Diphosgene
Title: Diphosgene
CAS Registry Number: 503-38-8
CAS Name: Carbonochloridic acid trichloromethyl ester
Additional Names: chloroformic acid trichloromethyl ester; trichloromethylchloroformate; trichloromethylcarbonochloridate
Molecular Formula: C2Cl4O2
Molecular Weight: 197.83
Percent Composition: C 12.14%, Cl 71.68%, O 16.17%
Line Formula: ClCOOCCl3
Literature References: Used in synthesis as substitute for phosgene, q.v. Prepn by photochlorination of methyl formate: W. Hentschel, J. Prakt. Chem. 36, 209 (1887); F. Grignard et al., C.R. Hebd. Seances Acad. Sci. 169, 1074 (1919); eidem, ibid. 1143; by photochlorination of methyl chloroformate: A. Kling et al., ibid. 1046; K. Kurita, Y. Iwakura, Org. Synth. 59, 195 (1980). Effect on air-blood barrier in rabbits, toxicity: E. Klika, A. Mysliveckova, Folia Morphol. (Prague) 19, 5 (1971), C.A. 75, 3433c (1971). Use in synthesis of isocyanides: G. Skorna, J. Ugi, Angew. Chem. Int. Ed. 16, 259 (1977).
Properties: Suffocating liquid. bp 128°. bp50 49°. d15 1.664. nD22 1.45664. Stable at room temp, decomposes to phosgene at ~300°C. LC100 in rabbits (10-20 minutes exposure to vapor): 0.9 mg/l air (Klika, Mysliveckova).
Boiling point: bp 128°; bp50 49°
Index of refraction: nD22 1.45664
Density: d15 1.664
Toxicity data: LC100 in rabbits (10-20 minutes exposure to vapor): 0.9 mg/l air (Klika, Mysliveckova)
Use: In organic synthesis; as war gas.

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