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185892

Sigma-Aldrich

Ethyl chloroformate

97%

Synonym(s):

Chloroformic acid ethyl ester

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About This Item

Linear Formula:
ClCOOC2H5
CAS Number:
541-41-3
Molecular Weight:
108.52
Beilstein:
385653
EC Number:
208-778-5
MDL number:
MFCD00000644
UNSPSC Code:
12352100
PubChem Substance ID:
24851187
NACRES:
NA.22

vapor density

3.74 (vs air)

Quality Level

200

vapor pressure

3.42 psi ( 20 °C)

Assay

97%

form

liquid

autoignition temp.

842 °F

refractive index

n20/D 1.395 (lit.)

bp

93 °C (lit.)

mp

−81 °C (lit.)

solubility

alcohol: miscible
benzene: miscible
chloroform: miscible
diethyl ether: miscible
water: insoluble

density

1.135 g/mL at 25 °C (lit.)

SMILES string

CCOC(Cl)=O

InChI

1S/C3H5ClO2/c1-2-6-3(4)5/h2H2,1H3

InChI key

RIFGWPKJUGCATF-UHFFFAOYSA-N

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Application

  • Ethyl chloroformate was used in the synthesis of nitrile oxides.
  • It was used as derivatization reagent to investigate stereochemical conversion of chiral non-steroidal anti-inflammatory drugs during derivatization reaction.
  • It was used to develop flexible template strategy for the generation of nanometer-scale templates via dip-pen nanolithography.
  • It was used as derivatization reagent in an enantiomeric analysis of amino acids by two-dimensional gas chromatography.
  • It was also used with ammonia and cyanuric chloride to convert carboxylic acids to nitriles.

Packaging

Derivatization reagent employed in an enantiomeric analysis of amino acids by two-dimensional gas chromatography. Also used with ammonia and cyanuric chloride to convert carboxylic acids to nitriles.

Signal Word

Danger

Hazard Statements

H225,H290,H302,H314,H330

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 2 - Met. Corr. 1 - Skin Corr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

60.8 °F

Flash Point(C)

16 °C

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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Sezin Erarpat et al.
Journal of separation science, 43(6), 1100-1106 (2019-12-21)
A green and fast analytical method for the determination of l-methionine in human plasma is presented in this study. Preconcentration of the analyte was carried out by switchable solvent liquid phase microextraction after ethyl chloroformate derivatization reaction. Instrumental detection of
M R Wright et al.
Journal of chromatography, 616(1), 59-65 (1993-06-23)
A potential problem with chiral derivatization is the possibility of stereochemical conversion during the derivatization reaction. This possibility has been examined using the non-steroidal anti-inflammatory drugs ibuprofen, ketoprofen, etodolac and flurbiprofen. To avoid possible interference from stereochemical impurities, male Sprague-Dawley
Melanie Junge et al.
Chirality, 19(3), 228-234 (2007-01-19)
The chiral separation of amino acids (AA) derivatised with ethyl chloroformate by using comprehensive two-dimensional gas chromatography is reported. A commercially available enantioselective capillary column (Chirasil-l-Val) has been tested as first-dimension column. Two nonenantioselective stationary phases (BPX50 and BP1) with
Tetrahedron Letters, 48, 1465-1465 (2007)
A convenient preparative method of nitrile oxides by the dehydration of primary nitro compounds with ethyl chloroformate or benzenesulfonyl chloride in the presence of triethylamine.
Shimizu T, et al.
Bulletin of the Chemical Society of Japan, 59(9), 2827-2831 (1986)
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