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613-90-1

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613-90-1 Usage

Chemical Properties

yellow to brown low melting mass

uses

Using benzoyl cyanide as an electrophile also gives selective acylation of the 3-position, as does levulinic acid in the presence of DCC. Benzoyl cyanide is used to study the mechanism of reduction of benzoyl cyanide in acetonitrile, N,N-dimethylformamide and acetonitrile. It undergoes hydrolysis by Rhodococcus sp. CCZU10-1 to form benzoylformic acid. Reagent for selective acylation of amino compounds.

Uses

Reagent for selective acylation of amino compounds.

Preparation

Benzoyl cyanide is prepared by treatment of benzoyl chloride with sodium cyanide under phase-transfer catalytic conditions. This process is also used to convert 4-methyl, 4-methoxy, and 4-chlorobenzoyl chlorides into the corresponding benzoyl cyanides, and similarly cinnamoyl chloride into cinnamoyl cyanide (98%).

Synthesis Reference(s)

Synthetic Communications, 15, p. 849, 1985 DOI: 10.1080/00397918508063881

General Description

Benzoyl cyanide is used to study the mechanism of reduction of benzoyl cyanide in acetonitrile, N,N-dimethylformamide and acetonitrile. It undergoes hydrolysis by Rhodococcus sp. CCZU10-1 to form benzoylformic acid.

Check Digit Verification of cas no

The CAS Registry Mumber 613-90-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,1 and 3 respectively; the second part has 2 digits, 9 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 613-90:
(5*6)+(4*1)+(3*3)+(2*9)+(1*0)=61
61 % 10 = 1
So 613-90-1 is a valid CAS Registry Number.
InChI:InChI=1/C8H5NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5H

613-90-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name benzoyl cyanide

1.2 Other means of identification

Product number -
Other names Benzeneacetonitrile, α-oxo-

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:613-90-1 SDS

613-90-1Synthetic route

(Benzoylmethylene)triphenylphosphorane
20913-05-7

(Benzoylmethylene)triphenylphosphorane

A

benzoyl cyanide
613-90-1

benzoyl cyanide

B

(Benzoylmethylen)triphenylphosphoniumnitrat

(Benzoylmethylen)triphenylphosphoniumnitrat

Conditions
ConditionsYield
With dinitrogen tetraoxide In tetrahydrofuran for 12h;A 94%
B 100%
bis(phenylethynyl)mercury
6077-10-7

bis(phenylethynyl)mercury

benzoyl cyanide
613-90-1

benzoyl cyanide

Conditions
ConditionsYield
With N-oxo-N-nitrosoamine In diethyl ether at -78℃;100%
(RS)-mandelonitrile
532-28-5, 613-88-7

(RS)-mandelonitrile

benzoyl cyanide
613-90-1

benzoyl cyanide

Conditions
ConditionsYield
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%
phenylglyoxal hydrate
1074-12-0

phenylglyoxal hydrate

benzoyl cyanide
613-90-1

benzoyl cyanide

Conditions
ConditionsYield
With 1-amino-2-oxo-4,6-diphenylpyridine In toluene at 110℃; for 6h;97%
nitro-phenyl-acetonitrile
25059-43-2

nitro-phenyl-acetonitrile

benzoyl cyanide
613-90-1

benzoyl cyanide

Conditions
ConditionsYield
With copper In benzene at 80℃; for 10h;97%
sodium cyanide
773837-37-9

sodium cyanide

benzoyl chloride
98-88-4

benzoyl chloride

benzoyl cyanide
613-90-1

benzoyl cyanide

Conditions
ConditionsYield
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
oxo-phenyl-acetaldehyde oxime
532-54-7

oxo-phenyl-acetaldehyde oxime

benzoyl cyanide
613-90-1

benzoyl cyanide

Conditions
ConditionsYield
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
benzoyl chloride
98-88-4

benzoyl chloride

bis(triphenylphosphine)iminium cyanide
65300-07-4

bis(triphenylphosphine)iminium cyanide

benzoyl cyanide
613-90-1

benzoyl cyanide

Conditions
ConditionsYield
In dichloromethane at -10℃; for 0.0833333h;92%
tri-n-butyltin cyanide
2179-92-2

tri-n-butyltin cyanide

benzoyl chloride
98-88-4

benzoyl chloride

A

benzoyl cyanide
613-90-1

benzoyl cyanide

B

tributyltin chloride

tributyltin chloride

Conditions
ConditionsYield
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
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

benzoyl chloride
98-88-4

benzoyl chloride

benzoyl cyanide
613-90-1

benzoyl cyanide

Conditions
ConditionsYield
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%
benzoyl chloride
98-88-4

benzoyl chloride

potassium ferrocyanide

potassium ferrocyanide

benzoyl cyanide
613-90-1

benzoyl cyanide

Conditions
ConditionsYield
With palladium diacetate at 150℃; for 4h; Green chemistry;91%
at 160℃; for 3h;
In ethanol at 160℃; for 3h; Green chemistry;
CYANAMID
420-04-2

CYANAMID

Benzoyl bromide
618-32-6

Benzoyl bromide

benzoyl cyanide
613-90-1

benzoyl cyanide

Conditions
ConditionsYield
With tin(ll) chloride In nitromethane at 242℃; for 4h; Concentration; Temperature;86%
4,4,4-trifluoro-3,3-dihydroxy-2-(hydroxyimino)-1-phenylbutan-1-one

4,4,4-trifluoro-3,3-dihydroxy-2-(hydroxyimino)-1-phenylbutan-1-one

benzoyl cyanide
613-90-1

benzoyl cyanide

Conditions
ConditionsYield
With acetic anhydride In chloroform for 1h; Reagent/catalyst; Reflux;85%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

benzaldehyde
100-52-7

benzaldehyde

benzoyl cyanide
613-90-1

benzoyl cyanide

Conditions
ConditionsYield
With silica gel supported bis(trimethylsilyl) chromate In dichloromethane for 2h; Heating;84%
iodobenzene
591-50-4

iodobenzene

carbon monoxide
201230-82-2

carbon monoxide

potassium cyanide
151-50-8

potassium cyanide

A

benzoyl cyanide
613-90-1

benzoyl cyanide

B

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
With iodophenylbis(triphenylphosphine)palladium In tetrahydrofuran at 100℃; under 15200 Torr; for 20h;A 83.2%
B 1.4 % Chromat.
potassium cyanide
151-50-8

potassium cyanide

benzoyl chloride
98-88-4

benzoyl chloride

benzoyl cyanide
613-90-1

benzoyl cyanide

Conditions
ConditionsYield
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
25438-37-3

phenyl(trimethylsiloxy)acetonitrile

benzoyl cyanide
613-90-1

benzoyl cyanide

Conditions
ConditionsYield
With N-Bromosuccinimide In pentane at 23℃; for 20h; Irradiation; indirect daylight irradiation;82%
benzoyl chloride
98-88-4

benzoyl chloride

Polymer-Supported Cyanide

Polymer-Supported Cyanide

benzoyl cyanide
613-90-1

benzoyl cyanide

Conditions
ConditionsYield
In benzene for 4h; Heating;82%
phenylacetonitrile
140-29-4

phenylacetonitrile

benzoyl cyanide
613-90-1

benzoyl cyanide

Conditions
ConditionsYield
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
2154-71-4

bis-trifluoromethyl-aminooxyl

phenylacetonitrile
140-29-4

phenylacetonitrile

A

benzoyl cyanide
613-90-1

benzoyl cyanide

B

N,N-bis(trifluoromethyl)hydroxylamine
359-63-7

N,N-bis(trifluoromethyl)hydroxylamine

C

perfluoro(2,4-dimethyl-3-oxa-2,4-diazapentane)
6141-72-6

perfluoro(2,4-dimethyl-3-oxa-2,4-diazapentane)

D

α-(bistrifluoromethylamino-oxy)benzyl cyanide
77228-18-3

α-(bistrifluoromethylamino-oxy)benzyl cyanide

Conditions
ConditionsYield
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
140-29-4

phenylacetonitrile

A

benzoyl cyanide
613-90-1

benzoyl cyanide

B

N,N-bis(trifluoromethyl)hydroxylamine
359-63-7

N,N-bis(trifluoromethyl)hydroxylamine

C

perfluoro(2,4-dimethyl-3-oxa-2,4-diazapentane)
6141-72-6

perfluoro(2,4-dimethyl-3-oxa-2,4-diazapentane)

D

α-(bistrifluoromethylamino-oxy)benzyl cyanide
77228-18-3

α-(bistrifluoromethylamino-oxy)benzyl cyanide

Conditions
ConditionsYield
With bis-trifluoromethyl-aminooxyl at 20℃; for 0.5h;A 4%
B 41%
C 5%
D 81%
bromo-phenyl-acetonitrile
5798-79-8

bromo-phenyl-acetonitrile

benzoyl cyanide
613-90-1

benzoyl cyanide

Conditions
ConditionsYield
With silver nitrate In acetonitrile at 50℃; for 5h;79%
benzoyl chloride
98-88-4

benzoyl chloride

potassium hexacyanoferrate(II)

potassium hexacyanoferrate(II)

benzoyl cyanide
613-90-1

benzoyl cyanide

Conditions
ConditionsYield
With PEG-400; potassium iodide; silver(I) iodide In N,N-dimethyl-formamide at 20℃; for 8h;78%
3-oxo-3-phenylpropanamide
3446-58-0

3-oxo-3-phenylpropanamide

benzoyl cyanide
613-90-1

benzoyl cyanide

Conditions
ConditionsYield
With tetraethylammonium bromide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In acetonitrile at 60℃; for 1.83333h;75%
potassium cyanide
151-50-8

potassium cyanide

benzoyl chloride
98-88-4

benzoyl chloride

A

benzoyl cyanide
613-90-1

benzoyl cyanide

B

α-Benzoyloxy-α-phenylmalononitrile
5467-94-7

α-Benzoyloxy-α-phenylmalononitrile

Conditions
ConditionsYield
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
81677-08-9

3-azido-5-phenyl-1,2,4-oxadiazole

benzoyl cyanide
613-90-1

benzoyl cyanide

Conditions
ConditionsYield
at 550℃; under 0.07 Torr;70%
(E)-2-hydroxyimino-3-oxo-3-phenylpropanoic acid

(E)-2-hydroxyimino-3-oxo-3-phenylpropanoic acid

benzoyl cyanide
613-90-1

benzoyl cyanide

Conditions
ConditionsYield
With dmap; acetyl chloride for 0.5h;70%
bis-trifluoromethyl-aminooxyl
2154-71-4

bis-trifluoromethyl-aminooxyl

α-(bistrifluoromethylamino-oxy)benzyl cyanide
77228-18-3

α-(bistrifluoromethylamino-oxy)benzyl cyanide

A

benzoyl cyanide
613-90-1

benzoyl cyanide

B

N,N-bis(trifluoromethyl)hydroxylamine
359-63-7

N,N-bis(trifluoromethyl)hydroxylamine

C

perfluoro(2,4-dimethyl-3-oxa-2,4-diazapentane)
6141-72-6

perfluoro(2,4-dimethyl-3-oxa-2,4-diazapentane)

D

αα-bis(bistrifluoromethylamino-oxy)benzyl cyanide
77228-19-4

αα-bis(bistrifluoromethylamino-oxy)benzyl cyanide

Conditions
ConditionsYield
at 20℃; for 5h;A 66%
B 45%
C 60%
D 28%
α-(bistrifluoromethylamino-oxy)benzyl cyanide
77228-18-3

α-(bistrifluoromethylamino-oxy)benzyl cyanide

A

benzoyl cyanide
613-90-1

benzoyl cyanide

B

N,N-bis(trifluoromethyl)hydroxylamine
359-63-7

N,N-bis(trifluoromethyl)hydroxylamine

C

perfluoro(2,4-dimethyl-3-oxa-2,4-diazapentane)
6141-72-6

perfluoro(2,4-dimethyl-3-oxa-2,4-diazapentane)

D

αα-bis(bistrifluoromethylamino-oxy)benzyl cyanide
77228-19-4

αα-bis(bistrifluoromethylamino-oxy)benzyl cyanide

Conditions
ConditionsYield
With bis-trifluoromethyl-aminooxyl at 20℃; for 5h;A 66%
B 45%
C 60%
D 28%
benzoyl cyanide
613-90-1

benzoyl cyanide

α-(diethoxyphosphinyl)benzyl diethyl phosphite
71572-20-8

α-(diethoxyphosphinyl)benzyl diethyl phosphite

4,5-dicyano-2-<α-(diethoxyphosphinyl)benzyloxy>-2,2-diethoxy-4,5-diphenyl-1,3,2λ5-dioxaphospholane

4,5-dicyano-2-<α-(diethoxyphosphinyl)benzyloxy>-2,2-diethoxy-4,5-diphenyl-1,3,2λ5-dioxaphospholane

Conditions
ConditionsYield
With amine hydrochlorides In diethyl ether at 0℃;100%
benzoyl cyanide
613-90-1

benzoyl cyanide

C11H16N2O9P(1-)*Li(1+)
115265-67-3

C11H16N2O9P(1-)*Li(1+)

C25H24N2O11P(1-)*Li(1+)
115264-98-7

C25H24N2O11P(1-)*Li(1+)

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide for 16h; Ambient temperature;100%
benzoyl cyanide
613-90-1

benzoyl cyanide

C20H36N4O8P(1-)*Li(1+)

C20H36N4O8P(1-)*Li(1+)

C34H44N4O10P(1-)*Li(1+)

C34H44N4O10P(1-)*Li(1+)

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide for 16h; Ambient temperature;100%
benzoyl cyanide
613-90-1

benzoyl cyanide

C21H36N6O7P(1-)*Li(1+)

C21H36N6O7P(1-)*Li(1+)

C35H44N6O9P(1-)*Li(1+)

C35H44N6O9P(1-)*Li(1+)

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide for 16h; Ambient temperature;100%
benzoyl cyanide
613-90-1

benzoyl cyanide

C21H36N6O7P(1-)*Li(1+)

C21H36N6O7P(1-)*Li(1+)

C35H44N6O9P(1-)*Li(1+)

C35H44N6O9P(1-)*Li(1+)

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide for 16h; Ambient temperature;100%
benzoyl cyanide
613-90-1

benzoyl cyanide

C21H36N6O7P(1-)*Li(1+)

C21H36N6O7P(1-)*Li(1+)

C35H44N6O9P(1-)*Li(1+)

C35H44N6O9P(1-)*Li(1+)

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide for 16h; Ambient temperature;100%
benzoyl cyanide
613-90-1

benzoyl cyanide

C21H36N6O8P(1-)*Li(1+)

C21H36N6O8P(1-)*Li(1+)

C35H44N6O10P(1-)*Li(1+)

C35H44N6O10P(1-)*Li(1+)

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide for 16h; Ambient temperature;100%
benzoyl cyanide
613-90-1

benzoyl cyanide

phosphorous acid 1-dimethoxyphosphoryl-ethyl ester dimethyl ester
69412-45-9

phosphorous acid 1-dimethoxyphosphoryl-ethyl ester dimethyl ester

4,5-dicyano-2-<α-(dimethoxyphosphinyl)ethoxy>-2,2-dimethoxy-4,5-diphenyl-1,3,2λ5-dioxaphospholane

4,5-dicyano-2-<α-(dimethoxyphosphinyl)ethoxy>-2,2-dimethoxy-4,5-diphenyl-1,3,2λ5-dioxaphospholane

Conditions
ConditionsYield
With amine hydrochlorides In diethyl ether at 0℃;100%
benzoyl cyanide
613-90-1

benzoyl cyanide

α-(dipropoxyphosphinyl)benzyl dipropyl phosphite
84923-87-5

α-(dipropoxyphosphinyl)benzyl dipropyl phosphite

tetrapropyl (α-cyano-α,α'-oxydibenzylidene)bisphosphonate
84923-90-0

tetrapropyl (α-cyano-α,α'-oxydibenzylidene)bisphosphonate

Conditions
ConditionsYield
With boron trifluoride diethyl etherate at 100 - 110℃; for 1.5h;100%
benzoyl cyanide
613-90-1

benzoyl cyanide

benzonitrile
100-47-0

benzonitrile

Conditions
ConditionsYield
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
613-90-1

benzoyl cyanide

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

2-hydroxy-2-phenylacetophenone

1,2-diphenyl-2-oxoethyl benzoate
1459-20-7

1,2-diphenyl-2-oxoethyl benzoate

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; Molecular sieve;100%
In acetone at 65℃; for 7h;70%
benzoyl cyanide
613-90-1

benzoyl cyanide

cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

2-cyclohexyl-2-hydroxyacetonitrile
100007-62-3, 107485-34-7, 4354-47-6

2-cyclohexyl-2-hydroxyacetonitrile

Conditions
ConditionsYield
With water In hexane; dimethyl sulfoxide at 20℃; for 24h;100%
benzoyl cyanide
613-90-1

benzoyl cyanide

Diacetone D-glucose
2595-05-3

Diacetone D-glucose

(+)-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-yl benzoate
29474-73-5

(+)-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranos-3-yl benzoate

Conditions
ConditionsYield
With triethylamine In acetonitrile at 0℃;100%
With triethylamine In acetonitrile at 20℃; for 15h;
benzoyl cyanide
613-90-1

benzoyl cyanide

1-(2-azido-phenyl)-ethanone
16714-26-4

1-(2-azido-phenyl)-ethanone

C15H9N5O2

C15H9N5O2

Conditions
ConditionsYield
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
613-90-1

benzoyl cyanide

u-2-amino-1-phenylpropan-1-ol
14838-15-4

u-2-amino-1-phenylpropan-1-ol

(1R*,2R*)-N-<(2-phenyl-2-hydroxy-1-methyl)ethyl>benzamide
4380-71-6, 5267-69-6, 5267-71-0, 38222-75-2, 38222-76-3, 126524-00-3, 134522-09-1

(1R*,2R*)-N-<(2-phenyl-2-hydroxy-1-methyl)ethyl>benzamide

Conditions
ConditionsYield
In dichloromethane for 15h; Ambient temperature;99.5%
4-HYDROXYPIPERIDINE
5382-16-1

4-HYDROXYPIPERIDINE

benzoyl cyanide
613-90-1

benzoyl cyanide

(4-hydroxy-1-piperidinyl)(phenyl)methanone
80213-01-0

(4-hydroxy-1-piperidinyl)(phenyl)methanone

Conditions
ConditionsYield
In dichloromethane at -10℃;99%
In dichloromethane Ambient temperature;95%
benzoyl cyanide
613-90-1

benzoyl cyanide

6-dimethylamino-9-(3-benzyloxy-2-hydroxypropyl)purine
86626-07-5

6-dimethylamino-9-(3-benzyloxy-2-hydroxypropyl)purine

9-(2-benzoyloxypropyl-3-benzyloxy)-6-dimethylaminopurine
86626-08-6

9-(2-benzoyloxypropyl-3-benzyloxy)-6-dimethylaminopurine

Conditions
ConditionsYield
With triethylamine In acetonitrile for 1h; Ambient temperature;99%
benzoyl cyanide
613-90-1

benzoyl cyanide

4-methoxyphenyl 4,6-O-benzylidene-β-D-galactopyranoside
176299-96-0

4-methoxyphenyl 4,6-O-benzylidene-β-D-galactopyranoside

4-methoxyphenyl 3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside
671194-39-1

4-methoxyphenyl 3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranoside

Conditions
ConditionsYield
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
613-90-1

benzoyl cyanide

dimethyl 2,2-di(but-2-yn-1-yl)malonate
107428-05-7

dimethyl 2,2-di(but-2-yn-1-yl)malonate

3-benzoyl-1,4-dimethyl-5,7-dihydro-[2]pyrindine-6,6-dicarboxylic acid dimethyl ester

3-benzoyl-1,4-dimethyl-5,7-dihydro-[2]pyrindine-6,6-dicarboxylic acid dimethyl ester

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In dichloromethane at 60℃; for 16h;99%
benzoyl cyanide
613-90-1

benzoyl cyanide

4,5-diphenyletheno-1,2,3-selenadiazole
27892-81-5

4,5-diphenyletheno-1,2,3-selenadiazole

(4,5-diphenyl-1,2-selenazol-3-yl)(phenyl)methanone

(4,5-diphenyl-1,2-selenazol-3-yl)(phenyl)methanone

Conditions
ConditionsYield
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%
benzoyl cyanide
613-90-1

benzoyl cyanide

1-(2-methylphenyl)piperidine
7250-70-6

1-(2-methylphenyl)piperidine

1-(2-methylphenyl)piperidine-2-carbonitrile

1-(2-methylphenyl)piperidine-2-carbonitrile

Conditions
ConditionsYield
With oxygen; lithium carbonate In acetonitrile at 20℃; for 24h; Irradiation;99%
benzoyl cyanide
613-90-1

benzoyl cyanide

2-Amino-1-phenylethanol
7568-93-6

2-Amino-1-phenylethanol

2-(benzoylamino)-1-phenylethanol
34119-82-9

2-(benzoylamino)-1-phenylethanol

Conditions
ConditionsYield
In dichloromethane for 15h; Ambient temperature;98%
benzoyl cyanide
613-90-1

benzoyl cyanide

benzyl azide
622-79-7

benzyl azide

(1-benzyl-1H-tetrazol-5-yl)phenylketone
120869-85-4

(1-benzyl-1H-tetrazol-5-yl)phenylketone

Conditions
ConditionsYield
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
613-90-1

benzoyl cyanide

1L-2,3,4-Tri-O-benzyl-1-C-hydroxymethyl-chiro-inositol
75348-12-8

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
81712-79-0

1L-7-O-Benzoyl-2,3,4-tri-O-benzyl-1-C-hydroxymethyl-chiro-inositol

Conditions
ConditionsYield
With triethylamine In dichloromethane at -15℃; for 20h;98%
benzoyl cyanide
613-90-1

benzoyl cyanide

(3R,5R)-3-Hydroxymethyl-5-((E)-2-methoxy-vinyl)-piperidine-1-carboxylic acid benzyl ester

(3R,5R)-3-Hydroxymethyl-5-((E)-2-methoxy-vinyl)-piperidine-1-carboxylic acid benzyl ester

(3R,5R)-3-Benzoyloxymethyl-5-((E)-2-methoxy-vinyl)-piperidine-1-carboxylic acid benzyl ester
284482-56-0

(3R,5R)-3-Benzoyloxymethyl-5-((E)-2-methoxy-vinyl)-piperidine-1-carboxylic acid benzyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Acylation;98%
benzoyl cyanide
613-90-1

benzoyl cyanide

1-styrenyloxytrimethylsilane
13735-81-4

1-styrenyloxytrimethylsilane

1,3-diphenylpropanedione
120-46-7

1,3-diphenylpropanedione

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran98%
With tetrabutyl ammonium fluoride In tetrahydrofuran98 % Spectr.
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 24h;
benzoyl cyanide
613-90-1

benzoyl cyanide

1(S)-[(2R)-1,4-dioxaspiro[4.5]decanyl]-3-buten-1-ol
164145-69-1

1(S)-[(2R)-1,4-dioxaspiro[4.5]decanyl]-3-buten-1-ol

(2R,3S)-1,2-O-cyclohexylidene-3-benzoyloxy-5-hexene
1197010-59-5

(2R,3S)-1,2-O-cyclohexylidene-3-benzoyloxy-5-hexene

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; for 5h;98%
benzoyl cyanide
613-90-1

benzoyl cyanide

di-isopropyl azodicarboxylate
2446-83-5

di-isopropyl azodicarboxylate

diisopropyl (Z)-2-(cyano(phenyl)methylene)hydrazine-1,1-dicarboxylate
1201947-31-0

diisopropyl (Z)-2-(cyano(phenyl)methylene)hydrazine-1,1-dicarboxylate

Conditions
ConditionsYield
With triphenylphosphine In toluene at 90℃; for 1h; Mitsunobu reaction; Inert atmosphere;98%

613-90-1Relevant articles and documents

Selective Monohydrocyanation of Diimine using Potassium Hexacyanoferrate(II)-Benzoyl Chloride Reagent System as a Cyanide Source

Li, Zheng,Wen, Fei,Yang, Jingya

, p. 1849 - 1853 (2016)

The selective monohydrocyanation of diimines using potassium hexacyanoferrate(II)-benzoyl chloride reagent system as a cyanide source under catalyst-free condition is described. The advantages of this protocol are the non-toxic, non-volatile and inexpensive cyanide source, high yield, and simple work-up procedure. [Figure not available: see fulltext.]

Sachs,Whittaker

, p. 501 (1901)

Metal-Free Transformation of Sulfonyl Oxime Ethers with Amines to Oxime Ethers

Zhang, Jia-Yuan,Hu, Jinglin,Li, Xiao-Xuan,Tang, Wei-Ke,Feng, Yi-Si

, p. 12676 - 12682 (2021/09/18)

Sulfonyl oxime ethers undergo facile radical substitutions with various amines to yield the corresponding oxime ethers. An efficient arylation of sulfonyl oxime ethers was accomplished under ambient temperature and metal-free conditions, with a wide range of functional group tolerance. Mechanistic investigations indicate that a phenyl radical is involved in the catalytic cycle.

Thiocyanate radical mediated dehydration of aldoximes with visible light and air

Ban, Yong-Liang,Dai, Jian-Ling,Jin, Xiao-Ling,Zhang, Qing-Bao,Liu, Qiang

supporting information, p. 9701 - 9704 (2019/08/15)

We developed a new means of activating aldoximes by an in situ generated thiocyanate radical from ammonium thiocyanate and molecular oxygen at room temperature. With a catalytic amount of organic dye aizenuranine as the photocatalyst, the dehydration of aldoximes proceeds smoothly under visible light irradiation, providing a simple to handle, excellent functional group tolerance, and metal-free protocol for a wide range of nitriles.

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