5370-25-2

Basic information

• Product Name: 2-Acetyl-5-bromothiophene
• Synonyms: 5-Bromo 2-acetylthiophene;Ethanone, 1-(5-bromo-2-thienyl)-;Ethanone,1-(5-bromo-2-thienyl)-;Ketone, 5-bromo-2-thienyl methyl;2-Acetyl-5-Bromo Thiophenone;2-ACETYL-5-BROMOTHIOPHENE ,98%;1-(5-Bromothiophene-2-yl)ethanone;2-Bromo-5-acetylthiophene
• CAS NO: 5370-25-2
• Molecular Formula: C₆H₅BrOS
• Molecular Weight: 205.07
• EINECS: 226-363-7
• Product Categories: Thiophenes;Sulphur Derivatives;Thiophene&Benzothiophene;Pyridines;Building Blocks;C4 to C6;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Heterocycle-oher series
• Mol File: 5370-25-2.mol
• Article Data: 29

Chemical Properties

• Melting Point: 94-96 °C(lit.)
• Boiling Point: 103 °C4 mm Hg(lit.)
• Flash Point: 103°C/4mm
• Appearance: Yellow/Crystalline Flakes or Powder
• Density: 1.649 (estimate)
• Vapor Pressure: 0.0189mmHg at 25°C
• Refractive Index: 1.583
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: soluble in Methanol
• Sensitive: Light Sensitive
• BRN: 113949
• CAS DataBase Reference: 2-Acetyl-5-bromothiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Acetyl-5-bromothiophene(5370-25-2)
• EPA Substance Registry System: 2-Acetyl-5-bromothiophene(5370-25-2)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 36/37/39-26-22
• RIDADR: UN2811
• WGK Germany: 3
• HazardClass: LIGHT SENSITIVE
• Hazardous Substances Data: 5370-25-2(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

2-Acetyl-5-bromothiophene was used as a starting reagent in the synthesis of bithiophene bis-imidazo[1,2-a]pyridine derivatives. It was also used in the preparation of phosphorus-containing fused bicyclic 5,6-membered compounds.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 18, p. 1345, 1981 DOI: 10.1002/jhet.5570180714Synthetic Communications, 11, p. 29, 1981 DOI: 10.1080/00397918108064279

InChI:InChI=1/C6H5BrOS/c1-4(8)5-2-3-6(7)9-5/h2-3H,1H3

Upstream product

• 1003-09-4 2-bromothiophene 
• 64-19-7 acetic acid 
• 872-55-9 2-ethylthiophene 
• 64992-14-9 acetic 2-cyanoacetic anhydride 
• 114773-97-6 2-(α-methoxyimino)ethylthiophene 
• 1956-45-2 2-acetylthiophene oxime 
• 88-15-3 2-Acetylthiophene 
• 141-82-2 malonic acid 
• 114774-05-9 5-bromo-2-(α-methoxyimino)ethylthiophene 
• 3141-27-3 2,5-dibromothiophen 
• 75-36-5 acetyl chloride 
• 128-08-5 N-Bromosuccinimide 
• 108-24-7 acetic anhydride 
• 109-63-7 trifluoroborane diethyl ether 

Downstream Products

• 326-07-8 1-(5-bromo-[2]thienyl)-2H,2H-heptafluoro-hexane-1,3-dione 
• 100586-94-5 1-(5-bromo-[2]thienyl)-ethanone-phenylhydrazone 
• 366-90-5 (2E)-1-(5-bromothiophen-2-yl)-3-(4-fluorophenyl)prop-2-en-1-one 
• 96464-11-8 (2E)-1-(5-bromothiophen-2-yl)-3-(4-chlorophenyl) prop-2-en-1-one 
• 96462-86-1 (2E)-1-(5-bromothiophen-2-yl)-3-phenyl prop-2-en-1-one 
• 107456-34-8 (2E)-1-(5-bromothiophen-2-yl)-3-(4-methoxyphenyl)prop-2-en-1-one 
• 174502-99-9 1-(5-bromo-[2]thienyl)-ethanone thiosemicarbazone 
• 107455-95-8 1-(5-bromo-[2]thienyl)-3t-(2-methoxy-phenyl)-propenone 
• 101102-63-0 (2E)-1-(5-bromothiophen-2-yl)-3-[4-(dimethylamino) phenyl]prop-2-en-1-one 
• 96463-50-2 1-(5-bromo-[2]thienyl)-3t-(3,4-dichloro-phenyl)-propenone 
• 7311-63-9 5-bromothiophene-2-carboxylic acid 
• 10531-44-9 2-(2-bromoacetyl)-5-bromothiophene 
• 2160-55-6 1-(5-bromo-4-nitro-thiophen-2-yl)-ethanone 
• 174502-99-9 1-(5-bromo-2-thienyl)ethanone-thiosemicarbazone 

Relevant articles and documents

Five-membered heterocyclic oxo carboxylic acid compound and medical application thereof

The invention relates to a five-membered heterocyclic oxo carboxylic acid compound and a medical application thereof. Specifically, the invention relates to a compound, a pharmaceutical salt, a prodrug, a hydrate, a solvate or a crystal form as shown in a formula (I), and also relates to a preparation method of the compound, a pharmaceutical composition containing the compound and an application of the pharmaceutical composition as a secretion regulator of interferon type I, especially as an STING agonist in preparation of medicines for preventing and/or treating I-type interferon related diseases.

Pyrazoles: 'one-pot' synthesis from arenes and carboxylic acids

A rapid and efficient method for 'one-pot' synthesis of pyrazoles from (hetero)arenes and carboxylic acids via successive formation of ketones and β-diketones followed by heterocyclization with hydrazine has been developed. The utility of the RCOOH/TfOH/TFAA acylation system for intermediate production of ketones and 1,3-diketones is a key feature of this approach. The preliminary evaluation of the anticancer activity of the synthesized pyrazoles is performed.

Metal-Free Aerobic Oxidative Selective C-C Bond Cleavage in Heteroaryl-Containing Primary and Secondary Alcohols

A transition-metal-free aerobic oxidative selective C-C bond-cleavage reaction in primary and secondary heteroaryl alcohols is reported. This reaction was highly efficient and tolerated various heteroaryl alcohols, generating a carboxylic acid derivative and a neutral heteroaromatic compound. Experimental studies combined with density functional theory calculations revealed the mechanism underlying the selective C-C bond cleavage. This strategy also provides an alternative simple approach to carboxylation reaction.