67869-13-0

Basic information

• Product Name: 2,3,5-TRIBROMO-4-METHYLTHIOPHENE
• Synonyms: 2,3,5-TRIBROMO-4-METHYLTHIOPHENE;Tribromomethylthiophene;3-Methyl-1,4,5-tribromothiophene
• CAS NO: 67869-13-0
• Molecular Formula: C₅H₃Br₃S
• Molecular Weight: 334.85
• EINECS: 267-441-0
• Product Categories: Thiophens
• Mol File: 67869-13-0.mol

Chemical Properties

• Melting Point: 31°C
• Boiling Point: 283°Cat760mmHg
• Flash Point: 31 °C
• Appearance: /
• Density: 2.329g/cm³
• Storage Temp.: Refrigerator
• CAS DataBase Reference: 2,3,5-TRIBROMO-4-METHYLTHIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,5-TRIBROMO-4-METHYLTHIOPHENE(67869-13-0)
• EPA Substance Registry System: 2,3,5-TRIBROMO-4-METHYLTHIOPHENE(67869-13-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 67869-13-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,3,5-Tribromo-4-methylthiophene is used as a synthetic intermediate for the development of diarylthiopheneacetyl guanidines. These compounds have been found to act as selective BACE1 inhibitors, which are important in the research and development of potential treatments for neurodegenerative diseases such as Alzheimer's.
Used in Chemical Research:
2,3,5-Tribromo-4-methylthiophene is also utilized as a reagent in the synthesis of photochromic dithienylthiazole derivatives. These photochromic compounds exhibit reversible color changes upon exposure to light, making them interesting for applications in various fields, including materials science, optoelectronics, and molecular switches.

Upstream product

• 616-44-4 3-Methylthiophene 
• 14282-76-9 2-bromo-3-methylthiophene 

Downstream Products

• 136877-24-2 3-methyl-2,4,5-trichlorothiophene 
• 174148-87-9 3-Methyl-thiophene-2,4-dicarbaldehyde 
• 1257070-67-9 2,4-dibromothiophene-3-carbaldehyde 
• 1435937-82-8 2,4-dibromo-5-((4-methoxyphenyl)sulfinyl)-3-methylthiophene 
• 1435937-98-6 (3,5-dibromo-4-methylthiophen-2-yl)(2,4-dichlorophenyl)methanone 
• 1435937-81-7 (3,5-dibromo-4-methylthiophen-2-yl)(4-methoxyphenyl)methanol 
• 1435937-80-6 4-(3,5-dibromo-4-methylthiophen-2-yl)benzonitrile 
• 266338-06-1 4-bromo-3-methylthiophene-2-carbonitrile 
• 334687-36-4 2-[5-(2-hydroxyethyl)-4-methylthiophen-3-ylmethyl]-3-phenylaminoacrylonitrile 

Relevant articles and documents

Synthesis and relative diatropicity of a remarkably aromatic thia[13]annulene

2,4-Bis(bromomethyl)-3-methylthiophene was synthesised as an intermediate to prepare the strained thiophenobenzophanediene 11, which readily thermally valence isomerizes to the novel thia[13]annulene 10. This thia-annulene is notably diatropic and shows about 40% of the ring current of the parent bridged [14]annulene 9, which is substantially more than an analogous oxaannulene, 18, and substantially less than the azaannulene 19.

Halogenation Using Quaternary Ammonium Polyhalides. XXXI. Halogenation of Thiophene Derivatives with Benzyltrimethylammonium Polyhalides

The reactions of thiophene derivatives with benzyltrimethylammonium tetrachloroiodate, benzyltrimethylammonium tribromide, and benzyltrimethylammonium dichloroiodate in acetic acid or in acetic acid-zinc chloride under mild conditions gave chloro-, bromo-, and iodo-substituted thiophene derivatives, respectively, in satifactory yields.