Chlorobenzilate

Title: Chlorobenzilate
CAS Registry Number: 510-15-6
CAS Name: 4-Chloro-a-(4-chlorophenyl)-a-hydroxybenzeneacetic acid ethyl ester
Additional Names: 4,4¢-dichlorobenzilic acid ethyl ester; ethyl 4,4¢-dichlorobenzilate; ethyl 2-hydroxy-2,2-bis(4-chlorophenyl)acetate; chlorbenzilat
Manufacturers' Codes: G-23922; compd 338
Trademarks: Acaraben; Akar; Folbex
Molecular Formula: C16H14Cl2O3
Molecular Weight: 325.19
Percent Composition: C 59.10%, H 4.34%, Cl 21.80%, O 14.76%
Literature References: Prepn: Häfliger, US 2745780 (1956 to Geigy); GB 831421 (1960 to Metal & Thermit). Toxicity study: T. B. Gaines, Toxicol. Appl. Pharmacol. 14, 515 (1969). Review of carcinogenic risk: IARC Monographs 30, 73-85 (1983).
Properties: Viscous liquid. The commercial product is yellow. bp0.04 146-148°. nD20 1.5727. Vapor press. at 20°: 2.2 ´ 10-6 mm. Slightly sol in water. Sol in most organic solvents. Incompatible with lime. LD50 in male, female rats (mg/kg): 1040, 1220 orally (Gaines).
Boiling point: bp0.04 146-148°
Index of refraction: nD20 1.5727
Toxicity data: LD50 in male, female rats (mg/kg): 1040, 1220 orally (Gaines)
CAUTION: Symptoms similar to DDT: See Clinical Toxicology of Commercial Products, R. E. Gosselin et al., Eds. (Williams & Wilkins, Baltimore, 5th ed., 1984) Section II, p 283.
Use: Acaricide in spider-mite control; synergist for DDT.
Status: This monograph has been retired and is no longer subject to revision or update.
Chlorocresol Chlorocyanohydrin Chlorodibromomethane Chlorofluorocarbons Chloroform

Chlorobenzilate[1]
Chlorobenzilate structure.png
Identifiers
CAS number 510-15-6
PubChem 10522
ChemSpider 10085
KEGG C14574 YesY
Jmol-3D images Image 1
Properties
Molecular formula C16H14Cl2O3
Molar mass 325.19 g mol−1
Appearance Colorless to pale yellow solid
Density 1.28 g/cm3
Melting point 37 °C; 99 °F; 310 K
Hazards
R-phrases R22 R50/53
S-phrases (S2) S60 S61
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Chlorobenzilate is a pesticide that is not currently used in the USA or Europe. It was originally developed by Ciba-Geigy and introduced in 1952.[2] It was used as an acaricide against mites on citrus trees, including deciduous fruit trees.[3] It has been detected as a residue on tomatoes found in Japanese markets in 2005.[4] It is a non-systemic pesticide that works through contact and as a neurotoxin: it disrupts the functioning of the nervous system.

In the pure state, chlorobenzilate is a colorless to pale yellow solid, but the commercial product is a brownish liquid.[3] It is only slightly soluble in water, but miscible with acetone, toluene and methanol.