Benzil

Base Information

• Chemical Name: Benzil
• CAS No.: 134-81-6
• Deprecated CAS: 16510-35-3,1056020-44-0,1056020-46-2,1056020-44-0,1056020-46-2
• Molecular Formula: C14H10O2
• Molecular Weight: 210.232
• Hs Code.: 2914.30
• European Community (EC) Number: 205-157-0
• NSC Number: 220315,4041
• UNII: S85X61172J
• DSSTox Substance ID: DTXSID3044380
• Nikkaji Number: J5.599I
• Wikipedia: Benzil
• Wikidata: Q818497
• Pharos Ligand ID: PPYXC92HBUHS
• Metabolomics Workbench ID: 57776
• ChEMBL ID: CHEMBL189886
• Mol file: 134-81-6.mol

Synonyms:benzil;diphenyl-alpha-beta-ketone;diphenylethane-1,2-dione;diphenylethanedione

Chemical Property of Benzil

Chemical Property:

• Appearance/Colour: yellow crystals or powder
• Vapor Pressure: 1 mm Hg ( 128.4 °C)
• Melting Point: 94-95 °C(lit.)
• Refractive Index: 1.594
• Boiling Point: 347 °C at 760 mmHg
• Flash Point: 142.559 °C
• PSA: 34.14000
• Density: 1.165 g/cm³
• LogP: 2.75220
• Storage Temp.: Store below +30°C.
• Solubility.: <0.5g/l
• Water Solubility.: 0.5 g/L (20 ºC)
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 210.068079557
• Heavy Atom Count: 16
• Complexity: 230

Purity/Quality:

99% ^*data from raw suppliers

Benzil ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Aromatic Ketones
• Canonical SMILES: C1=CC=C(C=C1)C(=O)C(=O)C2=CC=CC=C2
• 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.
• Uses: Organic synthesis; insecticide. 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.

Technology Process of Benzil

There total 1169 articles about Benzil 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: 86.0%

(1S,2R)-1,2-diphenylethane-1,2-diol (579-43-1) → benzaldehyde (100-52-7) + benzil (134-81-6)

Guidance literature:

With ^-Bu4N⁺ (MoO5PICO); In dichloromethane; at 50 ℃; for 10h;

DOI:10.1021/jo00298a052

Reference yield: 63.0%

(E)-1,2-diphenyl-ethene (103-30-0) → benzaldehyde (100-52-7) + benzil (134-81-6) + benzoic acid (65-85-0,8013-63-6)

Guidance literature:

With [Fe(2,2'-bipyridine)Cl₄][2,2'-bipyridine*H] encapsulation on Al-MCM-41; In N,N-dimethyl-formamide; acetonitrile; at 25 ℃; Temperature; Reagent/catalyst;

DOI:10.1039/c5ra04565g

Reference yield: 60.0%

benzyl alcohol (100-51-6,185532-71-2) → 1,2-diphenyl-1,2-ethanediol (492-70-6,655-48-1,2325-10-2,38270-73-4,52340-78-0,579-43-1) + 2-hydroxy-2-phenylacetophenone (119-53-9,579-44-2) + benzaldehyde (100-52-7) + benzil (134-81-6)

Guidance literature:

With air; 2,2'-thiobis(2,4-di-tert-butylphenol); triethylamine; copper(l) chloride; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1002/(SICI)1521-3773(19980904)37:16<2217::AID-ANIE2217>3.0.CO;2-D

upstream raw materials:

1,4-dioxane

ethyl nitrite

2-amino-1,1-diphenyl-ethanol; hydrochloride

n-Butyl nitrite

Downstream raw materials:

2,3-diphenylpyrido[3,2-b]pyrazine

2-(5-bromo-[2]thienyl)-2-hydroxy-1,2-diphenyl-ethanone

3-N-(2-morpholinoethyl)-5,5-diphenylhydantoin

2-(2-morpholino-ethylamino)-5,5-diphenyl-1,5-dihydro-imidazol-4-one

Refernces

• 1、 Jeena, Vineet,Naidoo, Shivani. "Molecular iodine/DMSO mediated oxidation of internal alkynes and primary alcohols using a one-pot, two step approach towards 2,4,5-trisubstituted imidazoles: Substrate scope and mechanistic studies". . . Retrieved 2020.
• 2、 Dittmer et al.. "-". . p. 2097,2101. Retrieved 1969.
• 3、 Ueyama, Norikazu,Oku, Hiroyuki,Nakamura, Akira. "cis-dioxobis(benzenedithiolato)tungsten(VI) and the related monooxotungsten(V) and -(IV) complexes. Models of tungsten oxidoreductases". . p. 7310 - 7311. Retrieved 1992.
• 4、 Khadem, Hassan El,Czubarow, Pawel,Sandstedt, Christian. "Action of Cu(II) salts on osazones: side reactions of osotriazole formation". . p. 327 - 330. Retrieved 1992.
• 5、 Mukai, Masahiro,Yamauchi, Seigo,Hirota, Noboru. "A Time-resolved EPR Study of One- and Two-Photon Processes in the Photochemical Reactions of Benzil". . p. 4411 - 4413. Retrieved 1989.
• 6、 Rao, H. Surya Prakash,Jothilingam,Vasantham,Scheeren, Hans W.. "Formic acid oxidatively cleaves 1,2,3,4-tetraaryl-2-butene-1,4-diones to 1,2-diaryl-1,2-ethanediones under microwave irradiation". . p. 4495 - 4497. Retrieved 2007.
• 7、 Wild, Ute,Sch?n, Florian,Himmel, Hans-J?rg. "Oxidation of Organic Molecules with a Redox-Active Guanidine Catalyst". . p. 16410 - 16413. Retrieved 2017.
• 8、 Bauer,D.P.,Macomber,R.S.. "-". . p. 1990 - 1992. Retrieved 1975.
• 9、 Kashimura, Shigenori. "Cathodic coupling of aliphatic esters. Useful reaction for the synthesis of 1,2-diketone and acyloin". . p. 4805 - 4808. Retrieved 1995.
• 10、 Saputra, Leo,Kojima, Takashi,Hara, Takayoshi,Ichikuni, Nobuyuki,Shimazu, Shogo. "Recyclable Pd-contained perovskite catalyst synthesized by a low temperature hydrothermal method for aerobic alcohol oxidation". . p. 132 - 138. Retrieved 2018.