Chloromethyl chloroformate

Chloromethyl chloroformate
Names


Preferred IUPAC name Chloromethyl carbonochloridate
Identifiers
CAS Number	22128-62-7^Y
3D model (JSmol)	Interactive image Interactive image
ChemSpider	56498^Y
ECHA InfoCard	100.040.707
PubChem CID	62754
CompTox Dashboard (EPA)	DTXSID9074567
InChI InChI=1S/C2H2Cl2O2/c3-1-6-2(4)5/h1H2^Y Key: JYWJULGYGOLCGW-UHFFFAOYSA-N^Y InChI=1/C2H2Cl2O2/c3-1-6-2(4)5/h1H2 Key: JYWJULGYGOLCGW-UHFFFAOYAF
SMILES ClC(OCCl)=O ClC(=O)OCCl
Properties
Chemical formula	C₂H₂Cl₂O₂
Molar mass	128.94 g·mol⁻¹
Appearance	Colorless liquid
Density	1.45 g/ml^[1]
Boiling point	107–108 °C (225–226 °F; 380–381 K)^[1]
Related compounds
Related chloroformates	Chloroethyl chloroformate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

Chemical compound

Chloromethyl chloroformate (CClO₂CH₂Cl), also known as palite gas,^[2] is a chemical compound developed into gas form and used for chemical warfare during World War I. It is a tearing agent designed to cause temporary blindness. It is a colorless liquid with a penetrating, irritating odor.

Industrially, chloromethyl chloroformate is used to manufacture other chemicals.

References

^ ^a ^b "Chloromethyl chloroformate". Sigma-Aldrich.
^ Auld, S.J.M. (February 4, 1918). "Methods of gas warfare". Journal of the Washington Academy of Sciences. 8 (3): 58. Bibcode:1918Natur.101R.215.. doi:10.1038/101215b0. JSTOR 24521564. S2CID 32522395.

Blood agents

Blister agents

Arsenicals	Ethyldichloroarsine (ED) Methyldichloroarsine (MD) Phenyldichloroarsine (PD) Lewisite (L) Lewisite 2 (L2) Lewisite 3 (L3)
Sulfur mustards	Levinstein mustard (EA-229) T Q CEES
Nitrogen mustards	HN1 HN2 HN3 TL-301
Nettle agents	Phosgene oxime (CX)
Other	KB-16 Dibutylchloromethyltin chloride Selenium oxychloride

Nerve agents

G-agents	Tabun (GA) Sarin (GB) Chlorosarin (ClGB) Thiosarin (SGB) Soman (GD) Chlorosoman (ClGD) Ethylsarin (GE) GH Cyclosarin (GF) GP Fluorotabun EA-1356 EA-4352 Crotylsarin
V-agents	EA-2192 EA-3148 VE VG VM VP VR VS VX EA-1763 Chinese VX V-sub x (GD-7)
GV agents	GV (EA-5365)
Novichok agents	A-208 A-232 A-234 A-242 A-262 C01-A035 C01-A039 C01-A042
Carbamates	Dimethylcarbamoyl fluoride EA-3887 EA-3887A EA-3966 EA-3990 EA-4056 T-1123 T-1152 T-1194 Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) TL-599 TL-1238 TL-1299 TL-1317 Miotine (AR-28/T-1843) 3152 CT 4-686-293-01 (Agent 1-10)
Other	Diisopropyl fluorophosphate Dicyclohexyl phosphorofluoridate EA-2012 EA-2054 EA-2098 EA-2613 2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate Neopentylene fluorophosphate Selenophos Phospholine R-16661 Ro 3-0422 Methanesulfonyl fluoride Dimefox (TL-792) MSPI
Precursors	Acetonitrile AT ATO AlP A.P.C. complex Chlorosarin Chlorosoman Cyclohexanol 1,8-Dibromooctane N,N-Diisopropylaminoethanol (KB) EA-1250 DIHP ZS DEHP EA-1224 Dimethylamidophosphoric dichloride Dimethylamidophosphoric dicyanide DMHP Ethylphosphonoselenoic dichloride Formaldoxime Nital 4-Hydroxycoumarin Isopropyl alcohol (TB) Methyldichlorophosphine (SW) Methylphosphonyl difluoride (difluoro) (DF) Methylphosphonyl dichloride (dichloro) Nitromethane OPA mixture Phosphoryl chloride Phosphorus pentachloride Phosphorus trichloride (TH) Pinacolone Pinacolyl alcohol Phenacyl chloride QL 2,4,5-Trichlorophenol 3,3,5-Trimethylcyclohexanol Triethyl phosphite Trimethyl phosphite TC TG