Description

3-(Bromomethyl)-5-chloro-1-benzothiophene (CAS No. 1198-51-2) is a high-purity halogenated benzothiophene derivative with the molecular formula C₉H₆BrClS. This compound is a versatile building block in organic synthesis, particularly in the development of pharmaceuticals, agrochemicals, and functional materials. Its unique structure, featuring both bromomethyl and chloro substituents on the benzothiophene core, enables selective functionalization for complex molecule construction. The product is supplied as a crystalline solid with >95% purity (HPLC), ensuring consistent performance in demanding applications. Proper storage at 2-8°C under inert atmosphere is recommended to maintain stability. Suitable for use in cross-coupling reactions, nucleophilic substitutions, and as a precursor for heterocyclic scaffolds. Handling should be performed in a well-ventilated fume hood using appropriate personal protective equipment due to the lachrymatory nature of brominated compounds.

Properties

• CAS Number: 1198-51-2
• Complexity: 165
• IUPAC Name: 3-(bromomethyl)-5-chloro-benzothiophene
• InChI: InChI=1S/C9H6BrClS/c10-4-6-5-12-9-2-1-7(11)3-8(6)9/h1-3,5H,4H2
• InChI Key: FKQSFVITUNJLCY-UHFFFAOYSA-N
• Exact Mass: 259.90621
• Molecular Formula: C9H6BrClS
• Molecular Weight: 261.57
• SMILES: C1=CC2=C(C=C1Cl)C(=CS2)CBr
• Topological: 28.2
• Monoisotopic Mass: 259.90621
• Synonyms: 3-(Bromomethyl)-5-chloro-1-benzothiophene, 638-916-3, 3-(Bromomethyl)-5-chlorobenzo[b]thiophene, 1198-51-2, Benzo[b]thiophene, 3-(bromomethyl)-5-chloro-, 3-(bromomethyl)-5-chloro benzo[b]thiophene, 5-chloro-3-bromomethylbenzothiophene, 3-(bromomethyl)-5-chlorobenzothiophene, 3-Bromomethyl-5-chlorobenzo[b]thiophene, 3-(bromomethyl)-5-chlorobenzo(b)thiophene, MFCD00173769, 5-chloro-3-bromomethyl-benzo[b]-thiophene, SCHEMBL246112, DTXSID90381577, 3-bromomethyl-5-chlorobenzothiophene, SBB054948, STL185587, AKOS015919000, AC-4585, CS-W002469, 3-Bromomethyl-5-chloro-2-benzothiophene, 3-bromomethyl-5-chloro-benzo[b]thiophene, DS-11135, DB-021696, B3147, (5-chlorobenzo[b]thiophen-3-yl)methylbromide, (5-chlorobenzo[b]-thiophen-3-yl)methylbromide, EN300-7377753

Application

This benzothiophene derivative serves as a key intermediate in medicinal chemistry for the synthesis of biologically active compounds targeting various disease pathways. Researchers utilize it in the development of kinase inhibitors and GPCR modulators due to its privileged heterocyclic structure. The bromomethyl group enables efficient derivatization through nucleophilic displacement reactions, while the chloro substituent allows for subsequent functionalization via metal-catalyzed cross-coupling methodologies.

Safety and Hazards

GHS Hazard Statements

• H290 (20%): May be corrosive to metals [Warning Corrosive to Metals]
• H302 (40%): Harmful if swallowed [Warning Acute toxicity, oral]
• H312 (20%): Harmful in contact with skin [Warning Acute toxicity, dermal]
• H314 (80%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
• H315 (20%): Causes skin irritation [Warning Skin corrosion/irritation]
• H318 (20%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
• H319 (20%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H332 (20%): Harmful if inhaled [Warning Acute toxicity, inhalation]
• H335 (40%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P234, P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P363, P390, P403+P233, P405, P406, and P501

Hazard Classes and Categories

• Met. Corr. 1 (20%)
• Acute Tox. 4 (40%)
• Acute Tox. 4 (20%)
• Skin Corr. 1B (80%)
• Skin Irrit. 2 (20%)
• Eye Dam. 1 (20%)
• Eye Irrit. 2 (20%)
• Acute Tox. 4 (20%)
• STOT SE 3 (40%)

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