1776-09-6

Basic information

• Product Name: 3-broMo-2,3-dihydrochroMen-4-one
• Synonyms: 3-broMo-2,3-dihydrochroMen-4-one;3-bromochroman-4-one;3-bromo-2,3-dihydro-4H-chromen-4-one
• CAS NO: 1776-09-6
• Molecular Formula: C₉H₇BrO₂
• Molecular Weight: 227.05468
• Mol File: 1776-09-6.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 319.598 °C at 760 mmHg
• Flash Point: 147.088 °C
• Appearance: /
• Density: 1.643 g/cm³
• CAS DataBase Reference: 3-broMo-2,3-dihydrochroMen-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-broMo-2,3-dihydrochroMen-4-one(1776-09-6)
• EPA Substance Registry System: 3-broMo-2,3-dihydrochroMen-4-one(1776-09-6)

Safety Data

• Hazardous Substances Data: 1776-09-6(Hazardous Substances Data)

Usage

General Description

3-Bromo-2,3-dihydrochromen-4-one is a chemical compound with the formula C9H7BrO2. It is a brominated derivative of 2,3-dihydrochromen-4-one, which is a type of flavonoid. 3-broMo-2,3-dihydrochroMen-4-one has potential biological activities in the areas of anti-inflammatory and antioxidant properties, as well as anti-cancer and anti-tumor effects. It is also being studied for its potential use in drug development and as a lead compound for designing new drugs with improved pharmacological properties. Its chemical structure and properties make it an interesting compound for further research and potential therapeutic applications.

Upstream product

• 98592-23-5 3,3-dibromo chroman-4-one 
• 49619-82-1 3-bromo-4H-chromen-4-one 
• 7170-38-9 3-phenoxypropanoic acid 
• 6180-61-6 3-phenoxypropanol 
• 108-95-2 phenol 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 119-84-6 C₆H₄(CH₂CH₂C(O)O) 

Downstream Products

• 106129-86-6 1-(2-hydroxyphenyl)-3-dimethylaminoprop-2-enone 
• 850797-12-5 (E)-3-(diethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one 
• 31877-68-6 2-amino-4H-<1>benzopyrano<4,3-d>thiazole 
• 35371-17-6 2-phenyl-1⁽³⁾,4-dihydro-chromeno[3,4-d]imidazole 
• 139449-21-1 3-phenylthio-2,3-dihydro-(4H)-benzopyran-4-one 
• 66125-10-8 2-(2-phenyl-pyrimidin-4-yl)-phenol 
• 454679-89-1 3-Brom-chromanol-(4) 
• 491-38-3 1-benzopyran-4(4H)-one 
• 402929-38-8 2,3-dihydro-3-(1H-1,2,4-triazol-1-yl)-4H-1-benzopyran-4-one 
• 80930-39-8 3-(2-Methyl-imidazol-1-yl)-chroman-4-one 
• 80930-45-6 2,3-dihydro-3-(1H-imidazol-1-yl)-4H-1-benzopyran-4-one 
• 59507-94-7 3-amino-4H-chromen-4-one 

Relevant articles and documents

Conformationally constrained analogs of n-substituted piperazinylquinolones: Synthesis and antibacterial activity of n-(2,3-dihydro-4-hydroxyimino-4h-1-benzopyran-3-yl)-piperazinylquinolones

A series of novel quinolone agents bearing a particular bulky and conformationally constrained bicyclic substituent (2,3-dihydro-4-hydroxyimino- 4H-1-benzopyran-3-yl- moiety) on the piperazine ring of 7-piperazinyl quinolones (norfloxacin, enoxacin, ciprofloxacin, and levofloxacin) were synthesized and evaluated against a panel of Gram-positive and Gram-negative bacteria. Among these derivatives, ciprofloxacin counterpart 9c, highly inhibited the tested Gram-positive bacteria, superior to that of the reference drugs, and displayed antibacterial activity at non-cytotoxic concentrations.

Chemoselective Hydrosilylation of the α,β-Site Double Bond in α,β- And α,β,γ,δ-Unsaturated Ketones Catalyzed by Macrosteric Borane Promoted by Hexafluoro-2-propanol

The B(C6F5)3-catalyzed chemoselective hydrosilylation of α,β- and α,β,γ,δ-unsaturated ketones into the corresponding non-symmetric ketones in mild reaction conditions is developed. Nearly 55 substrates including those bearing reducible functional groups such as alkynyl, alkenyl, cyano, and aromatic heterocycles are chemoselectively hydrosilylated in good to excellent yields. Isotope-labeling studies revealed that hexafluoro-2-propanol also served as a hydrogen source in the process.

Enantioselective Total Syntheses of Pallambins A–D

The first enantioselective total syntheses of (?)-pallambins A–D have been achieved in 15 or 16 steps from a known chiral cyclohexenone. Salient features of the syntheses include a palladium-catalyzed oxidative cyclization to assemble the [3.2.1]bicyclic moiety, an Eschenmoser–Claisen rearrangement/lactone formation sequence to construct the C ring, an intramolecular Wittig reaction to form the D ring, and individual transformations of pallambins C and D to generate pallambins A and B. The described synthesis avoids protecting-group manipulations through the design of highly chemo- and stereoselective transformations. During the course of this work, a palladium-catalyzed method for the dehydrobromination of α-bromoketones was developed, and the scope of this transformation was also investigated.

Synthesis of α,β-dibromo ketones by photolysis of α-bromo ketones with N-bromosuccinimide: Photoinduced β-bromination of α-bromo ketones

Irradiation of α-bromopropiophenones in the presence of NBS results in the formation of α,β-dibromopropiophenones, which can be viewed as β-bromination of α-bromopropiophenones. The reaction is believed to go through a series of reactions; photoinduced C–Br bond cleavage, elimination of HBr to give α,β-unsaturated ketone intermediates, and addition of Br2, which are formed by the reaction between HBr and NBS. From mechanistic studies of the reaction, we have also found a very convenient method for α-debromination of the α,β-dibromopropiophenones which is by simple irradiation of the dibromo ketones in acetone or 2-propanol without the use of any additives. Our results demonstrate that bromine can be added into or eliminated from the alpha, beta, or both positions to the carbonyl group by photochemical methods, which make synthetic options of bromine containing carbonyl compounds versatile.