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24964-64-5 Usage

Chemical Properties

white to light yellow cryst. powder or chunks

Uses

3-Cyanobenzaldehyde is used in the synthesis of 3-(6,6-dimethyl-5,6-dihydro-4H-benzo[7,8]chromeno[6,5-d]oxazol-2-yl)benzonitrile. It is an important raw material and intermediate used in organic synthesis, pharmaceuticals agrochemicals and dyestuff fields.

Check Digit Verification of cas no

The CAS Registry Mumber 24964-64-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,4,9,6 and 4 respectively; the second part has 2 digits, 6 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 24964-64:
(7*2)+(6*4)+(5*9)+(4*6)+(3*4)+(2*6)+(1*4)=135
135 % 10 = 5
So 24964-64-5 is a valid CAS Registry Number.

24964-64-5 Well-known Company Product Price

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  • Alfa Aesar

  • (A15943)  3-Cyanobenzaldehyde, 97%   

  • 24964-64-5

  • 1g

  • 223.0CNY

  • Detail
  • Alfa Aesar

  • (A15943)  3-Cyanobenzaldehyde, 97%   

  • 24964-64-5

  • 5g

  • 927.0CNY

  • Detail
  • Alfa Aesar

  • (A15943)  3-Cyanobenzaldehyde, 97%   

  • 24964-64-5

  • 25g

  • 3146.0CNY

  • Detail

24964-64-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-formylbenzonitrile

1.2 Other means of identification

Product number -
Other names 3-Cyanobenzaldehyde

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:24964-64-5 SDS

24964-64-5Synthetic route

3-(hydroxymethyl)benzonitrile
874-97-5

3-(hydroxymethyl)benzonitrile

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

Conditions
ConditionsYield
With N-hydroxyphthalimide; oxygen; 3-chlorobenzoate; cobalt(II) acetate In acetonitrile at 20℃; for 2h;98%
With fluorosulfonyl fluoride; potassium carbonate; dimethyl sulfoxide at 20℃; for 12h; chemoselective reaction;92%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; rac-Ala-OH; iron(II) bromide In 1,4-dioxane for 12h; Reflux; Green chemistry;89%
ethyl 3-cyanobenzoate
2463-16-3

ethyl 3-cyanobenzoate

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

Conditions
ConditionsYield
With n-butyllithium; diisobutylaluminium hydride; tert-butyl alcohol In tetrahydrofuran; hexane at 0℃;97%
3-(1,3-dioxolan-2-yl)-benzonitrile
153329-04-5

3-(1,3-dioxolan-2-yl)-benzonitrile

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

Conditions
ConditionsYield
In(OSO2CF3)3 In acetone at 100℃; for 0.0833333h; microwave irradiation;94%
With Ti(4+)-exchanged montmorillonite In water; acetone at 60℃; for 6h;95 % Chromat.
3-cyano-N,N-diethylbenzamide
131497-05-7

3-cyano-N,N-diethylbenzamide

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

Conditions
ConditionsYield
With zirconocene dichloride; lithium tri-t-butoxyaluminum hydride In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere;94%
m-bromobenzoic aldehyde
3132-99-8

m-bromobenzoic aldehyde

potassium ferrocyanide

potassium ferrocyanide

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

Conditions
ConditionsYield
With dichloro[bis{1-(dicyclohexylphosphanyl)piperidine}]palladium; sodium carbonate In 1-methyl-pyrrolidin-2-one at 140℃; for 6h; Inert atmosphere;93%
With hydrogen tetrachloropalladate; sodium phosphate In N,N-dimethyl-formamide at 120℃; for 8h; Inert atmosphere;65 %Spectr.
With tri-tert-butyl phosphine; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 15h; Inert atmosphere;92 %Chromat.
m-iodobenzaldehyde
696-41-3

m-iodobenzaldehyde

potassium ferrocyanide

potassium ferrocyanide

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 9h; Inert atmosphere;92%
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 9h; Inert atmosphere;92 %Chromat.
4-(methylamino)phenyl thiocyanate
33192-08-4

4-(methylamino)phenyl thiocyanate

3-Formylphenylboronic acid
87199-16-4

3-Formylphenylboronic acid

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

Conditions
ConditionsYield
With N,N,N-trimethyl-2-(sulfooxy)ethanaminium palladium(II) chloride; sodium carbonate In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; water for 2h;91%
3-(hydroxyimino)methylbenzonitrile
64847-76-3

3-(hydroxyimino)methylbenzonitrile

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

Conditions
ConditionsYield
With zinc(II) nitrate; silica gel for 0.0666667h; deoxymation; Irradiation;90%
2-methyl-3-thiocyanato-1H-indole
31418-19-6

2-methyl-3-thiocyanato-1H-indole

3-Formylphenylboronic acid
87199-16-4

3-Formylphenylboronic acid

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

Conditions
ConditionsYield
With N,N,N-trimethyl-2-(sulfooxy)ethanaminium palladium(II) chloride; sodium carbonate In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; water for 2h;90%
3-(bromomethyl)benzonitrile
28188-41-2

3-(bromomethyl)benzonitrile

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

Conditions
ConditionsYield
With pyridine N-oxide; silver(l) oxide In acetonitrile at 50℃;84%
With chloroform; hexamethylenetetramine Erhitzen des Reaktionsprodukts mit wss. Essigsaeure;
With potassium carbonate; dimethyl sulfoxide at 90℃; Kornblum Aldehyd Synthesis;
3-Cyanobenzoic acid
1877-72-1

3-Cyanobenzoic acid

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

Conditions
ConditionsYield
With thexylchloroborane-Me2SO4 In dichloromethane for 24h; Ambient temperature;83%
With palladium(II) acetylacetonate; hydrogen; 2,2-dimethylpropanoic anhydride; dicyclohexylphenylphosphine In tetrahydrofuran at 80℃; under 3750.38 Torr; for 20h; Inert atmosphere;78%
With P(p-CH3OC6H4)3; methylphenylsilane; 2,2-dimethylpropanoic anhydride; bis(dibenzylideneacetone)-palladium(0) In toluene at 80℃; for 20h; Schlenk technique; Inert atmosphere;63%
3-cyanostyrene
5338-96-5

3-cyanostyrene

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

Conditions
ConditionsYield
With tert.-butylhydroperoxide; water at 90℃; for 12h;81%
potassiumhexacyanoferrate(II) trihydrate

potassiumhexacyanoferrate(II) trihydrate

3-Chlorobenzaldehyde
587-04-2

3-Chlorobenzaldehyde

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

Conditions
ConditionsYield
With 2-[2-(dicyclohexylphosphino)-phenyl]-1-methyl-1H-indole; palladium diacetate; sodium carbonate; triethylamine In water; acetonitrile at 70℃; for 18h;71%
m-bromobenzoic aldehyde
3132-99-8

m-bromobenzoic aldehyde

K4[Fe(CN)6]

K4[Fe(CN)6]

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

Conditions
ConditionsYield
With sodium carbonate; palladium diacetate at 120℃; for 16h;66%
m-bromobenzoic aldehyde
3132-99-8

m-bromobenzoic aldehyde

dicyanozinc
557-21-1

dicyanozinc

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

Conditions
ConditionsYield
With water; tri tert-butylphosphoniumtetrafluoroborate; zinc; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In 1-methyl-pyrrolidin-2-one at 20℃; for 24h;65%
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,2-Ph2-3,4-bis(2,4,6-(t-Bu)3-phenylphophinidene)cyclobutene; zinc In various solvent(s) at 100℃; for 16h;61%
2,2-diethoxy acetic acid
20461-86-3

2,2-diethoxy acetic acid

3-cyanobromobenzene
6952-59-6

3-cyanobromobenzene

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

Conditions
ConditionsYield
With nickel(II) chloride hexahydrate; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; caesium carbonate; 4,4'-di-tert-butyl-2,2'-bipyridine In N,N-dimethyl-formamide at 20℃; for 24h; Schlenk technique; Inert atmosphere; Irradiation;60%
3-Methylbenzonitrile
620-22-4

3-Methylbenzonitrile

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

Conditions
ConditionsYield
With oxygen In water at 150℃; under 30002.4 Torr; for 2h;55%
With bromine at 150℃; Irradiation.UV-Licht; Erwaermen des Reaktionsprodukts mit Calciumcarbonat und Wasser;
Multi-step reaction with 2 steps
1: chromium trioxide, acetic acid
2: water
View Scheme
Multi-step reaction with 2 steps
1: chlorine / 150 °C
2: silver nitrate
View Scheme
C14H20N2O

C14H20N2O

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

Conditions
ConditionsYield
With methanesulfonic acid In [D3]acetonitrile at 20℃; for 24h; Molecular sieve;31%
2-acetonyl-5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinane
111011-80-4

2-acetonyl-5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinane

4-cyano-1-(dimorpholinomethyl)benzene
152401-79-1

4-cyano-1-(dimorpholinomethyl)benzene

A

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

B

(Z)-2,2-dimethyl-1,3-propanediyl α-acetyl-4-cyanostyrylphosphonate

(Z)-2,2-dimethyl-1,3-propanediyl α-acetyl-4-cyanostyrylphosphonate

C

(E)-2,2-dimethyl-1,3-propanediyl α-acetyl-4-cyanostyrylphosphonate

(E)-2,2-dimethyl-1,3-propanediyl α-acetyl-4-cyanostyrylphosphonate

Conditions
ConditionsYield
With chloroacetic acid In toluene for 3h; Ambient temperature; Yield given. Title compound not separated from byproducts;A 6%
B n/a
C n/a
3-(dichloromethyl)benzonitrile
93632-91-8

3-(dichloromethyl)benzonitrile

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

Conditions
ConditionsYield
With silver nitrate
3-(chloromethyl)benzonitrile
64407-07-4

3-(chloromethyl)benzonitrile

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

Conditions
ConditionsYield
With cuprous nitrate
potassium cyanide
151-50-8

potassium cyanide

m-aminobenzaldehyde
1709-44-0

m-aminobenzaldehyde

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

Conditions
ConditionsYield
With water; copper(II) sulfate
(3-Cyan-benzyl)-phenyl-sulfid
51229-53-9

(3-Cyan-benzyl)-phenyl-sulfid

A

diphenyl sulfide
139-66-2

diphenyl sulfide

B

1,2-bis(3-cyanophenyl)ethane
4381-01-5

1,2-bis(3-cyanophenyl)ethane

C

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

D

3-Methylbenzonitrile
620-22-4

3-Methylbenzonitrile

E

diphenyldisulfane
882-33-7

diphenyldisulfane

F

C22H16N2S

C22H16N2S

Conditions
ConditionsYield
In tert-butyl alcohol Mechanism; Irradiation;
3-[(dimethylamino)methyl]benzonitrile
42967-27-1

3-[(dimethylamino)methyl]benzonitrile

A

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

B

3-((methylamino)methyl)benzonitrile
90389-96-1

3-((methylamino)methyl)benzonitrile

Conditions
ConditionsYield
With iodosylbenzene; meso-tetraphenylporphyrin iron(III) chloride In benzene
With iodosylbenzene; meso-tetraphenylporphyrin iron(III) chloride In benzene relative rate of oxidation; other catalyst;
ethanedinitrile
460-19-5

ethanedinitrile

benzaldehyde
100-52-7

benzaldehyde

A

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

B

o-formylbenzonitrile
7468-67-9

o-formylbenzonitrile

C

benzonitrile
100-47-0

benzonitrile

D

4-cyanobenzaldehyde
105-07-7

4-cyanobenzaldehyde

Conditions
ConditionsYield
gaseous plasma of glow discharge; Yield given. Further byproducts given. Yields of byproduct given;
carbon monoxide
201230-82-2

carbon monoxide

benzonitrile
100-47-0

benzonitrile

A

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

B

4-Cyanobenzyl alcohol
874-89-5

4-Cyanobenzyl alcohol

C

o-formylbenzonitrile
7468-67-9

o-formylbenzonitrile

D

3-(hydroxymethyl)benzonitrile
874-97-5

3-(hydroxymethyl)benzonitrile

Conditions
ConditionsYield
RhCl(CO)(PMe3)2 under 760 Torr; for 16.5h; Ambient temperature; Irradiation; Yield given. Further byproducts given. Yields of byproduct given;
carbon monoxide
201230-82-2

carbon monoxide

benzonitrile
100-47-0

benzonitrile

A

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

B

o-formylbenzonitrile
7468-67-9

o-formylbenzonitrile

C

3-(hydroxymethyl)benzonitrile
874-97-5

3-(hydroxymethyl)benzonitrile

D

4-cyanobenzaldehyde
105-07-7

4-cyanobenzaldehyde

Conditions
ConditionsYield
RhCl(CO)(PMe3)2 under 760 Torr; for 16.5h; Ambient temperature; Irradiation; Yield given. Further byproducts given. Yields of byproduct given;
3-((Z)-2-Cyano-3-oxo-3-phenyl-propenyl)-benzonitrile
80540-90-5

3-((Z)-2-Cyano-3-oxo-3-phenyl-propenyl)-benzonitrile

A

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

B

Benzoylacetonitrile
614-16-4

Benzoylacetonitrile

Conditions
ConditionsYield
With hydrogenchloride; water In ethanol; water at 25℃; Rate constant; Thermodynamic data; ΔH(excit.), ΔS(excit), pH dependence of the rate of hydrolysis;
m-cyanobenzaldiacetate
221226-95-5

m-cyanobenzaldiacetate

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

Conditions
ConditionsYield
With water
3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

3-(hydroxyimino)methylbenzonitrile
64847-76-3

3-(hydroxyimino)methylbenzonitrile

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water at 25℃; for 1h; Cooling with ice;100%
With sodium hydroxide; hydroxylamine hydrochloride In ethanol; water at 25 - 30℃; for 1h;94%
With hydroxylamine In pyridine; ethanol90%
3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

tert‐butyl 3‐aminopiperidine‐1‐carboxylate
144243-24-3

tert‐butyl 3‐aminopiperidine‐1‐carboxylate

trifluoroacetic acid
76-05-1

trifluoroacetic acid

3-[3-(aminopiperidin-1-yl)methyl]benzonitrile bis(trifluoroacetate) salt

3-[3-(aminopiperidin-1-yl)methyl]benzonitrile bis(trifluoroacetate) salt

Conditions
ConditionsYield
Multistep reaction;100%
3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

debenzyldonepezil
120014-30-4

debenzyldonepezil

1-(3-cyanobenzyl)-4-[(5,6-dimethoxy-1-indanon)-2-yl]methylpiperidine

1-(3-cyanobenzyl)-4-[(5,6-dimethoxy-1-indanon)-2-yl]methylpiperidine

Conditions
ConditionsYield
Stage #1: 3-Cyanobenzaldehyde; debenzyldonepezil In 1,2-dichloro-ethane
Stage #2: With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃; for 3h;
100%
With sodium tris(acetoxy)borohydride; acetic acid In ethyl acetate; 1,2-dichloro-ethane
3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

3-(1,3-dioxolan-2-yl)-benzonitrile
153329-04-5

3-(1,3-dioxolan-2-yl)-benzonitrile

Conditions
ConditionsYield
With p-toluenesulfonic acid monohydrate In ethylene glycol; toluene100%
tryptamine
61-54-1

tryptamine

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

3-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b] indol-1-yl)benzonitrile
1171311-06-0

3-(2,3,4,9-tetrahydro-1H-pyrido[3,4-b] indol-1-yl)benzonitrile

Conditions
ConditionsYield
With trifluoroacetic acid In 1,1-dichloroethane Reflux;100%
With trifluoroacetic acid In dichloromethane at 20℃; for 24h; Pictet-Spengler Synthesis;18%
3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

(7-morpholin-4-yl-2-phenyl-pyrazolo[1,5-a]pyrimidin-5-yl)hydrazine trifluoroacetate

(7-morpholin-4-yl-2-phenyl-pyrazolo[1,5-a]pyrimidin-5-yl)hydrazine trifluoroacetate

N-(3-cyano-benzylidene)-N'-(7-morpholin-4-yl-2-phenyl-pyrazolo[1,5-a]pyrimidin-5-yl)-hydrazine
1232221-08-7

N-(3-cyano-benzylidene)-N'-(7-morpholin-4-yl-2-phenyl-pyrazolo[1,5-a]pyrimidin-5-yl)-hydrazine

Conditions
ConditionsYield
Stage #1: 3-Cyanobenzaldehyde; (7-morpholin-4-yl-2-phenyl-pyrazolo[1,5-a]pyrimidin-5-yl)hydrazine trifluoroacetate In ethanol at 1 - 30℃; for 1h;
Stage #2: With NH-silica gel In methanol; dichloromethane
100%
3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

1,3-diaminoguanidine hydrochloride
36062-19-8

1,3-diaminoguanidine hydrochloride

2,2'-bis[(3-cyanophenyl)methylene]carbonimidic dihydrazide monohydrochloride

2,2'-bis[(3-cyanophenyl)methylene]carbonimidic dihydrazide monohydrochloride

Conditions
ConditionsYield
In ethanol for 16h; Reflux;100%
In ethanol for 16h; Reflux;
3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

1,3-di(aminomethyl)benzene
1477-55-0

1,3-di(aminomethyl)benzene

Conditions
ConditionsYield
With ammonia; hydrogen In methanol at 100℃; under 37503.8 Torr; for 5h;100%
With ammonia; hydrogen In methanol at 80℃; under 22502.3 Torr; for 5h;74%
3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

tert-butyl 1-(2-bromobenzyl)hydrazine-1-carboxylate

tert-butyl 1-(2-bromobenzyl)hydrazine-1-carboxylate

C20H20BrN3O2

C20H20BrN3O2

Conditions
ConditionsYield
In ethanol at 20℃;100%
diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate
124931-12-0

diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

(E)-3-(3-cyanophenyl)-N-methoxy-N-methylacrylamide

(E)-3-(3-cyanophenyl)-N-methoxy-N-methylacrylamide

Conditions
ConditionsYield
Stage #1: diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate With sodium hydride In tetrahydrofuran at 20℃; Horner-Wadsworth-Emmons Olefination;
Stage #2: 3-Cyanobenzaldehyde In tetrahydrofuran at -78 - 20℃; Horner-Wadsworth-Emmons Olefination;
100%
3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

3-(hydroxymethyl)benzonitrile
874-97-5

3-(hydroxymethyl)benzonitrile

Conditions
ConditionsYield
With [Ir(2,2':6',2'’-terpyridine)(1,10-phenanthroline)Cl](PF6)2; sodium formate In ethanol; water at 100℃; for 0.333333h; Microwave irradiation; chemoselective reaction;99%
With sodium tetrahydroborate In ethanol for 0.666667h;98%
With sodium tetrahydroborate In tetrahydrofuran; methanol98%
3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

3-(hydrazonomethyl)benzonitrile

3-(hydrazonomethyl)benzonitrile

Conditions
ConditionsYield
With hydrazine hydrate In methanol at 20℃; for 1h;99%
With hydrazine hydrate In ethanol for 3h; Condensation; Heating;77%
With hydrazine hydrate In ethanol at 20℃; for 3h;77%
With hydrazine hydrate In ethanol at 20℃; for 3h; Inert atmosphere;77%
With hydrazine hydrate In ethanol at 20℃; for 3h; Inert atmosphere;
3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

3-cyanobenzaldehyde oxime
52707-53-6

3-cyanobenzaldehyde oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium acetate In ethanol at 20℃; for 3h;99%
With hydroxylamine hydrochloride
With hydroxylamine hydrochloride In pyridine; ethanol; water19.2 g (69%)
With hydroxylamine hydrochloride In pyridine; ethanol; water19.2 g (69%)
3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

allyl-trimethyl-silane
762-72-1

allyl-trimethyl-silane

3-[1-[(trimethylsilyl)oxy]-3-buten-1-yl]benzonitrile
1200328-46-6

3-[1-[(trimethylsilyl)oxy]-3-buten-1-yl]benzonitrile

Conditions
ConditionsYield
With Montmorillonite K10 clay In dichloromethane at 0 - 20℃; for 1.08333h; Hosomi-Sakurai reaction;99%
3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

C12H16NO3P

C12H16NO3P

Conditions
ConditionsYield
With barium hydroxide octahydrate In tetrahydrofuran at 20℃; for 0.25h; Pudovik Reaction;99%
3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

C18H13F6N3O2
1665286-80-5

C18H13F6N3O2

3-((4’-oxo-3’-(4-(trifluoromethoxy)phenyl)-7’-(trifluoromethyl)-3’,4’-dihydro-1‘H-spiro[azetidine-3,2’-quinazolin]-1-yl)methyl)benzonitrile
1620884-81-2

3-((4’-oxo-3’-(4-(trifluoromethoxy)phenyl)-7’-(trifluoromethyl)-3’,4’-dihydro-1‘H-spiro[azetidine-3,2’-quinazolin]-1-yl)methyl)benzonitrile

Conditions
ConditionsYield
With caesium carbonate In acetonitrile at 50℃; for 2h;99%
3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

4-amino-1-phenylpiperazine
14340-32-0

4-amino-1-phenylpiperazine

(E)-3-((4-phenylpiperazin-1-ylimino)methyl)benzonitrile

(E)-3-((4-phenylpiperazin-1-ylimino)methyl)benzonitrile

Conditions
ConditionsYield
In toluene at 100℃; for 6h;99%
3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

2-amino-1-benzylamine
4403-69-4

2-amino-1-benzylamine

3-(1,2,3,4-tetrahydroquinazolin-2-yl)benzonitrile

3-(1,2,3,4-tetrahydroquinazolin-2-yl)benzonitrile

Conditions
ConditionsYield
In methanol at 20℃; Pictet-Spengler Synthesis; Sealed tube;99%
trifluoroacetic acid-methyl ester
431-47-0

trifluoroacetic acid-methyl ester

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

sodium methylate
124-41-4

sodium methylate

3-cyanobenzaldehyde dimethyl acetal

3-cyanobenzaldehyde dimethyl acetal

Conditions
ConditionsYield
In methanol at 20℃; Inert atmosphere;99%
triphenyl phosphite
101-02-0

triphenyl phosphite

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

methyl carbamate
598-55-0

methyl carbamate

methyl ((3-cyanophenyl)(diphenoxyphosphoryl)methyl)carbamate

methyl ((3-cyanophenyl)(diphenoxyphosphoryl)methyl)carbamate

Conditions
ConditionsYield
With copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 20℃; for 16h; Oleksyszyn Synthesis;99%
methanol
67-56-1

methanol

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

trimethyl orthoformate
149-73-5

trimethyl orthoformate

3-cyanobenzaldehyde dimethyl acetal

3-cyanobenzaldehyde dimethyl acetal

Conditions
ConditionsYield
With hydrogenchloride In water at 20 - 45℃; for 3.08333h;98.9%
3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

malononitrile
109-77-3

malononitrile

2-(3-cyanobenzylidene)malononitrile
60595-33-7

2-(3-cyanobenzylidene)malononitrile

Conditions
ConditionsYield
In neat (no solvent) at 60℃; for 4h;98%
With dimethyl 3-methyl-9-oxo-7-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)-2,4-di(pyridin-2-yl)-3,7-diazabicyclo-[3.3.1]nonane-1,5-dicarboxylate In water at 40℃; for 2h; Knoevenagel Condensation;91%
In water at 100℃; for 0.05h; Microwave irradiation;82%
3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

ethyl bromoacetate
105-36-2

ethyl bromoacetate

ethyl (E)-3-(3-cyanophenyl)-2-propenoate
125873-00-9

ethyl (E)-3-(3-cyanophenyl)-2-propenoate

Conditions
ConditionsYield
With triphenylphosphine; nanocrystalline aerogel prepared MgO In N,N-dimethyl-formamide at 20℃; for 4h; Wittig reaction;98%
3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

benzene-1,3-dicarbonitrile
626-17-5

benzene-1,3-dicarbonitrile

Conditions
ConditionsYield
With hydroxylamine hydrochloride; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate; N,N-dimethyl-formamide at 100℃;98%
With hydroxylamine hydrochloride; zinc(II) oxide for 0.0166667h; Microwave irradiation; neat (no solvent);91%
Multi-step reaction with 2 steps
1: hydroxylamine hydrochloride
2: 19 percent Chromat. / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / acetonitrile / 0.5 h / Photolysis
View Scheme
3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

2-cyano-3-(3-cyanophenyl)propionic acid ethyl ester
773084-59-6

2-cyano-3-(3-cyanophenyl)propionic acid ethyl ester

Conditions
ConditionsYield
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; L-proline In ethanol at 25℃; cascade Knoevenagel olefination/hydrogenation reaction; Combinatorial reaction / High throughput screening (HTS); stereospecific reaction;98%
3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

cyclohexanone
108-94-1

cyclohexanone

(2S,1'R)-2-[1'-hydroxy-1'-(3-cyanophenyl)methyl]cyclohexanone
1202363-07-2

(2S,1'R)-2-[1'-hydroxy-1'-(3-cyanophenyl)methyl]cyclohexanone

Conditions
ConditionsYield
With (S)-N-{(R)-1-[3-(3,5-bis(trifluoromethyl)phenyl)ureido]-2-phenylethyl}pyrrolidine-2-carboxamide; 4-nitro-benzoic acid In toluene at -20℃; for 72h; Aldol Addition; enantioselective reaction;98%
Stage #1: 3-Cyanobenzaldehyde With (S)-N-(2-(adamantane-1-carboxamidophenyl))prolinamide; sodium chloride at 0℃; for 0.25h; Aldol Addition;
Stage #2: cyclohexanone for 48h; Aldol Addition; stereoselective reaction;
90%
With (2S)-N-[(2S,3S,4R,5S)-2-(tert-butyldiphenylsilyloxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]pyrrolidin-2-carboxamide In sodium chloride at 4℃; for 48h; Aldol condensation; optical yield given as %ee; enantioselective reaction;86%
ethanol
64-17-5

ethanol

3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

ethyl 3-cyanobenzoate
2463-16-3

ethyl 3-cyanobenzoate

Conditions
ConditionsYield
With 3-(7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methyl-1-(2,4,6-trimethylphenyl)-1H-imidazol-3-ium iodine salt; caesium carbonate In toluene at 60℃; for 3h;98%
With C22H29N2O(1+)*I(1-); caesium carbonate In toluene at 60℃; for 3h;95%
With potassium carbonate In water at 20℃; for 5h;65%
With potassium cyanide; potassium iodide at 75 - 80℃; for 24h;
3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

7-(benzo[b]thiophen-3-yl)-9-methoxy-2,3,4,5-tetrahydrobenzo[f][1,4]oxazepine

7-(benzo[b]thiophen-3-yl)-9-methoxy-2,3,4,5-tetrahydrobenzo[f][1,4]oxazepine

3-((7-(benzo[b]thiophen-3-yl)-9-methoxy-2,3-dihydrobenzo[f ][1,4]oxazepin-4(5H)-yl)methyl)benzonitrile

3-((7-(benzo[b]thiophen-3-yl)-9-methoxy-2,3-dihydrobenzo[f ][1,4]oxazepin-4(5H)-yl)methyl)benzonitrile

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; Suzuki Coupling;98%
3-Cyanobenzaldehyde
24964-64-5

3-Cyanobenzaldehyde

tert-butyldimethylsilyl cyanide
56522-24-8

tert-butyldimethylsilyl cyanide

3-{[(tert-butyldimethylsilyl)oxy](cyano)methyl}benzonitrile

3-{[(tert-butyldimethylsilyl)oxy](cyano)methyl}benzonitrile

Conditions
ConditionsYield
With cesium fluoride In acetonitrile at 25℃; for 12h; Inert atmosphere;98%

24964-64-5Relevant articles and documents

Method for reducing carboxylic acid into aldehyde compounds

-

Paragraph 0051-0054, (2020/02/27)

The invention discloses a method for reducing carboxylic acid into aldehyde compounds, and belongs to the field of organic chemical synthesis. Specifically, in an argon atmosphere, a carboxylic acid compound, a transition metal nickel compound, an anhydride compound, a ligand and a reducing agent are dissolved in an organic solvent, the mixture is heated and subjected to stirring reaction, after the reaction is finished, the pressure is reduced to remove the organic solvent, column chromatography separation is performed, and various aldehyde compounds are obtained. The method has the advantages of simple synthesis steps, mild reaction conditions, simplicity and easiness in operation, realization of successful reduction of the carboxylic acid compound into the aldehyde organic compounds, small use amount of the reaction catalyst, high product yield, and provision of a new approach for reduction of the carboxylic acid compound into the aldehyde compounds. Compared with a conventional method, the method has the advantages that raw materials are cheap, easy to obtain and environmentally friendly, substrate universality and functional group compatibility are improved, and the method hascertain innovativeness and unique research significance in organic synthesis methodology.

A Simple, Mild and General Oxidation of Alcohols to Aldehydes or Ketones by SO2F2/K2CO3 Using DMSO as Solvent and Oxidant

Zha, Gao-Feng,Fang, Wan-Yin,Leng, Jing,Qin, Hua-Li

supporting information, p. 2262 - 2267 (2019/04/17)

A practical, general and mild oxidation of primary and secondary alcohols to carbonyl compounds proceeds in yields of up to 99% using SO2F2 as electrophile in DMSO as both the oxidant and the solvent at ambient temperature. No moisture- and oxygen-free conditions are required. Stoichiometric amount of inexpensive K2CO3, which generates easy to separate by-products, is used as the base. Thus, 5-gram scale runs proceeded in nearly quantitative yields by a simple filtration as the work-up. The use of a polar solvent such as DMSO, which usually promotes competing Pummerer rearrangement, is also noteworthy. This protocol is compatible with a variety of common N-, O-, and S-functional groups on (hetero)arene, alkene and alkyne substrates (68 examples). The protocol was applied (99% yield) to a formal synthesis of the important cholesterol-lowering drug Rosuvastatin. (Figure presented.).

A Transition-Metal-Free One-Pot Cascade Process for Transformation of Primary Alcohols (RCH2OH) to Nitriles (RCN) Mediated by SO2F2

Jiang, Ying,Sun, Bing,Fang, Wan-Yin,Qin, Hua-Li

supporting information, p. 3190 - 3194 (2019/05/21)

A new transition-metal-free one-pot cascade process for the direct conversion of alcohols to nitriles was developed without introducing an “additional carbon atom”. This protocol allows transformations of readily available, inexpensive, and abundant alcohols to highly valuable nitriles.

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