2-CHLOROETHYL CHLOROFORMATE

PRODUCT IDENTIFICATION

CAS NO.

627-11-2

2-CHLOROETHYL CHLOROFORMATE 

EINECS NO. 210-982-4
FORMULA C3H4Cl2O2
MOL WT. 142.97
H.S. CODE  
TOXICITY Mouse LCLo (inhalation): 200mg/m3
SYNONYMS Carbonochloridic Acid 2-chloroethyl ester;  
2-Chloroethyl chloroformate; beta-Chloroethyl Chlorocarbonate (2-Chloroethoxy) carbonyl chloride; 2-Chlorethylester kyseliny chlormravenci; Chloroformic acid beta-chloroethyl ester;

SMILES

O(C(=O)Cl)CCCl

CLASSIFICATION

 

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE

colorless to slightly colored liquid

MELTING POINT -70 C
BOILING POINT 155 - 156 C
SPECIFIC GRAVITY

1.38 - 1.39

SOLUBILITY IN WATER 1.44E+04 mg/l at 25 C
AUTOIGNITION

 

pKa (Dissociation Constant at 20 C)
log Pow 0.88 (Octanol-water)
VAPOR PRESSURE (mmHg at 25 C)
HENRY'S LAW 1.10E-03 (atm-m3/mole at 25 C)
OH RATE 9.75E-13 (cm3/molecule-sec at 25 C Atmospheric )
pH  
VAPOR DENSITY  

AUTOIGNITION

 

REFRACTIVE INDEX

 

NFPA RATINGS  
FLASH POINT

79 C

STABILITY Stable under ordinary conditions

GENERAL DESCRIPTION & APPLICATIONS

Phosgene (carbonyl dichloride, COCl2) is a very reactive chemical intermediate to prepare isocyanates, chloroformates, isothiocyanates, isonitriles and acid chlorides as well as in the production of polymers including polyurethanes, polycarbonates, and polyureas. Phosgene , however, is extremely toxic gas associated strong safety hazards and handling precautions. It is listed on schedule 3 of the Chemical Weapons Convention. All production sites must be declared to the OPCW. Phosgene is almost entirely in captive consume in the production plant. Chloroformates are relatively less dangerous route to prepare important families of compounds, the carbonates and carbamates. Carbonates are prepared by reaction with alcohol (or phenol) and carbamates are by reaction with an amine ( primary or secondary). Chloroformates are starting materials to prepare carbonate and carbamate derivatives that are used in the pharmaceutical and agrochemical industry.

 

 

Chloroformates are esters of chloroformic acid, single acyl-halide derivative of carbonic acid (phosgene is the double acyl-halide derivative).  Chloroformic acid itself is too unstable to be handled for chemical reactions. However, many esters of this carboxylic acid are stable and these chloroformates are important reagents in organic chemistry. They are widely used as reagents in organic chemistry. Some important chloroformates are:

  • 4-Nitrophenyl chloroformate (CAS NO. 7693-46-1): a reagent for the synthesis of mixed, activated carbonates and thiocarbonates, activated urethanes, and other compounds. Used to synthesize a cleavable, heterobifunctional cross-linker for reversible conjugation of amines to thiol-modified DNA. Employed in the preparation of poly(oxyethylene) modified dextrans.
  • Fluorenylmethyloxycarbonylchloride (CAS No. 28920-43-6): a reagent for derivatizing amino acids and for introducing N-Fmoc amino acids for solid-phase peptide synthesis and for the synthesis of a bicyclic proline analog. FMOC protection is important in solid phase peptide synthesis because its removal with piperidine solution does not disturb the acid labile linker between the peptide and the resin. Very stable in acidic condition, and moderately stable in inorganic base.
  • Benzyl chloroformate (CAS No. 501-53-1): a reagent useful for the introduction of the carboxybenzyl (Cbz or Z) protecting group for amines. Easily deprotected under hydrogenation or triethyl silane.
  • Ethyl chloroformate (CAS No. 541-41-3): a reagent for the introduction of the ethyl carbamate protecting group and for the formation of carboxylic anhydrides. Used to convert carboxylic acids to nitriles.
  • Chloroethyl Chloroformate (2-Chloroethyl chloroformate: CAS No. 627-11-2, 1-Chloroethyl chloroformate:CAS No. 50893-53-3): a reagent for the selective N-dealkylation of tertiary amines. and for the synthesis of alkyl 1-chloroethyl carbonates. Useful in the synthesis of pharmaceuticals (e.g.: Cefpodoxime, Candesartan, Ampiroxicam, Bacampicillin)
SALES SPECIFICATION

APPEARANCE

colorless to slightly colored liquid

ASSAY (G.C)

98.0% min

COLOR (APHA)

50 max

TRANSPORTATION
PACKING 250kgs in Drum
HAZARD CLASS  
UN NO.  
OTHER INFORMATION