2,4,6-Cycloheptatriene-1-carbonitrile supplier

Name
2,4,6-Cycloheptatriene-1-carbonitrile
EINECS
CAS No. 13612-59-4
Article Data13
CAS DataBase
Density 1.005 g/cm³
Solubility
Melting Point
Formula C₈H₇N
Boiling Point 248.26 °C at 760 mmHg
Molecular Weight 117.15
Flash Point 87.563 °C
Transport Information
Appearance
Safety 36
Risk Codes 20/21/22
Molecular Structure
Hazard Symbols Xn
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;
PSA 23.79000
LogP 1.80838

Synthetic route

: tropylium hexachlorophosphate chloride

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

Conditions

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

: 151-50-8
potassium cyanide

: tropylium bromide

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

Conditions

Conditions	Yield
In water	81%

: 85807-68-7
4-diazo-1,2,3-triazole

: 71-43-2
benzene

A: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

B: 26902-53-4
3-Cyanocycloheptatrien

C: 19052-84-7
2-cyanocycloheptatriene

D: 19052-79-0
cycloheptatrienecarbonitrile

E: 1680-44-0
5-phenyl-1H-1,2,3-triazole

Conditions

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%

...Expand

: 85807-68-7
4-diazo-1,2,3-triazole

: 71-43-2
benzene

A: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

B: 19052-84-7
2-cyanocycloheptatriene

C: 19052-79-0
cycloheptatrienecarbonitrile

D: 1680-44-0
5-phenyl-1H-1,2,3-triazole

Conditions

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%

...Expand

: 85807-68-7
4-diazo-1,2,3-triazole

: 71-43-2
benzene

A: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

B: 26902-53-4
3-Cyanocycloheptatrien

C: 19052-79-0
cycloheptatrienecarbonitrile

D: 1680-44-0
5-phenyl-1H-1,2,3-triazole

Conditions

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

...Expand

: 1714-39-2
7-ethoxy-1,3,5-cycloheptatriene

: 151-50-8
potassium cyanide

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

Conditions

Conditions	Yield
With hydrogenchloride

: 13138-21-1
diazoacetonitrile

: 71-43-2
benzene

A: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

B: 26902-53-4
3-Cyanocycloheptatrien

C: 19052-84-7
2-cyanocycloheptatriene

D: 19052-79-0
cycloheptatrienecarbonitrile

Conditions

Conditions	Yield
Irradiation;

...Expand

: 140-90-9
sodium O-ethyl dithiocarbonate

: 69806-00-4, 69854-10-0, 113301-25-0, 113301-26-1
trans-8exo-cyano-oxa-bis-ς-homobenzene

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

Conditions

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

: 143-33-9
sodium cyanide

: 27081-10-3
tropylium tetrafluoroborate

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

: 113236-87-6
(1R,4R,5R,6R)-5-Hydroxy-4-thiocyanato-bicyclo[4.1.0]hept-2-ene-7-carbonitrile

A: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

: 69806-00-4, 69854-10-0, 113301-25-0, 113301-26-1
trans-8exo-cyano-oxa-bis-ς-homobenzene

Conditions

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

: 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

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

Conditions

Conditions	Yield
With pH8 buffer solution at 0℃;

: 151-50-8
potassium cyanide

tropylium perchlorate: tropylium perchlorate

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

: 69806-00-4, 69854-10-0, 113301-25-0, 113301-26-1
trans-8exo-cyano-oxa-bis-ς-homobenzene

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

Conditions

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

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

Conditions

Conditions	Yield
In dimethyl sulfoxide

: potassium cyanide

: 27081-10-3
tropylium tetrafluoroborate

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

Conditions

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

: 7677-24-9
trimethylsilyl cyanide

: 27081-10-3
tropylium tetrafluoroborate

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

Conditions

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

: 773837-37-9
sodium cyanide

: 544-25-2
Cyclohepta-1,3,5-triene

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

Conditions

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

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

: 19052-84-7
2-cyanocycloheptatriene

Conditions

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

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

: 35034-28-7
cyclohepta-2,4,6-trien-1-ylmethanamine

Conditions

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

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

: 74-89-5
methylamine

: 123686-89-5
(1RS)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carbonitrile

Conditions

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

: 918813-47-5
[5-(2-iodo-ethyl)-5-methyl-cyclopent-1-enyloxy]-trimethyl-silane

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

: 918813-48-6
(1R)-1-[2-(1-methyl-2-oxocyclopentyl)ethyl]cyclohepta-2,4,6-triene-1-carbonitrile

Conditions

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%

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

: 123686-89-5
(1RS)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carbonitrile

Conditions

Conditions	Yield
With sodium hydroxide; methylamine In methanol	70%

: 884866-01-7
1-(4-methylbenzensulfonyl)-4-phenyl-1H-1,2,3-triazole

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

: 1078739-38-4
2-(cyclohepta-2,4,6-trienyl)-4-phenyl-1-tosyl-1H-imidazole

Conditions

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

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

: 99028-91-8
bicyclo<3.2.0>hepta-2,6-diene-1-carbonitrile

Conditions

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

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

: 13274-43-6
4-methyl-1,2,4-triazoline-3,5-dione

A: 90652-50-9
anti-3-cyano-6,7-diaza-exo-tricyclo<3.2.2.02,4>non-9-ene-6,7-dicarboxylic acid methylimide

B: 90694-71-6
syn-3-cyano-6,7-diaza-exo-tricyclo<3.2.2.02,4>non-8-ene-6,7-dicarboxylic acid methylimide

Conditions

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

...Expand

: 27792-49-0, 40250-96-2
tricarbonyltrispyridinechromium(0)

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

A: 14740-77-3
pentacarbonyl(pyridine)chromium(0)

B: 12146-99-5, 12146-34-8, 12146-35-9
exo-NCC7H7Cr(CO)3

C: 12146-35-9, 12146-99-5, 12146-34-8
endo-(C7H7CN)Cr(CO)3

D: (C7H7CN)Cr(CO)5

Conditions

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

...Expand

: 64-17-5
ethanol

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

: 27332-37-2
ethyl cyclohepta-2,4,6-trienecarboxylate

Conditions

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

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

: aziridinium tetrafluoroborate

: 2-(1,3,5-Cycloheptatrien-7-yl)imidazolidin-2-ylium-tetrafluoroborat

Conditions

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

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

A: 50998-08-8, 69854-08-6, 122921-39-5
C8H7NO2

B: 50998-08-8
C8H7NO2

C: (1R,2R,3R,4S,5S)-6,7-Dioxa-tricyclo[3.2.2.02,4]non-8-ene-3-carbonitrile

D: (1R,2R,3S,4S,5S)-6,7-Dioxa-tricyclo[3.2.2.02,4]non-8-ene-3-carbonitrile

Conditions

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

...Expand

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

A: 50998-08-8, 69854-08-6, 122921-39-5
C8H7NO2

B: 7468-67-9
o-formylbenzonitrile

C: (1R,2R,3R,4S,5S)-6,7-Dioxa-tricyclo[3.2.2.02,4]non-8-ene-3-carbonitrile

D: (1R,2R,3S,4S,5S)-6,7-Dioxa-tricyclo[3.2.2.02,4]non-8-ene-3-carbonitrile

Conditions

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

...Expand

: 13463-40-6
iron pentacarbonyl

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

: 116852-14-3
tricarbonyl(1-4-η-6-cyanocyclohepta-1,3,5-triene)iron

Conditions

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%

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

: 123-54-6
acetylacetone

: 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

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

...Expand

: 16453-18-2
3,6-bis(trifluoromethyl)-1,2,4,5-tetrazine

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

: 137233-09-1
1-exo-Cyan-4,7-bis(trifluormethyl)-1a,5,7a,7b-tetrahydro-1H-cyclopropaphthalazin

: 137233-10-4
1-exo-Cyan-4,7-bis(trifluormethyl)-1a,7b-dihydro-1H-cyclopropaphthalazin

Conditions

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%

...Expand

: 16453-18-2
3,6-bis(trifluoromethyl)-1,2,4,5-tetrazine

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

: 137233-10-4
1-exo-Cyan-4,7-bis(trifluormethyl)-1a,7b-dihydro-1H-cyclopropaphthalazin

Conditions

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

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

: 4661-46-5
benzenediazonium-2-carboxylate hydrochloride

A: 151395-80-1
Exo-7-cyano-2,5-benzo-tricyclo[4.1.0]hept-3-ene

B: Endo-7-cyano-2,5-benzo-tricyclo<4.1.0>hept-3-ene

Conditions

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

...Expand

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

: 1-ethoxy-2,3-diphenylcyclopropenium fluoroborate

A: 19052-84-7
2-cyanocycloheptatriene

B: 79574-43-9
7-cyano-7-(ethoxy-1,3-diphenylcycloprop-2-en-1-yl)cycloheptatriene

Conditions

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

...Expand

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

: 1-ethoxy-2,3-diphenylcyclopropenium ion

: 79574-43-9
7-cyano-7-(ethoxy-1,3-diphenylcycloprop-2-en-1-yl)cycloheptatriene

Conditions

Conditions	Yield
With diisopropylamine In acetonitrile	21%

: 15321-51-4
diiron nonacarbonyl

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

: 116852-14-3
tricarbonyl(η4-1-cyanocycloheptatriene)iron

Conditions

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%

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

: 130-15-4
[1,4]naphthoquinone

A: 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

B: C18H13NO2

C: 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

D: C18H11NO2

Conditions

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

...Expand

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

: 18870-24-1
Tropontosylhydrazon-Na-salz

: (1S,2S,9S)-Tricyclo[7.4.1.02,8]tetradeca-3,5,7,10,12-pentaene-10-carbonitrile

Conditions

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

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

: 4440-40-8
cyclohepta-2,4,6-trienecarboxylic acid

Conditions

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

: 13612-59-4
cyclohepta-2,4,6-triene-1-carbonitrile

: 26902-48-7
cyclohepta-2,4,6-trienecarboxamide

Conditions

Conditions	Yield
With dihydrogen peroxide; sodium carbonate; acetone

2,4,6-Cycloheptatriene-1-carbonitrile Specification

The 2,4,6-Cycloheptatriene-1-carbonitrile, with the CAS registry number 13612-59-4, is also known as 7-Cyanocyclohetatriene. It belongs to the product categories of C8 to C9; Cyanides/Nitriles; Nitrogen Compounds. This chemical's molecular formula is C₈H₇N and formula weight is 117.15. What's more, its IUPAC name and systematic name are the same which is called cyclohepta-2,4,6-triene-1-carbonitrile.

Physical properties of 2,4,6-Cycloheptatriene-1-carbonitrile: (1)ACD/LogP: 1.02; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.02; (4)ACD/LogD (pH 7.4): 1.02; (5)ACD/BCF (pH 5.5): 3.52; (6)ACD/BCF (pH 7.4): 3.52; (7)ACD/KOC (pH 5.5): 85.63; (8)ACD/KOC (pH 7.4): 85.63; (9)#H bond acceptors: 1; (10)Index of Refraction: 1.542; (11)Molar Refractivity: 36.69 cm³; (12)Molar Volume: 116.5 cm³; (13)Surface Tension: 38.8 dyne/cm; (14)Density: 1 g/cm³; (15)Flash Point: 87.6 °C; (16)Enthalpy of Vaporization: 48.54 kJ/mol; (17)Boiling Point: 248.3 °C at 760 mmHg; (18)Vapour Pressure: 0.0245 mmHg at 25°C.

Preparation: this chemical can be prepared by cycloheptatrienylium; bromide and hydrocyanic acid; potassium salt. This reaction will need solvent H₂O. The yield is about 81%.

Uses of 2,4,6-Cycloheptatriene-1-carbonitrile: it can be used to produce 2-cyanocycloheptatriene at temperature of 5 - 20 °C. This reaction will need reagent KOH and solvent ethanol.

When you are using this chemical, please be cautious about it as the following:
This chemical may cause damage to health. It is harmful by inhalation, in contact with skin and if swallowed. Whenever you will contact it, please wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC=CC(C=C1)C#N
(2)InChI: InChI=1S/C8H7N/c9-7-8-5-3-1-2-4-6-8/h1-6,8H
(3)InChIKey: LADCKIXFXIKHQM-UHFFFAOYSA-N

Product Name

2,4,6-Cycloheptatriene-1-carbonitrile

Synthetic route

2,4,6-Cycloheptatriene-1-carbonitrile Specification

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