6975-71-9

Basic information

• Product Name: 1-Cyclohexene-1-acetonitrile
• Synonyms: Cyclohex-1-ene-1-acetonitrile;CYCLOHEX-1-ENYL-ACETONITRILE;1-CYCLOHEXENEACETONITRILE;1-CYCLOHEXENYLACETONITRILE;1-CYCLOHEXENACETONITRILE;1-CYCLOHEXENE-1-ACETONITRILE;AKOS MSC-0136;TIMTEC-BB SBB007680
• CAS NO: 6975-71-9
• Molecular Formula: C₈H₁₁N
• Molecular Weight: 121.18
• EINECS: 230-235-6
• Product Categories: Building Blocks;C8 to C9;Chemical Synthesis;Cyanides/Nitriles;Nitrogen Compounds;Organic Building Blocks
• Mol File: 6975-71-9.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 144 °C90 mm Hg(lit.)
• Flash Point: 183 °F
• Appearance: Clear yellow to orange/Liquid
• Density: 0.947 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.147mmHg at 25°C
• Refractive Index: n20/D 1.478(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1-Cyclohexene-1-acetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Cyclohexene-1-acetonitrile(6975-71-9)
• EPA Substance Registry System: 1-Cyclohexene-1-acetonitrile(6975-71-9)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-27-36/37/39-36/37-60-9
• RIDADR: 3276
• WGK Germany: 3
• TSCA: T
• HazardClass: 6.1
• Hazardous Substances Data: 6975-71-9(Hazardous Substances Data)

Usage

Chemical Properties

Clear yellow to orange liquid

Uses

1-Cyclohexenylacetonitrile is used as a reagent for the cost-effective synthesis of 5-substituted 1H-tetrazoles from nitriles and sodium azide.

InChI:InChI=1/C8H11N/c9-7-6-8-4-2-1-3-5-8/h4H,1-3,5-6H2

Synthetic route

2-(1-cyclohexenyl)ethylamine (3399-73-3) → 1-cyclohexenylacetonitrile (6975-71-9)

Conditions	Yield
With nickel(II) sulphate; sodium hydroxide; dipotassium peroxodisulfate In dichloromethane for 24h; Ambient temperature;	95%
With oxygen; RuHAP In toluene at 110℃; for 24h;	99 % Chromat.
With ammonium hydroxide; oxygen In tert-Amyl alcohol at 110℃; under 2250.23 Torr; for 15h; Autoclave; Green chemistry;	90 %Chromat.

(+/-)-2-(7-oxabicyclo[4.1.0]heptyl)ethanenitrile (29625-35-2) → 1-cyclohexenylacetonitrile (6975-71-9)

Conditions	Yield
With sodium iodide; tin(ll) chloride In ethanol for 0.05h; Reflux; Green chemistry;	85%

2-cyclohexylideneacetonitrile (4435-18-1, 76293-17-9) + sodium ethanolate (141-52-6) → 1-cyclohexenylacetonitrile (6975-71-9)

Conditions	Yield
at 25℃; Kinetics;

ethyl 2-cyano-2-cyclohexylideneacetate (6802-76-2) → 1-cyclohexenylacetonitrile (6975-71-9)

Conditions	Yield
With pyrex-glass at 510℃;

2-cyano-2-cyclohexylideneacetic acid (37107-50-9) → 1-cyclohexenylacetonitrile (6975-71-9)

Conditions	Yield
under 50 Torr; bei der Destillation;
With pyridine; copper
With pyridine; nitric acid
at 165 - 175℃;

cyano-cyclohex-1-enyl-acetic acid (112005-21-7) → 1-cyclohexenylacetonitrile (6975-71-9)

Conditions	Yield
under 90 Torr; durch Destillation;

cyclohexanone (108-94-1) + cyanoacetic acid (372-09-8) → 1-cyclohexenylacetonitrile (6975-71-9)

Conditions	Yield
With piperidine at 105℃;
With ammonium acetate; benzene Erhitzen des Reaktionsprodukts unter 35-45 Torr auf 165-175grad;
With ammonium acetate; benzene Erhitzen des Reaktionsprodukts unter 50-70 Torr auf 130-140grad;

2-cyclohexylideneacetonitrile (4435-18-1, 76293-17-9) → 1-cyclohexenylacetonitrile (6975-71-9)

Conditions	Yield
In N,N,N,N,N,N-hexamethylphosphoric triamide at 165℃; for 14h;

bromomalononitrile (1885-22-9) + cyclohexene (110-83-8) → 1-cyclohexenylacetonitrile (6975-71-9)

Conditions	Yield
(i) CH2N2, (ii) aq. HCl, AcOH; Multistep reaction;

2-(2-hydroxycyclohexyl)acetonitrile (90242-33-4) → 1-cyclohexenylacetonitrile (6975-71-9)

Conditions	Yield
With acetic anhydride for 6h; Heating; Yield given;

Δ1-cyclohexenyl-acetamide → 1-cyclohexenylacetonitrile (6975-71-9)

Conditions	Yield
With phosphorus pentachloride; trichlorophosphate

2-(cyanomethyl)cyclohexanone (42185-27-3) → 1-cyclohexenylacetonitrile (6975-71-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaBH4 / methanol; H2O / 1 h / Ambient temperature 2: acetic anhydride / 6 h / Heating View Scheme

cyclohexanone (108-94-1) + acetonitrile (75-05-8) → 2-cyclohexylideneacetonitrile (4435-18-1, 76293-17-9) + 1-cyclohexenylacetonitrile (6975-71-9)

Conditions	Yield
With potassium hydroxide Reflux;

methanol (67-56-1) + 1-cyclohexenylacetonitrile (6975-71-9) → methyl 1-cyclohexene-1-acetate (53723-52-7)

Conditions	Yield
With sulfuric acid for 72h; Heating;	99%
With sulfuric acid for 72h; Reflux;	84%
With sulfuric acid Heating;

1-cyclohexenylacetonitrile (6975-71-9) → 2-(cyclohex-1-en-1-yl)acetaldehyde (42370-81-0)

Conditions	Yield
With diisobutylaluminium hydride In toluene 1.) -78 deg C, 15 min, 2.) -78 deg C to r.t., 1 h, 3.) r.t., 1 h;	98%
Multi-step reaction with 2 steps 1: Raney nickel; methanol; acetic acid / Hydrogenation 2: diethyl ether; HCl; water View Scheme

1-cyclohexenylacetonitrile (6975-71-9) → 2-(1-cyclohexenyl)ethylamine (3399-73-3)

Conditions	Yield
With sodium bis(2-methoxyethoxy)aluminium dihydride In tetrahydrofuran at 15℃; for 21h; Solvent; Inert atmosphere; Green chemistry;	95%
With hydrogen In ethanol at 70℃; under 15001.5 Torr; Temperature; Pressure; Autoclave;	91.8%
With lithium aluminium tetrahydride In di-isopropyl ether 1.) 5 deg C, 1 h, 2.) RT, 2 h;	89.5%

1-cyclohexenylacetonitrile (6975-71-9) + rac-3-bromocyclohexene (1521-51-3) → 2-(cyclohex-1-en-1-yl)-N-(cyclohex-2-en-1-yl)acetamide

Conditions	Yield
With water; silver trifluoromethanesulfonate at 0℃; for 1h; Ritter Amidation; chemoselective reaction;	95%

1-cyclohexenylacetonitrile (6975-71-9) → (+/-)-2-(7-oxabicyclo[4.1.0]heptyl)ethanenitrile (29625-35-2)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃;	93%

1-cyclohexenylacetonitrile (6975-71-9) → 5-(cyclohexenylmethyl)-1H-tetrazole (1337922-05-0)

Conditions	Yield
With sodium azide In N,N-dimethyl-formamide at 120℃; for 14h;	93%

1-cyclohexenylacetonitrile (6975-71-9) → 2-cyclohexylideneacetonitrile (4435-18-1, 76293-17-9) + 2-(1-Cyclohexenyl)-3,3-pentamethylenglutarsaeuredinitril (38931-64-5)

Conditions	Yield
With P(MeNCH2CH2)3N In methanol at 50℃; for 0.166667h;	A 10% B 90%

1-cyclohexenylacetonitrile (6975-71-9) → 1-cyclohexenylacetic acid (18294-87-6)

Conditions	Yield
With sodium hydroxide In water for 20h; Heating;	85%
With potassium hydroxide Heating;	75%
With sodium hydroxide In ethanol for 18h; Heating;	74%

1-cyclohexenylacetonitrile (6975-71-9) → 1-cyclohexenylacetonitrile-d2

Conditions	Yield
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate; water-d2 at 70℃; for 24h; Inert atmosphere;	85%

1-cyclohexenylacetonitrile (6975-71-9) + diphenyl acetylene (501-65-5) → 2-(cyclohex-1-en-1-ylmethyl)-3,4,5,6-tetraphenylpyridine

Conditions	Yield
With 1,4-di(diphenylphosphino)-butane; cobalt(II) iodide; zinc In N,N-dimethyl acetamide at 80℃; for 24h; Inert atmosphere;	79%

1-cyclohexenylacetonitrile (6975-71-9) → (cyclohex-1-en-1-yl)-CH2-CO-NH2 (87143-30-4)

Conditions	Yield
With dihydrogen peroxide; hexadecyltrimethylammonium methanesulfonate; sodium hydroxide In water at 25℃; for 1h;	68%
With sulfuric acid; acetic acid
With sodium hydroxide; dihydrogen peroxide; dimethyl sulfoxide In methanol; water at 50℃; for 1h;	95 % Spectr.

1-cyclohexenylacetonitrile (6975-71-9) + mercaptoacetic acid (68-11-1) → (2-cyanomethylcyclohexylthio)acetic acid

Conditions	Yield
With azobisisobutyronitrile In acetic acid Irradiation;	67%

1-cyclohexenylacetonitrile (6975-71-9) → 2-(7-azabicyclo[4.1.0]heptan-1-yl)acetonitrile

Conditions	Yield
With pyridine; bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; hydroxylamine-O-sulfonic acid at 25℃; for 2.5h; chemoselective reaction;	59%

1-cyclohexenylacetonitrile (6975-71-9) → 2-oxo-6-cycloheptenecarbonitrile (190452-02-9)

Conditions	Yield
Stage #1: 1-cyclohexenylacetonitrile With ozone In dichloromethane at -78℃; Stage #2: With dimethylsulfide In dichloromethane at 20℃; for 36h; Inert atmosphere;	58%
With dimethylsulfide; toluene-4-sulfonic acid; ozone 1.) acetone, -78 deg C, 2.) CH2Cl2, room temperature, 5-30 h; Yield given. Multistep reaction;

2-aminopyridine (504-29-0) + 1-cyclohexenylacetonitrile (6975-71-9) → 2-cyclohexenyl-N-(pyridin-2-yl)acetimidamide (1606181-81-0)

Conditions	Yield
Stage #1: 2-aminopyridine; 1-cyclohexenylacetonitrile at 80 - 90℃; for 0.5h; Stage #2: With tin(IV) chloride at 100 - 110℃;	55%

bromobenzene (108-86-1) + 1-cyclohexenylacetonitrile (6975-71-9) → 2-(cyclohex-1-en-1-yl)-1-phenylethan-1-one (1017-23-8)

Conditions	Yield
With bis(cyclopentadienyl)titanium dichloride; chloro-trimethyl-silane; [nickel(II)dichloride(dimethoxyethane)]; trifluoroacetic acid; 4,4'-di-tert-butyl-2,2'-bipyridine; zinc In 1,4-dioxane at 60℃; chemoselective reaction;	55%

1-cyclohexenylacetonitrile (6975-71-9) + pent-4-ynyl-1-azide (199276-58-9) → 3-cyclohex-1-enylmethyl-6,7-dihydro-5H-pyrrolo[1,2-c]imidazole (1394843-48-1) + 5,6-ddihydro-4H-pyrrolo[1,2-c][1,2,3]triazole (1394843-37-8)

Conditions	Yield
With gold(III) chloride; methanesulfonic acid at 20℃; for 8h; Huisgen Cycloaddition; regioselective reaction;	A 50% B 13 %Spectr.

1-cyclohexenylacetonitrile (6975-71-9) + (trifluoromethyl)trimethylsilane (81290-20-2) → 2-(7,7-difluorobicyclo[4.1.0]heptan-1-yl)acetonitrile

Conditions	Yield
With sodium iodide In tetrahydrofuran for 8h; Reflux;	50%

1-cyclohexenylacetonitrile (6975-71-9) + cyclohexanone (108-94-1) → 3-oxo-1,2,3,4,5,6,7,8-octahydroisoquinoline-1-spiro-1'-cyclohexane

Conditions	Yield
With PPA at 100℃; for 0.25h;	42%

1-cyclohexenylacetonitrile (6975-71-9) + phenylmagnesium bromide → 2-(cyclohex-1-en-1-yl)-1-phenylethan-1-one (1017-23-8)

Conditions	Yield
Stage #1: 1-cyclohexenylacetonitrile; phenylmagnesium bromide In diethyl ether for 3h; Heating; Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether at 0 - 20℃;	33%

(CO)4Fe(Si(CH3)2C6H4Si(CH3)2) + 1-cyclohexenylacetonitrile (6975-71-9) → (CO)3Fe(C6H4Si(CH3)2N(Si(CH3)2)CHCHC6H9) (95192-88-4)

Conditions	Yield
In hexane Irradiation (UV/VIS); inert atmosphere, soln. of the compounds irradiated for 44 h at room temp. (Hg-lamp); crystd. from hexane, elem. anal.;	30%

1-cyclohexenylacetonitrile (6975-71-9) → 1-cyclohexene-1-carboxaldehyde (1192-88-7) + C8H11NO (1096537-67-5)

Conditions	Yield
With selenium(IV) oxide In dichloromethane at 20℃; for 24h; Inert atmosphere;	A 9% B 30%

1-cyclohexenylacetonitrile (6975-71-9) + benzaldehyde (100-52-7) → 1-phenyl-3-oxo-1,2,3,4,5,6,7,8-octahydroisoquinoline (80999-16-2) + 1-phenyl-3-oxo-1,2,3,5,6,7,8,8a-octahydroisoquinoline + 1-phenyl-3-oxo-1,2,3,4,6,7,8,8a-octahydroisoquinoline

Conditions	Yield
With methanesulfonic acid; phosphorus pentoxide for 0.166667h; Ambient temperature; Yields of byproduct given;	A 27% B n/a C n/a
With methanesulfonic acid; phosphorus pentoxide for 0.166667h; Ambient temperature; Yield given. Yields of byproduct given;	A 27% B n/a C n/a

pyridine-4-carbonitrile (100-48-1) + 1-cyclohexenylacetonitrile (6975-71-9) → (3-Pyridin-4-yl-cyclohex-1-enyl)-acetonitrile (100190-68-9) + (6-Pyridin-4-yl-cyclohex-1-enyl)-acetonitrile (89344-81-0)

Conditions	Yield
In acetonitrile for 1h; Product distribution; Mechanism; Irradiation; var. alkenes;	A 7.6% B 5.5%
In acetonitrile for 1h; Irradiation;	A 7.6% B 5.5%

1-cyclohexenylacetonitrile (6975-71-9) + benzaldehyde (100-52-7) → 1-phenyl-3-oxo-1,2,3,4,5,6,7,8-octahydroisoquinoline (80999-16-2) + 1-phenyl-3-oxo-2,3,4,4a,5,6,7,8-octahydroisoquinoline + 1-phenyl-3-oxo-1,2,3,5,6,7,8,8a-octahydroisoquinoline

Conditions	Yield
With PPA at 100℃; for 0.25h; Mechanism;	A n/a B 2% C n/a
With PPA; Polyphosphoric acid (PPA) at 100℃; for 0.25h;	A n/a B 2% C n/a

methyl magnesium iodide (917-64-6) + 1-cyclohexenylacetonitrile (6975-71-9) → 1-cyclohexenylacetone (768-50-3)

Conditions	Yield
With toluene ether

piperonal (120-57-0) + 1-cyclohexenylacetonitrile (6975-71-9) → 3-benzo[1,3]dioxol-5-yl-2-cyclohex-1-enyl-acrylonitrile

Conditions	Yield
With sodium ethanolate

ethanol (64-17-5) + 1-cyclohexenylacetonitrile (6975-71-9) + sodium ethanolate (141-52-6) → 2-cyclohexylideneacetonitrile (4435-18-1, 76293-17-9)

Conditions	Yield
Kinetics; Isomerisierung;

Upstream product

• 6802-76-2 ethyl 2-cyano-2-cyclohexylideneacetate 
• 108-94-1 cyclohexanone 
• 75-05-8 acetonitrile 
• 29625-35-2 (+/-)-2-(7-oxabicyclo[4.1.0]heptyl)ethanenitrile 
• 42185-27-3 2-(cyanomethyl)cyclohexanone 
• 3399-73-3 2-(1-cyclohexenyl)ethylamine 
• 90242-33-4 2-(2-hydroxycyclohexyl)acetonitrile 
• 1885-22-9 bromomalononitrile 
• 110-83-8 cyclohexene 
• 4435-18-1 2-cyclohexylideneacetonitrile 
• 372-09-8 cyanoacetic acid 
• 112005-21-7 cyano-cyclohex-1-enyl-acetic acid 
• 37107-50-9 2-cyano-2-cyclohexylideneacetic acid 
• 141-52-6 sodium ethanolate 

Downstream Products

• 768-50-3 1-cyclohexenylacetone 
• 53723-52-7 methyl 1-cyclohexene-1-acetate 
• 51072-34-5 N-(2-cyclohex-1-enylethyl)-2-(4-methoxyphenyl)-acetamide 
• 100190-68-9 (3-Pyridin-4-yl-cyclohex-1-enyl)-acetonitrile 
• 89344-81-0 (6-Pyridin-4-yl-cyclohex-1-enyl)-acetonitrile 
• 133412-65-4 Cyclohexen-1-yl-cyanacetaldehyd 
• 80999-16-2 1-phenyl-3-oxo-1,2,3,4,5,6,7,8-octahydroisoquinoline 
• 102557-64-2 2-cyclohex-1-enylmethyl-1,3-diphenyl-imidazolidine 
• 4435-18-1 2-cyclohexylideneacetonitrile 
• 6051-03-2 cis-hexahydrobenzofuran-2(3H)-one 
• 3399-73-3 2-(1-cyclohexenyl)ethylamine 
• 87143-30-4 (cyclohex-1-en-1-yl)-CH₂-CO-NH₂ 
• 4435-14-7 2-cyclohexylacetonitrile 
• 18294-87-6 1-cyclohexenylacetic acid 

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