Methyl 2-bromoacrylate
Basic information
- CAS
4519-46-4- Standard SMILES
C=C(Br)C(=O)OC- InChIKey
HVJXPDPGPORYKY-UHFFFAOYSA-N- Molecular formula
- C4H5BrO2
- Average molar mass
- 164.99 g/mol
- Monoisotopic mass
- 163.94729
Names & identifiers
- Preferred name
- Methyl 2-bromoacrylate
- IUPAC
- methyl 2-bromoprop-2-enoate
- English name
- Methyl alpha-bromoacrylate 95
- Molecular formula
- C4H5BrO2
- Molecular weight
- 164.99
Names & synonyms
Methyl 2-bromoacrylate4519-46-42-Propenoic acid, 2-bromo-, methyl esterDTXSID00282086RefChem:157304DTXCID50233240689-567-9HVJXPDPGPORYKY-UHFFFAOYSA-NInChI=1/C4H5BrO2/c1-3(5)4(6)7-2/h1H2,2Hmethyl 2-bromoprop-2-enoateMethyl alpha-bromoacrylateMFCD08276754
Show more names
Methyl α-bromoacrylatemethyl α-bromoacrylateMethyl alpha-bromoacrylate 95Methyl alpha-bromoacrylate 95%2-Bromopropenoic acid methyl ester2-bromopropyl-2-eneacidmethyl esterMethyl α-bromoacrylate, CAS 4519-46-4
Methyl2-bromoacrylateMethyl 2-bromoacrylate #methyl 2-bromo-2-propenoateSCHEMBL600306SCHEMBL7666124Methyl alpha-bromoacrylate, 95%NSC24144NSC-24144
Database identifiers
- CAS
4519-46-4- PubChem CID
- 229990
- DTXSID
DTXSID00282086- EC Number
- 689-567-9
- Nikkaji
- J132.165J
Properties
Computed structural properties
- XLogP
- 1.6
- Topological polar surface area
- 26.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 97.9
Physicochemical properties
- Boiling point
- 70 · 70-75 °C48 mm Hg(lit.)
- Density
- 1.556 g/mL · 1.556 g/mL at 25 °C(lit.)
- Flash point
- 134 °F · 134 °F
- storage temp.
- -20 °C · -20°C
- Appearance
- Colorless to light yellow Liquid
- InChI
- InChI=1S/C4H5BrO2/c1-3(5)4(6)7-2/h1H2,2H3
- InChIKey
- HVJXPDPGPORYKY-UHFFFAOYSA-N
- SMILES
- C(OC)(=O)C(Br)=C
- CAS DataBase Reference
- 4519 · 4519-46-4
- Comptox DTXSID
- 282086 · DTXSID00282086
- UNSPSC Code
- 12162002 · 12162002
- NACRES
- 23 · NA.23
- Symbol(GHS)
- 2 · GHS02,GHS07
- Signal word
- Warning
- Hazard statements
- 226 · H226-H315-H319-H335
- Precautionary statements
- 210 · P210-P302+P352-P305+P351+P338
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesFlam. Liq. 3 (100%)
Safety data
- PPE
- Eyeshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- ridadr
- UN 1993 3/PG 3
- hs_code
- 2916199590
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS02,GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- hazard_class
- 3
- Storage Class
- 3 - Flammable liquids
- packing_group
- Ⅲ
- target organs
- Respiratory system
- Hazard statements
- H226-H315-H319-H335
Chemistry & industry
Applications
UsesMethyl α-bromoacrylate can undergo radical copolymerization with vinyl triacetoxysilane (VTAS) in the presence of azobisisobutyronitrile as the initiator. Dibromocyclopropanation of methyl α-bromoacrylate can yield methyl 1,1,2-tribromocyclopropanecarboxylate. It may be reduced with zinc dust and deuterium oxide to synthesize. Methyl acrylate-α-d with a high isotopic purity. These may undergo conjugate addition with methoxide, thiolates, oxime anions, hydrazones and EtZnCl to afford ester enolates.
Upstream & downstream products
Upstream raw materials
Related reactions
3 records
Compound notes
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