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766-84-7

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766-84-7 Usage

Chemical Properties

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Check Digit Verification of cas no

The CAS Registry Mumber 766-84-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 7,6 and 6 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 766-84:
(5*7)+(4*6)+(3*6)+(2*8)+(1*4)=97
97 % 10 = 7
So 766-84-7 is a valid CAS Registry Number.
InChI:InChI=1/C7H4ClN/c8-7-3-1-2-6(4-7)5-9/h1-4H

766-84-7 Well-known Company Product Price

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  • Alfa Aesar

  • (A13237)  3-Chlorobenzonitrile, 99%   

  • 766-84-7

  • 10g

  • 559.0CNY

  • Detail
  • Alfa Aesar

  • (A13237)  3-Chlorobenzonitrile, 99%   

  • 766-84-7

  • 50g

  • 1852.0CNY

  • Detail
  • Alfa Aesar

  • (A13237)  3-Chlorobenzonitrile, 99%   

  • 766-84-7

  • 250g

  • 7439.0CNY

  • Detail

766-84-7SDS

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 3-Chlorobenzonitrile

1.2 Other means of identification

Product number -
Other names 3-chlorobenzylnitrile

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:766-84-7 SDS

766-84-7Synthetic route

(3‐cyanophenyl)boronic acid
150255-96-2

(3‐cyanophenyl)boronic acid

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With N-chloro-succinimide; copper(l) chloride In acetonitrile at 80℃; for 1h;98%
With N-chloro-succinimide In acetonitrile at 80℃; for 12h;97%
C14H10ClNO2

C14H10ClNO2

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With iron(III) chloride; 2,6-di-tert-butyl-4-methyl-phenol In dichloromethane; toluene at 20℃; for 0.0833333h;97%
With iron(III) chloride; 2,6-di-tert-butyl-4-methyl-phenol In toluene at 20℃; for 0.0833333h; Schlenk technique;85%
3-Chlorobenzaldehyde
587-04-2

3-Chlorobenzaldehyde

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With copper(II) oxide; hydroxylamine hydrochloride In neat (no solvent) for 0.0263889h; Mechanism; Reagent/catalyst; Microwave irradiation; Green chemistry;95%
With ammonium acetate; phenyltrimethylammonium tribromide In acetonitrile at 20℃; for 64h;94%
Stage #1: m-Chlorobenzaldehyde With ammonia In water at 20℃; for 0.166667h;
Stage #2: With tetra-N-butylammonium tribromide In water at 20℃; for 3h;
93%
m-chlorobenzylamine
4152-90-3

m-chlorobenzylamine

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With dmap; copper(l) iodide; 9-azabicyclo[3.3.1]nonane N-oxyl; oxygen; 4,4'-di-tert-butyl-2,2'-bipyridine In acetonitrile at 20℃; under 760.051 Torr; for 15h; Reagent/catalyst;95%
With 1-methyl-1H-imidazole; oxygen; copper(ll) bromide In dimethyl sulfoxide at 100℃; for 24h;90%
With potassium hydroxide; nickel copper formate; (Bu4N)2S2O8 In dichloromethane at 20℃; for 10h; Oxidation;87%
3-chlorobenzaldehyde oxime
34158-71-9

3-chlorobenzaldehyde oxime

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With acetonitrile for 1.5h; Reflux; Green chemistry;95%
Stage #1: 3-chlorobenzaldehyde oxime With Bromotrichloromethane; triphenylphosphine In dichloromethane for 0.416667h; Reflux;
Stage #2: With triethylamine In dichloromethane for 8h; Reflux;
81%
With 1,2-bis(3-fluorophenyl)diselane; dihydrogen peroxide In acetonitrile at 65℃; for 24h;80%
3-iodochlorobenzene
625-99-0

3-iodochlorobenzene

potassium ferrocyanide

potassium ferrocyanide

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 15h; Schlenk technique; Green chemistry;94%
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 13h;88%
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 1h; Inert atmosphere; Green chemistry;
With sodium carbonate In N,N-dimethyl-formamide at 120℃;
1-bromo-3-chlorobenzene
108-37-2

1-bromo-3-chlorobenzene

potassium ferrocyanide

potassium ferrocyanide

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With [Pd{C6H3(CH2CH2NH2)-4-OMe-5-κ2-C,N}(μ-Br)]2; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 0.05h; Microwave irradiation; chemoselective reaction;93%
With tri-tert-butyl phosphine; potassium carbonate In N,N-dimethyl-formamide at 120℃; for 17h; Inert atmosphere;69 %Chromat.
With sodium carbonate In N,N-dimethyl-formamide at 120℃; for 1h; Inert atmosphere; Green chemistry;
With sodium carbonate In N,N-dimethyl-formamide at 120℃;
1-bromo-3-chlorobenzene
108-37-2

1-bromo-3-chlorobenzene

potassium cyanide
151-50-8

potassium cyanide

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With tri-tert-butyl phosphine; tributyltin chloride; tris(dibenzylideneacetone)dipalladium (0) In acetonitrile at 80℃; for 17h;92%
potassium hexacyanoferrate(II)

potassium hexacyanoferrate(II)

1-bromo-3-chlorobenzene
108-37-2

1-bromo-3-chlorobenzene

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With CHF3O3S*C52H45NO2P2Pd; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 3.25h; chemoselective reaction;92%
3-iodochlorobenzene
625-99-0

3-iodochlorobenzene

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With sodium carbonate; potassium ferrocyanide In N,N-dimethyl-formamide at 120℃; for 6h;91%
3-chlorophenylboronic acid
63503-60-6

3-chlorophenylboronic acid

4-bromo-N-(4-chlorophenyl)-N-cyanobenzenesulfonamide

4-bromo-N-(4-chlorophenyl)-N-cyanobenzenesulfonamide

A

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

B

4-bromo-benzenesulfonic acid-(4-chloro-anilide)
6295-97-2

4-bromo-benzenesulfonic acid-(4-chloro-anilide)

Conditions
ConditionsYield
With Fe3O4/SiO2/(3-chloropropyl)trimethoxysilane/2,2′-(4,4′-(propane-1,3-diyl)bis(piperazine-4,1-diyl))- diethanamine/Pd In acetonitrile for 15h; Catalytic behavior; Reflux;A 91%
B n/a
3-chlorophenylboronic acid
63503-60-6

3-chlorophenylboronic acid

N-(4-chlorophenyl)-N-cyano-4-nitrobenzenesulfonamide

N-(4-chlorophenyl)-N-cyano-4-nitrobenzenesulfonamide

A

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

B

4-nitro-N-(4-chlorophenyl)benzenesulfonamide
16937-03-4

4-nitro-N-(4-chlorophenyl)benzenesulfonamide

Conditions
ConditionsYield
With Fe3O4/SiO2/(3-chloropropyl)trimethoxysilane/2,2′-(4,4′-(propane-1,3-diyl)bis(piperazine-4,1-diyl))- diethanamine/Pd In acetonitrile for 13h; Catalytic behavior; Reflux;A 91%
B n/a
3-chlorobenzamide
618-48-4

3-chlorobenzamide

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With C8H14N2O4S In dichloromethane for 1h; Reflux;90%
With vanadium oxide on hydrotalcite (V/HT) In 1,3,5-trimethyl-benzene for 24h; Reflux;89%
Stage #1: 3-chlorobenzamide With C39H45N2 In acetonitrile at 20℃; Schlenk technique; Glovebox; Inert atmosphere;
Stage #2: With phenylsilane In acetonitrile at 20℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube;
82%
m-chlorobenzyl alcohol
873-63-2

m-chlorobenzyl alcohol

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With ammonium acetate; iodine at 100℃; for 3h;90%
With 2,3'-bipyridine; ammonium hydroxide; copper(l) iodide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen In ethanol at 20℃; for 24h;85%
With potassium phosphate; ammonium formate In acetonitrile at 115℃; for 16h; Sealed tube; Green chemistry;82%
With copper(II) choride dihydrate; ammonium formate; potassium carbonate In neat (no solvent) at 135℃; under 760.051 Torr; for 24h; Sealed tube; Schlenk technique; Green chemistry;75%
1-bromo-3-chlorobenzene
108-37-2

1-bromo-3-chlorobenzene

potassiumhexacyanoferrate(II) trihydrate

potassiumhexacyanoferrate(II) trihydrate

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With [Pd{C6H4(CH2N(CH2Ph)2)}(μ-Br)]2; tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 0.0833333h; Microwave irradiation; chemoselective reaction;90%
With C20H28Br2N2O4Pd2; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 0.333333h; Inert atmosphere; Microwave irradiation; chemoselective reaction;58%
1-bromo-3-chlorobenzene
108-37-2

1-bromo-3-chlorobenzene

potassium hexacyanoferrate(II) hydrate

potassium hexacyanoferrate(II) hydrate

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With [Pd{C6H2(CH2CH2NH2)-(OMe)2-2,3}(μ-Br)]2; tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 130℃; for 0.0833333h; Microwave irradiation; Green chemistry; chemoselective reaction;90%
3-chlorophenylboronic acid
63503-60-6

3-chlorophenylboronic acid

N-(4-chlorophenyl)-N-cyano-4-methylbenzenesulfonamide
119986-58-2

N-(4-chlorophenyl)-N-cyano-4-methylbenzenesulfonamide

A

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

B

4-methyl-N-(4-chlorophenyl)benzenesulfonamide
2903-34-6

4-methyl-N-(4-chlorophenyl)benzenesulfonamide

Conditions
ConditionsYield
With Fe3O4/SiO2/(3-chloropropyl)trimethoxysilane/2,2′-(4,4′-(propane-1,3-diyl)bis(piperazine-4,1-diyl))- diethanamine/Pd In acetonitrile for 16h; Catalytic behavior; Reflux;A 90%
B n/a
3-iodochlorobenzene
625-99-0

3-iodochlorobenzene

2-(dimethylamino)malononitrile
19555-13-6

2-(dimethylamino)malononitrile

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With copper(II) orthophosphate In N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere; Sealed tube;89%
3-Chlorobenzaldehyde
587-04-2

3-Chlorobenzaldehyde

A

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

B

3-chlorobenzaldehyde oxime
34158-71-9

3-chlorobenzaldehyde oxime

Conditions
ConditionsYield
With hydroxylamine hydrochloride; FeOO280 In toluene for 7h; Condensation; dehydration; Heating;A 86%
B 14%
3-Cyanobenzoic acid
1877-72-1

3-Cyanobenzoic acid

A

3-cyanobromobenzene
6952-59-6

3-cyanobromobenzene

B

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With Bromotrichloromethane; trichloroisocyanuric acid; bromine at 10 - 120℃; for 0.5h; Photolysis;A 84%
B 10%
m-chlorobenzylamine
4152-90-3

m-chlorobenzylamine

A

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

B

N-(3-chlorobenzylidene)-1-(3-chlorophenyl)methylamine
161723-68-8

N-(3-chlorobenzylidene)-1-(3-chlorophenyl)methylamine

Conditions
ConditionsYield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; N,N-dimethylethylenediamine; copper(l) chloride In toluene at 80℃; for 24h; Sealed tube; Schlenk technique; chemoselective reaction;A 82%
B n/a
With iodine; tert-butylamine In acetonitrile for 6h; Ambient temperature;A 86 % Chromat.
B 9 % Chromat.
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; C63H51N2O3P2Ru(1+)*ClO4(1-); oxygen In toluene at 90℃; under 760.051 Torr; for 20h;A 50 %Chromat.
B 20 %Chromat.
3-chlorophenylacetic acid
1878-65-5

3-chlorophenylacetic acid

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With oxygen; copper(II) trifluoroacetate; urea In dimethyl sulfoxide at 110℃; for 38h; Green chemistry;80%
3'-Chloroacetophenone
99-02-5

3'-Chloroacetophenone

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With oxygen; copper(l) cyanide In dimethyl sulfoxide at 150℃;78%
3-chlorobenzoate
535-80-8

3-chlorobenzoate

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With aluminum oxide; aminosulfonic acid; urea for 0.0833333h; Irradiation;77%
With ammonium hydroxide; thionyl chloride 2.) dioxane, 3.) reflux; Multistep reaction;
N-cyano-N-phenyl-p-toluenesulfonamide
55305-43-6

N-cyano-N-phenyl-p-toluenesulfonamide

3-chlorophenylboronic acid
63503-60-6

3-chlorophenylboronic acid

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With hydroxo(1,5-cyclooctadiene)rhodium (I) dimer; potassium carbonate In 1,4-dioxane at 80℃; for 4h; Inert atmosphere;76%
3-Chlorobenzaldehyde
587-04-2

3-Chlorobenzaldehyde

A

3-chlorobenzamide
618-48-4

3-chlorobenzamide

B

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With [Ru(η6-C6Me6)Cl2(tris(dimethylamino)phosphine)]; hydroxylamine hydrochloride; sodium hydrogencarbonate In water at 100℃; for 7h; Inert atmosphere; Sealed tube; Green chemistry;A 74%
B n/a
1-bromo-3-chlorobenzene
108-37-2

1-bromo-3-chlorobenzene

2,2-dimethylmalononitrile
7321-55-3

2,2-dimethylmalononitrile

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
Stage #1: 1-bromo-3-chlorobenzene With TurboGrignard In tetrahydrofuran at 0℃; for 5h;
Stage #2: 2,2-dimethylmalononitrile In tetrahydrofuran at 0 - 23℃; for 1h;
73%
3-Carboxyphenol
99-06-9

3-Carboxyphenol

acetonitrile
75-05-8

acetonitrile

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

Conditions
ConditionsYield
With tetrachloromethane; bis(acetylacetonate)oxovanadium at 150℃; for 6h; Autoclave;72%
(E)-3-chlorobenzaldehyde oxime
3717-33-7, 34158-71-9, 4006-79-5

(E)-3-chlorobenzaldehyde oxime

acetonitrile
75-05-8

acetonitrile

A

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

B

3-(3-chlorophenyl)-5-methyl-1,2,4-oxadiazole
95124-66-6

3-(3-chlorophenyl)-5-methyl-1,2,4-oxadiazole

C

3-chlorobenzoate
535-80-8

3-chlorobenzoate

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate at 70℃; for 1h;A n/a
B 70%
C 7%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

3-chloro-N-hydroxy-benzamidine
22179-77-7

3-chloro-N-hydroxy-benzamidine

Conditions
ConditionsYield
With hydroxylamine monohydrate In ethanol at 90℃; for 1h; Sealed tube;100%
With sodium hydroxide; hydroxylamine hydrochloride In ethanol; water at 80℃; for 2h;85.9%
With hydroxylamine hydrochloride; sodium hydrogencarbonate In ethanol; water at 25℃; for 70h;80%
ethanol
64-17-5

ethanol

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

ethyl 3-chlorobenzimidate hydrochloride
60612-87-5

ethyl 3-chlorobenzimidate hydrochloride

Conditions
ConditionsYield
With hydrogenchloride at 0 - 20℃; for 16.33h;100%
With hydrogenchloride at 0 - 20℃; for 16.3333h;100%
With hydrogenchloride at 0 - 20℃; for 16.3333h;100%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

5-(m-chlorophenyl)tetrazole
41421-28-7

5-(m-chlorophenyl)tetrazole

Conditions
ConditionsYield
Stage #1: 3-chloro-benzonitrile With sodium azide In N,N-dimethyl-formamide at 120℃; for 36h;
Stage #2: With hydrogenchloride In water; ethyl acetate for 0.0833333h;
99%
With sodium azide at 120℃; for 0.0833333h;98%
With sodium azide at 130℃; for 6.75h; Catalytic behavior;98%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

3-chlorobenzamide
618-48-4

3-chlorobenzamide

Conditions
ConditionsYield
With water; potassium carbonate at 150℃; for 0.25h; Microwave irradiation;99%
With C12H24O16Ru3*2H2O In water at 110℃; for 1h; Catalytic behavior; Schlenk technique; Inert atmosphere; Autoclave;99%
With polystyrene-triethylenetetramine anchored ruthenium(II) complex; air In water at 90℃; for 7h; Green chemistry;95%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

3-chloro-benzylamine; hydrochloride
42365-42-4

3-chloro-benzylamine; hydrochloride

Conditions
ConditionsYield
Stage #1: 3-chloro-benzonitrile With [2,6-η6:η1-bis(2,4,6-trimethylphenyl)phenylthiolato]triethylphosphineruthenium(II)tetrakis[3,5-bis(trifluoromethyl)phenyl]borate; diethylphenylsilane at 20℃; for 18h; Glovebox; Inert atmosphere;
Stage #2: With hydrogenchloride In diethyl ether at 20℃; for 1h; Glovebox; Inert atmosphere;
99%
Stage #1: 3-chloro-benzonitrile With MnBr(CO)2[NH(CH2CH2P(iPr)2)2]; hydrogen; sodium t-butanolate In toluene at 120℃; under 37503.8 Torr; for 24h; Autoclave;
Stage #2: With hydrogenchloride In diethyl ether
96%
Stage #1: 3-chloro-benzonitrile With cobalt pivalate; 1,1,3,3-Tetramethyldisiloxane; tert-butylisonitrile at 80℃; for 24h;
Stage #2: With hydrogenchloride In diethyl ether at 20℃; for 0.5h;
95%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

phenylboronic acid
98-80-6

phenylboronic acid

3-phenylbenzonitrile
24973-50-0

3-phenylbenzonitrile

Conditions
ConditionsYield
With C16H36N(1+)*C32H25Cl2Fe2N2O3PdS(1-); potassium carbonate In water for 0.25h; Suzuki coupling; Microwave irradiation;99%
With caesium carbonate; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane for 1h; Suzuki-Miyaura coupling; Heating;98%
With potassium phosphate; 2-(diphenylphosphino)phenylferrocene; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 90℃; for 24h; Suzuki-Miyaura coupling;96%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

n-pentylmagnesium bromide
693-25-4

n-pentylmagnesium bromide

1-(3-chlorophenyl)hexan-1-one

1-(3-chlorophenyl)hexan-1-one

Conditions
ConditionsYield
Stage #1: 3-chloro-benzonitrile; n-pentylmagnesium bromide In tetrahydrofuran; diethyl ether at 0 - 20℃; Inert atmosphere;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; diethyl ether at 0 - 20℃;
99%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

pentafluorophenyl potassium carboxylate
58521-27-0

pentafluorophenyl potassium carboxylate

2′,3′,4′,5′,6′-pentafluorobiphenyl-3-carbonitrile

2′,3′,4′,5′,6′-pentafluorobiphenyl-3-carbonitrile

Conditions
ConditionsYield
With palladium diacetate; tricyclohexylphosphine In diethylene glycol dimethyl ether at 130℃; for 24h; Inert atmosphere; Sealed tube;99%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

pentylmagnesium chloride
6393-56-2

pentylmagnesium chloride

1-(3-chlorophenyl)hexan-1-one

1-(3-chlorophenyl)hexan-1-one

Conditions
ConditionsYield
Stage #1: 3-chloro-benzonitrile; pentylmagnesium chloride In tetrahydrofuran; diethyl ether at 20℃; for 144h; Inert atmosphere;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; diethyl ether at 0℃;
99%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

cyclopentylzinc bromide lithium chloride

cyclopentylzinc bromide lithium chloride

3-cyclopentylbenzonitrile

3-cyclopentylbenzonitrile

Conditions
ConditionsYield
With Pd-PEPPSI-IPrAn In tetrahydrofuran; 1,4-dioxane at 0 - 20℃; for 0.5h; Negishi Coupling; Schlenk technique; Inert atmosphere;99%
styrene
292638-84-7

styrene

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

(E)-3-styrylbenzonitrile
14064-35-8

(E)-3-styrylbenzonitrile

Conditions
ConditionsYield
With tetrakis[μ-1-[(3-methoxyphenyl)methyl]-2-phenyl-3-[2-oxo-2-[(2-phenolato-kO)aminokN]ethyl]-1H-imidazoliumato-kC4]tetrapalladium; tetrabutylammomium bromide; sodium acetate at 140℃; for 16h; Heck Reaction;99%
With tetrabutylammomium bromide; sodium acetate; C84H60N12O8Pd4 at 140℃; for 2h; Heck Reaction; Inert atmosphere; Schlenk technique;99%
4,5,6,7-Tetrahydrocyclohexa-1,2,3-selenadiazol
35676-30-3

4,5,6,7-Tetrahydrocyclohexa-1,2,3-selenadiazol

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

3-(3-chlorophenyl)-4,5,6,7-tetrahydrobenzo[d][1,2]selenazole

3-(3-chlorophenyl)-4,5,6,7-tetrahydrobenzo[d][1,2]selenazole

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%
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%
3,5,5-Trimethylcyclohex-2-en-1-one
78-59-1

3,5,5-Trimethylcyclohex-2-en-1-one

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

3-((5,5-dimethyl-3-oxocyclohex-1-en-1-yl)methyl)benzonitrile

3-((5,5-dimethyl-3-oxocyclohex-1-en-1-yl)methyl)benzonitrile

Conditions
ConditionsYield
With 2-(2,6-dimethoxyphenyl)-1-methyl-3-(diphenylphosphino)-1H-indole; palladium diacetate; lithium tert-butoxide In 1,4-dioxane at 100℃; for 1h; Schlenk technique; Inert atmosphere;99%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

benzaldehyde
100-52-7

benzaldehyde

N-benzyl-1-(3-chlorophenyl)methanaminium chloride

N-benzyl-1-(3-chlorophenyl)methanaminium chloride

Conditions
ConditionsYield
Stage #1: 3-chloro-benzonitrile; benzaldehyde With hydrogen In 2-methyltetrahydrofuran at 100℃; under 11251.1 Torr; for 20h; High pressure; Autoclave;
Stage #2: With hydrogenchloride In diethyl ether
99%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

ethylenediamine
107-15-3

ethylenediamine

2-(3-chlorophenyl)-4,5-dihydro-1H-imidazole
27429-86-3

2-(3-chlorophenyl)-4,5-dihydro-1H-imidazole

Conditions
ConditionsYield
With tetraphosphorus decasulfide for 0.0416667h; microwave irradiation;98%
With toluene-4-sulfonic acid for 0.416667h; Reflux; neat (no solvent);92%
With sulfur at 20℃; for 0.116667h; ultrasonic irradiation;89%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

propan-1-ol-3-amine
156-87-6

propan-1-ol-3-amine

2-(3-chlorophenyl)-5,6-dihydro-4H-1,3-oxazine
91552-24-8

2-(3-chlorophenyl)-5,6-dihydro-4H-1,3-oxazine

Conditions
ConditionsYield
With Montmorillonite K-10 for 7h; Microwave irradiation;98%
With montmorillonite KSF at 30℃; for 0.166667h; Sonication;98%
With phosphotungstic acid for 0.121667h; Microwave irradiation; chemoselective reaction;90%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

di(p-tolyl)borinic acid
66117-64-4

di(p-tolyl)borinic acid

4'-methyl-[1,1'-biphenyl]-3-carbonitrile
133909-96-3

4'-methyl-[1,1'-biphenyl]-3-carbonitrile

Conditions
ConditionsYield
With NiCl2(Tris-(4-methoxy-phenyl)-phosphin)2; potassium phosphate tribasic trihydrate; P(p-CH3OC6H4)3 In toluene at 110℃; for 5h; Inert atmosphere;98%
With bis(triphenylphosphine)nickel(II) chloride; potassium phosphate tribasic trihydrate; 1-n-butyl-3-methylimidazolim bromide In toluene at 110℃; for 6h; Inert atmosphere;93%
ethyl 5-phenyl-1,2,3-thiadiazole-4-carboxylate
60474-27-3

ethyl 5-phenyl-1,2,3-thiadiazole-4-carboxylate

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

ethyl 3-(3-chlorophenyl)-5-phenylisothiazole-4-carboxylate

ethyl 3-(3-chlorophenyl)-5-phenylisothiazole-4-carboxylate

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; chloro(1,5-cyclooctadiene)rhodium(I) dimer In chlorobenzene at 130℃; for 1h; Glovebox;98%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

3-chlorobenzoate
535-80-8

3-chlorobenzoate

Conditions
ConditionsYield
With benzene-1,2-dicarboxylic acid for 0.666667h; microwave-irradiation;97%
With potassium hydroxide In ethylene glycol at 170℃; for 7h;
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

2-Methylphenylboronic acid
16419-60-6

2-Methylphenylboronic acid

2'-methyl-[1,1'-biphenyl]-3-carbonitrile
253678-80-7

2'-methyl-[1,1'-biphenyl]-3-carbonitrile

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); potassium phosphate monohydrate; 2-(2-methoxyphenyl)-1-methyl-3-(diphenylphosphino)-1H-indole In 1,4-dioxane at 90℃; for 24h; Suzuki-Miyaura coupling; Inert atmosphere;97%
With (2’,4’,6’-triisopropyl-[1,1’-biphenyl]-2-yl)-diphenylphosphine; potassium phosphate; palladium diacetate In tetrahydrofuran at 20℃; for 24h; Suzuki-Miyaura coupling;94%
With potassium phosphate monohydrate; 1-methyl-2-(2-(dicyclohexylphosphino)phenyl)-1H-benzoimidazole; palladium diacetate In 1,4-dioxane; 1,3,5-trimethyl-benzene at 135℃; for 24h; Suzuki-Miyaura coupling; Inert atmosphere;81%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

1-propylmagnesium chloride
2234-82-4

1-propylmagnesium chloride

1-(3-chlorophenyl)butan-1-one
21550-08-3

1-(3-chlorophenyl)butan-1-one

Conditions
ConditionsYield
Stage #1: 3-chloro-benzonitrile; 1-propylmagnesium chloride; copper(l) chloride In tetrahydrofuran; diethyl ether for 0.5h; Heating / reflux;
Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether; water at 20℃;
Stage #3: With water; hydrogenchloride at 90℃; for 1h;
97%
Stage #1: 3-chloro-benzonitrile; 1-propylmagnesium chloride In tetrahydrofuran; diethyl ether at 0 - 20℃; Inert atmosphere;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; diethyl ether at 0 - 20℃;
88%
Stage #1: 3-chloro-benzonitrile; 1-propylmagnesium chloride In tetrahydrofuran; diethyl ether at 0 - 20℃; for 96h; Inert atmosphere;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; diethyl ether at 20℃; for 1h;
88%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

cyclohexylmagnesiumchloride
931-51-1

cyclohexylmagnesiumchloride

(3-chlorophenyl)(cyclohexyl)methanone
211985-77-2

(3-chlorophenyl)(cyclohexyl)methanone

Conditions
ConditionsYield
Stage #1: 3-chloro-benzonitrile; cyclohexylmagnesiumchloride; copper(l) chloride In tetrahydrofuran; diethyl ether for 0.5h; Heating / reflux;
Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether; water at 20℃;
Stage #3: With water; hydrogenchloride at 90℃; for 1h;
97%
carbon monoxide
201230-82-2

carbon monoxide

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

3-Cyanobenzoic acid
1877-72-1

3-Cyanobenzoic acid

Conditions
ConditionsYield
With 1,3-bis(dicyclohexylphosphino)propane bis(tetrafluoroborate) salt; water; palladium diacetate; potassium carbonate In dimethyl sulfoxide at 100℃; under 760.051 Torr; for 15h;97%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

m-cyanophenol
873-62-1

m-cyanophenol

Conditions
ConditionsYield
With dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; boric acid; palladium diacetate; caesium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; for 24h; Schlenk technique; Inert atmosphere;97%
With tris(6,6'-diamino-2,2'-bipyridine); 4,4-diphenyl-1,3,5,7,8-pentamethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene; Br2Ni*3H2O; water; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide; acetonitrile at 20℃; for 24h; Glovebox; Irradiation; Inert atmosphere;91%
With trans-di(μ-acetato)bis[o-(di-o-tolyl-phosphino)benzyl]dipalladium(II); C29H45Pt; potassium carbonate In water; N,N-dimethyl-formamide at 115℃; for 0.5h; Inert atmosphere; Microwave irradiation;90%
1,1,1,3,5,5,5-heptamethyltrisiloxan
1873-88-7

1,1,1,3,5,5,5-heptamethyltrisiloxan

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

C14H24ClNO2Si3

C14H24ClNO2Si3

Conditions
ConditionsYield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 2.9-dimethyl-1,10-phenanthroline In 1,4-dioxane at 100℃; for 20h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Sealed tube; regioselective reaction;97%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

3-chloro-N-hydroxybenzimidamide
22179-77-7

3-chloro-N-hydroxybenzimidamide

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium carbonate In ethanol; water for 6h; Reflux;96%
With hydroxylamine hydrochloride; potassium carbonate In ethanol
With hydroxylamine hydrochloride; sodium carbonate In ethanol Heating;
dimethyl diazomalonate
6773-29-1

dimethyl diazomalonate

3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

4-Carbomethoxy-5-methoxy-2-(3'-chlorophenyl)oxazole
109345-74-6

4-Carbomethoxy-5-methoxy-2-(3'-chlorophenyl)oxazole

Conditions
ConditionsYield
dirhodium tetraacetate In chloroform for 8h; Heating;96%
dirhodium tetraacetate In chloroform Heating;96%
3-chloro-benzonitrile
766-84-7

3-chloro-benzonitrile

3-chlorothiobenzamide
2548-79-0

3-chlorothiobenzamide

Conditions
ConditionsYield
With sodium monohydrogen sulfide x-hydrate; magnesium(II) chloride hexahydrate In N,N-dimethyl-formamide at 20℃; for 2h;96%
With diammonium sulfide; 1,6-bis(3-methylimidazolium-1-yl)hexane dichloride at 70℃; for 0.05h;94%
With diphosphorus pentasulfide; ethanol for 4h; Heating;88%

766-84-7Relevant articles and documents

Biomass chitosan-derived nitrogen-doped carbon modified with iron oxide for the catalytic ammoxidation of aromatic aldehydes to aromatic nitriles

Wang, Wei David,Wang, Fushan,Chang, Youcai,Dong, Zhengping

, (2020/11/24)

Nitrogen-doped carbon catalysts have attracted increasing research attention due to several advantages for catalytic application. Herein, cost-effective, renewable biomass chitosan was used to prepare a N-doped carbon modified with iron oxide catalyst (Fe2O3@NC) for nitrile synthesis. The iron oxide nanoparticles were uniformly wrapped in the N-doped carbon matrix to prevent their aggregation and leaching. Fe2O3@NC-800, which was subjected to carbonization at 800 °C, exhibited excellent activity, selectivity, and stability in the catalytic ammoxidation of aromatic aldehydes to aromatic nitriles. This study may provide a new method for the fabrication of an efficient and cost-effective catalyst system for synthesizing nitriles.

Unprecedented Catalysis of Cs+Single Sites Confined in y Zeolite Pores for Selective Csp3-H Bond Ammoxidation: Transformation of Inactive Cs+Ions with a Noble Gas Electronic Structure to Active Cs+Single Sites

Acharyya, Shankha S.,Ghosh, Shilpi,Iwasawa, Yasuhiro,Kaneko, Takuma,Sasaki, Takehiko,Yoshida, Yusuke

, p. 6698 - 6708 (2021/06/25)

We report the transformation of Cs+ ions with an inactive noble gas electronic structure to active Cs+ single sites chemically confined in Y zeolite pores (Cs+/Y), which provides an unprecedented catalysis for oxidative cyanation (ammoxidation) of Csp3-H bonds with O2 and NH3, although in general, alkali and alkaline earth metal ions without a moderate redox property cannot activate Csp3-H bonds. The Cs+/Y catalyst was proved to be highly efficient in the synthesis of aromatic nitriles with yields >90% in the selective ammoxidation of toluene and its derivatives as test reactions. The mechanisms for the genesis of active Cs+ single sites and the ammoxidation pathway of Csp3-H bonds were rationalized by density functional theory (DFT) simulations. The chemical confinement of large-sized Cs+ ions with the pore architecture of a Y zeolite supercage rendered the highest occupied molecular orbital (HOMO)-lowest unoccupied molecular orbital (LUMO) gap reduction, HOMO component change, and preferable coordination arrangement for the selective reaction promotion, which provides a trimolecular assembly platform to enable the coordination-promoted concerted ammoxidation pathway working closely on each Cs+ single site. The new reaction pathway without involvement of O2-dissociated O atom and lattice oxygen differs from the traditional redox catalysis mechanisms for the selective ammoxidation.

An overview on the progress and development on the palladium catalyzed direct cyanation

Heydari, Somayyeh,Habibi, Davood,Reza Faraji, Ali,keypour, Hassan,Mahmoudabadi, Masoumeh

, (2020/10/02)

Generation of the positive CN ion and the corresponding direct cyanation are both extremely important for cyanation of aromatic compounds. Hereby, we would like to report the simultaneous use of the new Pd nano-catalyst as well as the three types of the N-arylsulfonyl cyanamides (A, B and C) as potent reagents for the in situ generation of the positive CN ion for the direct cyanation of phenylboronic acids in acetonitrile at reflux conditions.

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