Description

5-Bromo-4-chloro-6-cyclopropylpyrimidine (CAS No. 27192-21-8) is a high-purity halogenated pyrimidine derivative with the molecular formula C₇H₆BrClN₂. This compound is a valuable heterocyclic building block for pharmaceutical and agrochemical research, featuring a reactive bromo-chloro substitution pattern and a cyclopropyl moiety that enhances steric and electronic modulation. Ideal for cross-coupling reactions, nucleophilic substitutions, and metal-catalyzed transformations, it is supplied as a crystalline solid with ≥95% purity (HPLC). Packaged under inert gas to ensure stability, it is suited for high-throughput screening and medicinal chemistry applications. Store at 2-8°C in a dry environment.

Properties

• CAS Number: 27192-21-8
• Complexity: 151
• IUPAC Name: 5-bromo-4-chloro-6-cyclopropyl-pyrimidine
• InChI: InChI=1S/C7H6BrClN2/c8-5-6(4-1-2-4)10-3-11-7(5)9/h3-4H,1-2H2
• InChI Key: UPVAFAYXZVOGHH-UHFFFAOYSA-N
• Exact Mass: 231.94029
• Molecular Formula: C7H6BrClN2
• Molecular Weight: 233.49
• SMILES: C1CC1C2=C(C(=NC=N2)Cl)Br
• Topological: 25.8
• Monoisotopic Mass: 231.94029
• Synonyms: 5-bromo-4-chloro-6-cyclopropylpyrimidine, 27192-21-8, 823-376-5, MFCD11047047, SCHEMBL16441737, WLZ3230, CBA19221, AKOS015149907, CS-47724, SY358371, 5-bromo-4-chloro-6-cyclopropyl-pyrimidine, EN300-3260154, Z1269163094

Application

5-Bromo-4-chloro-6-cyclopropylpyrimidine serves as a versatile intermediate in the synthesis of kinase inhibitors and antiviral agents due to its reactive halogen sites. Its cyclopropyl group facilitates the development of conformationally constrained bioactive molecules. Researchers utilize it in Suzuki-Miyaura and Buchwald-Hartwig couplings to construct complex heterocycles. It is also employed in crop protection chemistry for designing novel pesticides.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (50%): 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, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Irrit. 2A (50%)
• STOT SE 3 (50%)

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