(2S)-1-chloro-1-oxopropan-2-yl acetate

• ChemBase ID: 145841
• Molecular Formular: C5H7ClO3
• Molecular Mass: 150.56028
• Monoisotopic Mass: 150.00837176
• SMILES: C[C@@H](C(=O)Cl)OC(=O)C
• Canonical SMILES: CC(=O)O[C@H](C(=O)Cl)C
• InChI: InChI=1S/C5H7ClO3/c1-3(5(6)8)9-4(2)7/h3H,1-2H3/t3-/m0/s1
• InChIKey: ALHZEIINTQJLOT-VKHMYHEASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-chloro-1-oxopropan-2-yl acetate
• IUPAC Traditional name: (2S)-1-chloro-1-oxopropan-2-yl acetate
• Synonyms: AP-Cl; O-Acetyl-L-lactyl chloride; (S)-(-)-2-Acetoxypropionyl chloride; 2-过氧乙酰丙酰氯; (S)-(-)-2-乙酰氧基丙酰氯

Database IDs

• CAS Number: 36394-75-9
• MDL Number: MFCD00145252
• Beilstein Number: 1722943
• PubChem SID: 24845097; 162240043; 24868317
• PubChem CID: 11094804

CALCULATED PROPERTIES

• Acid pKa: 17.345482
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.5026255
• LogD (pH = 7.4): 0.5026255
• Log P: 0.5026255
• Molar Refractivity: 31.8498 cm^3
• Polarizability: 12.820691 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 50 °C/5 mmHg(lit.)
• Flash Point: 113 °C; 235.4 °F
• Density: 1.189 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.423; n20/D 1.423(lit.)
• Optical Rotation: [α]20/D -31°, c = 4 in chloroform; [α]20/D -33.0±2°, c = 4% in chloroform

Safety Information

• European Hazard Symbols: Corrosive (C)
• UN Number: 3265
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314
• GHS Precautionary statements: 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 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0%; ≥99.0% (AT); 97%
• Grade: for chiral derivatization
• Optical Purity: enantiomeric ratio: ≥97:3 (GC)
• Linear Formula: CH3CH(O2CCH3)COCl

DETAILS

Sigma Aldrich - 447056

Packaging
1, 5 g in glass bottle
Application
Frequently used chiral building block.1,2 Also used to resolve a bicyclic α-hydroxylactone3 and to prepare chiral phosphonates used in an enantiomeric excess assay of unprotected amino acids.4 Useful chiral derivatizing agent.5

Sigma Aldrich - 00877

Other Notes
Chiral derivatizing agent for the det. of enantiomeric purity of alcohols by GC or NMR1,2,3