| Identification | More | [Name]
ETHYL 2-(BROMOMETHYL)ACRYLATE | [CAS]
17435-72-2 | [Synonyms]
2-(BROMOMETHYL)ACRYLIC ACID ETHYL ESTER
ETHYL 2-(BROMOMETHYL)ACRYLATE
2-Propenoic acid, 2-(bromomethyl)-, ethyl ester
2-(Bromomethyl)-2-propenoic Acid Ethyl Ester
2-Carbethoxyallyl Bromide
Ethyl 2-(Bromomethyl)-2-propenoate
Ethyl 3-Bromo-2-(methylene)propanoate
Ethyl Bromomethacrylate
NSC 215252
Ethyl 2-(Bromomethyl)acrylate (stabilized with HQ) | [EINECS(EC#)]
628-033-1 | [Molecular Formula]
C6H9BrO2 | [MDL Number]
MFCD00031518 | [Molecular Weight]
193.04 | [MOL File]
17435-72-2.mol |
| Chemical Properties | Back Directory | [Appearance]
Colourless Oil | [Melting point ]
134-136℃ | [Boiling point ]
38 °C/0.8 mmHg (lit.) | [density ]
1.398 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.479(lit.)
| [Fp ]
178 °F
| [storage temp. ]
2-8°C
| [solubility ]
Chloroform (Sparingly), Ethyl Acetate (Slightly) | [form ]
Liquid | [color ]
Colorless to pale yellow | [Usage]
Intermediate used for the synthesis of aza inhibitors of chorismate mutase | [BRN ]
970108 | [InChI]
InChI=1S/C6H9BrO2/c1-3-9-6(8)5(2)4-7/h2-4H2,1H3 | [InChIKey]
MTCMFVTVXAOHNQ-UHFFFAOYSA-N | [SMILES]
C(OCC)(=O)C(CBr)=C | [CAS DataBase Reference]
17435-72-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [RIDADR ]
UN 2810 6.1 / PGII | [WGK Germany ]
3
| [F ]
10-19-23 | [HS Code ]
29161900 |
| Hazard Information | Back Directory | [Chemical Properties]
Colourless Oil | [Uses]
ETHYL 2-(BROMOMETHYL)ACRYLATE is an intermediate used for the synthesis of aza inhibitors of chorismate mutase.
| [General Description]
Ethyl 2-(bromomethyl)acrylate is an allylic alkylating reagent. | [Synthesis]
GENERAL STEPS: Phosphorus tribromide (0.51 mL, 5.4 mmol) was added slowly and dropwise to a stirred solution of ethyl 2-hydroxymethacrylate (2 g, 15.4 mmol) in ether (15 mL) at 0 °C. The reaction mixture was stirred at 0 °C for 3 h and subsequently warmed to room temperature. The reaction was quenched by the addition of water (5 mL) and the product was extracted with hexane (3 x 10 mL). The organic layers were combined, washed with brine (2 × 10 mL), dried over anhydrous MgSO4, filtered and concentrated in vacuum to afford ethyl 2-bromomethacrylate (2.4 g, 12.3 mmol, 82% yield) as a colorless liquid, which could be used in the next reaction without further purification. The product was characterized as follows: colorless oil; 1H NMR (400 MHz, CDCl3) δ 1.30 (t, J = 7.2 Hz, 3H, H6), 4.16 (s, 2H, H4), 4.24 (q, J = 7.0 Hz, 2H, H5), 5.92 (s, 1H, H1'), 6.30 (s, 1H, H1); 13C NMR ( 101 MHz, CDCl3) δ 14.1 (CH3, C6), 29.3 (CH2, C4), 61.2 (CH2, C5), 128.8 (CH2, C1), 137.6 (C, C2), 164.8 (C, C3); IR (νmax, cm-1) 1718 (C=O ester), 1628 (C=C alkene), 1182 (C-O ester), 523 (C-Br); HRMS-EI: m/z [M+H]+ calcd for C6H10BrO2: 192.9864, found: 192.6870. | [Purification Methods]
If it contains some free acid, add H2O, cool, and neutralise with NaHCO3 until evolution of CO2 ceases. Extract the mixture with Et2O (3x) and dry the combined extracts (Na2SO4, 3hours). Evaporate Et2O and distil the ester collecting fraction b 39-40o/0.9mm and check spectra. [Preparation and NMR: Ramarajan et al. Org Synth Coll Vol VII 211 1990, Beilstein 2 IV 1541.] | [References]
[1] Journal of Polymer Science, Part A: Polymer Chemistry, 2011, vol. 49, # 6, p. 1513 - 1516
[2] Angewandte Chemie - International Edition, 2016, vol. 55, # 5, p. 1872 - 1875
[3] Angew. Chem., 2016, vol. 128, # 5, p. 1904 - 1907,4
[4] Angewandte Chemie - International Edition, 2017, vol. 56, # 41, p. 12619 - 12623
[5] Angew. Chem., 2017, vol. 129, # 41, p. 12793 - 12797,5 |
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