ethyl 2-(bromomethyl)prop-2-enoate

• ChemBase ID: 78138
• Molecular Formular: C6H9BrO2
• Molecular Mass: 193.03846
• Monoisotopic Mass: 191.97859153
• SMILES: BrCC(=C)C(=O)OCC
• Canonical SMILES: CCOC(=O)C(=C)CBr
• InChI: InChI=1S/C6H9BrO2/c1-3-9-6(8)5(2)4-7/h2-4H2,1H3
• InChIKey: MTCMFVTVXAOHNQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2-(bromomethyl)prop-2-enoate
• IUPAC Traditional name: ethyl 2-(bromomethyl)prop-2-enoate
• Synonyms: 2-(Bromomethyl)-2-propenoic Acid Ethyl Ester; 2-Carbethoxyallyl Bromide; Ethyl 2-(Bromomethyl)-2-propenoate; Ethyl 2-(Bromomethyl)acrylate; Ethyl 3-Bromo-2-(methylene)propanoate; NSC 215252; Ethyl Bromomethacrylate; Ethyl 2-(bromomethyl)acrylate; Ethyl 2-(bromomethyl)prop-2-enoate; Ethyl 2-(bromomethyl)acrylate; ethyl 2-(bromomethyl)prop-2-enoate; 2-溴甲基丙烯酸乙酯

Database IDs

• CAS Number: 17435-72-2
• MDL Number: MFCD00031518
• Beilstein Number: 970108
• PubChem SID: 162042957; 24866620
• PubChem CID: 310620

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.9238491
• LogD (pH = 7.4): 1.9238491
• Log P: 1.9238491
• Molar Refractivity: 38.9754 cm^3
• Polarizability: 15.164677 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: Colourless Oil
• Boiling Point: 38 °C/0.8 mmHg(lit.); 38°C/0.8mm
• Flash Point: 177.8 °F; 81 °C; 81°C
• Density: 1.398; 1.398 g/mL at 25 °C(lit.)
• Refractive Index: 1.4790; n20/D 1.479; n20/D 1.479(lit.)
• Hydrophobicity(logP): 1.838

Safety Information

• Storage Warning: Corrosive/Keep Cold
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: 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: -20°C; 2-8°C

Product Information

• Purity: ≥95.0% (GC); 95%; 95+%; 98%
• Grade: purum
• Linear Formula: CH2=C(CH2Br)CO2CH2CH3

DETAILS

Sigma Aldrich - 425222

Packaging
1, 5 g in glass bottle

Sigma Aldrich - 17552

Caution
may discolor to brown on storage
Other Notes
Used for Reformatskii-type reactions giving α-methylene-γ-lactones1

Toronto Research Chemicals - E900390

Intermediate used for the synthesis of aza inhibitors of chorismate mutase.

REFERENCES

• Hediger, M.E., et al.: Bioorg. Med. Chem., 12, 4995 (2004).