ethyl 3-bromopropanoate

• ChemBase ID: 150587
• Molecular Formular: C5H9BrO2
• Molecular Mass: 181.02776
• Monoisotopic Mass: 179.97859153
• SMILES: CCOC(=O)CCBr
• Canonical SMILES: BrCCC(=O)OCC
• InChI: InChI=1S/C5H9BrO2/c1-2-8-5(7)3-4-6/h2-4H2,1H3
• InChIKey: FQTIYMRSUOADDK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 3-bromopropanoate
• IUPAC Traditional name: ethyl 3-bromopropanoate
• Synonyms: Ethyl 3-bromopropionate; ethyl 3-bromopropanoate; 3-Bromopropionic acid ethyl ester; 3-溴丙酸乙酯

Database IDs

• CAS Number: 539-74-2
• EC Number: 208-724-0
• MDL Number: MFCD00000251
• Beilstein Number: 1700933
• PubChem SID: 24847832; 162244748; 24850970
• PubChem CID: 68320

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.2392081
• LogD (pH = 7.4): 1.2392081
• Log P: 1.2392081
• Molar Refractivity: 34.5975 cm^3
• Polarizability: 13.633196 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 135-136 °C/50 mmHg(lit.); 67-71°C/10mm
• Flash Point: 158 °F; 70 °C; 79°C(174°F)
• Density: 1.412 g/mL at 25 °C(lit.); 1.416
• Refractive Index: 1.4520; n20/D 1.452(lit.); n20/D 1.453
• Hydrophobicity(logP): 1.443

Safety Information

• Storage Warning: Light Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26; 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335; H315-H319-H335-H227
• GHS Precautionary statements: P210-P305+P351+P338-P302+P352-P321-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: ≥95.0% (GC); 95%; 97%; 98%; 99%
• Grade: purum
• Linear Formula: BrCH2CH2COOC2H5

DETAILS

Sigma Aldrich - 128163

Packaging
25, 100 g in glass bottle

REFERENCES

• Undergoes a "homo-Reformatsky" coupling with carbonyl compounds leading to -lactones. The homoenolate can be generated with various lanthanide metals, La, Ce, Nd or Sm: J. Org. Chem., 55, 1628 (1990):
  
• Cyclopropanols may be synthesized by reaction of ?-halo esters with Grignard reagents and SmI₂: Tetrahedron Lett., 32, 7691 (1991).