Basic information Description Structure Preparation Applications Safety Supplier Related
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Benzil

Basic information Description Structure Preparation Applications Safety Supplier Related

Benzil Basic information

Product Name:
Benzil
Synonyms:
  • 1,2-DIPHENYLETHANEDIONE
  • 1,2-DIPHENYL-1,2 ETHANEDIONE
  • BENZIL
  • AURORA 14062
  • BIBENZOYL
  • DIPHENYL-A B-DIKETONE
  • DIPHENYLGLYOXAL
  • DIPHENYL DIKETONE
CAS:
134-81-6
MF:
C14H10O2
MW:
210.23
EINECS:
205-157-0
Product Categories:
  • B
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  • C13 to C14
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Mol File:
134-81-6.mol
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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.
InChIKey
WURBFLDFSFBTLW-UHFFFAOYSA-N
CAS DataBase Reference
134-81-6(CAS DataBase Reference)
NIST Chemistry Reference
Ethanedione, diphenyl-(134-81-6)
EPA Substance Registry System
Benzil (134-81-6)
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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
Toxicity
LD50 orally in Rabbit: 2710 mg/kg

MSDS

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Benzil Usage And Synthesis

Description

Benzil 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.

Structure

The 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.

Preparation

Benzyl 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+

Applications

Benzil 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 Properties

yellow crystals or powder

Uses

Organic synthesis; insecticide.

Uses

Benzil is used as a pharmaceutical intermediate and uv curing resin photosensitizer. In polymer chemistry, it is used as a photoinitiator. Further, it serves as a potent inhibitor of human carboxylesterases. It is used in the preparation of diketimines by reacting with amines. It is also involved in the famous benil-benzilic acid rearrangement. In addition this, it reacts with 1,3-diphenylacetone to get tetraphenylcyclopentadienone.

Definition

A 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).

Definition

ChEBI: An alpha-diketone that is ethane-1,2-dione substituted by phenyl groups at positions 1 and 2 respectively.

Synthesis Reference(s)

Journal of the American Chemical Society, 105, p. 7755, 1983 DOI: 10.1021/ja00364a054
Tetrahedron Letters, 30, p. 6267, 1989 DOI: 10.1016/S0040-4039(01)93869-9

Safety Profile

Low toxicity by ingestion. An eyeirritant. Combustible. When heated to decomposition itemits acrid smoke and irritating fumes.

Purification Methods

Crystallise 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.]

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