ethyl 2-chloro-2-oxoacetate

• ChemBase ID: 78090
• Molecular Formular: C4H5ClO3
• Molecular Mass: 136.5337
• Monoisotopic Mass: 135.9927217
• SMILES: O(C(=O)C(=O)Cl)CC
• Canonical SMILES: CCOC(=O)C(=O)Cl
• InChI: InChI=1S/C4H5ClO3/c1-2-8-4(7)3(5)6/h2H2,1H3
• InChIKey: OWZFULPEVHKEKS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2-chloro-2-oxoacetate
• IUPAC Traditional name: ethyl chloroglyoxylate
• Synonyms: mono-Ethyl oxalyl chloride; ethyl 2-chloro-2-oxoacetate; Ethyl chloroglyoxylate; Ethyl chloro(oxo)acetate; Monoethyl oxalyl chloride; Oxalic acid monoethyl ester chloride; mono-Ethyl oxalyl chloride; Ethyl chlorooxoacetate; Ethyl oxalyl chloride; 草酰氯单乙酯; 草酰氯单乙酯; 乙基乙二酰氯酯; 乙基草酰氯; 草酸单乙酯酰氯; 草酰氯乙酯; 草酸氯单乙酯

Database IDs

• CAS Number: 4755-77-5
• EC Number: 225-285-0
• MDL Number: MFCD00000706
• Beilstein Number: 506725
• PubChem SID: 24894549; 24886873; 162042914
• PubChem CID: 20884

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.0056134
• LogD (pH = 7.4): 1.0056134
• Log P: 1.0056134
• Molar Refractivity: 27.8148 cm^3
• Polarizability: 11.030652 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 134-135°C; 135 °C(lit.); 135°C
• Flash Point: 105.8 °F; 41 °C; 41°C; 41°C(105°F)
• Density: 1.222; 1.222 g/mL at 25 °C(lit.); 1.226; 1.227 g/mL at 20 °C
• Refractive Index: 1.4160; n20/D 1.416(lit.); n20/D 1.418

Safety Information

• Storage Warning: Corrosive/Flammable/Harmful/Irritant/Lachrymatory/Moisture Sensitive/Store under Argon; Moisture Sensitive
• European Hazard Symbols: Corrosive (C); X
• UN Number: 2920; UN2920
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 10-14-22-34-37; 10-34-37
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H314; H301-H335-H314-H318-H226
• GHS Precautionary statements: P210-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2920 8/PG 2

Product Information

• Purity: ≥97.0% (AT); 98%
• Grade: purum
• Linear Formula: ClCOCOOCH2CH3

DETAILS

Sigma Aldrich - E43101

Packaging
25, 100, 500 g in glass bottle

Sigma Aldrich - 75753

Other Notes
Reagent for a convenient preparation of α-oxoesters1

REFERENCES

• Reaction with imidazole, followed by a Grignard reagent, provides a route to ɑ-keto esters, generally in good yield: J. Org. Chem., 46, 211 (1981).
• In the presence of pyridine, electron-rich alkenes give 2-oxo-3-alkenoic esters: Synthesis, 137 (1986):