| Identification | More | [Name]
Ethyl 4-bromocrotonate | [CAS]
37746-78-4 | [Synonyms]
4-BROMOCROTONIC ACID ETHYL ESTER
ETHYL 4-BROMOCROTONATE
ETHYL TRANS-4-BROMO-2-BUTENOATE
TRANS-ETHYL-4-BROMOCROTONATE
Ethyl (2E)-4-bromo-2-butenoate
Ethyl (E)-4-bromo-2-butenoate
Ethyl gamma-bromocrotonate
Ethylbromocrotonatepract
ETHYL 4-BROMOCROTONATE, TECH., 75%
Ethyl 4-bromocrotonate, pract., 85%
2-Butenoic acid, 4-bromo-, ethyl ester, (2E)-
ETHYL 4-BROMOCROTONATE (4-BROMOCROTONIC ACID ETHYL ESTER)
4-bromo-trans-crotonic acid ethyl ester
trans-Ethyl-4-bromocrotonate, 97 %
(2E)-4-Bromo-2-butenoic acid ethyl ester
Ethyl (E)-4-bromobut-2-enoate
Ethyl 4-bromo-2-(E)-butenoate
Ethyl 4-bromocrotonate, 75%, tech. | [EINECS(EC#)]
629-265-6 | [Molecular Formula]
C6H9BrO2 | [MDL Number]
MFCD00000247 | [Molecular Weight]
193.04 | [MOL File]
37746-78-4.mol |
| Chemical Properties | Back Directory | [Appearance]
clear yellow liquid | [Boiling point ]
94-95 °C/12 mmHg (lit.) | [density ]
1.402 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.493(lit.)
| [Fp ]
207 °F
| [storage temp. ]
2-8°C
| [solubility ]
Chloroform (Sparingly), Methanol (Slightly) | [form ]
Liquid | [color ]
Clear light yellow to brown | [Specific Gravity]
1.402 | [Water Solubility ]
Insoluble in water. | [BRN ]
1721388 | [Stability:]
Light Sensitive | [InChI]
1S/C6H9BrO2/c1-2-9-6(8)4-3-5-7/h3-4H,2,5H2,1H3/b4-3+ | [InChIKey]
FHGRPBSDPBRTLS-ONEGZZNKSA-N | [SMILES]
CCOC(=O)\C=C\CBr | [CAS DataBase Reference]
37746-78-4(CAS DataBase Reference) | [NIST Chemistry Reference]
2-Butenoic acid, 4-bromo-, ethyl ester, (E)-(37746-78-4) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS05 | [Signal word ]
Danger | [Hazard statements ]
H314 | [Precautionary statements ]
P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363-P405 | [Hazard Codes ]
C,Xi | [Risk Statements ]
R34:Causes burns.
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 .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S24/25:Avoid contact with skin and eyes . | [RIDADR ]
UN 3265 8/PG 2
| [WGK Germany ]
3
| [F ]
10-19-23 | [HazardClass ]
8 | [PackingGroup ]
III | [HS Code ]
29161995 | [Storage Class]
8A - Combustible corrosive hazardous materials | [Hazard Classifications]
Skin Corr. 1B |
| Hazard Information | Back Directory | [Chemical Properties]
clear yellow liquid | [Uses]
Ethyl 4-bromocrotonate is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuffs. | [Synthesis]
General procedure for the synthesis of ethyl (E)-4-bromobut-2-enoate from ethyl crotonate: To a round-bottomed flask containing ethyl (2E)-but-2-enoate (10.9 g, 87.6 mmol) and carbon tetrachloride (100 mL), N-bromosuccinimide (NBS, 17 g, 96 mmol) and azobisisobutyronitrile (AIBN, 4.3 g, 26 mmol). The reaction mixture was stirred at 80 °C for 12 hours. After completion of the reaction, the reaction mixture was diluted with dichloromethane (DCM) and washed sequentially with saturated sodium bicarbonate solution, water and brine. The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent to give ethyl (E)-4-bromobut-2-enoate (7.5 g, 44% yield) as an oil. | [References]
[1] Journal of the American Chemical Society, 2001, vol. 123, # 21, p. 4966 - 4973
[2] Patent: WO2017/100668, 2017, A1. Location in patent: Page/Page column 150
[3] Patent: WO2018/103058, 2018, A1. Location in patent: Page/Page column 150
[4] Bulletin de la Societe Chimique de France, 1966, p. 1315 - 1324
[5] Journal of Organometallic Chemistry, 1973, vol. 60, p. 209 - 217 |
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