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inquiryCAS Number 613-90-1 Product Name Benzoyl Cyanide Synonyms Alpha-oxophenylacetonitrile; Benzoylcyanide; Oxo(phenyl)acetonitrile;
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inquiryBenzoyl cyanide Basic information Product Name: Benzoyl cyanide Synonyms: alpha-oxophenylacetonitrile;BENZOYL CYANIDE;PHENYLGLYOXYLONITRILE;alpha-oxo-benzeneacetoni
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inquiryBenzoyl cyanide Chemical Properties Melting point 28-31 °C(lit.) Boiling point 206 °C(lit.) density 1.106 g/mL at 25 °C(lit.) refractive index 1.4700 (estimate) Fp 184 °F Water Solubility slihtly soluble, decom
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(Benzoylmethylene)triphenylphosphorane
A
benzoyl cyanide
Conditions | Yield |
---|---|
With dinitrogen tetraoxide In tetrahydrofuran for 12h; | A 94% B 100% |
Conditions | Yield |
---|---|
With N-oxo-N-nitrosoamine In diethyl ether at -78℃; | 100% |
(RS)-mandelonitrile
benzoyl cyanide
Conditions | Yield |
---|---|
With methyl 3,5-bis((1H-1,2,4-triazol-1-yl)methyl)benzoate; oxygen; sodium acetate; nickel dibromide at 120℃; under 760.051 Torr; for 48h; | 97% |
With silica gel supported bis(trimethylsilyl) chromate In dichloromethane at 25℃; for 1.5h; | 96% |
With tert.-butylhydroperoxide; tris(triphenylphosphine)ruthenium(II) chloride In benzene for 3h; Ambient temperature; Var. Ru complexes, oxidants and solvents; | 87% |
Conditions | Yield |
---|---|
With 1-amino-2-oxo-4,6-diphenylpyridine In toluene at 110℃; for 6h; | 97% |
nitro-phenyl-acetonitrile
benzoyl cyanide
Conditions | Yield |
---|---|
With copper In benzene at 80℃; for 10h; | 97% |
Conditions | Yield |
---|---|
With water; Aliquat 336 In toluene at 60 - 85℃; for 5.5h; Temperature; | 96.9% |
Stage #1: sodium cyanide With tri(butyl)tetradecylphosphonium chloride; tetrabutylammomium bromide; copper(l) cyanide; copper(l) chloride In toluene for 3h; Reflux; Stage #2: benzoyl chloride In toluene at 100℃; for 6h; Temperature; Solvent; Reagent/catalyst; | 93% |
In ethyl acetate for 3h; Reflux; | 92% |
With Aliquat 336 In water at 7℃; for 0.0833333h; | 95 %Chromat. |
With tetrabutyl ammonium fluoride; zinc(II) iodide In o-xylene at 120℃; for 3h; | 123.9 g |
Conditions | Yield |
---|---|
With oxalyl dichloride; Triphenylphosphine oxide In ethyl acetate at 20℃; for 1h; | 93% |
With ammonium thiocyanate; fluorescein sodium salt In acetonitrile at 20℃; for 10h; Irradiation; | 74% |
With acetyl chloride at 20℃; | |
With acetic anhydride | |
With thionyl chloride |
Conditions | Yield |
---|---|
In dichloromethane at -10℃; for 0.0833333h; | 92% |
Conditions | Yield |
---|---|
In neat (no solvent) at 75℃; for 0.333333h; Product distribution; cyanating of acyl chlorides; | A 91.5% B n/a |
In neat (no solvent) at 75℃; for 0.333333h; | A 91.5 % Chromat. B n/a |
Conditions | Yield |
---|---|
tin(IV) chloride In dichloromethane for 2h; Ambient temperature; | 91% |
With titanium tetrachloride In dichloromethane at 20℃; for 2.5h; | 90% |
With zinc(II) iodide at 100℃; for 2h; Inert atmosphere; Neat (no solvent); neat (no solvent); | 89% |
Conditions | Yield |
---|---|
With palladium diacetate at 150℃; for 4h; Green chemistry; | 91% |
at 160℃; for 3h; | |
In ethanol at 160℃; for 3h; Green chemistry; |
Conditions | Yield |
---|---|
With tin(ll) chloride In nitromethane at 242℃; for 4h; Concentration; Temperature; | 86% |
benzoyl cyanide
Conditions | Yield |
---|---|
With acetic anhydride In chloroform for 1h; Reagent/catalyst; Reflux; | 85% |
Conditions | Yield |
---|---|
With silica gel supported bis(trimethylsilyl) chromate In dichloromethane for 2h; Heating; | 84% |
iodobenzene
carbon monoxide
potassium cyanide
A
benzoyl cyanide
B
benzonitrile
Conditions | Yield |
---|---|
With iodophenylbis(triphenylphosphine)palladium In tetrahydrofuran at 100℃; under 15200 Torr; for 20h; | A 83.2% B 1.4 % Chromat. |
Conditions | Yield |
---|---|
With AMBERLITE XAD-4 In water; benzene at 30℃; for 2h; | 83% |
With zinc(II) iodide; PEG400 In dichloromethane at 20℃; for 4.5h; | 76% |
With water In acetonitrile at 80℃; for 1.5h; effect of added water; various additives, various time, further aroyl chlorides; | 68% |
With water In acetonitrile at 80℃; for 1.5h; | 68% |
phenyl(trimethylsiloxy)acetonitrile
benzoyl cyanide
Conditions | Yield |
---|---|
With N-Bromosuccinimide In pentane at 23℃; for 20h; Irradiation; indirect daylight irradiation; | 82% |
Conditions | Yield |
---|---|
In benzene for 4h; Heating; | 82% |
Conditions | Yield |
---|---|
With methyl 3,5-bis((1H-1,2,4-triazol-1-yl)methyl)benzoate; oxygen; sodium acetate; nickel dibromide at 120℃; under 760.051 Torr; for 72h; | 82% |
With oxygen; copper diacetate In acetonitrile at 20 - 120℃; for 24h; Schlenk technique; Sealed tube; | 38% |
With oxygen; copper dichloride In toluene at 110℃; under 760.051 Torr; for 48h; Schlenk technique; | 35% |
With carbon tetrabromide; oxygen In water; ethyl acetate for 20h; Catalytic behavior; Solvent; Reagent/catalyst; Irradiation; | |
With tert.-butylhydroperoxide; C56H53ClN3P2Ru(1+)*F6P(1-) In benzene at 40℃; for 18h; Inert atmosphere; | 51 %Spectr. |
bis-trifluoromethyl-aminooxyl
phenylacetonitrile
A
benzoyl cyanide
B
N,N-bis(trifluoromethyl)hydroxylamine
C
perfluoro(2,4-dimethyl-3-oxa-2,4-diazapentane)
D
α-(bistrifluoromethylamino-oxy)benzyl cyanide
Conditions | Yield |
---|---|
at 20℃; for 0.5h; Mechanism; reactions with other benzyl derivatives (PhCH2Cl, PhCH2N3, and PhCH2OH); | A 4% B 41% C 5% D 81% |
at 20℃; for 0.5h; | A 4% B 41% C 5% D 81% |
phenylacetonitrile
A
benzoyl cyanide
B
N,N-bis(trifluoromethyl)hydroxylamine
C
perfluoro(2,4-dimethyl-3-oxa-2,4-diazapentane)
D
α-(bistrifluoromethylamino-oxy)benzyl cyanide
Conditions | Yield |
---|---|
With bis-trifluoromethyl-aminooxyl at 20℃; for 0.5h; | A 4% B 41% C 5% D 81% |
Conditions | Yield |
---|---|
With silver nitrate In acetonitrile at 50℃; for 5h; | 79% |
Conditions | Yield |
---|---|
With PEG-400; potassium iodide; silver(I) iodide In N,N-dimethyl-formamide at 20℃; for 8h; | 78% |
Conditions | Yield |
---|---|
With tetraethylammonium bromide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In acetonitrile at 60℃; for 1.83333h; | 75% |
potassium cyanide
benzoyl chloride
A
benzoyl cyanide
B
α-Benzoyloxy-α-phenylmalononitrile
Conditions | Yield |
---|---|
In acetonitrile at 50℃; for 1h; ultrasound; Title compound not separated from byproducts; | A 73% B 15 % Chromat. |
With sodium iodide In acetonitrile at 50℃; for 2h; ultrasound; Title compound not separated from byproducts; | A 88 % Chromat. B 4.2 % Chromat. |
3-azido-5-phenyl-1,2,4-oxadiazole
benzoyl cyanide
Conditions | Yield |
---|---|
at 550℃; under 0.07 Torr; | 70% |
benzoyl cyanide
Conditions | Yield |
---|---|
With dmap; acetyl chloride for 0.5h; | 70% |
bis-trifluoromethyl-aminooxyl
α-(bistrifluoromethylamino-oxy)benzyl cyanide
A
benzoyl cyanide
B
N,N-bis(trifluoromethyl)hydroxylamine
C
perfluoro(2,4-dimethyl-3-oxa-2,4-diazapentane)
D
αα-bis(bistrifluoromethylamino-oxy)benzyl cyanide
Conditions | Yield |
---|---|
at 20℃; for 5h; | A 66% B 45% C 60% D 28% |
α-(bistrifluoromethylamino-oxy)benzyl cyanide
A
benzoyl cyanide
B
N,N-bis(trifluoromethyl)hydroxylamine
C
perfluoro(2,4-dimethyl-3-oxa-2,4-diazapentane)
D
αα-bis(bistrifluoromethylamino-oxy)benzyl cyanide
Conditions | Yield |
---|---|
With bis-trifluoromethyl-aminooxyl at 20℃; for 5h; | A 66% B 45% C 60% D 28% |
benzoyl cyanide
α-(diethoxyphosphinyl)benzyl diethyl phosphite
Conditions | Yield |
---|---|
With amine hydrochlorides In diethyl ether at 0℃; | 100% |
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide for 16h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide for 16h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide for 16h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide for 16h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide for 16h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide for 16h; Ambient temperature; | 100% |
benzoyl cyanide
phosphorous acid 1-dimethoxyphosphoryl-ethyl ester dimethyl ester
Conditions | Yield |
---|---|
With amine hydrochlorides In diethyl ether at 0℃; | 100% |
benzoyl cyanide
α-(dipropoxyphosphinyl)benzyl dipropyl phosphite
tetrapropyl (α-cyano-α,α'-oxydibenzylidene)bisphosphonate
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate at 100 - 110℃; for 1.5h; | 100% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In benzene at 120℃; for 12h; Product distribution; other acyl cyanides, var. solvents, temp. and time; | 100% |
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 180℃; for 24h; Temperature; Glovebox; Inert atmosphere; Sealed tube; | 95 %Chromat. |
benzoyl cyanide
2-hydroxy-2-phenylacetophenone
1,2-diphenyl-2-oxoethyl benzoate
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 20℃; Molecular sieve; | 100% |
In acetone at 65℃; for 7h; | 70% |
benzoyl cyanide
cyclohexanecarbaldehyde
2-cyclohexyl-2-hydroxyacetonitrile
Conditions | Yield |
---|---|
With water In hexane; dimethyl sulfoxide at 20℃; for 24h; | 100% |
benzoyl cyanide
Diacetone D-glucose
(+)-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-yl benzoate
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 0℃; | 100% |
With triethylamine In acetonitrile at 20℃; for 15h; |
Conditions | Yield |
---|---|
Stage #1: 1-(2-azido-phenyl)-ethanone With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Stage #2: benzoyl cyanide In tetrahydrofuran for 1h; Stage #3: With 4-toluenesulfonyl azide; triethylamine In acetonitrile | 100% |
Stage #1: 1-(2-azido-phenyl)-ethanone With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: benzoyl cyanide In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #3: With 4-toluenesulfonyl azide; triethylamine In acetonitrile Inert atmosphere; | 551 mg |
benzoyl cyanide
u-2-amino-1-phenylpropan-1-ol
(1R*,2R*)-N-<(2-phenyl-2-hydroxy-1-methyl)ethyl>benzamide
Conditions | Yield |
---|---|
In dichloromethane for 15h; Ambient temperature; | 99.5% |
4-HYDROXYPIPERIDINE
benzoyl cyanide
(4-hydroxy-1-piperidinyl)(phenyl)methanone
Conditions | Yield |
---|---|
In dichloromethane at -10℃; | 99% |
In dichloromethane Ambient temperature; | 95% |
benzoyl cyanide
6-dimethylamino-9-(3-benzyloxy-2-hydroxypropyl)purine
9-(2-benzoyloxypropyl-3-benzyloxy)-6-dimethylaminopurine
Conditions | Yield |
---|---|
With triethylamine In acetonitrile for 1h; Ambient temperature; | 99% |
benzoyl cyanide
4-methoxyphenyl 4,6-O-benzylidene-β-D-galactopyranoside
4-methoxyphenyl 3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside
Conditions | Yield |
---|---|
With dmap In dichloromethane at -78℃; for 4h; Molecular sieve; Inert atmosphere; regioselective reaction; | 99% |
With triethylamine In acetonitrile at 20℃; for 0.5h; | 75% |
benzoyl cyanide
dimethyl 2,2-di(but-2-yn-1-yl)malonate
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In dichloromethane at 60℃; for 16h; | 99% |
benzoyl cyanide
4,5-diphenyletheno-1,2,3-selenadiazole
Conditions | Yield |
---|---|
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (S,S)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane In 1,4-dioxane at 100℃; for 6h; | 99% |
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; (S,S)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane In 1,4-dioxane at 100℃; for 6h; | 99% |
Conditions | Yield |
---|---|
With oxygen; lithium carbonate In acetonitrile at 20℃; for 24h; Irradiation; | 99% |
benzoyl cyanide
2-Amino-1-phenylethanol
2-(benzoylamino)-1-phenylethanol
Conditions | Yield |
---|---|
In dichloromethane for 15h; Ambient temperature; | 98% |
Conditions | Yield |
---|---|
at 120℃; for 60h; Huisgen 1,3-dipolar cycloaddition; | 98% |
In acetonitrile at 100℃; under 7500600 Torr; for 25h; | 90% |
With 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 100℃; for 85h; | 50% |
benzoyl cyanide
1L-2,3,4-Tri-O-benzyl-1-C-hydroxymethyl-chiro-inositol
1L-7-O-Benzoyl-2,3,4-tri-O-benzyl-1-C-hydroxymethyl-chiro-inositol
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at -15℃; for 20h; | 98% |
benzoyl cyanide
(3R,5R)-3-Benzoyloxymethyl-5-((E)-2-methoxy-vinyl)-piperidine-1-carboxylic acid benzyl ester
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Acylation; | 98% |
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran | 98% |
With tetrabutyl ammonium fluoride In tetrahydrofuran | 98 % Spectr. |
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 24h; |
benzoyl cyanide
1(S)-[(2R)-1,4-dioxaspiro[4.5]decanyl]-3-buten-1-ol
(2R,3S)-1,2-O-cyclohexylidene-3-benzoyloxy-5-hexene
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0℃; for 5h; | 98% |
benzoyl cyanide
di-isopropyl azodicarboxylate
diisopropyl (Z)-2-(cyano(phenyl)methylene)hydrazine-1,1-dicarboxylate
Conditions | Yield |
---|---|
With triphenylphosphine In toluene at 90℃; for 1h; Mitsunobu reaction; Inert atmosphere; | 98% |
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