Description

4-Bromo-3-phenyl-1H-pyrazole (CAS No. 13808-65-6) is a high-purity heterocyclic organic compound with the molecular formula C₉H₇BrN₂. This brominated pyrazole derivative features a phenyl substituent at the 3-position, making it a versatile intermediate for pharmaceutical, agrochemical, and materials science research. Its well-defined structure (IUPAC name: 4-bromo-5-phenyl-1H-pyrazole) ensures consistent reactivity in cross-coupling reactions, metal-catalyzed transformations, and as a building block for bioactive molecules. Available in >98% purity (HPLC), this compound is supplied in sealed packaging under inert conditions to ensure stability. Ideal for medicinal chemistry, ligand synthesis, and structural studies.

Properties

• CAS Number: 13808-65-6
• Complexity: 145
• IUPAC Name: 4-bromo-5-phenyl-1H-pyrazole
• InChI: InChI=1S/C9H7BrN2/c10-8-6-11-12-9(8)7-4-2-1-3-5-7/h1-6H,(H,11,12)
• InChI Key: ZJFUSLGMGSYTRY-UHFFFAOYSA-N
• Exact Mass: 221.97926
• Molecular Formula: C9H7BrN2
• Molecular Weight: 223.07
• SMILES: C1=CC=C(C=C1)C2=C(C=NN2)Br
• Topological: 28.7
• Monoisotopic Mass: 221.97926
• Synonyms: 4-Bromo-3-phenyl-1H-pyrazole, 13808-65-6, 4-bromo-3-phenylpyrazole, DTXSID40415917, DTXCID70366766, 819-245-7, 4-bromo-5-phenyl-1H-pyrazole, 4-Bromo-3-phenyl-1(2)H-pyrazole, 1H-Pyrazole, 4-bromo-3-phenyl-, MFCD09027561, Pyrazole, 4-bromo-3-phenyl- (8CI); 4-Bromo-3-phenylpyrazole, bromophenylpyrazole, bromophenyl pyrazole, SCHEMBL518672, SCHEMBL27217094, pyrazole, 4-bromo-3(5)phenyl-, BBL034977, SBB074355, STL428816, AKOS010654600, AKOS017342828, AKOS025394350, CS-W020606, AS-31006, PD144686, SY055857, EN300-312755, Z815438332, InChI=1/C9H7BrN2/c10-8-6-11-12-9(8)7-4-2-1-3-5-7/h1-6H,(H,11,12

Application

4-Bromo-3-phenyl-1H-pyrazole serves as a key precursor in Suzuki-Miyaura and Buchwald-Hartwig coupling reactions for drug discovery. Researchers utilize it to develop kinase inhibitors and antimicrobial agents due to its privileged pyrazole scaffold. The compound is also employed in coordination chemistry to synthesize transition metal complexes for catalytic applications.

Safety and Hazards

GHS Hazard Statements

• H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (50%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (50%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• STOT SE 3 (50%)

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