13195-50-1

Basic information

• Product Name: 2-Bromo-5-nitrothiophene
• Synonyms: LABOTEST-BB LT00455100;2-BROMO-5-NITROTHIOPHENE;2-Bromo-5-nitrothiophene ,98%;2-Nitro-5-bromothiophene;5-Nitro-2-bromothiophene;2-Bromo-5-Nitrothiophene 99%
• CAS NO: 13195-50-1
• Molecular Formula: C₄H₂BrNO₂S
• Molecular Weight: 208.03
• EINECS: 236-155-8
• Product Categories: Heterocycles;Thiophene&Benzothiophene;Miscellaneous;Halogenated Heterocycles;Heterocyclic Building Blocks;Thiophenes;ThiophenesBuilding Blocks
• Mol File: 13195-50-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 44-48 °C(lit.)
• Boiling Point: 235-237°C
• Flash Point: 235-237°C
• Appearance: white to light yellow crystal powder
• Density: 1.945 g/cm³
• Vapor Pressure: 0.0295mmHg at 25°C
• Refractive Index: 1.647
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• BRN: 120955
• CAS DataBase Reference: 2-Bromo-5-nitrothiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-5-nitrothiophene(13195-50-1)
• EPA Substance Registry System: 2-Bromo-5-nitrothiophene(13195-50-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 13195-50-1(Hazardous Substances Data)

Usage

Description

2-Bromo-5-nitrothiophene is a heteroaryl halide derived from thiophene through a process of bromination followed by nitration. It is characterized by its white to light yellow crystal powder appearance and is utilized in the synthesis of various organic compounds, particularly oligothiophene precursors. These precursors are essential in the generation of (porphinato)zinc(II)-based chromophores, which have potential applications in the field of chemistry and materials science.

Uses

Used in Chemical Synthesis:
2-Bromo-5-nitrothiophene is used as a key intermediate in the synthesis of various organic compounds, including:
1. 3-bromo-4-(5-nitro-2-thienyl)-6-ethoxypyridine
2. 5-chloro-2-methoxy-4-(5-nitrothien-2-yl)-pyridine
3. 5-(5-nitrothien-2-yl)pyrimidine
4. 2-methoxy-5-(5-nitrothien-2-yl)pyrimidine
These synthesized compounds can be further utilized in the development of pharmaceuticals, dyes, and other specialty chemicals.
Used in the Preparation of Oligothiophene Precursors:
2-Bromo-5-nitrothiophene is used as a building block for the preparation of oligothiophene precursors, which are essential in the synthesis of (porphinato)zinc(II)-based chromophores. These chromophores have potential applications in the field of chemistry and materials science, particularly in the development of advanced materials with unique optical and electronic properties.
Used in Research and Development:
Due to its unique chemical properties and reactivity, 2-Bromo-5-nitrothiophene is also used in research and development for exploring new synthetic pathways, understanding its reactivity with various reagents, and discovering novel applications in different industries.

InChI:InChI=1/C4H2BrNO2S/c5-3-1-2-4(9-3)6(7)8/h1-2H

Upstream product

• 609-40-5 2-nitrothiophene 
• 7726-95-6 bromine 
• 1003-09-4 2-bromothiophene 

Downstream Products

• 13053-81-1 2-acetylaminothiophene 
• 91392-92-6 5,5'-diacetyldiamino-2,2'-dithienyl 
• 13195-53-4 2-nitro-5-phenylsulfanyl-thiophene 
• 79929-25-2 5-nitro-2-thienyl-4'-nitrophenylsulfide 
• 609-40-5 2-nitrothiophene 
• 41085-77-2 2,2'-dinitro-5,5'-dithienyl 
• 2160-38-5 2-bromo-3,5-dinitro-thiophene 
• 190966-86-0 2-Cyclohexylsulfanyl-5-nitro-thiophene 
• 190966-75-7 2-Nitro-5(4-fluoro)phenoxythiophene 
• 190966-80-4 2-(3-Chloro-phenoxy)-5-nitro-thiophene 
• 190966-71-3 2-(3-Fluoro-phenoxy)-5-nitro-thiophene 
• 190966-81-5 2-(2,3-Dimethyl-phenoxy)-5-nitro-thiophene 
• 190966-72-4 2-(2,4-Difluoro-phenoxy)-5-nitro-thiophene 
• 190966-85-9 2-(3-Isopropyl-phenoxy)-5-nitro-thiophene 

Relevant articles and documents

Studies on the biological activity of some nitrothiophenes

The biological activity of nineteen substituted thiophenes (3) have been assessed by evaluating the minimum inhibitory concentration required to inhibit the growth of E. coli, M. luteus and A. niger. The series displays a wide range of activities with 2-chloro-3,5-dinitrothiophene (3a) or 2-bromo-3,5- dinitrothiophene (3c) showing the highest activity against all three organisms, while the simplest compound of the series, 2-nitrothiophene (3s) shows the smallest activity in each case. The mode of action of 3a and 3c is thought to involve nucleophilic attack by intracellular thiols at the 2-position of the heterocyclic ring leading to displacement of halogen, but other active derivatives, such as 2,4-dinitrothiophene (3h) and 5-nitrothiophene-2- carbaldehyde (3d) which have no displaceable halogen or leaving group are thought to act by forming Meisenheimer complexes. The Royal Society of Chemistry 2006.

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Anisotropic organic compounds

STR1 The invention describes liquid crystalline compounds or formula (I), where A, D and G are independently selected from phenyl, thiophene, hydrogenated phenyl, chlorinated phenyl and fluorinated phenyl, B and E are independently selected from a single bond C= C. C C.C00, azoxy and diazo, k and m are independently selected from 1 and 0, such that m+n is 1 or 2, and R1 and R2 are independently selected from R, R0, alkynyl, thioalkyl, hydrogen, CN, NCS and SCN; provided that at least one of R1 and R2 is selected from CN, NCS and SCN and that at least one of A, D and G is phenyl; and excluding where at least one of R1 and R2 is independently selected as CN and one of A, D or G is not thiophene, and where m is 0, A, and D are phenyl, B is a single bond and only one of R1 or R2 is NCS. Also described are compounds suitable for inclusion in a device utilizing pretransitional characteristics of liquid crystalline materials in the isotropic phase, of general formula (II) where J and Y are independently selected from phenyl, thiophene, hydrogenated phenyl, chlorinated phenyl and fluorinated phenyl, X is selected from C= C. C C.COO azoxy and diazo, k is 1 or 0 and R3 and R4 are independently selected from R, RO, alkynyl, thioalkyl, hydrogen, CN, NCS and SCN; provided that at least one of R3 and R4 is selected from CN, NCS and SCN and that at least one of J and Y is phenyl.

COMPLEXES DE MEISENHEIMER TRIFLUOROMETHYLSULFONYLES. IV. TRIFLONES HETEROCYCLIQUES A CINQ CHAINONS. MISE EN EVIDENCE CINETIQUE D'UN EFFET ANORMAL DU GROUPE SO2CF3.

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