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E43101

Sigma-Aldrich

Ethyl chlorooxoacetate

98%

Synonym(s):

mono-Ethyl oxalyl chloride, Ethyl chloroglyoxylate, Monoethyl oxalyl chloride, Oxalic acid monoethyl ester chloride

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About This Item

Linear Formula:
ClCOCOOCH2CH3
CAS Number:
4755-77-5
Molecular Weight:
136.53
Beilstein:
506725
EC Number:
225-285-0
MDL number:
MFCD00000706
UNSPSC Code:
12352101
PubChem Substance ID:
24894549
NACRES:
NA.22
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Quality Level

100

Assay

98%

form

liquid

reaction suitability

reagent type: oxidant

refractive index

n20/D 1.416 (lit.)

bp

135 °C (lit.)

density

1.222 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)C(Cl)=O

InChI

1S/C4H5ClO3/c1-2-8-4(7)3(5)6/h2H2,1H3

InChI key

OWZFULPEVHKEKS-UHFFFAOYSA-N

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Application

Ethyl chlorooxoacetate can be used for the synthesis of:
  • α-keto esters.[1]
  • Functionalized 3-pyrolin-2-ones.[2]
  • Substituted arylglyoxylic acids via Friedel–Crafts acylation.[3]
  • Substituted 9,10-phenanthrenequinones.[4]
  • Quinoxalinone derivatives.[5]

Signal Word

Danger

Hazard Statements

H226,H314,H335

Hazard Classifications

Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

105.8 °F - closed cup

Flash Point(C)

41 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBL3643
STBK9719
WXBD1736V
WXBD1185V
STBJ3928

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Synthesis of arylglyoxylic acids and their collision-induced dissociation.
Wadhwa K, et al.
Synthetic Communications, 38(24), 4434-4444 (2008)
Microwave assisted synthesis of novel imidazo [2, 1-b] thiazole derivative attached to quinoxalinones.
Mukherjee C, et al.
Tetrahedron Letters, 53(45), 6008-6014 (2012)
A Convenient Synthesis of alpha-Keto Esters Using Ethyl 2-Pyridyl Oxalate.
Lee, Jae In
J. Korean Chem. Soc., 48(1), 103-103 (2004)
A one-pot synthesis of functionalised 3-pyrolin-2-ones by a four-component reaction between triphenylphosphine, primary amines, dimethyl acetylenedicarboxylate and ethyl chlorooxoacetate.
Anary-Abbasinejad M, et al.
J. Chem. Res. (M), 2007(10), 574-574 (2007)
An Efficient and Scalable Synthesis of Substituted Phenanthrenequinones by Intramolecular Friedel- Crafts Reaction of Imidazolides.
Yoshikawa N, et al.
Organic Letters, 9(21), 4103-4106 (2007)
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