| Identification | More | [Name]
3-Bromo-4-methylbenzonitrile | [CAS]
42872-74-2 | [Synonyms]
3-BROMO-4-METHYLBENZONITRILE 97
3-Bromo-4-methylbenzonitrile 98%
3-Bromo-4-methylbenzonitrile
4-methyl-3-bromobenzonitrile | [Molecular Formula]
C8H6BrN | [MDL Number]
MFCD06797818 | [Molecular Weight]
196.04 | [MOL File]
42872-74-2.mol |
| Chemical Properties | Back Directory | [Melting point ]
41-45 °C (lit.) | [Boiling point ]
259.1±20.0 °C(Predicted) | [density ]
1.51±0.1 g/cm3(Predicted) | [Fp ]
>230 °F
| [storage temp. ]
Sealed in dry,Room Temperature | [form ]
fused solid | [Appearance]
White to off-white Solid | [Water Solubility ]
Insoluble in water. | [InChI]
InChI=1S/C8H6BrN/c1-6-2-3-7(5-10)4-8(6)9/h2-4H,1H3 | [InChIKey]
VXUMRYMTYKDWMO-UHFFFAOYSA-N | [SMILES]
C(#N)C1=CC=C(C)C(Br)=C1 | [CAS DataBase Reference]
42872-74-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S36:Wear suitable protective clothing . | [RIDADR ]
UN3439 | [WGK Germany ]
3
| [Hazard Note ]
Harmful | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
2926907090 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white crystalline | [Uses]
Used as pharmaceutical intermediate. | [Synthesis]
General procedure for the synthesis of 3-bromo-4-methylbenzonitrile from 4-methylbenzonitrile: 4-methylbenzonitrile (168 g, 1.46 mol) was dissolved in a mixed solution of H2SO4/H2O (800 mL, 1:1, v/v/v) at 10 °C and N-bromosuccinimide (NBS, 256 g, 1.43 mol) was added slowly. The reaction mixture was stirred under light-avoiding conditions for 48 hours. After completion of the reaction, the mixture was filtered and the filter cake was collected. The filter cake was dissolved in ethyl acetate (1000 mL) and the organic layer was washed sequentially with water and saturated saline. Subsequently, it was neutralized with NaOH solution to pH=7 and washed again with saturated saline. The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to give 3-bromo-4-methylbenzonitrile (276.5 g, 89% yield) as a yellow solid. | [References]
[1] Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, # 2, p. 217 - 223
[2] Zhurnal Organicheskoi Khimii, 1988, vol. 24, # 2, p. 248 - 255
[3] Patent: WO2011/22337, 2011, A1. Location in patent: Page/Page column 103-104
[4] Synlett, 2007, # 14, p. 2179 - 2184
[5] Organic Letters, 2006, vol. 8, # 4, p. 645 - 647 |
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