ethyl 3-chloro-3-oxopropanoate

• ChemBase ID: 89656
• Molecular Formular: C5H7ClO3
• Molecular Mass: 150.56028
• Monoisotopic Mass: 150.00837176
• SMILES: O(CC)C(=O)CC(=O)Cl
• Canonical SMILES: CCOC(=O)CC(=O)Cl
• InChI: InChI=1S/C5H7ClO3/c1-2-9-5(8)3-4(6)7/h2-3H2,1H3
• InChIKey: KWFADUNOPOSMIJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 3-chloro-3-oxopropanoate
• IUPAC Traditional name: ethyl 3-chloro-3-oxopropanoate
• Synonyms: Ethyl malonyl chloride; Ethyl 3-chloro-3-oxopropionate; Ethyl (chloroformyl)acetate; Ethyl malonyl chloride; Malonic acid monoethyl ester chloride; ethyl 3-chloro-3-oxopropanoate; 乙基-3-氯-3-氧丙酸酯; 氯甲酰乙酸乙酯; 丙二酸单乙酯酰氯; 氯甲酰乙酸乙酯

Database IDs

• CAS Number: 36239-09-5
• EC Number: 252-934-5
• MDL Number: MFCD00000736
• Beilstein Number: 636215
• PubChem SID: 162076519; 24882592; 24850040
• PubChem CID: 118931

CALCULATED PROPERTIES

• Acid pKa: 8.094882
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.70381266
• LogD (pH = 7.4): 0.6251065
• Log P: 0.7049144
• Molar Refractivity: 32.364 cm^3
• Polarizability: 12.818835 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 188 - 190°C
• Boiling Point: 79-80 °C/25 mmHg(lit.); 79-80°C/25mm; 83°C/22mm
• Flash Point: 147.2 °F; 64 °C; 67°C(152°F)
• Density: 1.176 g/mL at 25 °C(lit.); 1.189; 1.196 g/mL at 20 °C
• Refractive Index: 1.4290; n20/D 1.429(lit.); n20/D 1.430
• Hydrophobicity(logP): 0.641

Safety Information

• Storage Warning: Corrosive; Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 3265; UN3265
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 3; II
• Risk Statements: 14-34
• Safety Statements: 26-36/37/39-45; 7-26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318-H227
• GHS Precautionary statements: P210-P260-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 3265 8/PG 3
• Supplemental Hazard Statements: Reacts violently with water.
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (HPLC); 95%
• Grade: purum; technical grade
• Linear Formula: CH3CH2OCOCH2COCl

DETAILS

Sigma Aldrich - 163872

Application
Employed in the synthesis of 3-pyrrolin-2-ones via amidation with propargylamines and subsequent base catalyzed 5-exo-dig cyclization.1
Versatile acylating agent for propargyl alcohols, hydrazines, and amines.
Packaging
5, 25 g in glass bottle

Sigma Aldrich - 63398

Caution
may discolor to brown on storage

REFERENCES

• Useful synthetic building block, e.g. in an oxazole synthesis: J. Med. Chem., 36, 3871 (1993):
  
• Formation of amides has been used in the syntheses of 1,2,4-triazine-3,6-diones, and of a vicinal tricarbonyl amide derivative of L-phenylalanine: J. Org. Chem., 60, 5992 (1995); 61, 1872 (1996).