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Benzil

Basic information Description Structure Preparation Applications Safety Related Supplier
Benzil Basic information
  • Product Name:Benzil
  • CAS:134-81-6
  • MF:C14H10O2
  • MW:210.23
  • EINECS:205-157-0
  • Mol File:134-81-6.mol
Benzil Chemical Properties
  • Melting point:94-95 °C(lit.)
  • Boiling point:346 °C
  • Density 1,521 g/cm3
  • vapor pressure 1 mm Hg ( 128.4 °C)
  • refractive index 1.5681 (estimate)
  • Flash point:346-348°C
  • storage temp. Store below +30°C.
  • solubility <0.5g/l
  • form Crystalline Powder
  • color White
  • Water Solubility 0.5 g/L (20 ºC)
  • Merck 14,1078
  • BRN 608047
  • Stability:Stable. Combustible. Incompatible with strong oxidizing agents.
  • InChIKeyWURBFLDFSFBTLW-UHFFFAOYSA-N
  • CAS DataBase Reference134-81-6(CAS DataBase Reference)
  • NIST Chemistry ReferenceEthanedione, diphenyl-(134-81-6)
  • EPA Substance Registry SystemBenzil (134-81-6)
Safety Information
  • Hazard Codes Xi
  • Risk Statements 36/37/38
  • Safety Statements 26-36-37/39
  • WGK Germany 2
  • RTECS DD1925000
  • 10
  • Hazard Note Irritant
  • TSCA Yes
  • HS Code 29143900
  • ToxicityLD50 orally in Rabbit: 2710 mg/kg
MSDS
Benzil Usage And Synthesis
  • DescriptionBenzil also known as 1,2-diphenylethane-1,2-dione is an organic compound with the molecular formula (C6H5CO)2. The compound belongs to the group of organic compounds known as stilbenes which contains a 1,2-diphenylethylene moiety. Benzyl is yellow in color and is one of the most common diketones.
  • StructureThe most noticeable feature in Benzil’s structure is the long carbon-carbon bond of 1.54 Å, which shows there is no pi-bonding between the two carbonyl centers. Although the par of benzoyl groups are twisted with respect to the other with a dihedral angler of 117o, the PhCO are planar.
  • PreparationBenzyl is synthesized from benzoin, for instance with copper (II) acetate.
    PhC(O)CH(OH)Ph + 2 Cu2+ → PhC(O)C(O)Ph + 2 H+ + 2 Cu+
  • ApplicationsBenzil is utilized as an intermediate in pharmaceuticals and UV curing resin photosensitizer. Benzyl is mostly used in the free-radical curing of polymer networks. Benzyl is decomposed by ultraviolet radiation that generates free-radical species within the material, leading to the formation of cross-links. It is normally employed as a photoinitiator in polymer chemistry. In addition, Benzil is a potent inhibitor of human carboxylesterases, which are enzymes involved in the hydrolysis of many drugs used clinically as well as carboxylesters. It is also used in the synthesis of diketimines by reaction with amines. Benzyl is also used as an intermediate in the famous benil-benzilic acid arrangement. Further, it reacts with 1,3-diphenylacetone to get tetraphenylcyclopentadienone.
  • Chemical Propertiesyellow crystals or powder
  • UsesOrganic synthesis; insecticide.
  • DefinitionA reaction in which benzil (1,2- diphenylethan-1,2-dione) is treated with hydroxide and then with acid to give benzilic acid (2-hydroxy-2,2-diphenylethanoic acid):
    C6H5.CO.CO.C6H5
    (C6H5)2C(OH).COOH
    The reaction, which involves migration of a phenyl group (C6H5-) from one carbon atom to another, was the first rearrangement reaction to be described (by Justus von Liebig in 1828).
  • DefinitionChEBI: An alpha-diketone that is ethane-1,2-dione substituted by phenyl groups at positions 1 and 2 respectively.
  • Safety ProfileLow toxicity by ingestion. An eyeirritant. Combustible. When heated to decomposition itemits acrid smoke and irritating fumes.
  • Purification MethodsCrystallise benzil from *benzene after washing with alkali. (Crystallisation from EtOH did not free benzil from material reacting with alkali.) [Hine & Howarth J Am Chem Soc 80 2274 1958.] It has also been crystallised from CCl4, diethyl ether or EtOH [Inoue et al. J Chem Soc, Faraday Trans 1 82 523 1986]. [Beilstein 7 IV 2502.]
Benzil Preparation Products And Raw materials
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