methyl 2-(bromomethyl)prop-2-enoate

• ChemBase ID: 149343
• Molecular Formular: C5H7BrO2
• Molecular Mass: 179.01188
• Monoisotopic Mass: 177.96294146
• SMILES: COC(=O)C(=C)CBr
• Canonical SMILES: COC(=O)C(=C)CBr
• InChI: InChI=1S/C5H7BrO2/c1-4(3-6)5(7)8-2/h1,3H2,2H3
• InChIKey: CFTUQSLVERGMHL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 2-(bromomethyl)prop-2-enoate
• IUPAC Traditional name: methyl 2-(bromomethyl)prop-2-enoate
• Synonyms: Methyl 2-(bromomethyl)acrylate; Methyl 2-(bromomethyl)acrylate; 2-(溴甲基)丙烯酸甲酯

Database IDs

• CAS Number: 4224-69-5
• MDL Number: MFCD00011697
• Beilstein Number: 1852481
• PubChem SID: 24850506; 162243510; 24858262
• PubChem CID: 521093

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.5670412
• LogD (pH = 7.4): 1.5670412
• Log P: 1.5670412
• Molar Refractivity: 34.2268 cm^3
• Polarizability: 13.377831 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 35-37 °C/1.3 mmHg(lit.)
• Flash Point: 172 °F; 172.4 °F; 78 °C
• Density: 1.489 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.490; n20/D 1.490(lit.)

Safety Information

• RTECS: AS4900000
• European Hazard Symbols: Irritant (Xi)
• UN Number: 2810
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 36/37/38; 37/38-41
• Safety Statements: 26-36; 26-36/37/39
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H318-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2810 6.1/PG 2
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥95.0% (GC); 95+%; 97%
• Grade: purum
• Linear Formula: H2C=C(CH2Br)CO2CH3

DETAILS

Sigma Aldrich - 302546

Application
Substrate employed in enantioselective syntheses of β-amino acids.1,2
Packaging
1, 5 g in glass bottle

Sigma Aldrich - 17553

Other Notes
Reagent used for the synthesis of α-methylene-γ-butyrolactones from ketones and of corresponding butyrolactams from imines1,2,3,4,5; Preparation of fused piperidines from cyclic ketones6,7