1503-49-7

Basic information

• Product Name: 4-CYANOBENZOPHENONE
• Synonyms: 4-CYANOBENZOPHENONE;4-BENZOYLBENZONITRILE;P-CYANOBENZOPHENONE;4-Cyano-benzophenon;Benzonitrile, 4-benzoyl-;benzophenone-4-carbonitrile;4-Cyanobenzophenone,98%
• CAS NO: 1503-49-7
• Molecular Formula: C₁₄H₉NO
• Molecular Weight: 207.23
• EINECS: 216-126-6
• Product Categories: Aromatic Benzophenones & Derivatives (substituted);Building Blocks;C10 to C27;Chemical Synthesis;Cyanides/Nitriles;Nitrogen Compounds;Organic Building Blocks
• Mol File: 1503-49-7.mol
• Article Data: 180

Chemical Properties

• Melting Point: 110-114 °C(lit.)
• Boiling Point: 346.25°C (rough estimate)
• Flash Point: 181.8 °C
• Appearance: /
• Density: 1.1259 (rough estimate)
• Vapor Pressure: 6.95E-06mmHg at 25°C
• Refractive Index: 1.4700 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Insoluble in water.
• BRN: 641181
• CAS DataBase Reference: 4-CYANOBENZOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CYANOBENZOPHENONE(1503-49-7)
• EPA Substance Registry System: 4-CYANOBENZOPHENONE(1503-49-7)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36
• RIDADR: 3439
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 1503-49-7(Hazardous Substances Data)

Usage

Description

4-Cyanobenzophenone is a benzophenone derivative characterized by its slightly yellow crystalline powder appearance. It can be synthesized by treating 4-cyanobenzoyl chloride with benzene, and its reduction under electrochemical conditions results in the formation of 4-t-butyl-benzophenone and 1-(4-cyanophenyl)-2,2-dimethyl-1-phenylpropan-1-ol. 4-CYANOBENZOPHENONE is known for its efficiency as a triplet sensitizer in the photoisomerization of norbornadiene (N) to quadricyclane (Q) and vice versa.

Uses

Used in Photochemistry:
4-Cyanobenzophenone is used as a triplet sensitizer for the photoisomerization of norbornadiene (N) to quadricyclane (Q) and Q to N. Its efficiency in this application has been assessed and found to be effective in facilitating the isomerization process.
Used in Chemical Synthesis:
In the chemical industry, 4-Cyanobenzophenone can be utilized as a starting material or intermediate for the synthesis of various compounds, taking advantage of its unique chemical properties and reactivity.
Used in Research and Development:
Due to its role in photoisomerization and its chemical properties, 4-Cyanobenzophenone may be employed in research and development settings to study the behavior of molecules under different conditions and to develop new methodologies or applications in photochemistry and related fields.

Synthesis Reference(s)

The Journal of Organic Chemistry, 41, p. 1187, 1976 DOI: 10.1021/jo00869a023Tetrahedron Letters, 26, p. 4819, 1985 DOI: 10.1016/S0040-4039(00)94960-8

InChI:InChI=1/C14H9NO/c15-10-11-6-8-13(9-7-11)14(16)12-4-2-1-3-5-12/h1-9H

Upstream product

• 15190-10-0 morpholin-4-yl-phenyl-acetonitrile 
• 1194-02-1 4-fluorobenzonitrile 
• 134-84-9 4-Methylbenzophenone 
• 32752-54-8 4-(bromomethyl)benzophenone 
• 100-58-3 phenylmagnesium bromide 
• 105-07-7 4-cyanobenzaldehyde 
• 623-00-7 4-bromobenzenecarbonitrile 
• 82102-37-2 9-methyl-9H-fluorene-9-carbonyl chloride 
• 201230-82-2 carbon monoxide 
• 36800-95-0 p-cyanophenyl p-toluenesulfonate 
• 98-80-6 phenylboronic acid 
• 640-60-8 toluene-4-sulfonic acid phenyl ester 
• 126747-14-6 4-cyanophenylboronic acid 
• 17763-67-6 Phenyl triflate 

Downstream Products

• 611-95-0 4-carboxybenzophenone 
• 7664-41-7 ammonia 
• 15796-82-4 4,4'-di-tert-butylbenzophenone 
• 73831-64-8 1-(4-tert-Butyl-phenyl)-2,2-dimethyl-1-phenyl-propan-1-ol 
• 73841-13-1 (4-tert-Butyl-phenyl)-[5,6-di-tert-butyl-3'-(4-tert-butyl-benzoyl)-bicyclohexyl-2,2'-dien-2-yl]-methanone 
• 69677-75-4 (4-benzoylphenyl)(p-tolyl)methanone 
• 20912-50-9 4-benzoylbenzaldehyde 
• 58-72-0 Triphenylethylene 
• 838-13-1 p-cyanobenzophenone hydrazone 
• 434940-62-2 4-(Cyclopenta-2,4-dienylidene-phenyl-methyl)-benzonitrile 
• 73831-69-3 4-(1-hydroxy-2,2-dimethyl-1-phenylpropyl)benzonitrile 
• 22679-54-5 4-tert-butylbenzophenone 
• 78024-99-4 (Z)-4,4′-(1,2-diphenylethene-1,2-diyl)dibenzonitrile 
• 78025-01-1 trans-1,2-di(4-cyanophenyl)-1,2-diphenylethylene 

Relevant articles and documents

-

-

C(acyl)-C(sp2) and C(sp2)-C(sp2) Suzuki-Miyaura cross-coupling reactions using nitrile-functionalized NHC palladium complexes

Application of N-heterocyclic carbene (NHC) palladium complexes has been successful for the modulation of C-C coupling reactions. For this purpose, a series of azolium salts (1a-f) including benzothiazolium, benzimidazolium, and imidazolium, bearing a CN-substituted benzyl moiety, and their (NHC)2PdBr2 (2a-c) and PEPPSI-type palladium (3b-f) complexes have been systematically prepared to catalyse acylative Suzuki-Miyaura coupling reaction of acyl chlorides with arylboronic acids to form benzophenone derivatives in the presence of potassium carbonate as a base and to catalyse the traditional Suzuki-Miyaura coupling reaction of bromobenzene with arylboronic acids to form biaryls. All the synthesized compounds were fully characterized by Fourier Transform Infrared (FTIR), and 1H and 13C NMR spectroscopies. X-ray diffraction studies on single crystals of 3c, 3e and 3f prove the square planar geometry. Scanning Electron Microscopy (SEM), energy dispersive X-ray spectroscopy (EDS), metal mapping analyses and thermal gravimetric analysis (TGA) were performed to get further insights into the mechanism of the Suzuki-Miyaura cross coupling reactions. Mechanistic studies have revealed that the stability and coordination of the complexes by the CN group are achieved by the removal of pyridine from the complex in catalytic cycles. The presence of the CN group in the (NHC)Pd complexes significantly increased the catalytic activities for both reactions.

Feeding Carbonylation with CO2via the Synergy of Single-Site/Nanocluster Catalysts in a Photosensitizing MOF

Solar-driven carbonylation with CO2 replacing toxic CO as a C1 source is of considerable interest; however it remains a great challenge due to the inert CO2 molecule. Herein, we integrate cobalt single-site and ultrafine CuPd nanocluster catalysts into a