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

• 6068-72-0 4-cyanobenzoyl chlorIde 
• 71-43-2 benzene 
• 1137-41-3 (4-aminophenyl)(phenyl)methanone 
• 201230-82-2 carbon monoxide 
• 3058-39-7 4-iodobenzonitrile 
• 383-35-7 ethyldifluorophenylsilane 
• 934-56-5 trimethyl(phenyl)stannane 
• 841-76-9 triphenylaluminium 
• 62673-29-4 phenyl(diisobutyl)aluminium 
• 58482-37-4 triphenylaluminium etherate 
• 15190-10-0 morpholin-4-yl-phenyl-acetonitrile 
• 1194-02-1 4-fluorobenzonitrile 
• 619-65-8 4-cyanobenzoic Acid 
• 623-00-7 4-bromobenzenecarbonitrile 

Downstream Products

• 76509-32-5 4-cyanobenzophenone ethylene acetal 
• 22679-54-5 4-tert-butylbenzophenone 
• 73831-69-3 4-(1-hydroxy-2,2-dimethyl-1-phenylpropyl)benzonitrile 
• 434940-62-2 4-(Cyclopenta-2,4-dienylidene-phenyl-methyl)-benzonitrile 
• 76509-33-6 4-acetylbenzophenone ethylene acetal 
• 73060-15-8 4-<3-(4-(N,N-dimethylamino)phenyl)propyl>benzophenone 
• 76509-34-7 4-<3-(4-(N,N-dimethylamino)phenyl)-1-oxopropyl>benzophenone ethylene acetal 
• 1259107-03-3 (E)-4-(2-fluoro-1-phenylvinyl)benzonitrile 
• 1314172-46-7 phenyl-[4-(1H-tetrazol-5-yl)-phenyl]-methanone 
• 69677-75-4 (4-benzoylphenyl)(p-tolyl)methanone 
• 20912-50-9 4-benzoylbenzaldehyde 
• 1022-45-3 2-phenyl-4(3H)-quinazolinone 
• 23405-48-3 4-methylthiobenzophenone 
• 26960-81-6 (4-(dodecylthio)phenyl)(phenyl)methanone 

Relevant articles and documents

-

-

Aromatization as an Impetus to Harness Ketones for Metallaphotoredox-Catalyzed Benzoylation/Benzylation of (Hetero)arenes

Herein we report ketones as feedstock materials in radical cross-coupling reactions under Ni/photoredox dual catalysis. In this approach, simple condensation first converts ketones into prearomatic intermediates that then act as activated radical sources for cross-coupling with aryl halides. Our strategy enables the direct benzylation/benzoylation of (hetero)arenes under mild reaction conditions with high functional group tolerance.

Novelmeta-benzothiazole and benzimidazole functionalised POCOP-Ni(ii) pincer complexes as efficient catalysts in the production of diarylketones

The synthesis of four novel non-symmetric Ni(ii)-POCOP pincer complexesmeta-functionalized with either benzothiazole or benzimidazole at the central aryl ring is described. All complexes were fully characterised in solution by various analytical techniques and the molecular structures in the solid state of complexes1b,2aand2bwere unequivocally determined by single crystal X-ray diffraction analysis. In addition, the Ni(ii)-POCOP pincer complexes were efficiently used as catalysts in the synthesis of diarylketones by cross-coupling reactions of functionalized benzaldehydes and boronic acid derivatives under relatively mild conditions. An important aspect of this transformation is the dependence on the steric properties of the donor groups (OPR2) of the pincer ligands, the more active compounds having the phosphinitos bearing isopropyl groups (1aand2a) than those containingtert-butyl substituents (1band2b).