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Sigma-Aldrich

2-Chloroethyl chloroformate

97%

Synonym(s):

2-Chloroethoxycarbonyl chloride

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About This Item

Linear Formula:
ClCOOCH2CH2Cl
CAS Number:
627-11-2
Molecular Weight:
142.97
Beilstein:
506639
EC Number:
210-982-4
MDL number:
MFCD00000646
UNSPSC Code:
12352100
PubChem Substance ID:
24855215
NACRES:
NA.22

vapor pressure

0.23 psi ( 20 °C)

Assay

97%

form

liquid

refractive index

n20/D 1.446 (lit.)

bp

155-156 °C (lit.)

density

1.385 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

ClCCOC(Cl)=O

InChI

1S/C3H4Cl2O2/c4-1-2-7-3(5)6/h1-2H2

InChI key

SVDDJQGVOFZBNX-UHFFFAOYSA-N

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Application

2-Chloroethyl chloroformate has been used in the synthesis of:
  • (4S)-4-hydroxymethyl-N-[(αR)-α-methylbenzyl]-2-oxazolidinone
  • propargyl dienamide (ll), a precursor of allenic dienamide
  • (±)-7-(2-chloroethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-6,7-dihydro-5H-pyrrolo-[3,4-b]-pyrazin-5-one

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H314,H331

Hazard Classifications

Acute Tox. 3 Inhalation - Eye Dam. 1 - 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)

158.0 °F - closed cup

Flash Point(C)

70 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Asymmetric synthesis of the 4-hydroxymethyl-2-oxazolidinone from the serinol derivative and chloroformates.
Sugiyama S, et al.
Tetrahedron Letters, 40(42), 7489-7492 (1999)
Enzymatic resolution of new carbonate intermediates for the synthesis of (< i> S</i>)-(+)-zopiclone.
Solares LF, et al.
Tetrahedron Asymmetry, 13(23), 2577-2582 (2002)
A new approach to pyrrolophenanthridone alkaloids via allene intramolecular cycloaddition: Total synthesis of Hippadine.
Hayakawa K, et al.
Tetrahedron Letters, 28(47), 5895-5898 (1987)

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