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66230-04-4

Basic Information
CAS No.: 66230-04-4
Name: Esfenvalerate
Article Data: 11
Molecular Structure:
Molecular Structure of 66230-04-4 (Esfenvalerate)
Formula: C25H22ClNO3
Molecular Weight: 419.908
Synonyms: Sumidan;a-Sum;Benzeneaceticacid, 4-chloro-a-(1-methylethyl)-, cyano(3-phenoxyphenyl)methyl ester,[S-(R*,R*)]-;(S)-a-Cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)isovalerate;(S,S)-Fenvalerate;1S,1'S-Fenvalerate;Asana;Asana XL;Aa;Fenvalerate a;OMS 3023;S 1844;S 5602Aa;Sumi-Gold;Sumi-alfa;Sumi-alpha;Sumicidin Aa;
Density: 1.21 g/cm3
Melting Point: 59 °C
Boiling Point: 538.9 °C at 760 mmHg
Flash Point: 279.7 °C
Solubility: 0.002 mg l-1 (25 °C)
Appearance: White crystalline solid
Hazard Symbols: ToxicT, DangerousN
Risk Codes: 23/25-43-50/53
Safety: 24-36/37/39-45-60-61
Transport Information: UN 2811
PSA: 59.32000
LogP: 6.67998
Synthetic route
143-33-9

sodium cyanide

66230-05-5

S-(+)-2-(4-chlorophenyl)isovaleryl chloride

39515-51-0

3-Phenoxybenzaldehyde

66230-04-4

esfenvalerate

Conditions
ConditionsYield
With N-butyl-N,N-dimethyl-(α-phenyl)ethylammonium bromide In water; 1,2-dichloro-ethane at 0 - 5℃; for 2.25h;36%
956498-38-7

α-cyano-3-phenoxybenzyl S-(+)-2-(4-chlorophenyl)isovalerate

A

67614-32-8

(R)-α-cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)-3-methylbutyrate

B

66230-04-4

esfenvalerate

Conditions
ConditionsYield
With ammonia In methanol at -19 - 17℃; for 17 - 260h; Purification / work up; Resolution of racemate;A n/a
B 23%
Stage #1: α-cyano-3-phenoxybenzyl S-(+)-2-(4-chlorophenyl)isovalerate In n-heptane; toluene for 2h; Heating / reflux; Resolution of racemate;
Stage #2: In methanol at -16 - 0℃; for 65 - 240h; Purification / work up;
iron rust In methanol at -5 - 12℃; for 30h; Purification / work up; Resolution of racemate;
66230-05-5

S-(+)-2-(4-chlorophenyl)isovaleryl chloride

39515-47-4, 52315-06-7, 61826-76-4, 71962-66-8

(S)-m-phenoxybenzaldehyde cyanohydrin

66230-04-4

esfenvalerate

Conditions
ConditionsYield
With pyridine
66230-05-5

S-(+)-2-(4-chlorophenyl)isovaleryl chloride

39515-47-4, 52315-06-7, 61826-76-4, 71962-66-8

(S)-m-phenoxybenzaldehyde cyanohydrin

A

66230-04-4

esfenvalerate

B

66267-77-4

[R]-alpha-cyano-3-phenoxybenzyl [S]-2-(4-chlorophenyl)-2-isopropyl-acetate

Conditions
ConditionsYield
With pyridine In dichloromethane a) 0 deg C 1 h, b) r.t., overnight; Yield given. Title compound not separated from byproducts;
39515-47-4

2-hydroxy-2-(3-phenoxyphenyl)acetonitrile

66230-05-5

S-(+)-2-(4-chlorophenyl)isovaleryl chloride

A

66230-04-4

esfenvalerate

B

66267-77-4

[R]-alpha-cyano-3-phenoxybenzyl [S]-2-(4-chlorophenyl)-2-isopropyl-acetate

Conditions
ConditionsYield
With pyridine In dichloromethane for 0.5h; Acylation;A 495 mg
B 645 mg
51631-50-6

2-(4-chlorophenyl)-3-methyl-(2SR)-butanoyl chloride

39515-47-4, 52315-06-7, 61826-76-4, 71962-66-8

(S)-m-phenoxybenzaldehyde cyanohydrin

A

67614-32-8

(R)-α-cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)-3-methylbutyrate

B

66230-04-4

esfenvalerate

Conditions
ConditionsYield
With pyridine In hexane; acetate buffer at 0℃; pH=4.5; Title compound not separated from byproducts;
298702-31-5

(S)-(+)-cyano(3-phenoxyphenyl)methyl butyrate

66230-04-4

esfenvalerate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Pseudomonas cepacia lipase gelozyme; AcOH; 1-butanol / hexane / 3 h / 20 °C / Enzymatic reaction
2: pyridine / acetate buffer; hexane / 0 °C / pH 4.5
View Scheme
2012-74-0, 55291-27-5, 55332-38-2, 63640-09-5

2-(4-chlorophenyl)-3-methylbutyric acid

66230-04-4

esfenvalerate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: via (S)-(-)-α-methylbenzylamine salt
2: SOCl2; DMF / CHCl3 / 1 h / 60 °C
3: 495 mg / pyridine / CH2Cl2 / 0.5 h
View Scheme
55332-38-2

S-isopropyl-4-chlorophenylacetic acid

66230-04-4

esfenvalerate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: SOCl2; DMF / CHCl3 / 1 h / 60 °C
2: 495 mg / pyridine / CH2Cl2 / 0.5 h
View Scheme
39515-51-0

3-Phenoxybenzaldehyde

66230-04-4

esfenvalerate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: HCl / tetrahydrofuran; H2O / 0.5 h / 20 °C
2: 495 mg / pyridine / CH2Cl2 / 0.5 h
View Scheme
Multi-step reaction with 3 steps
2: Candida cylindracea lipase / H2O / 23 h / 30 °C / pH 5
3: pyridine
View Scheme
Multi-step reaction with 3 steps
2: 49 percent / Arthrobacter lipase / H2O / 23 h / 40 °C / further lipases and immobilized Arthrobacter lipase; effect of pH, temperature and (S)/(R) mixture of the acetate
3: pyridine
View Scheme
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  • EsfenvalerateCAS NO.: 66230-04-4

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    EsfenvalerateCAS NO.: 66230-04-4

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Consensus Reports

IARC Cancer Review: Group 3 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 53 (1991),p. 309.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 53 (1991),p. 309.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human No Available Data IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 53 (1991),p. 309.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) .

Specification

The IUPAC name of Fenvalerate alpha is [(S)-cyano-(3-phenoxyphenyl)methyl](2S)-2-(4-chlorophenyl)-3-methylbutanoate. With the CAS registry number 66230-04-4, it is also named as Esfenvalerate; Benzeneacetic acid, 4-chloro-alpha-(1-methylethyl)-, (S)-cyano(3-phenoxyphenyl)methyl ester, (alphaS)-. The product's categories are insecticide; EQ - EZMethod specific; pesticides;Alpha sort; endocrine disruptors (draft) alphabetic; EPA; oeko-tex standard 100; pesticides& metabolites; pyrethroids. It is white crystalline solid which is soluble in acetone, acetonitrile, chloroform, ethyl acetate, dimethyl formamide, dimethyl sulfoxide, xylene and other organic solvents. Fenvalerate alpha is a kind of pesticide which is highly toxic. It will produce toxic nitrogen oxide and chloride gas when buring. In addition, the storage environment should be ventilate, low-temperature and dry.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 6.68; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 6.68; (4)ACD/LogD (pH 7.4): 6.68; (5)ACD/BCF (pH 5.5): 69665.47; (6)ACD/BCF (pH 7.4): 69665.47; (7)ACD/KOC (pH 5.5): 101909.01; (8)ACD/KOC (pH 7.4): 101909.01; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 8; (12)Index of Refraction: 1.586; (13)Molar Refractivity: 116.44 cm3; (14)Molar Volume: 346.7 cm3; (15)Polarizability: 46.16×10-24 cm3; (16)Surface Tension: 47.3 dyne/cm; (17)Enthalpy of Vaporization: 81.62 kJ/mol; (18)Vapour Pressure: 1.11E-11 mmHg at 25°C; (19)Rotatable Bond Count: 8; (20)Exact Mass: 419.128821; (21)MonoIsotopic Mass: 419.128821; (22)Topological Polar Surface Area: 59.3; (23)Heavy Atom Count: 30; (24)Complexity: 586.

Uses of Fenvalerate alpha: It is used for control of a wide range of insect pests on cotton, maize, groundnuts, soya beans, sugar cane, sunflowers, sorghum, fruit trees, vegetables, ornamentals, and noncrop land.

When you are using this chemical, please be cautious about it as the following:
It is toxic by inhalation and if swallowed and may cause sensitization by skin contact, so people should avoid contact with skin.. It is also very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) This material and its container must be disposed of as hazardous waste and avoid release to the environment.

People can use the following data to convert to the molecule structure.
1. SMILES: Clc1ccc(cc1)[C@@H](C(=O)O[C@H](C#N)c3cccc(Oc2ccccc2)c3)C(C)C;
2. InChI: InChI=1/C25H22ClNO3/c1-17(2)24(18-11-13-20(26)14-12-18)25(28)30-23(16-27)19-7-6-10-22(15-19)29-21-8-4-3-5-9-21/h3-15,17,23-24H,1-2H3/t23-,24+/m1/s1.

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rabbit LD50 skin > 2gm/kg (2000mg/kg)   Farm Chemicals Handbook. Vol. -, Pg. C27, 1991.
rat LD50 oral 325mg/kg (325mg/kg)   Farm Chemicals Handbook. Vol. -, Pg. C287, 1991.
rat LD50 skin > 5gm/kg (5000mg/kg)   Farm Chemicals Handbook. Vol. -, Pg. C287, 1991.