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766-05-2

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766-05-2 Usage

Uses

Cyclohexanecarbonitrile was used as model substrate in rhodium-catalyzed direct ortho-arylation reactions of phenylazoles using arylboron reagents. It was used as probe in the synthesis of an asymmetric, C-magnesiated nitrile.

Synthesis Reference(s)

Journal of the American Chemical Society, 93, p. 4318, 1971 DOI: 10.1021/ja00746a052Tetrahedron Letters, 25, p. 3301, 1984 DOI: 10.1016/S0040-4039(01)81369-1The Journal of Organic Chemistry, 54, p. 4476, 1989 DOI: 10.1021/jo00279a047

Check Digit Verification of cas no

The CAS Registry Mumber 766-05-2 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, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 766-05:
(5*7)+(4*6)+(3*6)+(2*0)+(1*5)=82
82 % 10 = 2
So 766-05-2 is a valid CAS Registry Number.
InChI:InChI=1/C7H11N/c8-6-7-4-2-1-3-5-7/h7H,1-5H2

766-05-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name Cyclohexanecarbonitrile

1.2 Other means of identification

Product number -
Other names tetrahydrobenzonitrile

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:766-05-2 SDS

766-05-2Synthetic route

cyclohexanecarbaldoxime
4715-11-1

cyclohexanecarbaldoxime

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

Conditions
ConditionsYield
With nickel(II) chloride dihydrate In acetonitrile at 80℃; Molecular sieve; Inert atmosphere;100%
With MIL-100 (Fe)-NH4F In o-xylene at 153 - 160℃; for 1h; Dean-Stark; Inert atmosphere;97%
With phosphoric acid diethyl ester 2-phenylbenzimidazol-1-yl ester; triethylamine In acetonitrile at 20℃; for 0.916667h;94%
N(C4H9)4(1+)*Cu(1+)*2CN(1-)=(N(C4H9)4)[Cu(CN)2]

N(C4H9)4(1+)*Cu(1+)*2CN(1-)=(N(C4H9)4)[Cu(CN)2]

cyclohexyl chloride
542-18-7

cyclohexyl chloride

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide In acetonitrile at 20℃; for 4h; Reagent/catalyst; Inert atmosphere; UV-irradiation;98%
cyclohexylmethylamine
3218-02-8

cyclohexylmethylamine

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

Conditions
ConditionsYield
With pyridine; Oxone; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; Pyridine hydrobromide In dichloromethane at 20℃; for 12h; Green chemistry;97%
With pyridine; 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate In dichloromethane at 20℃; for 12h; Inert atmosphere;95%
With water; potassium hydroxide at 25℃; pH=13.6; Electrochemical reaction;95%
cyclohexanylcarbonyl chloride
2719-27-9

cyclohexanylcarbonyl chloride

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

Conditions
ConditionsYield
With sulfonamide In sulfolane at 120℃; for 3h;95%
1-cyclohexanecarboxaldehyde N,N-dimethylhydrazone
19888-79-0

1-cyclohexanecarboxaldehyde N,N-dimethylhydrazone

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

Conditions
ConditionsYield
With pyridine; dihydrogen peroxide; acetic acid; methyltrioxorhenium(VII) In water; acetonitrile for 0.25h;95%
Multi-step reaction with 2 steps
1: benzene / 7 h / Heating
2: NaOMe / methanol / 4 h / Heating
View Scheme
cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

Conditions
ConditionsYield
With ammonia at 210℃; Inert atmosphere;95%
With nitrogen; ammonia at 240℃; Heating;88%
With ammonium hydroxide; dihydrogen peroxide In water; acetonitrile at 50℃; for 8h;76%
cyclohexanecarbaldehyde
2043-61-0

cyclohexanecarbaldehyde

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

Conditions
ConditionsYield
With ammonia; iodine In tetrahydrofuran; water at 20℃; for 0.166667h;94%
Stage #1: cyclohexanecarbaldehyde With 3 A molecular sieve; hydroxylamine hydrochloride; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 20℃; for 10h;
Stage #2: With ethyl phosphodichloridite In dichloromethane at 20℃; for 5h; Further stages.;
92%
With bismuth(lll) trifluoromethanesulfonate; acetylhydroxamic acid In acetonitrile for 24h; Reflux;88%
cyclohexylcarboxamide
1122-56-1

cyclohexylcarboxamide

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

Conditions
ConditionsYield
With trichloromethyl chloroformate In various solvent(s) 0-5 deg C then heated to 60 deg C, 5 min;93%
With lead acetate In dichloromethane for 12h; Reflux;90%
With oxalyl dichloride; triethylamine In dimethyl sulfoxide; acetonitrile at 20℃; for 0.666667h; Swern Oxidation;87%
Dimethyl-dithiocarbamic acid 1-cyano-cyclohexyl ester
61540-43-0

Dimethyl-dithiocarbamic acid 1-cyano-cyclohexyl ester

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene at 80℃; for 5h;93%
methanesulfonyl cyanide
24225-08-9

methanesulfonyl cyanide

Cyclohexanecarboxylic acid 2-thioxo-2H-pyridin-1-yl ester
105398-69-4

Cyclohexanecarboxylic acid 2-thioxo-2H-pyridin-1-yl ester

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

Conditions
ConditionsYield
In dichloromethane at 0℃; Irradiation;90%
N-cyanoimidazole
36289-36-8

N-cyanoimidazole

cyclohexylmagnesium bromide
931-50-0

cyclohexylmagnesium bromide

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

Conditions
ConditionsYield
In tetrahydrofuran at -78℃; for 0.5h; cyanation;90%
(E)-N-(cyclohexylmethylidene)hydroxylamine
30950-35-7

(E)-N-(cyclohexylmethylidene)hydroxylamine

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

Conditions
ConditionsYield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 4 A molecular sieve In acetonitrile at 80℃; for 0.166667h;90%
Cyclohexanethiol
1569-69-3

Cyclohexanethiol

tetra-n-butylammonium cyanide
10442-39-4

tetra-n-butylammonium cyanide

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

Conditions
ConditionsYield
With triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 20℃; for 5h;90%
2-(cyclohexyloxy)tetrahydro-2H-pyran
709-83-1

2-(cyclohexyloxy)tetrahydro-2H-pyran

tetra-n-butylammonium cyanide
10442-39-4

tetra-n-butylammonium cyanide

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

Conditions
ConditionsYield
With triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile for 7h; Heating;90%
cyclohexane
110-82-7

cyclohexane

3-oxo-1λ3-benzo[d][1,2]iodaoxole-1(3H)-carbonitrile
172876-96-9

3-oxo-1λ3-benzo[d][1,2]iodaoxole-1(3H)-carbonitrile

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

Conditions
ConditionsYield
With tert-Butyl peroxybenzoate In ethyl acetate at 110℃; for 16h; Solvent; Temperature; Reagent/catalyst; Time; Sealed tube; Inert atmosphere; Glovebox;90%
P-toluenesulfonyl cyanide
19158-51-1

P-toluenesulfonyl cyanide

Cyclohexanecarboxylic acid 2-thioxo-2H-pyridin-1-yl ester
105398-69-4

Cyclohexanecarboxylic acid 2-thioxo-2H-pyridin-1-yl ester

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

Conditions
ConditionsYield
In dichloromethane at 0℃; Irradiation;88%
Cyclohexanecarboxylic acid
98-89-5

Cyclohexanecarboxylic acid

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

Conditions
ConditionsYield
With thionyl chloride; sulfonamide In sulfolane at 120℃; for 3h;88%
With sulfuric acid; acetonitrile at 95℃; for 4h;59%
Multi-step reaction with 2 steps
1.1: thionyl chloride / tetrahydrofuran / 1 h / 50 °C
1.2: 0.08 h / 0 °C
2.1: palladium diacetate; Selectfluor; acetonitrile / 18 h / 20 °C
View Scheme
With indium(III) chloride; acetonitrile at 200℃; under 11251.1 Torr; for 14h;86 %Chromat.
1-(1-Cyanocyclohexyl)-2-carbomethoxyhydrazine
61827-29-0

1-(1-Cyanocyclohexyl)-2-carbomethoxyhydrazine

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

Conditions
ConditionsYield
With sodium cyanide In methanol at 17℃; for 4.7h; electrolysis;86%
cyclohexylmethylamine
3218-02-8

cyclohexylmethylamine

A

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

B

cyclohexylcarboxamide
1122-56-1

cyclohexylcarboxamide

C

Cyclohexanecarboxylic acid
98-89-5

Cyclohexanecarboxylic acid

Conditions
ConditionsYield
With water; oxygen at 140℃; under 3800.26 Torr; for 24h;A n/a
B 86%
C n/a
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

cyclohexanylcarbonyl chloride
2719-27-9

cyclohexanylcarbonyl chloride

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine In toluene at 110℃; for 1h; Schlenk technique; Inert atmosphere;86%
P-toluenesulfonyl cyanide
19158-51-1

P-toluenesulfonyl cyanide

cyclohexylzinc iodide
121883-35-0

cyclohexylzinc iodide

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 25℃;84%
1-(1-Cyanocyclohexyl)-2-acetylhydrazine
27702-91-6

1-(1-Cyanocyclohexyl)-2-acetylhydrazine

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

Conditions
ConditionsYield
With sodium cyanide In methanol at 17℃; for 4.7h; electrolysis;83%
tetra-n-butylammonium cyanide
10442-39-4

tetra-n-butylammonium cyanide

cyclohexanol
108-93-0

cyclohexanol

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

Conditions
ConditionsYield
With triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 20℃; for 0.166667h;83%
2-cyclohexyl-1,3-dioxolane
4362-48-5

2-cyclohexyl-1,3-dioxolane

A

cyclohexanecarbaldoxime
4715-11-1

cyclohexanecarbaldoxime

B

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

Conditions
ConditionsYield
With hydroxylamine hydrochloride; toluene-4-sulfonic acid In ethanol for 2h; Heating;A 8%
B 81%
Allyl 1-cyanocyclohexanecarboxylate
102804-62-6

Allyl 1-cyanocyclohexanecarboxylate

A

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

B

cyclohex-1-enecarbonitrile
1855-63-6

cyclohex-1-enecarbonitrile

Conditions
ConditionsYield
tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine In various solvent(s) for 1h; Heating; Yields of byproduct given;A n/a
B 81%
pyridin-2-yl cyanate
175351-40-3

pyridin-2-yl cyanate

cyclohexylmagnesium bromide
931-50-0

cyclohexylmagnesium bromide

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

Conditions
ConditionsYield
In tetrahydrofuran at 0℃; for 0.166667h;80%
N'-[1-Cyclohexyl-meth-(Z)-ylidene]-N,N-dimethyl-hydrazine
10424-96-1

N'-[1-Cyclohexyl-meth-(Z)-ylidene]-N,N-dimethyl-hydrazine

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

Conditions
ConditionsYield
With dihydrogen peroxide; sodium carbonate; acetonitrile at 55℃; for 18h;80%
methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

P-toluenesulfonyl cyanide
19158-51-1

P-toluenesulfonyl cyanide

(Prop-2-ene-1-sulfonyl)-cyclohexane

(Prop-2-ene-1-sulfonyl)-cyclohexane

A

methyl cyclohexylcarboxylate
4630-82-4

methyl cyclohexylcarboxylate

B

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

Conditions
ConditionsYield
Stage #1: carbon monoxide; P-toluenesulfonyl cyanide; (Prop-2-ene-1-sulfonyl)-cyclohexane With 1,1'-azobis(1-cyanocyclohexanenitrile) In n-heptane at 100℃; under 98800 Torr;
Stage #2: methanol In n-heptane at 20℃;
A 80%
B 15%
dimethylbromosulphonium bromide
50450-21-0

dimethylbromosulphonium bromide

cyclohexylcarboxamide
1122-56-1

cyclohexylcarboxamide

A

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

B

dimethyl sulfoxide
67-68-5

dimethyl sulfoxide

Conditions
ConditionsYield
In acetonitrile for 3h; Reflux;A 80%
B n/a
cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

2-ethyl-1-bromobutane
3814-34-4

2-ethyl-1-bromobutane

1-(2-ethylbutyl)cyclohexane-1-carbonitrile

1-(2-ethylbutyl)cyclohexane-1-carbonitrile

Conditions
ConditionsYield
Stage #1: cyclohexane carbonitrile With n-butyllithium; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide In tetrahydrofuran; hexane at -15 - 8℃;
Stage #2: 2-ethyl-1-bromobutane In tetrahydrofuran; hexane at 3 - 26℃; Product distribution / selectivity;
100%
Stage #1: cyclohexane carbonitrile With methylmagnesium chloride; diethylamine In tetrahydrofuran at 20 - 25℃; for 1.5h;
Stage #2: 2-ethyl-1-bromobutane In tetrahydrofuran at 45 - 50℃; for 2h; Product distribution / selectivity;
97.6%
With methylmagnesium chloride; diethylamine In tetrahydrofuran at 45.3 - 70.2℃; for 2.25h; Product distribution / selectivity; Inert atmosphere;95%
cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

allyl bromide
106-95-6

allyl bromide

1-allylcyclohexane-1-nitrile
676132-37-9

1-allylcyclohexane-1-nitrile

Conditions
ConditionsYield
Stage #1: cyclohexane carbonitrile With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: allyl bromide In tetrahydrofuran at -78 - 20℃; Inert atmosphere;
100%
Stage #1: cyclohexane carbonitrile With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h;
Stage #2: allyl bromide In tetrahydrofuran at 20℃;
94%
Stage #1: cyclohexane carbonitrile With lithium diisopropyl amide In tetrahydrofuran Inert atmosphere;
Stage #2: allyl bromide Inert atmosphere;
90%
cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

aniline
62-53-3

aniline

N-(cyclohexylmethyl)aniline
79952-92-4

N-(cyclohexylmethyl)aniline

Conditions
ConditionsYield
With ammonium acetate; hydrogen; palladium on activated charcoal In methanol at 20℃; for 24h;100%
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h;99%
ethanol
64-17-5

ethanol

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

ethyl cyclohexanecarboximidate hydrochloride
43002-69-3

ethyl cyclohexanecarboximidate hydrochloride

Conditions
ConditionsYield
With hydrogenchloride at 0 - 20℃; for 12h; Inert atmosphere;100%
With hydrogenchloride In 1,4-dioxane at 20℃; for 48h;74%
With hydrogenchloride for 3h; Inert atmosphere; Cooling with ice;73%
methanol
67-56-1

methanol

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

methyl cyclohexanecarboximidate
66493-03-6

methyl cyclohexanecarboximidate

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether at 0℃; for 0.333333h;100%
With hydrogenchloride at 0℃; for 0.333333h;
cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

cyclohexylcarboxamide
1122-56-1

cyclohexylcarboxamide

Conditions
ConditionsYield
With [RuH(tBu-PNP(-))(CO)]; water In tert-butyl alcohol at 50℃; for 24h;99%
With water; tricyclohexylphosphine; {Rh(OMe)(cod)}2 In isopropyl alcohol at 25℃; for 72h;96%
With N-ethyl-N-hydroxy-ethanamine; water; copper diacetate In ethanol at 35℃; for 3h;89%
cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

cyclohexylmethylamine
3218-02-8

cyclohexylmethylamine

Conditions
ConditionsYield
With [Ru(H)(BH4)(CO)(PPh3)(3-(di-tert-butylphosphino)-N-((1-methyl-1H-imidazol-2 yl)methyl)propylamine)]; hydrogen In isopropyl alcohol at 70℃; for 3h; Inert atmosphere; Autoclave;99%
With ammonia; hydrogen In toluene at 120℃; under 22502.3 Torr; for 16h; Autoclave;92%
With hydrogen In ethanol at 88℃; under 37503.8 Torr; for 0.5h;91%
benzyl bromide
100-39-0

benzyl bromide

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

1-benzylcyclohexanecarbonitrile
104367-54-6

1-benzylcyclohexanecarbonitrile

Conditions
ConditionsYield
Stage #1: cyclohexane carbonitrile With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.5h;
Stage #2: benzyl bromide In tetrahydrofuran; hexane at -78 - 20℃;
99%
Stage #1: cyclohexane carbonitrile With lithium diisopropyl amide In tetrahydrofuran at -78 - 20℃; for 1h;
Stage #2: benzyl bromide With methyl cyanoformate In tetrahydrofuran at -78 - 20℃; for 2h; chemoselective reaction;
98%
cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

dimethyl sulfate
77-78-1

dimethyl sulfate

Phenyl azide
622-37-7

Phenyl azide

C14H18N4

C14H18N4

Conditions
ConditionsYield
Stage #1: cyclohexane carbonitrile With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.333333h;
Stage #2: Phenyl azide With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran at -78 - 20℃; for 1h;
Stage #3: dimethyl sulfate at 20℃; for 1h;
99%
cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

dimethyl sulfate
77-78-1

dimethyl sulfate

Phenyl azide
622-37-7

Phenyl azide

C14H18N4

C14H18N4

Conditions
ConditionsYield
Stage #1: cyclohexane carbonitrile With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.333333h;
Stage #2: Phenyl azide With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran at -78 - 20℃; for 1h;
Stage #3: dimethyl sulfate at -78℃; for 1h;
99%
2-fluoropyridine
372-48-5

2-fluoropyridine

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

1-(pyridin-2-yl)cyclohexanecarbonitrile

1-(pyridin-2-yl)cyclohexanecarbonitrile

Conditions
ConditionsYield
With potassium hexamethylsilazane In toluene at 60℃; for 2h;99%
iodobenzene
591-50-4

iodobenzene

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

Cyclohexyl phenyl ketone
712-50-5

Cyclohexyl phenyl ketone

Conditions
ConditionsYield
Stage #1: iodobenzene; cyclohexane carbonitrile With iodine; magnesium In tetrahydrofuran at 83 - 85℃;
Stage #2: With sulfuric acid In water at 20 - 25℃; for 2h;
99%
cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

o-toluidine
95-53-4

o-toluidine

2-cyclohexylcarbonyl-6-methylaniline
205990-43-8

2-cyclohexylcarbonyl-6-methylaniline

Conditions
ConditionsYield
Stage #1: cyclohexane carbonitrile; o-toluidine With boron trichloride In toluene at 20℃; for 1h; Addition;
Stage #2: With aluminium trichloride In acetonitrile for 5h; Rearrangement; Heating;
Stage #3: With hydrogenchloride In acetonitrile for 2.5h; Hydrolysis; Heating;
98.4%
cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

aniline
62-53-3

aniline

N'-phenylcyclohexanecarboximidamide

N'-phenylcyclohexanecarboximidamide

Conditions
ConditionsYield
With aluminium trichloride98%
With aluminum (III) chloride at 120℃;
cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

cyclohexanecarboximidamide hydrochloride
2498-48-8

cyclohexanecarboximidamide hydrochloride

Conditions
ConditionsYield
Stage #1: cyclohexane carbonitrile With hydrogenchloride; methanol In diethyl ether at 0℃;
Stage #2: With ammonia In ethanol
98%
Multi-step reaction with 2 steps
1: 31 g / HCl (gas) / diethyl ether; methanol / 0 °C
2: 9 g / NH3 / ethanol / 24 h / 0 °C
View Scheme
Stage #1: cyclohexane carbonitrile With hydrogenchloride; ethanol for 3h; Pinner Amidine Synthesis; Inert atmosphere; Cooling with ice;
Stage #2: With ammonia In methanol at 20℃; for 24h; Pinner Amidine Synthesis; Inert atmosphere;
835 mg
cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

tert-butyl alcohol
75-65-0

tert-butyl alcohol

cyclohexanecarboxylic acid N-t-butylamide
6941-24-8

cyclohexanecarboxylic acid N-t-butylamide

Conditions
ConditionsYield
With 1-methyl-3-(4-sulfonylbutyl)-1H-imidazol-3-ium trifluoromethanesulfonate at 60℃; for 5h; Ritter reaction; Inert atmosphere; Ionic liquid;98%
With silica boron-sulfuric acid nanoparticles at 20℃; for 0.333333h; Ritter reaction; Neat (no solvent);91%
pinacolborane

pinacolborane

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

C23H45B2N

C23H45B2N

Conditions
ConditionsYield
With sodium triethylborohydride In neat (no solvent) at 20℃; for 3h; Inert atmosphere; Glovebox; Green chemistry;98%
bromobenzene
108-86-1

bromobenzene

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

Cyclohexyl phenyl ketone
712-50-5

Cyclohexyl phenyl ketone

Conditions
ConditionsYield
Stage #1: bromobenzene; cyclohexane carbonitrile With iodine; magnesium In tetrahydrofuran at 80 - 85℃;
Stage #2: With sulfuric acid In water at 20 - 25℃; for 2h;
98%
bromostyrene
103-64-0

bromostyrene

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

p-toluidine
106-49-0

p-toluidine

C29H33N3

C29H33N3

Conditions
ConditionsYield
With gallium(III) trichloride; 2,4-lutidine In 2-methyltetrahydrofuran; isopropyl alcohol at 85℃; for 4h; Reagent/catalyst; Solvent; Inert atmosphere;97.6%
4-(2-bromo-vinyl)-anisole
27570-08-7, 60592-52-1, 6303-59-9

4-(2-bromo-vinyl)-anisole

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

aniline
62-53-3

aniline

C29H33N3O

C29H33N3O

Conditions
ConditionsYield
With gallium(III) trichloride; 2,4-lutidine In 2-methyltetrahydrofuran; isopropyl alcohol at 70℃; for 6h; Reagent/catalyst; Solvent; Inert atmosphere;97.5%
1-(2-bromovinyl)-4-chlorobenzene
66482-29-9, 66482-30-2, 125428-11-7

1-(2-bromovinyl)-4-chlorobenzene

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

aniline
62-53-3

aniline

C28H30ClN3

C28H30ClN3

Conditions
ConditionsYield
With gallium(III) trichloride; 2,4-lutidine In 2-methyltetrahydrofuran; isopropyl alcohol at 80℃; for 5h; Reagent/catalyst; Solvent; Inert atmosphere;97.3%
(E)-(5-bromopent-3-en-2-yloxy)tertbutyldimethylsilane
1372806-96-6

(E)-(5-bromopent-3-en-2-yloxy)tertbutyldimethylsilane

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

C18H33NOSi
1372806-98-8

C18H33NOSi

Conditions
ConditionsYield
Stage #1: cyclohexane carbonitrile With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: (E)-(5-bromopent-3-en-2-yloxy)tertbutyldimethylsilane In tetrahydrofuran; hexane at -78 - 25℃;
97%
acetic acid tert-butyl ester
540-88-5

acetic acid tert-butyl ester

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

cyclohexanecarboxylic acid N-t-butylamide
6941-24-8

cyclohexanecarboxylic acid N-t-butylamide

Conditions
ConditionsYield
With silica sulfuric acid at 60℃; for 3.08333h; Reagent/catalyst; Temperature; Ritter Amidation; Green chemistry;97%
4-bromobut-1-yne
38771-21-0

4-bromobut-1-yne

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

1-(but-3-yn-1-yl)cyclohexane-1-carbonitrile

1-(but-3-yn-1-yl)cyclohexane-1-carbonitrile

Conditions
ConditionsYield
Stage #1: cyclohexane carbonitrile With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: 4-bromobut-1-yne In tetrahydrofuran; hexane at -78 - 24℃; for 14h; Inert atmosphere;
97%
cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

chlorobenzene
108-90-7

chlorobenzene

Cyclohexyl phenyl ketone
712-50-5

Cyclohexyl phenyl ketone

Conditions
ConditionsYield
Stage #1: cyclohexane carbonitrile; chlorobenzene With iodine; magnesium In tetrahydrofuran at 85℃;
Stage #2: With sulfuric acid In water at 20 - 25℃; for 2h;
97%
methanol
67-56-1

methanol

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

methyl cyclohexanecarboximidate hydrochloride
94052-40-1

methyl cyclohexanecarboximidate hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In hexane at 0℃; for 3h;96%
With hydrogenchloride; diethyl ether
With hydrogenchloride In methanol; diethyl ether at 0℃;31 g
2-Iodobenzyl bromide
40400-13-3

2-Iodobenzyl bromide

cyclohexane carbonitrile
766-05-2

cyclohexane carbonitrile

1-(2-iodobenzyl)cyclohexanecarbonitrile
445006-90-6

1-(2-iodobenzyl)cyclohexanecarbonitrile

Conditions
ConditionsYield
Stage #1: cyclohexane carbonitrile With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: 2-Iodobenzyl bromide In tetrahydrofuran; hexane at -78 - 20℃; Further stages.;
96%

766-05-2Relevant articles and documents

Method for dehydrating primary amide into nitriles under catalysis of cobalt

-

Paragraph 0096-0098, (2021/06/21)

The invention provides a method for dehydrating primary amide into nitrile. The method comprises the following steps: mixing primary amide (II), silane, sodium triethylborohydride, aminopyridine imine tridentate nitrogen ligand cobalt complex (I) and a reaction solvent under the protection of inert gas, carrying out reacting at 60-100 DEG C for 6-24 hours, and post-treating reaction liquid to obtain a nitrile compound (III). According to the invention, an effective method for preparing nitrile compounds by cobalt-catalyzed primary amide dehydration reaction by using the novel aminopyridine imine tridentate nitrogen ligand cobalt complex catalyst is provided; and compared with existing methods, the method has the advantages of simple operation, mild reaction conditions, wide application range of reaction substrates, high selectivity, stable catalyst, high efficiency, and relatively high practical application value in synthesis.

A new reagent for efficient synthesis of nitriles from aldoximes using methoxymethyl bromide

ULUDAG, Nesimi,GIDEN, Ozge NUR

, p. 993 - 998 (2021/02/05)

This study outlines an efficient, high-yielding, and rapid method by which to access diverse nitriles from aldoximes with methoxymethyl bromide (MOM-Br) in THF. It represents the first application of MOM-Br as a deoximation reagent to synthesize nitriles. The reaction was performed at reflux to ensure excellent yield (79-96%) of the nitriles within 20-45 minutes. Furthermore, this method has been successfully applied to the synthesis of the synthesis precursor of aromatic, heteroaromatic, cyclic, and acyclic aliphatic.

A Titanium-Catalyzed Reductive α-Desulfonylation

Kern, Christoph,Selau, Jan,Streuff, Jan

supporting information, p. 6178 - 6182 (2021/03/16)

A titanium(III)-catalyzed desulfonylation gives access to functionalized alkyl nitrile building blocks from α-sulfonyl nitriles, circumventing traditional base-mediated α-alkylation conditions and strong single electron donors. The reaction tolerates numerous functional groups including free alcohols, esters, amides, and it can be applied also to the α-desulfonylation of ketones. In addition, a one-pot desulfonylative alkylation is demonstrated. Preliminary mechanistic studies indicate a catalyst-dependent mechanism involving a homolytic C?S cleavage.

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