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23181

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/REAXYS Number:
506426
EC Number:
244-793-3
MDL number:
MFCD00077688
UNSPSC Code:
12352100
PubChem Substance ID:
57648023
NACRES:
NA.22

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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

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1 of 4

This Item
2326172640035660
Chloromethyl chloroformate ≥98.0% (GC)

Sigma-Aldrich

23181

Chloromethyl chloroformate

Trichloromethyl chloroformate ≥97.0% (GC)

Sigma-Aldrich

23261

Trichloromethyl chloroformate

2-(Chloromethyl)benzoic acid ≥97.0% (GC)

Sigma-Aldrich

726400

2-(Chloromethyl)benzoic acid

Bis(2-chloroethyl) ether puriss., ≥99.0% (GC)

Sigma-Aldrich

35660

Bis(2-chloroethyl) ether

assay

≥98.0% (GC)

assay

≥97.0% (GC)

assay

≥97.0% (GC)

assay

≥99.0% (GC)

Quality Level

200

Quality Level

100

Quality Level

-

Quality Level

200

form

liquid

form

-

form

crystals

form

liquid

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

-

bp

107-108 °C (lit.)

bp

20 °C/10 mmHg (lit.)

bp

-

bp

65-67 °C/15 mmHg (lit.)

density

1.450 g/mL at 20 °C

density

1.639 g/mL at 20 °C

density

-

density

1.22 g/mL at 25 °C (lit.)

Application

Chloromethyl chloroformate was used as key reactant in the synthesis of:
  • novel aminocarbonyloxymethyl esters of diclofenac and flufenamic acid[1]
  • highly water-soluble monomethoxypoly(ethyleneglycol) prodrugs of cyclosporin A[2]
  • series of 3-acyloxymethyloxycarbonyl-1-aryl-3-methyltriazenes[3]

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

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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
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
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
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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