13612-59-4

Basic information

• Product Name: 2,4,6-Cycloheptatriene-1-carbonitrile
• Synonyms: 1,3,5-Cycloheptatriene-7-carbonitrile;1-Cyano-2,4,6-cycloheptatriene;2,4,6-Cycloheptatrienecarbonitrile;7-Cyano-1,3,5-cycloheptatriene;7-Cyanocycloheptatriene;7-cyanotropilidene;2,4,6-CYCLOHEPTATRIENE-1-CARBONITRILE, 9 5%;2,4,6-CYCLOHEPTATRIENE-1-CARBONITRILE 95%
• CAS NO: 13612-59-4
• Molecular Formula: C₈H₇N
• Molecular Weight: 117.15
• Product Categories: C8 to C9;Cyanides/Nitriles;Nitrogen Compounds
• Mol File: 13612-59-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 51-53 °C1.5 mm Hg(lit.)
• Flash Point: 185 °F
• Appearance: /
• Density: 1.017 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0245mmHg at 25°C
• Refractive Index: n20/D 1.533(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2,4,6-Cycloheptatriene-1-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-Cycloheptatriene-1-carbonitrile(13612-59-4)
• EPA Substance Registry System: 2,4,6-Cycloheptatriene-1-carbonitrile(13612-59-4)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 13612-59-4(Hazardous Substances Data)

Usage

Uses

2,4,6-Cycloheptatriene-1-carbonitrile (7-cyanocycloheptatriene ) may be used in the synthesis of 7-carbomethoxycycloheptatriene. It may be used as model compound for EPR and intramolecular proton transfer studies of cycloheptatriene radicals and anions. It can also be used to generate dihydroazocines and hydrooxocins.

General Description

2,4,6-Cycloheptatriene-1-carbonitrile (7-Cyanocycloheptatriene) is a 7-substituted cycloheptatriene. Its synthesis by reacting tropylium cation with cyanide anion has been described. 2,4,6-cycloheptatriene-1-carbonitrile affords toluene or toluonitrile during flash photolysis studies. Its diamagnetic susceptibility has been determined, which is useful for the derivation of its susceptibility exaltation. It reacts with acetyl acetone in the presence of Mn(OAc)3 to form products derived from the norcaradiene structure.

InChI:InChI=1/C8H7N/c9-7-8-5-3-1-2-4-6-8/h1-6,8H

Synthetic route

tropylium hexachlorophosphate chloride → cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4)

Conditions	Yield
In benzene at 20℃; for 0.25h; Substitution; cyanation;	90%

potassium cyanide (151-50-8) + tropylium bromide → cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4)

Conditions	Yield
In water	81%

4-diazo-1,2,3-triazole (85807-68-7) + benzene (71-43-2) → cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4) + 3-Cyanocycloheptatrien (26902-53-4) + 2-cyanocycloheptatriene (19052-84-7) + cycloheptatrienecarbonitrile (19052-79-0) + 5-phenyl-1H-1,2,3-triazole (1680-44-0)

Conditions	Yield
for 6h; Heating; other 4-diazo-1,2,3-triazole derivatives, photolysis;	A n/a B n/a C n/a D n/a E 53%

4-diazo-1,2,3-triazole (85807-68-7) + benzene (71-43-2) → cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4) + 2-cyanocycloheptatriene (19052-84-7) + cycloheptatrienecarbonitrile (19052-79-0) + 5-phenyl-1H-1,2,3-triazole (1680-44-0)

Conditions	Yield
for 6h; Heating; Further byproducts given;	A n/a B n/a C n/a D 53%
for 3h; Irradiation; Further byproducts given;	A n/a B n/a C n/a D 26%

4-diazo-1,2,3-triazole (85807-68-7) + benzene (71-43-2) → cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4) + 3-Cyanocycloheptatrien (26902-53-4) + cycloheptatrienecarbonitrile (19052-79-0) + 5-phenyl-1H-1,2,3-triazole (1680-44-0)

Conditions	Yield
for 3h; Irradiation; Further byproducts given;	A n/a B n/a C n/a D 26%

7-ethoxy-1,3,5-cycloheptatriene (1714-39-2) + potassium cyanide (151-50-8) → cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4)

Conditions	Yield
With hydrogenchloride

diazoacetonitrile (13138-21-1) + benzene (71-43-2) → cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4) + 3-Cyanocycloheptatrien (26902-53-4) + 2-cyanocycloheptatriene (19052-84-7) + cycloheptatrienecarbonitrile (19052-79-0)

Conditions	Yield
Irradiation;

sodium O-ethyl dithiocarbonate (140-90-9) + trans-8exo-cyano-oxa-bis-ς-homobenzene (69806-00-4, 69854-10-0, 113301-25-0, 113301-26-1) → cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4)

Conditions	Yield
In isopropyl alcohol at 0℃; for 48h; Yield given;

sodium cyanide (143-33-9) + tropylium tetrafluoroborate (27081-10-3) → cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4)

(1R,4R,5R,6R)-5-Hydroxy-4-thiocyanato-bicyclo[4.1.0]hept-2-ene-7-carbonitrile (113236-87-6) → cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4) + trans-8exo-cyano-oxa-bis-ς-homobenzene (69806-00-4, 69854-10-0, 113301-25-0, 113301-26-1)

Conditions	Yield
With triethylamine In ethyl acetate var. reag.: K2CO3;
With triethylamine In ethyl acetate Product distribution; K2CO3;

2-((1R,2R,3R,6R)-7-Cyano-2-hydroxy-bicyclo[4.1.0]hept-4-en-3-yl)-isothiourea; compound with sulfuric acid (113236-90-1) → cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4)

Conditions	Yield
With pH8 buffer solution at 0℃;

potassium cyanide (151-50-8) + tropylium perchlorate → cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4)

trans-8exo-cyano-oxa-bis-ς-homobenzene (69806-00-4, 69854-10-0, 113301-25-0, 113301-26-1) → cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 13 percent / H2SO4 / diethyl ether / 0 °C 2: pH8 buffer solution / 0 °C View Scheme

potassium cyanide + tropylium bromide → cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4)

Conditions	Yield
In dimethyl sulfoxide

potassium cyanide + tropylium tetrafluoroborate (27081-10-3) → cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4)

Conditions	Yield
With 18-crown-6 ether In [D3]acetonitrile for 0.0833333h; Inert atmosphere;

trimethylsilyl cyanide (7677-24-9) + tropylium tetrafluoroborate (27081-10-3) → cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4)

Conditions	Yield
In [D3]acetonitrile for 0.25h; Inert atmosphere;

sodium cyanide (773837-37-9) + Cyclohepta-1,3,5-triene (544-25-2) → cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4)

Conditions	Yield
Stage #1: Cyclohepta-1,3,5-triene With bromine In chloroform Stage #2: Heating; Stage #3: sodium cyanide In water

cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4) → 2-cyanocycloheptatriene (19052-84-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 45℃; for 30h;	96%
With N-ethyl-N,N-diisopropylamine In acetonitrile at 44℃; for 5h; Rate constant; Product distribution; Mechanism; Ea, ΔF(excit.), ΔH(excit.), ΔS(excit.); other amines; other temp. and solvents;
With potassium hydroxide In ethanol

cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4) → cyclohepta-2,4,6-trien-1-ylmethanamine (35034-28-7)

Conditions	Yield
With lithium aluminium tetrahydride at 0℃; for 2h;	95%

cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4) + methylamine (74-89-5) → (1RS)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carbonitrile (123686-89-5)

Conditions	Yield
In tert-butyl alcohol at 85℃; for 24h;	87%

[5-(2-iodo-ethyl)-5-methyl-cyclopent-1-enyloxy]-trimethyl-silane (918813-47-5) + cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4) → (1R)-1-[2-(1-methyl-2-oxocyclopentyl)ethyl]cyclohepta-2,4,6-triene-1-carbonitrile (918813-48-6)

Conditions	Yield
Stage #1: cyclohepta-2,4,6-triene-1-carbonitrile With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.166667h; Stage #2: [5-(2-iodo-ethyl)-5-methyl-cyclopent-1-enyloxy]-trimethyl-silane With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran at -20℃; for 16h;	71%

cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4) → (1RS)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carbonitrile (123686-89-5)

Conditions	Yield
With sodium hydroxide; methylamine In methanol	70%

1-(4-methylbenzensulfonyl)-4-phenyl-1H-1,2,3-triazole (884866-01-7) + cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4) → 2-(cyclohepta-2,4,6-trienyl)-4-phenyl-1-tosyl-1H-imidazole (1078739-38-4)

Conditions	Yield
With rhodium (II) octanoate dimer In chloroform at 140℃; for 0.25h; Microwave irradiation;	67%

cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4) → bicyclo<3.2.0>hepta-2,6-diene-1-carbonitrile (99028-91-8)

Conditions	Yield
for 9.5h; Ambient temperature; Irradiation;	62%

cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4) + 4-methyl-1,2,4-triazoline-3,5-dione (13274-43-6) → anti-3-cyano-6,7-diaza-exo-tricyclo<3.2.2.02,4>non-9-ene-6,7-dicarboxylic acid methylimide (90652-50-9) + syn-3-cyano-6,7-diaza-exo-tricyclo<3.2.2.02,4>non-8-ene-6,7-dicarboxylic acid methylimide (90694-71-6)

Conditions	Yield
In diethyl ether; acetone at 0℃; for 0.5h;	A 55% B 8%

tricarbonyltrispyridinechromium(0) (27792-49-0, 40250-96-2) + cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4) → pentacarbonyl(pyridine)chromium(0) (14740-77-3) + exo-NCC7H7Cr(CO)3 (12146-99-5, 12146-34-8, 12146-35-9) + endo-(C7H7CN)Cr(CO)3 (12146-35-9, 12146-99-5, 12146-34-8) + (C7H7CN)Cr(CO)5

Conditions	Yield
In diethyl ether in the presence of BF3;;	A n/a B 53% C 12% D 20%

ethanol (64-17-5) + cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4) → ethyl cyclohepta-2,4,6-trienecarboxylate (27332-37-2)

Conditions	Yield
With sulfuric acid for 35h; Heating;	46.3%

cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4) + aziridinium tetrafluoroborate → 2-(1,3,5-Cycloheptatrien-7-yl)imidazolidin-2-ylium-tetrafluoroborat

Conditions	Yield
at 100℃; for 20h;	30%

cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4) → C8H7NO2 (50998-08-8, 69854-08-6, 122921-39-5) + C8H7NO2 (50998-08-8) + (1R,2R,3R,4S,5S)-6,7-Dioxa-tricyclo[3.2.2.02,4]non-8-ene-3-carbonitrile + (1R,2R,3S,4S,5S)-6,7-Dioxa-tricyclo[3.2.2.02,4]non-8-ene-3-carbonitrile

Conditions	Yield
With hematoporphyrin In acetone Irradiation; Further byproducts given;	A 20% B 2% C 24% D 28%

cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4) → C8H7NO2 (50998-08-8, 69854-08-6, 122921-39-5) + o-formylbenzonitrile (7468-67-9) + (1R,2R,3R,4S,5S)-6,7-Dioxa-tricyclo[3.2.2.02,4]non-8-ene-3-carbonitrile + (1R,2R,3S,4S,5S)-6,7-Dioxa-tricyclo[3.2.2.02,4]non-8-ene-3-carbonitrile

Conditions	Yield
With hematoporphyrin In acetone Irradiation; Further byproducts given;	A 20% B 3% C 24% D 28%

iron pentacarbonyl (13463-40-6) + cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4) → tricarbonyl(1-4-η-6-cyanocyclohepta-1,3,5-triene)iron (116852-14-3)

Conditions	Yield
In not given Irradiation (UV/VIS); C7H7CN and Fe(CO)5 were irradiated externally with a 60 W fluorescent lamp through Pyrex at 115°C for 23 h.; Then filtered through Celite and the filtrate was concentrated and chromatographed on silica gel. Elem. anal.;	28%

cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4) + acetylacetone (123-54-6) → rel-(3aR,5aR,6S,6aS,6bR)-1-acetyl-2-methyl-5a,6,6a,6b-tetrahydro-3aH-cyclopropa[3,4]benzo[1,2-b]furan-6-carbonitrile + rel-(3aR,5aR,6R,6aS,6bR)-1-acetyl-2-methyl-5a,6,6a,6b-tetrahydro-3aH-cyclopropa[3,4]benzo[1,2-b]furan-6-carbonitrile + rel-(1S,2R,5S,6S,7R)-7-cyano-5-(2,4-dioxopentan-3-yl)bicyclo[4.1.0]hept-3-en-2-yl acetate + rel-(1S,2S,5S,6S,7R)-7-cyano-5-(2,4-dioxopentan-3-yl)bicyclo[4.1.0]hept-3-en-2-yl acetate

Conditions	Yield
With manganese(III) triacetate dihydrate In acetic acid at 80℃; Inert atmosphere;	A 25% B 28% C 8% D 8%

3,6-bis(trifluoromethyl)-1,2,4,5-tetrazine (16453-18-2) + cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4) → 1-exo-Cyan-4,7-bis(trifluormethyl)-1a,5,7a,7b-tetrahydro-1H-cyclopropaphthalazin (137233-09-1) + 1-exo-Cyan-4,7-bis(trifluormethyl)-1a,7b-dihydro-1H-cyclopropaphthalazin (137233-10-4)

Conditions	Yield
In chloroform for 15h; Mechanism; Heating; other 7-substituted cycloheptatrienes;	A 26% B 15%
In chloroform for 15h; Heating;	A 26% B 15%

3,6-bis(trifluoromethyl)-1,2,4,5-tetrazine (16453-18-2) + cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4) → 1-exo-Cyan-4,7-bis(trifluormethyl)-1a,7b-dihydro-1H-cyclopropaphthalazin (137233-10-4)

Conditions	Yield
In dichloromethane for 168h; Heating;	22%

cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4) + benzenediazonium-2-carboxylate hydrochloride (4661-46-5) → Exo-7-cyano-2,5-benzo-tricyclo[4.1.0]hept-3-ene (151395-80-1) + Endo-7-cyano-2,5-benzo-tricyclo<4.1.0>hept-3-ene

Conditions	Yield
In 1,2-dichloro-ethane for 48h; Heating;	A 22% B 16%

cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4) + 1-ethoxy-2,3-diphenylcyclopropenium fluoroborate → 2-cyanocycloheptatriene (19052-84-7) + 7-cyano-7-(ethoxy-1,3-diphenylcycloprop-2-en-1-yl)cycloheptatriene (79574-43-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile for 10.5h; Ambient temperature;	A n/a B 21%

cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4) + 1-ethoxy-2,3-diphenylcyclopropenium ion → 7-cyano-7-(ethoxy-1,3-diphenylcycloprop-2-en-1-yl)cycloheptatriene (79574-43-9)

Conditions	Yield
With diisopropylamine In acetonitrile	21%

diiron nonacarbonyl (15321-51-4) + cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4) → tricarbonyl(η4-1-cyanocycloheptatriene)iron (116852-14-3)

Conditions	Yield
In toluene C7H7CN is reacted with Fe2(CO)9 in toluene at reflux temp. for 1 h, allowed to cool; chromd. (Al2O3, toluene-ethyl acetate (3:1)), evapd. in vac., treated with Et2O and 60% HPF6 soln., filtered, washed with Et2O, deprotonated inacetone soln. with Et3N, extd. with Et2O-water, org. layer sepd., dried, evapd., distd.; elem. anal.;	20%

cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4) + [1,4]naphthoquinone (130-15-4) → 14-exo-cyano-1S(R),12R(S),13R(S),15S(R)-pentacyclo[10.3.2.02,11.04,9.013,15]heptadeca-4,6,8,16-tetraene-3,10-dione + C18H13NO2 + 14-exo-cyano-1S(R),12R(S),13R(S),15S(R)-pentacyclo[10.3.2.02,11.04,9.013,15]heptadeca-4,6,8,16-tetraene-3,10-dione + C18H11NO2

Conditions	Yield
In chloroform at 95℃; for 432h; Further byproducts given;	A n/a B n/a C 8% D n/a

cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4) + Tropontosylhydrazon-Na-salz (18870-24-1) → (1S,2S,9S)-Tricyclo[7.4.1.02,8]tetradeca-3,5,7,10,12-pentaene-10-carbonitrile

Conditions	Yield
In diethylene glycol dimethyl ether at 120℃; for 0.25h;	7%

cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4) → cyclohepta-2,4,6-trienecarboxylic acid (4440-40-8)

Conditions	Yield
With hydrogenchloride; methanol; diethyl ether anschliessend mit H2O behandeln und Behandeln des Reaktionsprodukts mit NaHCO3 in wss. Methanol und anschliessend mit wss. NaOH;
Multi-step reaction with 2 steps 1: 46.3 percent / conc. H2SO4 / 35 h / Heating 2: 74 percent / HaHCO3, H2O / methanol / 2 h / Heating View Scheme
Multi-step reaction with 2 steps 1: HCl 2: aq. NaOH, NaHCO3 / methanol View Scheme
Multi-step reaction with 2 steps 2: aq. H2SO4 View Scheme

cyclohepta-2,4,6-triene-1-carbonitrile (13612-59-4) → cyclohepta-2,4,6-trienecarboxamide (26902-48-7)

Conditions	Yield
With dihydrogen peroxide; sodium carbonate; acetone

Upstream product

• 151-50-8 potassium cyanide 
• 1714-39-2 7-ethoxy-1,3,5-cycloheptatriene 
• 13138-21-1 diazoacetonitrile 
• 71-43-2 benzene 
• 773837-37-9 sodium cyanide 
• 544-25-2 Cyclohepta-1,3,5-triene 
• 7677-24-9 trimethylsilyl cyanide 
• 27081-10-3 tropylium tetrafluoroborate 
• 69806-00-4 trans-8exo-cyano-oxa-bis-?-homobenzene 
• 85807-68-7 4-diazo-1,2,3-triazole 
• 113236-90-1 2-((1R,2R,3R,6R)-7-Cyano-2-hydroxy-bicyclo[4.1.0]hept-4-en-3-yl)-isothiourea; compound with sulfuric acid 
• 113236-87-6 (1R,4R,5R,6R)-5-Hydroxy-4-thiocyanato-bicyclo[4.1.0]hept-2-ene-7-carbonitrile 
• 143-33-9 sodium cyanide 
• 140-90-9 sodium O-ethyl dithiocarbonate 

Downstream Products

• 4440-40-8 cyclohepta-2,4,6-trienecarboxylic acid 
• 26902-48-7 cyclohepta-2,4,6-trienecarboxamide 
• 25230-72-2 tropylium perchlorate 
• 32399-46-5 7-(methoxycarbonyl)cycloheptatriene 
• 1078739-38-4 2-(cyclohepta-2,4,6-trienyl)-4-phenyl-1-tosyl-1H-imidazole 
• 13466-55-2 tropan-2β-ol 
• 78386-47-7 tropan-2β-yl toluene-p-sulphonate 
• 78386-50-2 phenyl 2-cyano-8-azabicyclo<3.2.1>oct-2-ene-8-carboxylate 
• 78386-51-3 N-phenoxycarbonylnortropan-2-on 
• 13466-55-2 tropan-2α-ol 
• 78477-91-5 8-methyl-8-azabicyclo[3.2.1]octan-2-one 
• 32399-48-7 cycloheptatriene-7-carbonyl chloride 
• 32399-49-8 N,N-dimethyl-1,3,5-cycloheptatriene-7-carboxamide 
• 103-82-2 phenylacetic acid 

Relevant articles and documents

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