53317-05-8

Basic information

• Product Name: 3,4,5-tribromo-2-thenoic acid
• Synonyms: 3,4,5-tribromo-2-thenoic acid;3,4,5-Tribromo-2-thiophenecarboxylic acid;Einecs 258-475-7;3,4,5-Tribromo-thiophene-2-carboxylic acid
• CAS NO: 53317-05-8
• Molecular Formula: C₅HBr₃O₂S
• Molecular Weight: 364.83724
• EINECS: 258-475-7
• Mol File: 53317-05-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 259 °C
• Boiling Point: 396.3°Cat760mmHg
• Flash Point: 193.5°C
• Appearance: /
• Density: 2.606g/cm³
• Vapor Pressure: 5.44E-07mmHg at 25°C
• Refractive Index: 1.708
• PKA: 2.89±0.10(Predicted)
• CAS DataBase Reference: 3,4,5-tribromo-2-thenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,5-tribromo-2-thenoic acid(53317-05-8)
• EPA Substance Registry System: 3,4,5-tribromo-2-thenoic acid(53317-05-8)

Safety Data

• Hazardous Substances Data: 53317-05-8(Hazardous Substances Data)

Usage

General Description

3,4,5-tribromo-2-thenoic acid is a chemical compound with the molecular formula C4HBr3O2. It is a derivative of acrylic acid and is characterized by the presence of three bromine atoms on the aromatic ring. The compound is often used as a building block in the synthesis of other organic compounds and is also used as a precursor in the production of pharmaceuticals and agrochemicals. Its unique structure and functional groups make it a valuable intermediate in organic chemistry and it has potential applications in various fields including medicinal and materials chemistry. Additionally, 3,4,5-tribromo-2-thenoic acid has been investigated for its potential biological activities and is of interest to researchers in the field of chemical biology and drug discovery.

InChI:InChI=1/C5HBr3O2S/c6-1-2(7)4(8)11-3(1)5(9)10/h(H,9,10)

Upstream product

• 3141-24-0 2,3,5-tribromothiophene 
• 124-38-9 carbon dioxide 
• 3958-03-0 Tetrabromothiophene 
• 7311-66-2 3,4-dibromo-2-thiophenecarboxylic acid 

Downstream Products

• 943324-11-6 3,4-dibromo-5-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-2-thiophenecarboxylic acid 
• 115871-50-6 <2H9>valeric acid 
• 3141-25-1 2,3,4-tribromothiophene 
• 24647-80-1 Methyl-3,4,5-tribrom-2-thiophencarboxylat 
• 16694-18-1 4-bromo-thiophene-2-carboxylic acid 

Relevant articles and documents

Unusual ligand-dependent chemoselective Suzuki-Miyaura cross-coupling reactions of 3-bromo-4-trifloyl-thiophenes

An unusual ligand-dependent chemoselective Suzuki-Miyaura cross-coupling reaction for 3-bromo-4-trifloyl-thiophenes was discovered. Pd(PPh 3)4 showed selectivity for triflate over bromide, whereas the selectivity was reversed for Pd(tBu3P)2.

Synthesis of Thieno--, -- and --thiophenes and Thieno--, -- and --thienopyrimidin-7(6H)-ones Starting from Thiophene

3-Bromo-, 3,5-dibromo- and 3,4,5-tribromo-2-thienyllithium have been prepared by bromine ->lithium exchange and converted into a number of thiophene derivatives, including the corresponding 2-carbaldehydes.The aldehydes have been converted into the corresponding thiophene-2-carbonitriles.Metallation of 2,5-dibromo- or 2,4,5-tribromo-thiophene with LDA occured at a vacant 3-position but the resulting 3-lithiated thiophenes rearranged (mechanism discussed) to 3,5-dibromo- and 3,4,5-tribromo-2-thienyllithium, which were quenched with various electrophiles.Attempts to dilithiate 2,5-dibromothiophene with LDA were unsuccessful. 3,4-Dibromo-2,5-dilithiothiophene was prepared from 2,3,4,5-tetrabromothiophene but it failed to yield the 2,5-dicarbaldehyde with N,N-dimethylformamide.The title thienothiophenes were prepared by reaction of a 3-bromothiophene-2-carbaldehyde, a 2-bromothiophene-3-carbaldehyde (prepared by bromination of a thiophene-3-carbaldehyde) or a 4-bromothiophene-3-carbaldehyde, or a corresponding nitrile, with ethyl 2-sulfanylacetate or 2-sulfanylacetamide.Thienothiophenes carrying an o-aminocarboxamide substitution pattern gave the title thienothienopyrimidinones with triethyl orthoformate.

The electroreduction of halogenated thiophenes

Electroreduction of polyhalothiophenes results in the preferential reduction of the α-halogen atoms.Preparative electrochemical reduction of these compounds at controlled potential can be used to synthesize 2,3,4-trihalo, 3,4-dihalo, and 3-halothiophenes.Experimental conditions were developed under which these reductions could be done selectively, giving good yields of the desired products.Electroreduction of tetrabromothiophene can also lead to the formation of a polybromodithyenyl mercury compound.