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Benzophenone

Base Information Edit
  • 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
Benzophenone

Synonyms:benzophenone

Suppliers and Price of Benzophenone
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • TRC
  • Benzophenone
  • 250g
  • $ 100.00
  • TRC
  • Benzophenone
  • 1g
  • $ 55.00
  • TCI Chemical
  • Benzophenone >99.0%(GC)
  • 25g
  • $ 17.00
  • TCI Chemical
  • Benzophenone >99.0%(GC)
  • 500g
  • $ 34.00
  • SynQuest Laboratories
  • Benzophenone
  • 500 g
  • $ 40.00
  • SynQuest Laboratories
  • Benzophenone
  • 1 kg
  • $ 50.00
  • SynQuest Laboratories
  • Benzophenone
  • 100 g
  • $ 20.00
  • Sigma-Aldrich
  • Benzophenone ReagentPlus?, 99%
  • 25 g
  • $ 11.50
  • Sigma-Aldrich
  • Benzophenone 99%
  • 25g-a
  • $ 11.20
  • Sigma-Aldrich
  • Benzophenone for synthesis. CAS No. 119-61-9, EC Number 204-337-6., for synthesis
  • 8018010005
  • $ 15.90
Total 308 raw suppliers
Chemical Property of Benzophenone Edit
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:

99.5%min *data from raw suppliers

Benzophenone *data from reagent suppliers

Safty Information:
  • Pictogram(s): IrritantXi,DangerousN,FlammableF HarmfulXn 
  • 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]
  • General Description Benzophenone, also known as diphenyl ketone or phenyl ketone, is a versatile organic compound widely used in chemical synthesis, photochemistry, and as a precursor in pharmaceuticals and polymerization processes. It serves as a chromophore in photochemical studies, participates in ethynylation reactions under ball milling conditions, and is involved in the synthesis of anti-malarial agents, vitamin E amines, and organometallic complexes. Its derivatives, such as benzophenone imines, exhibit intramolecular general-base catalysis in hydrolysis reactions. Benzophenone's structural adaptability makes it valuable in diverse applications, including drug development, photopolymerization, and organic synthesis.
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:
Guidance literature:
With methyloxirane; In 1,2-dichloro-ethane; for 0.75h; Mechanism; Heating;
DOI:10.1016/S0040-4039(00)98960-3
Guidance literature:
With tetrachloromethane; Yields of byproduct given; Ambient temperature; Irradiation;
DOI:10.1016/S0040-4039(00)82327-8
Guidance literature:
With potassium hydroxide; oxygen; In 1,2-dimethoxyethane; at 20 ℃; for 0.5h;
DOI:10.1007/BF00957947
Refernces Edit

Structure-activity relationships of novel anti-malarial agents: Part 5. N-(4-acylamino-3-benzoylphenyl)-[5-(4-nitrophenyl)-2-furyl]acrylic acid amides

10.1016/S0960-894X(02)01003-X

The study focuses on the structure-activity relationships of novel anti-malarial agents, specifically N-(4-acylamino-3-benzoylphenyl)-[5-(4-nitrophenyl)-2furyl]acrylic acid amides. The researchers developed a lead compound, benzophenone 4g, which was modified by replacing the tolylacetyl residue at the 2-amino group with various acyl residues to determine their influence on anti-malarial activity. The chemicals used included 2-amino-5-nitrobenzophenone, acid chlorides for acylation, SnCl2?2H2O for reduction, and 3-[5-(4-nitrophenyl)-2-furyl]acrylic acid chloride for further acylation. The purpose of these chemicals was to synthesize and test a series of compounds to identify the optimal acyl residue structure for high anti-malarial activity, with the aim of overcoming drug resistance in Plasmodium falciparum, the causative agent of malaria. The study found that a phenylacetic acid substructure substituted in its para-position with methyl or similar-sized substituents was essential for high activity, with the trifluoromethyl-substituted derivative showing the most potent activity.

Structural effects on the photodissociation of alkoxyamines

10.1039/c0ob01207f

The study investigates the structural effects on the photodissociation of alkoxyamines, which are compounds used in various fields including organic synthesis, fluorescence probes, and controlled polymerization processes. The researchers focused on the photochemical properties of six selected alkoxyamines, examining how their chemical structures influence the selectivity of bond cleavage and the efficiency of nitroxide formation. The alkoxyamines were studied using techniques such as ESR (Electron Spin Resonance) and laser flash photolysis to understand their behavior under light irradiation. Key chemicals used in the study include alkoxyamines with a benzophenone chromophore, which serves as a light-absorbing group, and various trapping agents to prevent back-reaction of radicals. The purpose of these chemicals was to investigate the photodissociation process and the generation of radicals, which are crucial for applications in photopolymerization and other photochemical reactions.

Efficient synthesis of vitamin E amines

10.1002/ejoc.200900088

The study presents a novel and efficient method for synthesizing Vitamin E amines (tocopheramines and tocotrienamines) in enantiopure form. These compounds are significant due to their potential biological and antioxidant properties, making them valuable for applications in food additives, polymer stabilizers, and pharmaceuticals. The synthesis involves Pd-catalyzed N-arylation reactions on triflates derived from the corresponding phenols. Key chemicals used include Pd(OAc)2 and rac-BINAP as catalysts, NaOtBu or Cs2CO3 as bases, and benzylamine or benzophenone imine as nitrogen sources. The process involves converting natural tocopherols and tocotrienols into their triflate derivatives, followed by amination to introduce the nitrogen function at the 6-position of the chromane ring. The study optimizes the reaction conditions to achieve high yields and purity of the final products, demonstrating a significant improvement over previous methods. The synthesized compounds are of interest for further investigation into their antioxidant and therapeutic properties, with preliminary results showing promising antiproliferative effects on cancer cell lines.

Direct Exploitation of the Ethynyl Moiety in Calcium Carbide Through Sealed Ball Milling

10.1002/ejoc.202000612

The study explores a novel method for the direct exploitation of the ethynyl moiety in calcium carbide (CaC2) through sealed ball milling, which allows for the reaction of CaC2 with organic electrophiles without the need for additives or catalysts. The primary chemicals used in the study include calcium carbide (CaC2) and various ketones, such as benzophenone, 2-naphthyl phenyl ketone, 4,4′-dichlorobenzophenone, and others, which serve as substrates for ethynylation reactions. Additionally, aryl halides like 9-bromophenanthrene and 2-fluoro-1,4-dimethoxybenzene were used to investigate the feasibility of alkynylation under ball milling conditions. The purpose of these chemicals is to demonstrate a practical and cost-effective alternative method for introducing ethynyl functionalities into organic molecules, which is synthetically valuable and has potential applications in organic synthesis.

A titanacyclobutane precursor to alkyl-substituted titanium-carbene complexes

10.1021/om00135a016

The research focuses on the synthesis and characterization of organometallic compounds, specifically metallacycles and titanium-carbene complexes. The purpose of the study was to prepare a titanacyclobutane precursor, which was then reacted with benzophenone to yield an organic product, and further reacted with phosphines to obtain phosphine adducts of an α-substituted titanium-carbene complex. The researchers also succeeded in creating a heterobimetallic alkylidene complex by reacting the metallacycle with dimethylaluminum chloride. The conclusions drawn from the study indicate that the observed reactivity of the metallacycle is consistent with productive cleavage of the metal-containing ring, leading to the formation of titanium-carbene complexes. The chemicals used in the process include 3,3-dimethylcyclopropene, Tebbe reagent, (dimethylamino)pyridine (DMAP), benzophenone, phosphines (PMeR2, where R = Me, Ph), and dimethylaluminum chloride, among others. The study provides insights into the reactivity of metallacycles and their potential as precursors to titanium-carbene compounds.

INTRAMOLECULAR GENERAL-BASE CATALYSIS OF SCHIFF-BASED HYDROLYSIS BY TERTIARY AMINO GROUPS.

10.1021/ja00367a016

The research investigates the kinetics of the hydrolysis of Schiff bases derived from benzophenone and various amines in aqueous solution. The purpose is to understand the mechanism of hydrolysis, particularly the role of intramolecular general-base catalysis by tertiary amino groups. The key chemicals used include Schiff bases such as benzophenone imine derivatives (la-j) with different substituents like aminoethyl, morpholine, piperazine, and pyridine groups. The study found that Schiff bases with an internal tertiary amino group at the p-position from the imino nitrogen atom showed significant intramolecular general-base catalysis of water attack on the protonated Schiff bases. The rate enhancement due to this intramolecular catalysis was correlated with the pKa of the internal catalyst, with effective concentrations of the internal bases estimated to range from 340 to 40 M. The research concludes that the enhanced reactivity in the hydrolysis of these Schiff bases is primarily due to intramolecular general-base catalysis by the tertiary amino groups, rather than other possible mechanisms such as nucleophilic participation through a 1,3-imidazolidinium intermediate.

Femtosecond-Picosecond Laser Photolysis Studies on Reduction Process of Excited Benzophenone with N-Methyldiphenylamine in Acetonitrile Solution

10.1021/j100199a042

The photoreduction of benzophenone (BP) and N-methyldiphenylamine (MDPA) in acetonitrile solution was investigated using femtosecond-picosecond laser photolysis and time-resolved transient absorption spectroscopy. The formation and reactivity of ion pairs (IPs) generated by electron transfer (ET) between BP and MDPA were investigated, with a focus on the different reactivity differences based on the IP generation mode and the energy gaps of formation and recombination reactions. The results indicate that the reactivity of ion pairs, including charge recombination and proton transfer, depends largely on their generation pathways and the energy gaps involved.

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