| Identification | More | [Name]
2-AMINO-5-BROMOBENZONITRILE | [CAS]
39263-32-6 | [Synonyms]
2-AMINO-5-BROMBENZONITRILE
2-AMINO-5-BROMOBENZENECARBONITRILE
2-AMINO-5-BROMOBENZONITRILE
4-Bromo-2-cyanoaniline
2-AMINO-5-BROMOBENZONITRILE 97%
5-Bromoanthranilonitrile | [EINECS(EC#)]
254-387-8 | [Molecular Formula]
C7H5BrN2 | [MDL Number]
MFCD00158946 | [Molecular Weight]
197.03 | [MOL File]
39263-32-6.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powder | [Melting point ]
96-100 °C(lit.) | [Boiling point ]
288.4±25.0 °C(Predicted) | [density ]
1.6480 (rough estimate) | [refractive index ]
1.5500 (estimate) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [solubility ]
Soluble in methanol. | [form ]
Crystalline Powder | [pka]
1.11±0.10(Predicted) | [color ]
Off-white to pale brown | [InChI]
InChI=1S/C7H5BrN2/c8-6-1-2-7(10)5(3-6)4-9/h1-3H,10H2 | [InChIKey]
OATYCBHROMXWJO-UHFFFAOYSA-N | [SMILES]
C(#N)C1=CC(Br)=CC=C1N | [CAS DataBase Reference]
39263-32-6(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 .
R43:May cause sensitization by skin contact.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S36/37:Wear suitable protective clothing and gloves .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S22:Do not breathe dust . | [RIDADR ]
3439 | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
6.1 | [HazardClass ]
IRRITANT | [PackingGroup ]
III | [HS Code ]
29269090 |
| Hazard Information | Back Directory | [Description]
2-Amino-5-bromo-benzonitrile is a heterocyclic building block.1,2 It has been used in the synthesis of copper-ligand coordination complexes and 4-amino-3-benzimidazol-2-ylhydroquinolin-2-one-based multi-targeted receptor tyrosine kinase (RTK) inhibitors with anticancer activity. | [Chemical Properties]
white to light yellow crystal powder | [Uses]
2-Amino-5-bromobenzonitrile can react with Oxalic acid dimethyl ester to get 5-Bromo-N-methylanthranilonitrile. | [Synthesis]
The general procedure for the synthesis of 2-amino-5-bromobenzonitrile from 2-aminobenzonitrile was as follows: 2-aminobenzonitrile (11.8 g, 0.1 mol) was dissolved in acetic acid (120 ml) and ammonium bromide (10.3 g, 0.105 mol) and hydrogen peroxide (10.2 ml, 35% aqueous solution, 0.105 mol) were added sequentially. The reaction mixture was stirred at room temperature for about 1 hour, followed by continued stirring for 24 hours until LCMS analysis confirmed the completion of the reaction. Upon completion of the reaction, the acetic acid was removed by concentration and the residue was stirred with 30% aqueous sodium hydroxide solution to alkaline. The resulting solid was collected by filtration, washed with water and dried. The dried solid was dissolved in an excess of dichloromethane, the solution was concentrated until a precipitate began to appear and left to crystallize completely. The crystals were collected by filtration and washed with a small amount of dichloromethane to afford the target compound 2-amino-5-bromobenzonitrile as an off-white crystalline solid (19.2 g, 97% yield).1HNMR data: δ 7.61 (1H, d, J=2.5 Hz), 7.43 (1H, dd, J=9,2.5 Hz), 6.75 (1H, d, J=9 Hz), 6.28 ( 2H, br s); LC-MS retention time: 2.24 min. | [References]
[1] Canadian Journal of Chemistry, 2009, vol. 87, # 2, p. 440 - 447
[2] Patent: WO2007/80401, 2007, A1. Location in patent: Page/Page column 26
[3] Synthetic Communications, 2010, vol. 40, # 6, p. 868 - 876
[4] Synthetic Communications, 2010, vol. 40, # 21, p. 3226 - 3232
[5] Molecular Crystals and Liquid Crystals (1969-1991), 1991, vol. 206, p. 205 - 221 |
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