Description

4-Amino-3-bromobenzonitrile (CAS No. 50397-74-5) is a high-purity aromatic compound with the molecular formula C₇H₅BrN₂. This specialized chemical features both an amino (–NH₂) and a cyano (–CN) functional group on a brominated benzene ring, making it a versatile intermediate for synthetic organic chemistry and pharmaceutical research. Its molecular weight of 197.04 g/mol and precise structure (IUPAC name: 4-amino-3-bromobenzonitrile) ensure consistent reactivity in cross-coupling reactions, nucleophilic substitutions, and heterocycle synthesis. Available in >98% purity (HPLC), it is supplied as a crystalline solid with strict QC protocols to meet research-grade standards. Ideal for medicinal chemistry, agrochemical development, and material science applications.

Properties

• CAS Number: 50397-74-5
• Complexity: 160
• IUPAC Name: 4-amino-3-bromo-benzonitrile
• InChI: InChI=1S/C7H5BrN2/c8-6-3-5(4-9)1-2-7(6)10/h1-3H,10H2
• InChI Key: POESQIHWIIWNJL-UHFFFAOYSA-N
• Exact Mass: 195.96361
• Molecular Formula: C7H5BrN2
• Molecular Weight: 197.03
• SMILES: C1=CC(=C(C=C1C#N)Br)N
• Topological: 49.8
• Monoisotopic Mass: 195.96361
• Synonyms: 4-Amino-3-bromobenzonitrile, 50397-74-5, DTXSID10363931, DTXCID00314977, 626-815-7, 3-Bromo-4-aminobenzonitrile, 2-Bromo-4-cyanoaniline, MFCD01861386, 4-amino-3-bromobenzenecarbonitrile, benzonitrile, 4-amino-3-bromo-, 4-amino-3-brombenzonitrile, 4-Amino-3-bromo-benzonitrile, 4-amino-3-bromobenzonitile, 4-amino-3-bromobenzo-nitrile, SCHEMBL616196, POESQIHWIIWNJL-UHFFFAOYSA-N, 4-Amino-3-bromobenzonitrile, 97%, SBB016927, AKOS001466128, AC-1795, CS-W002840, FA64097, PS-5927, 4-azanyl-3-bromanyl-benzenecarbonitrile, NCGC00341249-01, SY018639, DB-022326, A1961, ST50406062, EN300-30639, AB01153928-03, A828100, Z315898992

Application

4-Amino-3-bromobenzonitrile serves as a key building block in Suzuki-Miyaura and Buchwald-Hartwig coupling reactions for pharmaceutical intermediates. Its bromo and cyano groups enable selective functionalization in the synthesis of kinase inhibitors and agrochemicals. Researchers also utilize it to construct fused heterocycles like indoles and quinolines for drug discovery programs.

Safety and Hazards

GHS Hazard Statements

• H302 (95.3%): Harmful if swallowed [Warning Acute toxicity, oral]
• H317 (97.7%): May cause an allergic skin reaction [Warning Sensitization, Skin]

Precautionary Statements

• P261, P264, P270, P272, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, and P501

Hazard Classes and Categories

• Acute Tox. 4 (95.3%)
• Skin Sens. 1 (97.7%)

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