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Benzil
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134-81-6 Usage

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 ?, 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/ja00364a054Tetrahedron 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.]
InChI:InChI=1/C14H10O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10H

134-81-6 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (A12579)  Benzil, 98%    134-81-6 100g 246.0CNY Detail
Alfa Aesar (A12579)  Benzil, 98%    134-81-6 500g 661.0CNY Detail
Alfa Aesar (A12579)  Benzil, 98%    134-81-6 2500g 1697.0CNY Detail

134-81-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name benzil

1.2 Other means of identification

Product number -
Other names Benzil

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:134-81-6 SDS

134-81-6Synthetic route

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

benzil
134-81-6

benzil

Conditions
ConditionsYield
With pyridine chromium peroxide In benzene for 0.1h; Product distribution; Heating; effect of various chromium(VI) based oxidants;100%
With pyridine chromium peroxide In benzene for 0.1h; Heating;100%
With 4-dimethylaminopyridine tribromide In dichloromethane for 0.25h; Ambient temperature;100%
diphenyl acetylene
501-65-5

diphenyl acetylene

benzil
134-81-6

benzil

Conditions
ConditionsYield
With sodium periodate; sulfuric acid; C31H29Br2N3Ru*CH2Cl2 In water; acetonitrile at 25℃; for 0.5h; Inert atmosphere; Schlenk technique;100%
With sodium periodate; sulfuric acid; ruthenium-carbon composite In water; acetonitrile at 25℃; for 0.5h; Catalytic behavior; Reagent/catalyst; Temperature; Time; Solvent; Green chemistry;100%
With SO3-dioxane at 60℃; for 0.25h;99%
1,2-diphenyl-2-thioxoethanone
16939-18-7

1,2-diphenyl-2-thioxoethanone

benzil
134-81-6

benzil

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In diethyl ether for 1h; oxidation with nitric acid;100%
1,2-diphenyl-2-(trimethylsilyloxy)ethanone
26205-39-0

1,2-diphenyl-2-(trimethylsilyloxy)ethanone

benzil
134-81-6

benzil

Conditions
ConditionsYield
With copper nitrate - dinitrogen tetroxide adduct In tetrachloromethane for 0.75h; Oxidation; Heating;100%
With aluminium trichloride; silver bromate In acetonitrile for 0.4h; Heating;98%
With Montmorillonite K10; ferric nitrate Oxidation; deprotection; Irradiation;95%
(2RS)-(+/-)-2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1,2-diphenylethanone
180295-26-5

(2RS)-(+/-)-2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1,2-diphenylethanone

benzil
134-81-6

benzil

Conditions
ConditionsYield
With copper nitrate - dinitrogen tetroxide adduct In tetrachloromethane for 1h; Oxidation; Heating;100%
With N-hydroxyphthalimide; oxygen; cobalt(II) benzoate In acetonitrile at 20℃; for 9h;93%
With manganese(IV) oxide; aluminium trichloride In acetonitrile for 0.333333h; Oxidation; Heating;40%
[(6-Ph2TPA)Ni(PhC(O)C(OH)C(O)Ph)]ClO4

[(6-Ph2TPA)Ni(PhC(O)C(OH)C(O)Ph)]ClO4

A

[(6-Ph2TPA)Ni(O2CPh)]ClO4
932703-85-0

[(6-Ph2TPA)Ni(O2CPh)]ClO4

B

phenacyl benzoate
33868-50-7

phenacyl benzoate

C

carbon monoxide
201230-82-2

carbon monoxide

D

benzil
134-81-6

benzil

E

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With oxygenA 100%
B n/a
C n/a
D n/a
E n/a
[(bnpapa)Ni(PhC(O)C(OH)C(O)Ph)]ClO4

[(bnpapa)Ni(PhC(O)C(OH)C(O)Ph)]ClO4

A

phenacyl benzoate
33868-50-7

phenacyl benzoate

B

carbon monoxide
201230-82-2

carbon monoxide

C

[(bnpapa)Ni(O2CPh)]ClO4

[(bnpapa)Ni(O2CPh)]ClO4

D

benzil
134-81-6

benzil

E

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With oxygen In acetonitrile at 20℃;A n/a
B n/a
C 100%
D 12%
E 11 mg
Conditions
ConditionsYield
With Me2Se*NCS; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene 1.)1h 0 deg C, 1h room temperature, 2.) 4h room temperature;99%
With octahydro-2,5-epiminopentalen-7-yloxidanyl; acetic acid; sodium nitrite In acetonitrile at 20℃; for 4h; air;99%
With 9-benzyl-9-norazaadamantane N-oxyl; oxygen; acetic acid; sodium nitrite In acetonitrile at 20℃; for 4h; Catalytic behavior; Concentration; Reagent/catalyst; Solvent; Temperature; Time;99.3%
2-bromo-2'-hydroxy-diphenyl-2-methylethanone

2-bromo-2'-hydroxy-diphenyl-2-methylethanone

benzil
134-81-6

benzil

Conditions
ConditionsYield
Stage #1: 2-bromo-2'-hydroxy-diphenyl-2-methylethanone With potassium chloride at 60 - 76℃; for 4.33h;
Stage #2: With dimethyltitanocene; isopentyl butanoate for 4.5h; Temperature;
99.3%
phenyl benzyl ketone
451-40-1

phenyl benzyl ketone

benzil
134-81-6

benzil

Conditions
ConditionsYield
With hydrogen bromide; dimethyl sulfoxide at 55℃; for 24h;99%
With C14H14N6O2; oxygen; sodium acetate; palladium diacetate at 120℃; under 760.051 Torr; for 48h;97%
With potassium hydrogencarbonate; dimethyl sulfoxide at 80℃;96%
1,2-diphenyl-2-methylthio-1-ethanone
32368-19-7

1,2-diphenyl-2-methylthio-1-ethanone

benzil
134-81-6

benzil

Conditions
ConditionsYield
With CuCl2*2H2O In water; acetone for 1h; Heating;99%
2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

2-nitro-aniline
88-74-4

2-nitro-aniline

A

2,3-diphenylquinoxaline
1684-14-6

2,3-diphenylquinoxaline

B

benzil
134-81-6

benzil

Conditions
ConditionsYield
With sodium hydroxide In toluene at 120℃; for 3h; Inert atmosphere; Sealed tube;A 99%
B 50%
2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

A

dimethylsulfide
75-18-3

dimethylsulfide

B

benzil
134-81-6

benzil

Conditions
ConditionsYield
With antimonypentachloride; dimethyl sulfoxide In nitromethane; benzene for 2h; Heating;A n/a
B 98.7%
1,1'-(1,2-ethanediyl)bisbenzene
103-29-7

1,1'-(1,2-ethanediyl)bisbenzene

benzil
134-81-6

benzil

Conditions
ConditionsYield
With oxygen; silica gel; 4-aminoperbenzoic acid In dichloromethane at 20℃; for 9h;98%
With graphite oxide In chloroform at 120℃; for 24h;17%
With oxygen; graphite oxide In chloroform at 120℃; for 24h; Sealed tube;17%
With selenium(IV) oxide at 200℃;
Multi-step reaction with 2 steps
1: SeO2 / 200 °C / sowie auf 300grad
2: SeO2 / 200 °C
View Scheme
2,2'-Diphenyl-[2,2']bi[[1,3]dithiolanyl]
78576-73-5

2,2'-Diphenyl-[2,2']bi[[1,3]dithiolanyl]

benzil
134-81-6

benzil

Conditions
ConditionsYield
With t-butyl bromide; dimethyl sulfoxide at 70 - 75℃; for 4h;98%
With trimethylsilyl iodide; dimethyl sulfoxide In tetrachloromethane at 75 - 80℃; for 6h;98%
With fluorosulfonylchloride In diethyl ether; water Ambient temperature;86%
4-iodoxybiphenyl
91493-19-5

4-iodoxybiphenyl

diphenyl acetylene
501-65-5

diphenyl acetylene

A

4-iodo-biphenyl
1591-31-7

4-iodo-biphenyl

B

benzil
134-81-6

benzil

Conditions
ConditionsYield
In nitrobenzene at 170℃; for 5h;A 98%
B 34.5%
2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

A

benzil
134-81-6

benzil

B

Ph3Sb

Ph3Sb

Conditions
ConditionsYield
With (2 equiv); triphenylantimony dibromide; triethylamine In chloroform-d1 for 17h; Product distribution; Mechanism; reactions of α-hydroxyketones and esters in presence of var. bases;A 98%
B n/a
cis-[(1,4,7-trimethyl-1,4,7-triazacyclononane)(CF3COO)Ru(VI)O2]ClO4

cis-[(1,4,7-trimethyl-1,4,7-triazacyclononane)(CF3COO)Ru(VI)O2]ClO4

diphenyl acetylene
501-65-5

diphenyl acetylene

acetonitrile
75-05-8

acetonitrile

A

[(1,4,7-trimethyl-1,4,7-triazacyclononane)(CF3CO2)Ru(II)(CH3CN)2]ClO4

[(1,4,7-trimethyl-1,4,7-triazacyclononane)(CF3CO2)Ru(II)(CH3CN)2]ClO4

B

benzil
134-81-6

benzil

Conditions
ConditionsYield
In acetonitrile; trifluoroacetic acid excess diphenylacetylene was treated with cis-((Cn*)(CF3CO2)Ru(VI)O2)ClO4 in 0.2M CF3COOH/MeCN soln. at room temp.; recrystn. from MeCN/Et2O; elem. anal.;A 92%
B 98%
(S,S)-hydrobenzoin
2325-10-2

(S,S)-hydrobenzoin

benzil
134-81-6

benzil

Conditions
ConditionsYield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In N,N-dimethyl-formamide at 23 - 25℃; for 4h;98%
1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

benzil
134-81-6

benzil

Conditions
ConditionsYield
With aluminum (III) chloride; Oxone In water at 20℃; for 24h;98%
With iodine; dimethyl sulfoxide; copper(ll) bromide for 8h; Catalytic behavior; Reagent/catalyst; Schlenk technique; Heating;95%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; acetic acid; copper(I) bromide at 100℃; for 2h; Mechanism; Reagent/catalyst; Temperature;90%
Conditions
ConditionsYield
With bis(1-CH2Ph-3,5,7-3N-1-N(1+)tricyclo[3.3.1.13,7]decaneS2O8 In acetonitrile for 0.333333h; Oxidation; Heating;97%
With KMnO4/alumina at 50℃; for 0.5h;97%
With Cu(NO3)2-SiO2 for 0.133333h; oxime cleavage; microwave irradiation;95%
(E)-1,2-dichlorostilbene
951-86-0

(E)-1,2-dichlorostilbene

A

benzil
134-81-6

benzil

B

valeric acid
109-52-4

valeric acid

Conditions
ConditionsYield
With ruthenium(IV) oxide; sodium periodate In dichloromethane; water; acetonitrile for 0.5h; Ambient temperature;A 97%
B n/a
benzoin oxime
441-38-3

benzoin oxime

benzil
134-81-6

benzil

Conditions
ConditionsYield
With Cu(NO3)2-SiO2 for 0.0833333h; Oxidation; oxime cleavage; microwave irradiation;97%
With water; Dess-Martin periodane In dichloromethane at 5 - 20℃; for 0.333333h;92%
With quinolinium monofluorochromate(VI) In dichloromethane for 5h; Product distribution; Oxidation; Heating;85%
With imidazolium fluorochromate In acetonitrile at 20℃; for 0.5h; Oxidation;79%
α-iodo-α-phenylacetophenone
24242-77-1

α-iodo-α-phenylacetophenone

benzil
134-81-6

benzil

Conditions
ConditionsYield
With dimethyl sulfoxide at 100℃; for 2h;97%
With dimethyl sulfoxide at 100℃; for 2h;97%
With dimethyl sulfoxide at 130℃; for 1h;90%
(R,R)-hydroxybenzoin
52340-78-0

(R,R)-hydroxybenzoin

benzil
134-81-6

benzil

Conditions
ConditionsYield
With oxone; C18H17IN2O7PolS(1-)*Na(1+); tetra(n-butyl)ammonium hydrogensulfate In acetonitrile at 70℃; for 18h; Reagent/catalyst; Solvent; Sealed tube; Green chemistry;97%
(E)-1,2-diphenyl-ethene
103-30-0

(E)-1,2-diphenyl-ethene

benzil
134-81-6

benzil

Conditions
ConditionsYield
With water; iodine; oxygen In acetonitrile at 140℃; for 20h; Reagent/catalyst; Solvent; Temperature; Sealed tube; chemoselective reaction;96%
With tert.-butylhydroperoxide; [Ru2Cl(3,6-bis(1-(2-pyridylmethyl)imidazol-2-yliden-3-yl)pyridazine)(CH3CN)4](PF6)3; sodium iodide In water; acetonitrile at 20℃; for 0.166667h; Catalytic behavior; Reagent/catalyst; Solvent;92%
With tert.-butylhydroperoxide; (p-cymene)ruthenium(II) chloride; tetrabutylammonium iodide In water; toluene; acetonitrile at 20℃; for 1h;91%
desyl bromide
1484-50-0

desyl bromide

benzil
134-81-6

benzil

Conditions
ConditionsYield
With 4-methoxypyridine; lithium carbonate In N,N-dimethyl acetamide at 25℃; for 24h; Irradiation;96%
With 4-methoxypyridine; tris(2,2'-bipyridine)ruthenium dichloride; lithium carbonate In N,N-dimethyl acetamide at 25℃; for 24h; Irradiation;81%
With Amberlyst A-26; nitrate form In benzene for 2h; Heating;80%
(benzoylphenylmethylene)triphenylphosphorane
30416-76-3

(benzoylphenylmethylene)triphenylphosphorane

benzil
134-81-6

benzil

Conditions
ConditionsYield
With potassium permanganate; magnesium sulfate In toluene at 50 - 60℃; for 20h;96%
With N-Sulfonyloxaziridine 3 In dichloromethane at 25℃; for 0.5h;76%
(Z)-1,2,3,4-tetraphenyl-2-butene-1,4-dione
7510-34-1, 10496-80-7, 6313-26-4

(Z)-1,2,3,4-tetraphenyl-2-butene-1,4-dione

benzil
134-81-6

benzil

Conditions
ConditionsYield
With formic acid; sulfuric acid for 0.0333333h; microwave irradiation;96%
(1S,2R)-1,2-diphenylethane-1,2-diol
579-43-1

(1S,2R)-1,2-diphenylethane-1,2-diol

benzil
134-81-6

benzil

Conditions
ConditionsYield
With N-iodo-succinimide; 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methyl)urea In chloroform at 24℃; Concentration; Reagent/catalyst; Solvent;95%
With 4-acetylamino-2,2,6,6-tetramethylpiperidine-N-oxyl; toluene-4-sulfonic acid In dichloromethane at 18℃; 1.) 0 deg C, 1 h, 2.) room temp., 72 h;88%
With aluminium(III) phenoxide; p-benzoquinone; benzene
4-methyl-1,2-diaminobenzene
496-72-0

4-methyl-1,2-diaminobenzene

benzil
134-81-6

benzil

2,3-diphenyl-6-methylquinoxaline
16107-85-0

2,3-diphenyl-6-methylquinoxaline

Conditions
ConditionsYield
at 100℃; for 0.25h;100%
With gallium(III) triflate In ethanol at 20℃; for 0.0833333h;100%
With aluminum oxide at 20℃; for 0.166667h; neat (no solvent);100%
1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

benzil
134-81-6

benzil

2,3-diphenylquinoxaline
1684-14-6

2,3-diphenylquinoxaline

Conditions
ConditionsYield
With gallium(III) triflate In acetonitrile at 20℃; for 0.0833333h; Reactivity; Solvent; Time; Concentration;100%
With PEG-400 at 110℃; for 0.166667h; Neat (no solvent);100%
With zirconium(IV) chloride In methanol at 20℃; for 0.0833333h;100%
biphenyl-3,4-diamine
4458-39-3

biphenyl-3,4-diamine

benzil
134-81-6

benzil

2,3,6-triphenylquinoxaline
85877-63-0

2,3,6-triphenylquinoxaline

Conditions
ConditionsYield
With gallium(III) triflate In ethanol at 20℃; for 0.0833333h;100%
With 1,1,1,3',3',3'-hexafluoro-propanol at 20℃; for 1h;92%
With acetic acid
benzil
134-81-6

benzil

4-Nitrophenylene-1,2-diamine
99-56-9

4-Nitrophenylene-1,2-diamine

6-nitro-2,3-diphenylquinoxaline
7466-45-7

6-nitro-2,3-diphenylquinoxaline

Conditions
ConditionsYield
at 160℃; for 0.25h;100%
H6P2W18O62 In acetic acid at 20℃; for 0.0833333h;98%
at 120℃; for 0.0583333h; Microwave irradiation;98%
benzil
134-81-6

benzil

2-hydroxy-2-phenylacetophenone
119-53-9

2-hydroxy-2-phenylacetophenone

Conditions
ConditionsYield
With titanium(III) chloride In acetone at 0℃; for 1h;100%
Stage #1: benzil With sodium tetrahydroborate at 70℃; for 1.5h; Ball milling; neat (no solvent);
Stage #2: With water regiospecific reaction;
100%
With hydrogen; palladium In methanol at 20℃; under 3800 Torr; for 46h;98%
benzil
134-81-6

benzil

malononitrile
109-77-3

malononitrile

2-(2-oxo-1,2-diphenylethylidene)malononitrile
23195-86-0

2-(2-oxo-1,2-diphenylethylidene)malononitrile

Conditions
ConditionsYield
With third generation polystyrene supported poly(amidoamine) dendrimer In ethanol at 50℃; for 2h; Knoevenagel condensation;100%
With N,N-dimethyl-aniline In ethanol
With potassium carbonate In ethanol for 8h; Reflux;
benzil
134-81-6

benzil

phosphorous acid trimethyl ester
121-45-9

phosphorous acid trimethyl ester

2,2,2-trimethoxy-4,5-diphenyl-2,2-dihydro-1,3,2-dioxaphospholene
4850-55-9

2,2,2-trimethoxy-4,5-diphenyl-2,2-dihydro-1,3,2-dioxaphospholene

Conditions
ConditionsYield
100%
In benzene
acetaldehyde
75-07-0

acetaldehyde

benzil
134-81-6

benzil

2,3-dihydroxy-1,2-diphenyl-1-butanone

2,3-dihydroxy-1,2-diphenyl-1-butanone

Conditions
ConditionsYield
With titanium(III) chloride In acetone at 0℃; for 1h; Product distribution; Mechanism; various reaction conditions;100%
With titanium(III) chloride In acetone at 0℃; for 1h;100%
acetaldehyde
75-07-0

acetaldehyde

benzil
134-81-6

benzil

2,4-dimethyl-5-benzoyl-5-phenyl-1,3-dioxolane

2,4-dimethyl-5-benzoyl-5-phenyl-1,3-dioxolane

Conditions
ConditionsYield
With titanium(III) chloride In acetone at 40℃; for 1h;100%
4,5-Diamino-6-(2-hydroxy-ethylamino)-2H-pyridazin-3-one
132635-33-7

4,5-Diamino-6-(2-hydroxy-ethylamino)-2H-pyridazin-3-one

acetic acid
64-19-7

acetic acid

benzil
134-81-6

benzil

Acetic acid 2-(8-oxo-2,3-diphenyl-7,8-dihydro-pyrazino[2,3-d]pyridazin-5-ylamino)-ethyl ester
133219-06-4

Acetic acid 2-(8-oxo-2,3-diphenyl-7,8-dihydro-pyrazino[2,3-d]pyridazin-5-ylamino)-ethyl ester

Conditions
ConditionsYield
for 6h; Heating;100%
propionaldehyde
123-38-6

propionaldehyde

benzil
134-81-6

benzil

2,3-dihydroxy-1,2-diphenyl-1-pentanone

2,3-dihydroxy-1,2-diphenyl-1-pentanone

Conditions
ConditionsYield
With titanium(III) chloride In acetone at 0℃; for 1h;100%
4,5-Diamino-6-(2-hydroxy-2-phenyl-ethylamino)-2-methyl-2H-pyridazin-3-one
132635-37-1

4,5-Diamino-6-(2-hydroxy-2-phenyl-ethylamino)-2-methyl-2H-pyridazin-3-one

benzil
134-81-6

benzil

8-(2-Hydroxy-2-phenyl-ethylamino)-6-methyl-2,3-diphenyl-6H-pyrazino[2,3-d]pyridazin-5-one
133219-13-3

8-(2-Hydroxy-2-phenyl-ethylamino)-6-methyl-2,3-diphenyl-6H-pyrazino[2,3-d]pyridazin-5-one

Conditions
ConditionsYield
In acetic acid Ambient temperature;100%
benzil
134-81-6

benzil

<1,2-2H2>-1,2-diphenyl-1,2-ethanediol
36239-19-7

<1,2-2H2>-1,2-diphenyl-1,2-ethanediol

Conditions
ConditionsYield
With sodium borodeuteride In methanol for 1h; Ambient temperature;100%
With sodium borodeuteride; water-d2 In tetrahydrofuran at 0℃; for 1h;100%
With lithium aluminium deuteride In diethyl ether at 20℃; for 4h;9.7 g
benzil
134-81-6

benzil

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With bis(acetylacetonate)oxovanadium; oxygen; acetic acid at 80℃; under 760.051 Torr; for 8h; Sealed tube;100%
With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 1h;99%
With Oxone In water; acetonitrile for 48h; Reflux;97%
4,5-dimethyl-1,2-phenylenediamine
3171-45-7

4,5-dimethyl-1,2-phenylenediamine

benzil
134-81-6

benzil

6,7-dimethyl-2,3-diphenylquinoxaline
13362-56-6

6,7-dimethyl-2,3-diphenylquinoxaline

Conditions
ConditionsYield
With aluminum oxide at 20℃; for 0.166667h; neat (no solvent);100%
With amberlyst-15 In water at 70℃; for 0.2h;99%
In benzene for 2h; cyclocondensation; Heating;97%
1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

benzil
134-81-6

benzil

dibenzo[a,c]phenacine
215-64-5

dibenzo[a,c]phenacine

Conditions
ConditionsYield
Product distribution; Further Variations:; Temperatures; in melt; solid-state reaction;100%
at 20℃; for 1h; solid-state reaction;
2-methyl-1H-indole-3-carbaldehyde
5416-80-8

2-methyl-1H-indole-3-carbaldehyde

benzil
134-81-6

benzil

3-(4,5-diphenyl-1H-imidazol-2-yl)-2-methyl-1H-indole
662150-78-9

3-(4,5-diphenyl-1H-imidazol-2-yl)-2-methyl-1H-indole

Conditions
ConditionsYield
With ammonium acetate; acetic acid Reflux;100%
With ammonium acetate In acetic acid
With ammonium acetate In acetic acid for 3 - 5h; Heating / reflux;
With ammonium acetate In ethanol for 5h; Reflux;
oxybis(diphenylborane)
4426-21-5

oxybis(diphenylborane)

benzamidine monohydrochloride
1670-14-0

benzamidine monohydrochloride

benzil
134-81-6

benzil

1,3,3,5,7-pentaphenyl-2,4-dioxa-8-aza-6-azonia-3-boratabicyclo{3.3.3}oct-6-ene
115438-41-0

1,3,3,5,7-pentaphenyl-2,4-dioxa-8-aza-6-azonia-3-boratabicyclo{3.3.3}oct-6-ene

Conditions
ConditionsYield
With sodium hydroxide In ethanol room temp.; crystn. from reaction mixt., washing (ethanol, ether), or evapn., extraction (hot ethanol), crystn. on cooling; elem. anal.;100%
5-bromo-1H-indole-3-carboxaldehyde
877-03-2

5-bromo-1H-indole-3-carboxaldehyde

benzil
134-81-6

benzil

C23H16BrN3
331979-15-8

C23H16BrN3

Conditions
ConditionsYield
With ammonium acetate; acetic acid Reflux;100%
With ammonium acetate In neat (no solvent) for 0.233333h; Microwave irradiation; Green chemistry;92%
(S)-1-phenylethanol
1445-91-6

(S)-1-phenylethanol

benzil
134-81-6

benzil

(1S,3R,4S)-1-methyl-3,4-diphenyl-3,4-dihydro-1H-isochromene-3,4-diol

(1S,3R,4S)-1-methyl-3,4-diphenyl-3,4-dihydro-1H-isochromene-3,4-diol

Conditions
ConditionsYield
Stage #1: (S)-1-phenylethanol With sec.-butyllithium In diethyl ether; hexane
Stage #2: benzil In diethyl ether; hexane at -40 - 20℃; for 24h; Inert atmosphere;
100%
3,4,5-trimethoxy-benzaldehyde
86-81-7

3,4,5-trimethoxy-benzaldehyde

benzil
134-81-6

benzil

urea
57-13-6

urea

4,5‐diphenyl‐2‐(3,4,5‐trimethoxyphenyl)‐1H‐imidazole
190780-24-6

4,5‐diphenyl‐2‐(3,4,5‐trimethoxyphenyl)‐1H‐imidazole

Conditions
ConditionsYield
With ammonium acetate; zinc(II) chloride at 70 - 110℃; for 0.5h; Green chemistry;100%
beryllium(II) chloride
7787-47-5

beryllium(II) chloride

benzil
134-81-6

benzil

[BeCl2(benzil)]

[BeCl2(benzil)]

Conditions
ConditionsYield
In dichloromethane at 20℃; Sealed tube; Schlenk technique;100%

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Dianionic Oxy‐Cope Rearrangement with Benzil (cas 134-81-6) Derivatives: meso‐Selective 3,3‐Coupling of Two Tetrahydrofuran Moieties09/29/2019

Benzil and its derivatives naphthil and pyridil have been found to undergo a dianionic oxy‐Cope rearrangement upon reaction with 2‐lithio‐4,5‐dihydrofuran to give 3,3′‐octahydrobifuranyls selectively as the meso diastereomers. The diastereoselectivity is explained based on the reaction mec...detailed

Unexpected differences in the reactivity between MPh2Cl2 (M=Pb or Sn) and Benzil (cas 134-81-6) bis(thiosemicarbazone). X-ray crystal structure of Benzil (cas 134-81-6) bis(thiosemicarbazonate)lead(II)10/01/2019

The differences in the reactivity of diphenyllead and diphenyltin dichloride with benzil bis(thiosemicarbazone) LH 6 are explored. The reaction of PbPh 2 Cl 2 afforded the complex [Pb(LH 4 )] 1, containing the ligand doubly deprotonated and without the phenyl grou...detailed

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