Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

View All Documentation

23181

Sigma-Aldrich

Chloromethyl chloroformate

≥98.0% (GC)

Synonym(s):

1-Chloromethyl chloroformate, Chloroformic acid chloromethyl ester, Chloromethoxycarbonyl chloride, Chloromethyl carbonochloridate, Chloromethyl chlorocarbonate

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
ClCOOCH2Cl
CAS Number:
22128-62-7
Molecular Weight:
128.94
Beilstein/REAXYS Number:
506426
EC Number:
244-793-3
MDL number:
MFCD00077688
UNSPSC Code:
12352100
PubChem Substance ID:
57648023
NACRES:
NA.22

Quality Level

200

assay

≥98.0% (GC)

form

liquid

refractive index

n20/D 1.428

bp

107-108 °C (lit.)

density

1.450 g/mL at 20 °C

functional group

chloro

storage temp.

2-8°C

SMILES string

ClCOC(Cl)=O

InChI

1S/C2H2Cl2O2/c3-1-6-2(4)5/h1H2

InChI key

JYWJULGYGOLCGW-UHFFFAOYSA-N

Application

Chloromethyl chloroformate was used as key reactant in the synthesis of:
  • novel aminocarbonyloxymethyl esters of diclofenac and flufenamic acid
  • highly water-soluble monomethoxypoly(ethyleneglycol) prodrugs of cyclosporin A
  • series of 3-acyloxymethyloxycarbonyl-1-aryl-3-methyltriazenes

pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

signalword

Danger

hcodes

H314,H331

Hazard Classifications

Acute Tox. 3 Inhalation - Skin Corr. 1B

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

203.0 °F - closed cup

flash_point_c

95 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCCG7018
BCCG1934
BCCD3374
BCCB9095
BCBZ1772

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Hoon Cho et al.
Archives of pharmacal research, 27(6), 662-669 (2004-07-31)
The highly water-soluble monomethoxypoly(ethyleneglycol) (mPEG) prodrugs of cyclosporin A (CsA) were synthesized. These prodrugs were prepared by initially preparing intermediate in the form of carbonate at the 3'-positions of CsA with chloromethyl chloroformate, in the presence of a base to
Lina Ribeiro et al.
Archiv der Pharmazie, 340(1), 32-40 (2007-01-09)
Aminocarbonyloxymethyl ester prodrugs are known to undergo rearrangement in aqueous solutions to form the corresponding N-acylamine side product via an O-->N intramolecular acyl transfer from the carbamate conjugate base. Novel aminocarbonyloxymethyl esters of diclofenac and flufenamic acid containing amino acid
Keivan Sadrerafi et al.
Drug design, development and therapy, 12, 987-995 (2018-05-08)
Our previous study indicated that carborane containing small-molecule 1-(hydroxymethyl)-7-(4'-(trans-3″-(3'″-pyridyl)acrylamido)butyl)-1,7-dicarbadodecaborane (hm-MC4-PPEA), was a potent inhibitor of nicotinamide phosphoribosyltransferase (Nampt). Nampt has been shown to be upregulated in most cancers and is a promising target for the treatment of many different types
E Carvalho et al.
Bioorganic & medicinal chemistry, 8(7), 1719-1725 (2000-09-08)
A series of 3-acyloxymethyloxycarbonyl-1-aryl-3-methyltriazenes 5 was synthesised by the sequential reaction of 1-aryl-3-methyltriazenes with (i) chloromethyl chloroformate, (ii) NaI in dry acetone, and (iii) either the silver carboxylate or the carboxylic acids in the presence of silver carbonate. The hydrolysis

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service