ethyl (2E)-4-bromobut-2-enoate

• ChemBase ID: 122905
• Molecular Formular: C6H9BrO2
• Molecular Mass: 193.03846
• Monoisotopic Mass: 191.97859153
• SMILES: C(=O)(/C=C/CBr)OCC
• Canonical SMILES: CCOC(=O)/C=C/CBr
• InChI: InChI=1S/C6H9BrO2/c1-2-9-6(8)4-3-5-7/h3-4H,2,5H2,1H3/b4-3+
• InChIKey: FHGRPBSDPBRTLS-ONEGZZNKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2E)-4-bromobut-2-enoate; ethyl 4-bromobut-2-enoate
• IUPAC Traditional name: ethyl (2E)-4-bromobut-2-enoate; ethyl 4-bromobut-2-enoate
• Synonyms: ethyl 4-bromobut-2-enoate; Ethyl 4-bromocrotonate; Ethyl trans-4-bromo-2-butenoate; 4-Bromocrotonic acid ethyl ester; (E)-ethyl 4-bromobut-2-enoate; Ethyl trans-4-bromo-2-butenoate; Ethyl 4-bromocrotonate; 4-溴丁烯酸乙酯; 反式-4-溴-2-丁烯酸乙酯; 4-溴巴豆酸乙酯

Database IDs

• CAS Number: 37746-78-4
• MDL Number: MFCD00000247
• Beilstein Number: 1721388
• PubChem SID: 24850208; 162217258; 24894407
• PubChem CID: 5373944

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.9149336
• LogD (pH = 7.4): 1.9149336
• Log P: 1.9149336
• Molar Refractivity: 40.2918 cm^3
• Polarizability: 15.164297 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 94-95 °C/12 mmHg(lit.); 94-95°C/12mm
• Flash Point: 206.6 °F; 97 °C; 97°C(206°F)
• Density: 1.4 g/mL at 20 °C(lit.); 1.402; 1.402 g/mL at 25 °C(lit.)
• Refractive Index: 1.4930; n20/D 1.49; n20/D 1.493(lit.)
• Hydrophobicity(logP): 1.858

Safety Information

• European Hazard Symbols: Corrosive (C)
• UN Number: 3265; UN1760
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; III
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318
• 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 3265 8/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ~75% (GC); 75%; 95%; 95+%; tech. 80%
• Grade: technical; technical grade
• Linear Formula: BrCH2CH=CHCO2C2H5
• Empirical Formula (Hill Notation): C6H9BrO2

DETAILS

Sigma Aldrich - E13830

Packaging
5, 25 g in glass bottle

REFERENCES

• Reacts with sulfur-stabilized carbanions, e.g. from Benzyl phenyl sulfone, L04201, by conjugate addition with concomitant displacement of Br^-, to give cyclopropane esters: Tetrahedron Lett., 4603 (1979):
  
• Reformatsky-type reactions can occur with or without allylic rearrangement: Liebigs Ann. Chem., 709, 29 (1967); Chem. Lett., 161 (1982); Synthesis, 305 (1990).