3-bromopropanoic acid

• ChemBase ID: 69451
• Molecular Formular: C3H5BrO2
• Molecular Mass: 152.9746
• Monoisotopic Mass: 151.9472914
• SMILES: C(=O)(CCBr)O
• Canonical SMILES: OC(=O)CCBr
• InChI: InChI=1S/C3H5BrO2/c4-2-1-3(5)6/h1-2H2,(H,5,6)
• InChIKey: DHXNZYCXMFBMHE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-bromopropanoic acid
• IUPAC Traditional name: propanoic acid, 3-bromo-
• Synonyms: 3-Bromopropionic acid; 3-bromopropanoic acid; 3-Bromopropionic acid; beta-Bromopropionic acid; β-Propionic Acid; 3-溴丙酸

Database IDs

• CAS Number: 590-92-1
• EC Number: 209-694-1
• MDL Number: MFCD00002763
• Beilstein Number: 1071333
• Merck Index: 141433
• PubChem SID: 24850955; 162035177; 24850957; 24846536
• PubChem CID: 11553

CALCULATED PROPERTIES

• Acid pKa: 3.2381432
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -1.5048802
• LogD (pH = 7.4): -2.70198
• Log P: 0.7365061
• Molar Refractivity: 25.0798 cm^3
• Polarizability: 9.895464 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 g/mL, clear; Soluble in water, alcohol, ether, chloroform, benzene
• Melting Point: 57-63°C; 58-62 °C; 58-62 °C(lit.); 60-64 °C; 61 - 63°C; 61-63°C
• Boiling Point: 140-142°C/45mm
• Flash Point: 150.8 °F; 65.5°C; 65°C(149°F); 66 °C
• Density: 1.48 g/ml; 1.48 g/mL at 25 °C(lit.); 1.480
• Hydrophobicity(logP): 0.538

Safety Information

• Storage Condition: 0°C
• Storage Warning: Corrosive/Highly Flammable; IRRITANT
• RTECS: UE7875000
• European Hazard Symbols: Corrosive (C); Flammable (F); X
• UN Number: 1759; 3261; UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Australian Hazchem: 2X
• Risk Statements: 11-34; 22-34; R:34
• Safety Statements: 26-36/37/39-45; S:26-27/28-36/37/39-46-64
• EU Classification: C10
• EU Hazard Identification Number: 8B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: false; 是
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H314-H318; H314
• GHS Precautionary statements: P260-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95% (GC); ≥99.0% (GC); 95%; 95+%; 97%
• Grade: puriss.; technical
• Linear Formula: BrCH2CH2COOH

DETAILS

MP Biomedicals - 02150523

Crystalline
Enzyme alkylating agent

Sigma Aldrich - 101281

Application
Quaternization agent in amperometric biosensors.1 Alkylates mercaptans and other sulfur containing compounds.2,3
Packaging
100 g in glass bottle

Sigma Aldrich - 18180

Other Notes
Alkylates the ε-amino group of lysine in proteins1

REFERENCES

• Reacts with alkyllithiums to give a dilithio-derivative, which adds to carbonyl compounds giving -hydroxy acids. Acid-catalyzed lactonization gives -lactones in modest overall yield: Tetrahedron Lett., 883 (1978).