methyl 4-bromobut-2-enoate

• ChemBase ID: 75129
• Molecular Formular: C5H7BrO2
• Molecular Mass: 179.01188
• Monoisotopic Mass: 177.96294146
• SMILES: O(C(=O)/C=C/CBr)C
• Canonical SMILES: COC(=O)/C=C/CBr
• InChI: InChI=1S/C5H7BrO2/c1-8-5(7)3-2-4-6/h2-3H,4H2,1H3
• InChIKey: RWIKCBHOVNDESJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 4-bromobut-2-enoate; methyl (2E)-4-bromobut-2-enoate
• IUPAC Traditional name: methyl 4-bromobut-2-enoate; methyl (2E)-4-bromobut-2-enoate
• Synonyms: Methyl (2E)-4-bromobut-2-enoate; Methyl trans-4-bromocrotonate 97%; Methyl 4-bromocrotonate; Methyl trans-4-bromo-2-butenoate; Methyl 4-bromocrotonate; METHYL γ-BROMOCROTONATE; Methyl 4-bromocrotonate; 4-Bromocrotonic acid methyl ester; (E)-methyl 4-bromobut-2-enoate; 4-溴代巴豆酸甲酯; 反式-4-溴-2-丁烯酸甲酯; 4-溴代巴豆酸甲酯; 4-溴巴豆酸甲酯

Database IDs

• CAS Number: 1117-71-1; 6000-00-6
• EC Number: 214-251-0
• MDL Number: MFCD00000246
• Beilstein Number: 1745755
• PubChem SID: 24896822; 162040047; 24850117
• PubChem CID: 5369175

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.5581256
• LogD (pH = 7.4): 1.5581256
• Log P: 1.5581256
• Molar Refractivity: 35.5432 cm^3
• Polarizability: 13.377459 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 70 °C/0.03 mmHg(lit.); 83-85 °C/13 mmHg(lit.); 83-85°C/13mm; 83-85°C/13mm
• Flash Point: 197.6 °F; 91°C(195°F); 92 °C
• Density: 1.498 g/mL at 20 °C(lit.); 1.522; 1.522 g/mL at 25 °C(lit.); 1.524
• Refractive Index: 1.5010; n20/D 1.501; n20/D 1.501(lit.)

Safety Information

• Storage Warning: Irritant/Light Sensitive/Keep Cold/Store under Argon
• RTECS: GQ3120000
• European Hazard Symbols: Corrosive (C); Irritant (Xi)
• UN Number: UN1760
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: III
• Risk Statements: 34; 36/37/38; 37/38-41
• Safety Statements: 20-26-36/37/39-45-60; 26; 26-39
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger; Warning
• GHS Hazard statements: H314-H318-H227; H315-H318-H335; H315-H319-H335
• GHS Precautionary statements: P210-P260-P303+P361+P353-P305+P351+P338-P405-P501A; P261-P280-P305 + P351 + P338; P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90% (GC); 85%; 95%; 95+%; 96%; tech. 85%
• Grade: technical; technical grade
• Impurities: ~3% methyl cis-4-bromo-2-butenoate; <15% 2(5H)-furanone
• Contains: silver wool as stabilizer
• Linear Formula: BrCH2CH=CHCO2CH3; BrCH2CH=CHCOOCH3

DETAILS

MP Biomedicals - 05221260

MP Biomedicals Rare Chemical collection

Sigma Aldrich - M32100

Packaging
5, 25, 100 g in glass bottle

Sigma Aldrich - 16505

Packaging
5, 25 mL in glass bottle

REFERENCES

• Undergoes a vinylogous Reformatsky reaction with carbonyl compounds, to give δ-hydroxy-ɑ?-unsaturated esters: Liebigs Ann. Chem., 709, 29 (1967). Use of a Zn-Ag couple allows Reformatsky coupling to be carried out with or without allylic rearrangement depending on whether ether or THF is used as the solvent: Synth. Commun., 19, 2355 (1989). For a review of the Reformatsky synthesis, see: Synthesis, 571 (1989).