Benzophenone

Base Information

• Chemical Name: Benzophenone
• CAS No.: 119-61-9
• Deprecated CAS: 852361-03-6,1711678-21-5,445389-89-9
• Molecular Formula: C13H10O
• Molecular Weight: 182.222
• Hs Code.: 29143900
• European Community (EC) Number: 204-337-6
• ICSC Number: 0389
• NSC Number: 8077
• UN Number: 1224
• UNII: 701M4TTV9O
• DSSTox Substance ID: DTXSID0021961
• Nikkaji Number: J2.481C
• Wikipedia: Benzophenone
• Wikidata: Q409482
• RXCUI: 18997
• Metabolomics Workbench ID: 45232
• ChEMBL ID: CHEMBL90039
• Mol file: 119-61-9.mol

Synonyms:benzophenone

Chemical Property of Benzophenone

Chemical Property:

• Appearance/Colour: Orange crystals
• Vapor Pressure: 1 mm Hg ( 108 °C)
• Melting Point: 47-51 °C(lit.)
• Refractive Index: 1.5893
• Boiling Point: 305.4 °C at 760 mmHg
• Flash Point: 123.7 °C
• PSA: 17.07000
• Density: 1.11 g/cm³
• LogP: 2.91760
• Storage Temp.: Refrigerator
• Solubility.: ethanol: soluble100mg/mL, clear, colorless (80% ethanol)
• Water Solubility.: insoluble (
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 182.073164938
• Heavy Atom Count: 14
• Complexity: 165
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99.0%, ^*data from raw suppliers

Benzophenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,N,F Xn
• Hazard Codes: Xi,N,Xn,F
• Statements: 36/37/38-52/53-50/53-67-65-62-51/53-48/20-11-40
• Safety Statements: 26-61-37/39-29-60-36-62-36/37-33-16-9

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Benzophenones
• Canonical SMILES: C1=CC=C(C=C1)C(=O)C2=CC=CC=C2
• Inhalation Risk: Evaporation at 20 °C is negligible; a nuisance-causing concentration of airborne particles can, however, be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance is mildly irritating to the skin.
• Effects of Long Term Exposure: The substance may have effects on the liver and kidneys, resulting in impaired functions. Tumours have been detected in experimental animals but may not be relevant to humans.
• History: Discovery by Carl Graebe (1874): Benzophenone was first described by Carl Graebe at the University of K枚nigsberg in Prussia in 1874. Graebe detailed its reduction with hydroiodic acid and elemental phosphorus to form diphenylmethane.; Approval for Use in Sunscreens (1980s): The US Food and Drug Administration (FDA) approved the use of benzophenone in sunscreen products in the 1980s. It is recognized as a broad-spectrum ultraviolet (UV) radiation absorber and is permitted for use in sunscreens by both the European Union and the FDA.
• Production method: Acylation: Reaction of benzoyl chloride with excess benzene to produce benzophenone.; Atmospheric Oxidation: Oxidation of diphenylmethane by air in a copper-catalyzed reaction to yield benzophenone.; Carbon Tetrachloride Method: The reaction of benzene with carbon tetrachloride in the presence of anhydrous aluminum chloride to form diphenyldichloromethane, followed by hydrolysis to produce benzophenone.; Distillation: Distillation of calcium benzoate to obtain benzophenone.; Friedel鈥揅rafts Acylation: Reaction of aromatic compounds with Lewis acids (e.g., BF3, AlCl3, TiCl4, or ZnCl2) to generate benzophenone and its derivatives.
• Utilized as a photosensitizer: Benzophenone, a paradigmatic organic molecule for photosensitization, utilized as a photosensitizer in various contexts, including its application in photoprotection strategies and understanding photobiological risks associated with UV exposure. It has also found applications in medicinal chemistry due to its presence in naturally occurring molecules with diverse biological activities, as well as in synthetic compounds with medicinal properties. Additionally, benzophenone motifs are used in perfumes and as photoinitiators. [Benzophenone Photosensitized DNA Damage, Acc. Chem. Res. 2012, 45, 9, 1558鈥?1570]
• Applications of Benzophenone crystals: Benzophenone crystals have potential applications in organic nonlinear optical (NLO) materials for optical signal processing, telecommunications, optical data storage, and terahertz (THz) generation. The high-quality phase-matched second harmonic generation (SHG) single crystal is particularly of interest in the field of organic NLO materials.; Benzophenone (BP) single crystals could be grown using two different methods: the Sankaranarayanan鈥揜amasamy (SR) method and the slow evaporation solution technique (SEST). The SR method resulted in the growth of a high-quality, unidirectional crystal with specific dimensions (1060 mm length and 55 mm diameter). This method is highlighted for its advantages over the SEST method, including directional growth, which reduces the density of dislocations, leading to higher mechanical stability and better optical quality.[The growth of benzophenone crystals by Sankaranarayanan鈥揜amasamy (SR) method and slow evaporation solution technique (SEST): A comparative investigation, Materials Research Bulletin Volume 47, Issue 3, March 2012, Pages 826-835]
• Prohibited for use as food additives: Benzophenone is a mutagen, carcinogen, and endocrine disruptor. Its presence in food products or food packaging is banned in the United States. Under California Proposition 65, there is no safe harbor for benzophenone in any personal care products, including sunscreens, anti-aging creams, and moisturizers. [Benzophenone Accumulates over Time from the Degradation of Octocrylene in Commercial Sunscreen Products, Chem. Res. Toxicol. 2021, 34, 4, 1046鈥?1054]

Technology Process of Benzophenone

There total 3404 articles about Benzophenone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

2,2-diphenyl-1,3-oxathiolane (33735-40-9) + 2-carboxybenzene diazonium chloride (4661-46-5) → benzophenone (119-61-9) + phenylthioethylene (1822-73-7)

Guidance literature:

With methyloxirane; In 1,2-dichloro-ethane; for 0.75h; Mechanism; Heating;

DOI:10.1016/S0040-4039(00)98960-3

Reference yield: 80.0%

C23H16N2O2 (115993-91-4) → 4-chloroquinoline (611-35-8) + benzophenone (119-61-9) + hexachloroethane (67-72-1) + benzophenone azine (983-79-9)

Guidance literature:

With tetrachloromethane; Yields of byproduct given; Ambient temperature; Irradiation;

DOI:10.1016/S0040-4039(00)82327-8

Reference yield: 30.0%

1-(diphenylmethyl)-4-nitrobenzene (2945-12-2) → benzophenone (119-61-9) + 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0)

Guidance literature:

With potassium hydroxide; oxygen; In 1,2-dimethoxyethane; at 20 ℃; for 0.5h;

DOI:10.1007/BF00957947

upstream raw materials:

3,3,4,4-tetraphenyl-β-thiolactone

(E)-1,2-diphenyl-ethene

ethanol

(2,6-dimethylphenyl)(diphenylmethylene)phosphine

Downstream raw materials:

benzhydrylidenehydrazide of benzilic acid

diphenyl(pyridin-3-yl)methanol

diphenyl(pyridin-4-yl)methanol

1,1-diphenyl-2-pyrazin-2-yl-ethanol

Refernces

• 1、 Haselbach, Edwin,Vauthey, Eric,Suppan, Paul. "COMPARISON OF PHOTOINDUCED ELECTRON TRANSFER REACTIONS OF AROMATIC CARBONYL VS. CYANO COMPOUNDS WITH ELECTRON DONORS IN CONDENSED PHASE: THE IMPORTANCE OF THE SPIN STATE OF THE GEMINATE ION PAIR FOR OBTAINING HIGH ION YIELDS.". . p. 7335 - 7344. Retrieved 1988.
• 2、 Yin, Weiyan,He, Haifeng,Zhang, Yani,Long, Tong. "Ligand-free palladium-catalyzed aerobic oxidative coupling of carboxylic anhydrides with arylboronic acids". . p. 2402 - 2406. Retrieved 2014.
• 3、 Zeiss. "-". . . Retrieved 1951.
• 4、 Barton, Derek H. R.,Jaszberenyi, Joseph Cs.,Shinada, Tetsuro. "Oxidation of phenylhydrazones of α-keto esters with hypervalent organoiodine reagents". . p. 7191 - 7194. Retrieved 1993.
• 5、 Komissarov,Nazarov,Yamilova. "Mechanism of thermal decomposition of diphenyldiazomethane in the presence of oxygen". . p. 261 - 264. Retrieved 1997.
• 6、 Nazarov,Chainikova,Krupin,Khursan,Kalinichenko,Komissarov. "Kinetics, products, and mechanism of the reaction of diphenylcarbonyl oxide with sulfoxides". . p. 1496 - 1500. Retrieved 2000.
• 7、 Tice, Colin M.,Michelotti, Enrique L.,Mata, Ernesto G.,Nicolàs, Ernesto,Garcia, Javier,Albericio, Fernando. "Solid phase synthesis of α-acylamino-α,α-disubstituted ketones". . p. 7491 - 7494. Retrieved 2002.
• 8、 Mueller-Westerhoff, Ulrich T.,Zhou, Ming. "A simple synthesis of symmetrical α-diones from organometallic reagents and 1,4-dimethyl-piperazine-2,3-dione". . p. 571 - 574. Retrieved 1992.
• 9、 Maruyama, Kazuhiro,Hayami, Jun-ichi,Katagiri, Toshimasa. "TWO INTERMEDIATES OBSERVED IN THE GRIGNARD REACTION WITH BENZOPHENONE". . p. 601 - 604. Retrieved 1986.
• 10、 Iranpoor, Nasser,Firouzabadi, Habib,Etemadi-Davan, Elham. "Phosphine-free NiBr2-catalyzed synthesis of unsymmetrical diaryl ketones via carbonylative cross-coupling of aryl iodides with Ph3SnX (X = Cl, OEt)". . p. 282 - 287. Retrieved 2015.