(2S)-2-bromopropanoic acid

• ChemBase ID: 144740
• Molecular Formular: C3H5BrO2
• Molecular Mass: 152.9746
• Monoisotopic Mass: 151.9472914
• SMILES: C[C@@H](C(=O)O)Br
• Canonical SMILES: C[C@@H](C(=O)O)Br
• InChI: InChI=1S/C3H5BrO2/c1-2(4)3(5)6/h2H,1H3,(H,5,6)/t2-/m0/s1
• InChIKey: MONMFXREYOKQTI-REOHCLBHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-bromopropanoic acid
• IUPAC Traditional name: (2S)-2-bromopropanoic acid
• Synonyms: (S)-(-)-2-Bromopropionic acid; (2S)-2-Bromopropanoic Acid; (S)-α-Bromopropionic Acid; (-)-α-Bromopropanoic Acid; L-α-Bromopropionic Acid; L-2-Bromopropionic Acid; (S)-(-)-2-Bromopropionic Acid; (S)-2-Bromopropanoic Acid; (S)-2-Bromopropionic Acid; (S)-2-Bromopropionic Acid; (S)-(-)-2-BROMOPROPIONIC ACID; (S)-(-)-2-溴丙酸

Database IDs

• CAS Number: 32644-15-8
• MDL Number: MFCD00137325
• Beilstein Number: 1720261
• PubChem SID: 24850951; 162238952; 24864033
• PubChem CID: 642232

CALCULATED PROPERTIES

• Acid pKa: 2.8647847
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -1.515819
• LogD (pH = 7.4): -2.4203494
• Log P: 1.0682576
• Molar Refractivity: 24.8743 cm^3
• Polarizability: 9.901194 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Colourless Liquid
• Melting Point: -35 °C(lit.)
• Boiling Point: 78 °C/4 mmHg(lit.); 90-95°C
• Flash Point: 102 °C; 215.6 °F
• Density: 1.696 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.470; n20/D 1.475
• Optical Rotation: [α]20/D -25°, neat; [α]20/D -26.5±2°, neat

Safety Information

• European Hazard Symbols: Corrosive (C)
• UN Number: 3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2
• Risk Statements: 22-34
• Safety Statements: 26-36/37/39-45
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-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 3261 8/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.5% (sum of enantiomers, GC); 98%; 99%
• Grade: purum
• Linear Formula: CH3CH(Br)CO2H

DETAILS

Sigma Aldrich - 385514

Packaging
5 g in glass bottle
Application
Used for the direct enantiomeric assay of carboxylic acids by proton NMR.1

Sigma Aldrich - 18167

Caution
may discolor to brownish on storage
Other Notes
Chiral building block; synthesis of N-substituted D-alanines with amines1,2; Preparation of chiral ethers and esters3,4

Toronto Research Chemicals - B686670

(S)-2-Bromopropionic Acid is an intermediate in the synthesis of structural analogs of the antimitotic tripeptides hemiasterlins as antitumor agents.

REFERENCES

• Gamble, W., et al.: Bioorg. Med. Chem., 7, 1611 (1999)