(2S)-2-chloropropanoic acid

• ChemBase ID: 85856
• Molecular Formular: C3H5ClO2
• Molecular Mass: 108.5236
• Monoisotopic Mass: 107.99780708
• SMILES: OC(=O)[C@H](C)Cl
• Canonical SMILES: C[C@@H](C(=O)O)Cl
• InChI: InChI=1S/C3H5ClO2/c1-2(4)3(5)6/h2H,1H3,(H,5,6)/t2-/m0/s1
• InChIKey: GAWAYYRQGQZKCR-REOHCLBHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-chloropropanoic acid
• IUPAC Traditional name: (-)-2-chloropropionic acid
• Synonyms: (S)-2-Chloropropanoic acid; D-(α)-Chloropropionic Acid; (2R)-2-Chloropropionic Acid; D-2-Chloropropionic Acid; D-Chloropropionic Acid; (R)-(+)-2-Chloropropionic Acid; L-(α)-Chloropropionic Acid; (S)-(-)-2-Chloropropionic Acid; L-α-Chloropropionic acid; (S)-(-)-2-Chloropropanoic acid; (S)-(-)-2-Chloropropionic acid; (2S)-2-Chloropropionic acid; (2S)-2-Chloropropanoic acid; (S)-(-)-2-chloropropanoic acid; L-α-氯丙酸; (S)-(-)-2-氯丙酸

Database IDs

• CAS Number: 29617-66-1; 7474-05-7
• EC Number: 411-150-5
• MDL Number: MFCD00064205
• Beilstein Number: 1720257
• PubChem SID: 24858499; 162072972
• PubChem CID: 107915

CALCULATED PROPERTIES

• Acid pKa: 3.4175816
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -1.1879898
• LogD (pH = 7.4): -2.515642
• Log P: 0.8827623
• Molar Refractivity: 21.8908 cm^3
• Polarizability: 8.7767315 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol; Water
• Apperance: Colourless Oil; Pale Yellow Oil
• Melting Point: 4°C; 4°C
• Boiling Point: 185-188 °C; 185-188°C; 187°C; 77 °C/10 mmHg(lit.); 77°C/10mm
• Flash Point: 107°C; 107°C(225°F); 140 °F; 60 °C
• Density: 1.249; 1.249 g/mL at 25 °C(lit.); 1.258 g/mL at 20 °C(lit.); 1.270
• Refractive Index: 1.4345; 1.4347; n20/D 1.4347(lit.); n20/D 1.436
• Optical Rotation: [α]20/D -14±0.5°, neat; [α]25/D -14°, neat

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: Corrosive/Harmful
• RTECS: UA2451950
• European Hazard Symbols: Corrosive (C); X
• UN Number: 2511; UN2511
• German water hazard class: 1
• Hazard Class: 8
• Packing Group: 3; III
• Risk Statements: 21/22-35
• Safety Statements: 23-26-28-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H312-H314; H314-H318-H302-H312
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-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 2511 8/PG 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥98.5% (sum of enantiomers, GC); 97%; 98%; 99%
• Grade: puriss.
• Linear Formula: CH3CH(Cl)CO2H
• Empirical Formula (Hill Notation): C3H5ClO2

DETAILS

Sigma Aldrich - 306797

Packaging
1 g in glass bottle

Sigma Aldrich - 26155

Other Notes
Chiral building block; it is used in the synthesis of muramic acid derivatives 1,2; Preparation of its tert-butyl ester and reaction with protected amino acid cesium salts to depsipeptides 3