Description

3-(2-Bromoacetyl)benzonitrile (CAS No. 50916-55-7) is a high-purity organic compound with the molecular formula C₉H₆BrNO. This brominated aromatic nitrile is a versatile building block in synthetic organic chemistry, particularly in the development of pharmaceuticals, agrochemicals, and advanced materials. Its structure features a reactive bromoacetyl group adjacent to a benzonitrile moiety, making it an excellent electrophile for nucleophilic substitution reactions, cyclizations, and cross-coupling methodologies. Suitable for researchers in medicinal chemistry and material science, this compound is rigorously tested for purity and stability, ensuring reliable performance in demanding applications. Available in various quantities with detailed analytical data (GC/MS, NMR, HPLC) upon request.

Properties

• CAS Number: 50916-55-7
• Complexity: 218
• IUPAC Name: 3-(2-bromoacetyl)benzonitrile
• InChI: InChI=1S/C9H6BrNO/c10-5-9(12)8-3-1-2-7(4-8)6-11/h1-4H,5H2
• InChI Key: XWCGNFLHRINYCE-UHFFFAOYSA-N
• Exact Mass: 222.96328
• Molecular Formula: C9H6BrNO
• Molecular Weight: 224.05
• SMILES: C1=CC(=CC(=C1)C(=O)CBr)C#N
• Topological: 40.9
• Monoisotopic Mass: 222.96328
• Synonyms: 3-(2-Bromoacetyl)benzonitrile, 50916-55-7, DTXSID70370989, DTXCID10322023, 673-013-8, 3-Cyanophenacyl bromide, 2-Bromo-3′-cyanoacetophenone, 3-CYANOPHENACYLBROMIDE, 3-(2-bromoacetyl)benzenecarbonitrile, 3-(bromoacetyl)benzonitrile, MFCD00833267, CHEMBL1801626, Benzonitrile, 3-(bromoacetyl)-, 3-(2-bromo-acetyl)-benzonitrile, m-Cyanophenacyl bromide, 3-bromoacetylbenzonitrile, 3-bromoacetyl-benzonitrile, EZR7UV88N3, SCHEMBL38645, 2-bromo-3′-cyano-acetophenone, XWCGNFLHRINYCE-UHFFFAOYSA-N, Benzonitrile, 3-(2-bromoacetyl)-, 2-bromo-1-(3-cyanophenyl)ethanone, BCP27177, 1-(3-Cyanophenyl)-2-bromoethanone, BDBM50347524, SBB051663, STL183350, AKOS004911132, AC-23048, PD136222, SY050581, 3-(2-bromoacetyl)benzonitrile, AldrichCPR, DB-008301, A7546, B4079, CS-0186704, ST51041835, EN300-68614, 12X-0924, Z1095336216

Application

3-(2-Bromoacetyl)benzonitrile is widely used as a key intermediate in the synthesis of heterocyclic compounds, including indoles and quinolines, which are prevalent in drug discovery. Its reactive bromoacetyl group enables facile functionalization for the development of kinase inhibitors and other bioactive molecules. Researchers also employ it in material science for constructing conjugated systems or as a precursor for photoactive compounds. Its stability and selectivity make it ideal for multi-step synthetic routes.

Safety and Hazards

GHS Hazard Statements

• H301+H311+H331 (20%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
• H301 (60%): Toxic if swallowed [Danger Acute toxicity, oral]
• H302+H312+H332 (20%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
• H302 (40%): Harmful if swallowed [Warning Acute toxicity, oral]
• H311 (60%): Toxic in contact with skin [Danger Acute toxicity, dermal]
• H312 (20%): Harmful in contact with skin [Warning Acute toxicity, dermal]
• H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
• H318 (40%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
• H331 (60%): Toxic if inhaled [Danger Acute toxicity, inhalation]
• H332 (20%): Harmful if inhaled [Warning Acute toxicity, inhalation]

Precautionary Statements

• P260, P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P361+P364, P362+P364, P363, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 3 (60%)
• Acute Tox. 4 (40%)
• Acute Tox. 3 (60%)
• Acute Tox. 4 (20%)
• Skin Corr. 1B (100%)
• Eye Dam. 1 (40%)
• Acute Tox. 3 (60%)
• Acute Tox. 4 (20%)

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Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.