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23181

Sigma-Aldrich

Chloromethyl chloroformate

≥98.0% (GC)

Synonym(s):

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

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About This Item

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

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

Signal Word

Danger

Hazard Statements

H314,H331

Hazard Classifications

Acute Tox. 3 Inhalation - Skin Corr. 1B

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

203.0 °F - closed cup

Flash Point(C)

95 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG7018
BCCG1934
BCCD3374
BCCB9095
BCBZ1772

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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
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

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