20099-89-2

Basic information

• Product Name: 4-CYANOPHENACYL BROMIDE
• Synonyms: 4-(2-BROMOACETYL)BENZONITRILE;4-CYANOPHENACYL BROMIDE;4-(BROMOACETYL)BENZONITRILE;2-BROMO-4'-CYANOACETOPHENONE;BUTTPARK 41\03-55;cyanophenacylbromide;p-Bromoacetylbenzonitrile;4-Cyanophenacyl bromide 97%
• CAS NO: 20099-89-2
• Molecular Formula: C₉H₆BrNO
• Molecular Weight: 224.05
• EINECS: -0
• Product Categories: C8 to C9;Cyanides/Nitriles;Nitrogen Compounds;intermediates
• Mol File: 20099-89-2.mol
• Article Data: 61

Chemical Properties

• Melting Point: 92-96 °C(lit.)
• Boiling Point: 342.4 °C at 760 mmHg
• Flash Point: 160.9 °C
• Appearance: Off-white to light yellow/Crystalline Powder
• Density: 1.56 g/cm³
• Refractive Index: 1.59
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: soluble in Methanol
• BRN: 2087648
• CAS DataBase Reference: 4-CYANOPHENACYL BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CYANOPHENACYL BROMIDE(20099-89-2)
• EPA Substance Registry System: 4-CYANOPHENACYL BROMIDE(20099-89-2)

Safety Data

• Hazard Codes: C
• Statements: 20/21/22-34
• Safety Statements: 26-27-36/37/39-45
• RIDADR: UN 2928 6.1/PG 2
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 20099-89-2(Hazardous Substances Data)

Usage

Description

4-CYANOPHENACYL BROMIDE, also known as 2-Bromo-4'-cyanoacetophenone, is an off-white to light yellow crystalline powder synthesized from ethylbenzene via aerobic photooxidation using aqueous HBr. It is a chemical compound with potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
4-CYANOPHENACYL BROMIDE is used as an intermediate in the synthesis of novel Glycogen synthase kinase 3 (GSK-3) inhibitors for the irreversible inhibitory activity of GSK-3. This makes it a valuable compound in the development of new drugs targeting GSK-3 related diseases.
Used in Chemical Synthesis:
4-CYANOPHENACYL BROMIDE is used as a key building block in the synthesis of various organic compounds, such as 3-acylindolizines, (2R,3R)-3-[4-(4-cyanophenyl)thiazol-2-yl]-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol, and 1-[2-(4-cyanophenyl)-2-oxoethyl]-1,10-phenanthrolinium bromide. These synthesized compounds have potential applications in various fields, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C10H7BrO/c1-2-8-3-5-9(6-4-8)10(12)7-11/h1,3-6H,7H2

Upstream product

• 1443-80-7 4-cyanophenyl methyl ketone 
• 67-56-1 methanol 
• 25309-65-3 4-ethylbenzonitrile 
• 157729-39-0 4-(2-bromoethynyl)-benzonitrile 
• 100-47-0 benzonitrile 
• 598-21-0 2-Bromoacetyl bromide 
• 3435-51-6 4-ethenylbenzonitrile 
• 105-07-7 4-cyanobenzaldehyde 

Downstream Products

• 100537-59-5 4-[(pyridine-3-sulfonyl)-acetyl]-benzonitrile 
• 103962-24-9 4-(2-[1,2,4]triazol-1-ylacetyl)benzonitrile 
• 115505-06-1 ω-ethythio-p-cyanoacetophenone 
• 114751-55-2 4-[2-(4-Butyl-phenyl)-imidazo[2,1-b][1,3,4]thiadiazol-6-yl]-benzonitrile 
• 114751-56-3 2-<4-butylcyclohexyl>-6-<4-cyanophenyl>imidazo-<2,1-b>-1,3,4-thiadiazole 
• 52695-39-3 4-oxiran-2-ylbenzonitrile 
• 1443-80-7 4-cyanophenyl methyl ketone 
• 85554-13-8 (±)-4-(2-bromo-1-hydroxyethyl)benzonitrile 
• 60694-92-0 1-(4-cyanophenyl)-2-iodoethanone 
• 1097210-25-7 (S)-4-(2-bromo-1-hydroxyethyl)benzonitrile 
• 96855-39-9 p-cyano-α-(bromomethyl)benzenemethanol 
• 94020-34-5 ethyl 2-acetyl-4-(4-cyanophenyl)-4-oxobutanoate 
• 138470-03-8 6-<5-<2-(4-Cyanphenacyloxy)-phenyl>-1,2,4-dithiazol-3-yliden>-2,4-cyclohexadien-1-on 
• 13367-81-2 10-methylacridinium cation 

Relevant articles and documents

Unexpected ritter reaction during acid-promoted 1,3-dithiol-2-one formation

A series of aryl-substituted 1,3-dithiol-2-ones was prepared by the Bhattacharya-Hortmann cyclization method. Unexpectedly, a Ritter reaction occurred during the acid-catalyzed cyclization at the cyano group of the aryl substituents and 1,3-dithiol-2-ones bearing a carboxy or a carboxamide group could be selectively obtained (see 1 and 2a in Scheme 1). The formation of the acid or the amide functionality was temperature-dependent so that the one or the other group could be introduced selectively by modifying the reaction temperature. Copyright

High Chemo-/Stereoselectivity for Synthesis of Polysubstituted Monofluorinated Pyrimidyl Enol Ether Derivatives

A novel intramolecular Smiles rearrangement of α-fluoro-β-keto-pyrimidylsulfones (usually used as a carbon nucleophile) was developed, providing a versatile avenue for synthesis of tri/tetra-substituted monofluorinated pyrimidyl enol ethers. Among these, diverse (Z)-monofluorovinylsulfones and sulfinates were efficiently assembled by adding extra electrophile and fine-tuning reaction conditions. The process is triggered by a keto-enol tautomerism from enol oxyanion to pyrimidine 2-carbon, completely different from the classical carbon nucleophilic addition reaction approach.

An umpolung oxa-[2,3] sigmatropic rearrangement employing arynes for the synthesis of functionalized enol ethers

An oxa-[2,3] sigmatropic rearrangement involving arynes is reported featuring the umpolung of ketones, where the C=O bond polarity is reversed. The in situ-generated sulfur ylides from β-keto thioethers and arynes undergo efficient rearrangement allowing the facile and robust synthesis of functionalized enol ethers in high yields and excellent functional group compatibility. Preliminary mechanistic studies rule out the possibility of Pummerer-type rearrangement operating in this case.

Oxidation Potential-Guided Electrochemical Radical-Radical Cross-Coupling Approaches to 3-Sulfonylated Imidazopyridines and Indolizines

Oxidation potential-guided electrochemical radical-radical cross-coupling reactions between N-heteroarenes and sodium sulfinates have been established. Thus, simple cyclic voltammetry measurement of substrates predicts the likelihood of successful radical-radical coupling reactions, allowing the simple and direct synthetic access to 3-sulfonylated imidazopyridines and indolizines. The developed electrochemical radical-radical cross-coupling reactions to sulfonylated N-heteroarenes boast the green synthetic nature of the reactions that are oxidant- and metal-free.