52645-53-1 structure, C21H20Cl2O3

permethrin

CAS No.

52645-53-1

Formula:

C21H20Cl2O3

Basic Info

Permethrin is a medication and chemical widely used as an insecticide, acaricide, and insect repellent. Permethrin is a first-line treatment for scabies. It is used as a cream.
It belongs to the family of synthetic chemicals called pyrethroids and functions as a neurotoxin, affecting neuron membranes by prolonging sodium channel activation. It is not known to rapidly harm most mammals or birds, but is toxic to fish and cats. In cats it may induce hyperexcitability, tremors, seizures, and death. In general, it has a low mammalian toxicity and is poorly absorbed by skin.
It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system.

Formula
C21H20Cl2O3
Molecular Weight
391.288
Exact Mass
390.079
LogP
6.1133
PSA
35.53
Synonyms

3-Dichloroacetyl-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline

(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate

3-phenoxybenzyl (1RS,3RS

3-phenoxybenzyl (1RS)-cis-trans-3-(2,2-dichlorovinyl)-2,2- dimethylcyclopropanecarboxylate

Permethrin (isomers)

1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate

Permethrin (cis/trans)

Permethrin

(3-phenoxyphenyl)methyl (1Ξ,3Ξ)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate

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Properties

Appearance & Physical State
colourless crystals (but the technical productis normally supplied as a pale brown liquid)
Density
1.19
Boiling Point
465.9ºC at 760mmHg
Melting Point
34-35ºC
Flash Point
159.4ºC
Water Solubility
insoluble
Stability
Stable. Incompatible with strong oxidising agents.
Storage Condition
0-6ºC

Safety Info

RTECS
GZ1255000
Safety Statements
S13; S24; S36/37/39; S60; S61; S45; S36/37; S16; S7; S26
Risk Statements
R20/22
HS Code
2916209022
RIDADR
UN1230 3/PG 2

MSDS

SDS 1.0
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SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name permethrin

1.2 Other means of identification

Product number -
Other names 3-phenoxybenzyl (1RS,3RS

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Veterinary Drug: INSECTICIDE
Uses advised against no data available

1.4 Supplier's details

Company MOLBASE (Shanghai) Biotechnology Co., Ltd.
Address Floor 4 & 5, Building 12, No. 1001 North Qinzhou Road,
Xuhui District, Shanghai, China
Telephone +86(21)64956998
Fax +86(21)54365166

1.5 Emergency phone number

Emergency phone number +86-400-6021-666
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin sensitization, Category 1

Acute toxicity - Inhalation, Category 4

Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H302 Harmful if swallowed

H317 May cause an allergic skin reaction

H332 Harmful if inhaled

H410 Very toxic to aquatic life with long lasting effects

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.

P272 Contaminated work clothing should not be allowed out of the workplace.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P271 Use only outdoors or in a well-ventilated area.

P273 Avoid release to the environment.

Response

P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/…if you feel unwell.

P330 Rinse mouth.

P302+P352 IF ON SKIN: Wash with plenty of water/...

P333+P313 If skin irritation or rash occurs: Get medical advice/attention.

P321 Specific treatment (see ... on this label).

P362+P364 Take off contaminated clothing and wash it before reuse.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P312 Call a POISON CENTER/doctor/…if you feel unwell.

P391 Collect spillage.

Storage

none

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

3.Composition/information on ingredients

3.1 Substances

Chemical name Common names and synonyms CAS number EC number Concentration
permethrin permethrin 52645-53-1 none 100%

4.First-aid measures

4.1 Description of necessary first-aid measures

General advice

Consult a physician. Show this safety data sheet to the doctor in attendance.

If inhaled

Fresh air, rest.

In case of skin contact

Remove contaminated clothes. Rinse and then wash skin with water and soap.

In case of eye contact

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

If swallowed

Rinse mouth. Refer for medical attention .

4.2 Most important symptoms/effects, acute and delayed

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Inhalation of material may be harmful. Contact may cause burns to skin and eyes. Inhalation of Asbestos dust may have a damaging effect on the lungs. Fire may produce irritating, corrosive and/or toxic gases. Some liquids produce vapors that may cause dizziness or suffocation. Runoff from fire control may cause pollution. (ERG, 2016)

4.3 Indication of immediate medical attention and special treatment needed, if necessary

Skin decontamination. Wash skin promptly with soap and water ... . If irritant or paresthetic effects occur, obtain treatment by a physician. Because volatilization of pyrethroids apparently accounts for paresthesia affecting the face, strenuous measures should be taken (ventilation, protective face mask and hood) to avoid vapor contact with the face and eyes. Vitamin E oil preparations (dL-alpha tocopheryl acetate) are uniquely effective in preventing and stopping the paresthetic reaction. They are safe for application to the skin under field conditions. Corn oil is somewhat effective, but possible side effects with continuing use make it less suitable. Vaseline is less effective than corn oil. Zinc oxide actually worsens the reaction. /Pyrethroids/

5.Fire-fighting measures

5.1 Extinguishing media

Suitable extinguishing media

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: SMALL FIRE: Dry chemical, CO2, water spray or regular foam. LARGE FIRE: Water spray, fog or regular foam. Do not scatter spilled material with high-pressure water streams. Move containers from fire area if you can do it without risk. Dike fire-control water for later disposal. FIRE INVOLVING TANKS: Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. (ERG, 2016)

5.2 Specific hazards arising from the chemical

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Some may burn but none ignite readily. Containers may explode when heated. Some may be transported hot. For UN3508, be aware of possible short circuiting as this product is transported in a charged state. (ERG, 2016)

5.3 Special protective actions for fire-fighters

Wear self-contained breathing apparatus for firefighting if necessary.

6.Accidental release measures

6.1 Personal precautions, protective equipment and emergency procedures

Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8.

6.2 Environmental precautions

Personal protection: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Do NOT wash away into sewer. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

6.3 Methods and materials for containment and cleaning up

Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

7.Handling and storage

7.1 Precautions for safe handling

Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2.

7.2 Conditions for safe storage, including any incompatibilities

Provision to contain effluent from fire extinguishing. Separated from food and feedstuffs. Keep in a well-ventilated room.

8.Exposure controls/personal protection

8.1 Control parameters

Occupational Exposure limit values

no data available

Biological limit values

no data available

8.2 Appropriate engineering controls

Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.

8.3 Individual protection measures, such as personal protective equipment (PPE)

Eye/face protection

Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).

Skin protection

Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it.

Respiratory protection

Wear dust mask when handling large quantities.

Thermal hazards

no data available

9.Physical and chemical properties

Physical state colourless crystals (but the technical productis normally supplied as a pale brown liquid)
Colour Colorless crystals to a viscous liquid; Color, white to pale yellow
Odour no data available
Melting point/ freezing point 34-35ºC
Boiling point or initial boiling point and boiling range 465.9ºC at 760mmHg
Flammability Combustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.
Lower and upper explosion limit / flammability limit no data available
Flash point 159.4ºC
Auto-ignition temperature no data available
Decomposition temperature no data available
pH no data available
Kinematic viscosity no data available
Solubility In water:insoluble
Partition coefficient n-octanol/water (log value) no data available
Vapour pressure 5.18X10-8 mm Hg at 25°C (OECD Method 104)
Density and/or relative density 1.19
Relative vapour density no data available
Particle characteristics no data available

10.Stability and reactivity

10.1 Reactivity

no data available

10.2 Chemical stability

Stable to heat (> or = 2 yr at 50°C), more stable in acid than alkaline media with optimum stability ca. pH 4; some photochemical degradation has been observed in laboratory studies but field data indicate this does not adversely affect biological performances.

10.3 Possibility of hazardous reactions

A pyrethroid derivative.

10.4 Conditions to avoid

no data available

10.5 Incompatible materials

no data available

10.6 Hazardous decomposition products

When heated to decomp it emits toxic fumes of /hydrogen chloride/.

11.Toxicological information

Acute toxicity

  • Oral: LD50 Rat oral 1,500 mg/kg
  • Inhalation: no data available
  • Dermal: LD50 Rat percutaneous > 4000 mg/kg

Skin corrosion/irritation

no data available

Serious eye damage/irritation

no data available

Respiratory or skin sensitization

no data available

Germ cell mutagenicity

no data available

Carcinogenicity

The /Environmental Protection/ Agency classified permethrin as "Likely to be Carcinogenic to Humans" by the oral route. This classification was based on two reproducible benign tumor types (lung and liver) in the mouse, equivocal evidence of carcinogenicity in Long-Evans rats, and supporting structural activity relationships (SAR) information. For the purpose of risk characterization, a low dose extrapolation model (Q1*) was used. The Q1* is 9.6 x 10-3 (mg/kg/day)-1 and was derived from the female mouse lung (adenoma and/or carcinoma) tumors

Reproductive toxicity

no data available

STOT-single exposure

no data available

STOT-repeated exposure

no data available

Aspiration hazard

no data available

12.Ecological information

12.1 Toxicity

  • Toxicity to fish: LC50; Species: Pimephales promelas (fathead minnow); Conditions: flow through bioassay with measured concentrations, 25.4°C, dissolved oxygen 7.5 mg/L, hardness 45.7 mg/L calcium carbonate, alkalinity 41.6 mg/L calcium carbonate, and pH 7.1; Concentration: 16.0 mg/L for 96 hr (confidence limit 8.71- 29.6 mg/L)
  • Toxicity to daphnia and other aquatic invertebrates: LC50; Species: Daphnia magna (Water flea); Conditions: freshwater, static, 22°C, pH 8.2-8.3, hardness 162-178 mg/L CaCO3, alkalinity 107-114 mg/L CaCO3, dissolved oxygen 7.8-8.1 mg/L; Concentration: 12.4 ug/L for 24 hr /formulation
  • Toxicity to algae: no data available
  • Toxicity to microorganisms: no data available

12.2 Persistence and degradability

AEROBIC: The half-life of permethrin in aerobically incubated soil is less than 4 weeks, and the degradation of the trans isomer is more rapid than the cis isomer(1). Permethrin was stable in sterile Hagerstown silty clay loam indicating that any degradation probably was microbial(2); as expected ester hydrolysis predominated in non-sterile soil(2). In two Japanese soils, both the 1R, trans- and 1R, cis-isomers were rapidly degraded under dry conditions with half-lives of less than 2 days(2). The half-life in a sediment-seawater solution was less than 2.5 days; under sterile conditions there was no significant change in permethrin concentration(3). Aerobic incubation of 14C-labeled cis- and trans-isomers and stereo-isomers of permethrin in turfgrass soil and coverground soil from California resulted in losses of 68.6-78.9% and 86.3-90.4% after 14 days for the cis- and trans-isomers respectively, and 93.0-99.2% and 95.4-98.5% after 56 days for the cis- and trans-isomers respectively(4); degradation products included cyclopropanoic acid, 3-phenoxybenzoic acid and 3-phenoxybenzyl alcohol(4); degradation losses in sediment were greater under aerobic conditions compared to anaerobic conditions after 14 days (trans-isomers had 76.2-81.2% loss under aerobic conditions and 65.7-74.1% loss under anaerobic conditions)(4). Stereo-isomers of cis-permethrin had half-lives of 139-141 days when incubated in sterilized soil or sediments and half-lives of 99-126 days in non-sterile aerobic or anaerobic soil or sediments(5).

12.3 Bioaccumulative potential

The BCF values for permethrin in rainbow trout (Oncorhynchus mykiss) and sheepshead minnow (Cyprinodon vagiegatus) were approximately 560 and 480, respectively(1,2). According to a classification scheme(3), these BCF values suggest the potential for bioconcentration in aquatic organisms is high(SRC). A BCF of 1,900 was also reported for oysters(2). Insect BCF values after 6 hr of exposure to sublethal permethrin concentrations were 18, 30, 7, 4, and 24 for black fly, caddisfly, damsefly, water scavenger, and mayfly, respectively(4).

12.4 Mobility in soil

Koc values for permethrin range from 10,471 to 86,000 that were measured in a variety of different soils including silt loam, sandy loam, sediments and sand(1); the selected Koc value (for use in modeling) is 39,300(1). Koc values for silt loam (Ohio), sandy loam (Wisconsin), sediment (Georgia), and sand (Florida) were 19,300 (Kd = 236; organic matter, 0.71%), 20,900 (Kd = 217; organic matter, 0.60%), 44,700 (Kd = 401; organic matter, 0.91%), and 60,900 (Kd = 140; organic matter, 0.13%), respectively(1). The Kd for permethrin was measured to be 400 on a red earth soil from Australia with an organic matter content of 1.09%(2) which corresponds to a Koc of about 63,100(SRC). According to a classification scheme(3), these Koc values suggest that permethrin is expected to be immobile in soil(SRC). The distribution coefficients (Kd) for permethrin on clean (i.e., without organic matter) montomorillonite, aluminum oxide and kaolinite clay mineral surfaces were 61, 41, and 5 ml/g, respectively(4).

12.5 Other adverse effects

no data available

13.Disposal considerations

13.1 Disposal methods

Product

The material can be disposed of by removal to a licensed chemical destruction plant or by controlled incineration with flue gas scrubbing. Do not contaminate water, foodstuffs, feed or seed by storage or disposal. Do not discharge to sewer systems.

Contaminated packaging

Containers can be triply rinsed (or equivalent) and offered for recycling or reconditioning. Alternatively, the packaging can be punctured to make it unusable for other purposes and then be disposed of in a sanitary landfill. Controlled incineration with flue gas scrubbing is possible for combustible packaging materials.

14.Transport information

14.1 UN Number

ADR/RID: UN1230 IMDG: UN1230 IATA: UN1230

14.2 UN Proper Shipping Name

ADR/RID: METHANOL
IMDG: METHANOL
IATA: METHANOL

14.3 Transport hazard class(es)

ADR/RID: 3 IMDG: 3 IATA: 3

14.4 Packing group, if applicable

ADR/RID: II IMDG: II IATA: II

14.5 Environmental hazards

ADR/RID: yes IMDG: yes IATA: yes

14.6 Special precautions for user

no data available

14.7 Transport in bulk according to Annex II of MARPOL 73/78 and the IBC Code

no data available

15.Regulatory information

15.1 Safety, health and environmental regulations specific for the product in question

Chemical name Common names and synonyms CAS number EC number
permethrin permethrin 52645-53-1 none
European Inventory of Existing Commercial Chemical Substances (EINECS) Listed.
EC Inventory Listed.
United States Toxic Substances Control Act (TSCA) Inventory Not Listed.
China Catalog of Hazardous chemicals 2015 Not Listed.
New Zealand Inventory of Chemicals (NZIoC) Listed.
Philippines Inventory of Chemicals and Chemical Substances (PICCS) Listed.
Vietnam National Chemical Inventory Listed.
Chinese Chemical Inventory of Existing Chemical Substances (China IECSC) Listed.

16.Other information

Information on revision

Creation Date Aug 18, 2017
Revision Date Aug 18, 2017

Abbreviations and acronyms

  • CAS: Chemical Abstracts Service
  • ADR: European Agreement concerning the International Carriage of Dangerous Goods by Road
  • RID: Regulation concerning the International Carriage of Dangerous Goods by Rail
  • IMDG: International Maritime Dangerous Goods
  • IATA: International Air Transportation Association
  • TWA: Time Weighted Average
  • STEL: Short term exposure limit
  • LC50: Lethal Concentration 50%
  • LD50: Lethal Dose 50%
  • EC50: Effective Concentration 50%

References

  • IPCS - The International Chemical Safety Cards (ICSC), website: http://www.ilo.org/dyn/icsc/showcard.home
  • HSDB - Hazardous Substances Data Bank, website: https://toxnet.nlm.nih.gov/newtoxnet/hsdb.htm
  • IARC - International Agency for Research on Cancer, website: http://www.iarc.fr/
  • eChemPortal - The Global Portal to Information on Chemical Substances by OECD, website: http://www.echemportal.org/echemportal/index?pageID=0&request_locale=en
  • CAMEO Chemicals, website: http://cameochemicals.noaa.gov/search/simple
  • ChemIDplus, website: http://chem.sis.nlm.nih.gov/chemidplus/chemidlite.jsp
  • ERG - Emergency Response Guidebook by U.S. Department of Transportation, website: http://www.phmsa.dot.gov/hazmat/library/erg
  • Germany GESTIS-database on hazard substance, website: http://www.dguv.de/ifa/gestis/gestis-stoffdatenbank/index-2.jsp
  • ECHA - European Chemicals Agency, website: https://echa.europa.eu/

Disclaimer: The above information is believed to be correct but does not purport to be all inclusive and shall be used only as a guide. The information in this document is based on the present state of our knowledge and is applicable to the product with regard to appropriate safety precautions. It does not represent any guarantee of the properties of the product. We as supplier shall not be held liable for any damage resulting from handling or from contact with the above product.

Spectrum

NMR Spectrum 1H NMR : Predict
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Analysis Methods

Kovats' RI, non-polar column, isothermal
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Column Shape
Capillary
Active Phase(℃)
OV-1
Retention index
2632.
Temperature Control
220.
Method
isothermal
Comments
 
Reference
Erdmann, F.Rochholz, G.Schütz, H.Retention-indices on OV-1 of approximately 170 commonly used pesticidesMikrochim. Acta1992, 106, 3-6, 219-226.
Kovats' RI, non-polar column, custom temperature program
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Column Shape
Packed
Active Phase(℃)
SE-30
Retention index
2634.
Temperature Control
Method
custom temperature program
Comments
N2, Chromosorb W HP; Column length: 2. m; Program: not specified
Reference
Osselton, M.D.Snelling, R.D.Chromatographic Identification of PesticidesJ. Chromatogr.1986, 368, 265-271.
Normal alkane RI, non-polar column, custom temperature program
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Column Shape
Capillary
Active Phase(℃)
5 % Phenyl methyl siloxane
Retention index
2711.
Temperature Control
Method
custom temperature program
Comments
30. m/0.25 mm/0.25 μm, Helium; Program: 50 0C(1 min) <sup> </sup>25 0C/min -&gt; 125 0C <sup> </sup>10 0C/min -&gt; 300 0C (10 min)
Reference
Department of Food Safety, Ministry of HealthWelfareAnalytical methods for residual compositional substances of agricultural chemicals, feed aadditives, and veterinary drugs in foods2006, retrieved from http://www.mhlw.go.jp/english/topics/foodsafety/positivelist060228/de/060526-1a.pdf.
Normal alkane RI, non-polar column, custom temperature program
expand collapse
Column Shape
Capillary
Active Phase(℃)
5 % Phenyl methyl siloxane
Retention index
2706.
Temperature Control
Method
custom temperature program
Comments
30. m/0.25 mm/0.25 μm, Helium; Program: 50 0C(1 min) <sup> </sup>25 0C/min -&gt; 125 0C <sup> </sup>10 0C/min -&gt; 300 0C (10 min)
Reference
Department of Food Safety, Ministry of HealthWelfareAnalytical methods for residual compositional substances of agricultural chemicals, feed aadditives, and veterinary drugs in foods2006, retrieved from http://www.mhlw.go.jp/english/topics/foodsafety/positivelist060228/de/060526-1a.pdf.
Normal alkane RI, non-polar column, custom temperature program
expand collapse
Column Shape
Capillary
Active Phase(℃)
OV-1
Retention index
2657.
Temperature Control
Method
custom temperature program
Comments
Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified
Reference
Waggott, A.Davies, I.W.Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf.

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