Description

1-Bromo-4-isocyanobenzene (CAS No. 33554-73-3) is a high-purity aromatic isocyanate compound with the molecular formula C₇H₄BrN. This specialized chemical is widely utilized in organic synthesis, pharmaceutical research, and materials science due to its reactive isocyano (-NC) and bromo (-Br) functional groups. Its precise structure enables selective cross-coupling reactions, making it a valuable intermediate for constructing complex molecules. Suitable for Suzuki, Stille, and other palladium-catalyzed couplings, this compound is rigorously tested for purity (typically ≥95% by GC or HPLC) and is available in sealed ampules or bulk packaging under inert conditions to ensure stability. Store in a cool, dry place away from moisture and incompatible reagents.

Properties

• CAS Number: 33554-73-3
• Complexity: 127
• IUPAC Name: 1-bromo-4-isocyano-benzene
• InChI: InChI=1S/C7H4BrN/c1-9-7-4-2-6(8)3-5-7/h2-5H
• InChI Key: UVXCIFWBXFTMOD-UHFFFAOYSA-N
• Exact Mass: 180.95271
• Molecular Formula: C7H4BrN
• Molecular Weight: 182.02
• SMILES: [C-]#[N+]C1=CC=C(C=C1)Br
• Topological: 4.4
• Monoisotopic Mass: 180.95271
• Synonyms: 1-bromo-4-isocyanobenzene, 33554-73-3, DTXSID00373741, DTXCID00324773, 883-972-6, MFCD04117594, 4-bromophenyl-isocyanide, SCHEMBL997985, LCZC3172, BBL020634, STK893324, AKOS001476182, GS-0287, SY273932, DB-048438, E78470, EN300-1176974

Application

1-Bromo-4-isocyanobenzene serves as a versatile building block in medicinal chemistry for synthesizing bioactive molecules and heterocyclic scaffolds. It is employed in metal-catalyzed cross-coupling reactions to introduce both bromo and isocyano functionalities into target structures. Researchers also use it to develop advanced materials, such as conductive polymers or metal-organic frameworks (MOFs), leveraging its dual reactivity.

Safety and Hazards

GHS Hazard Statements

• H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
• H311 (100%): Toxic in contact with skin [Danger Acute toxicity, dermal]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H331 (100%): Toxic if inhaled [Danger Acute toxicity, inhalation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

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

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