3075. 1,3-Dichloropropene

Nomenclature

CAS number: 542-75-6
1,3-Dichloro-1-propene; α,γ-dichloropropylene; 1,3-dichloropropylene; γ-chloroallyl chloride; 1,3-D; Curfew (Dow AgroSci.); Telone II (Dow AgroSci.).
C3H4Cl2; mol wt 110.97.
C 32.47%, H 3.63%, Cl 63.90%.

Description and references

Prepd from 1,2,3-trichloropropane with NaOH: Friedel, Silva, Compt. Rend. 75, 81 (1872); Reboul, Ann. Chim. [3] 60, 37 (1860); from 3-chloro-2-propen-1-ol with PCl3: Kirrmann et al., Bull. Soc. Chim. Fr. [5] 1, 860 (1934); from acrolein with PCl5: van Romburgh, ibid. [2] 36, 549 (1881); from 3,3-dichloropropene by isomerization with conc HCl: idem, ibid. The usual industrial prepn is from 1,3-dichloro-2-propanol by dehydration with POCl3 or with P2O5 in benzene: Hurd, Webb, J. Am. Chem. Soc. 58, 2191 (1936). Prepn of stereoisomers: L. F. Hatch, A. C. Moore, ibid. 66, 285 (1944). Configuration: H. A. Smith, W. H. King, ibid. 70, 3528 (1948); L. F. Hatch, R. H. Perry, ibid. 71, 3262 (1949). Persistence in soil: I. J. Thomason, M. V. McKenry, Hilgardia 42, 393 (1974). GC determn of isomers in rat blood: P. E. Kastl, E. A. Hermann, J. Chromatogr. 265, 277 (1983). Toxicity study: T. R. Torkelson, F. Oyen, Am. Ind. Hyg. Assoc. J. 38, 217 (1977). Review of toxicology and human exposure: Toxicological Profile for 1,3-Dichloropropene (PB93-110765, 1992) 151 pp.

Chemical structure

Properties

Liquid with chloroform odor. d25 1.220. bp 108°. nD22 1.4735. Technical product is mixture of isomers. LD50 (92% technical product) in male, female rats (mg/kg): 713, 470 orally (10% soln in corn oil); in rabbits (mg/kg): 504 dermally (Torkelson, Oyen).

Derivative

(E)-Form.

Nomenclature

CAS number: 10061-02-6

Properties

bp 112.0°. d420 1.217. n420 1.4730.

Derivative

(Z)-Form.

Nomenclature

CAS number: 10061-01-5

Properties

bp 104.3°. d420 1.224. n420 1.4682.

Caution

Potential symptoms of overexposure are irritation of skin, eyes, and respiratory system; eye and skin burns; lacrimation; headache, dizziness, coma; gasping, refusal to breathe, cough, substernal pain; possible liver, kidney and heart injury. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 100; Clinical Toxicology of Commercial Products, R. E. Gosselin et al., Eds. (Williams & Wilkins, Baltimore, 5th Ed., 1984) Section III, pp 141-142. The technical grade is reasonably anticipated to be a human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-93.

Use

Soil fumigant; nematocide. In manuf of pesticides.