Cyanocyclobutane supplier | CasNO.4426-11-3

Name
Cyanocyclobutane
EINECS 224-606-1
CAS No. 4426-11-3
Article Data20
CAS DataBase
Density 0.93 g/cm³
Solubility Slightly soluble in water.
Melting Point
Formula C5H7 N
Boiling Point 156.1 °C at 760 mmHg
Molecular Weight 81.1173
Flash Point 44.3 °C
Transport Information 3275
Appearance Colorless liquid
Safety 3/7-9-16-36/37/39
Risk Codes 11-20/21/22
Molecular Structure
Hazard Symbols R10:Flammable.; R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.;
Synonyms Cyanocyclobutane;Cyclobutanenitrile
PSA 23.79000
LogP 1.31008

Synthetic route

: 6280-87-1
δ-chlorovaleronitrile

A: 4426-11-3
cyclobutanecarbonitrile

B: 1-chloro-4,8-dicyanooctane

Conditions

Conditions	Yield
With sodium hydroxide; tetrabutyl-ammonium chloride In tetrahydrofuran at 67℃; for 6h; Rate constant;	A 90% B 10 % Chromat.
With sodium hydroxide; tetrabutyl-ammonium chloride In tetrahydrofuran at 67℃; for 6h;	A 90% B 10 % Chromat.

: 5414-21-1
5-bromopentan-1-nitrile

: 4426-11-3
cyclobutanecarbonitrile

Conditions

Conditions	Yield
With oxygen; tetraethylammonium perchlorate In N,N-dimethyl-formamide at 20℃; electroreduction at -1.1 V;	72%
With sodium hydroxide; tetrabutyl-ammonium chloride In tetrahydrofuran at 67℃; for 3h; Rate constant;
With N,N-Dimethylamino acetonitrile
With sodium hydroxide; tetrabutyl-ammonium chloride In tetrahydrofuran at 67℃; for 3h; Yield given;

: 61540-42-9
Dimethyl-dithiocarbamic acid 1-cyano-cyclobutyl ester

: 4426-11-3
cyclobutanecarbonitrile

Conditions

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene at 80℃; for 5h;	71%

: 1189-71-5
isocyanate de chlorosulfonyle

: 3721-95-7
Cyclobutanecarboxylic acid

: 4426-11-3
cyclobutanecarbonitrile

Conditions

Conditions	Yield
In dichloromethane; N,N-dimethyl-formamide	66.5%

: 6280-87-1
δ-chlorovaleronitrile

: 4426-11-3
cyclobutanecarbonitrile

Conditions

Conditions	Yield
With sodium amide
With lithium diethylamide In N,N,N,N,N,N-hexamethylphosphoric triamide at -70℃;

: 1503-98-6
cyclobutyl amide

: 4426-11-3
cyclobutanecarbonitrile

Conditions

Conditions	Yield
With phosphorus pentoxide durch Destillation;
With phosphorus pentoxide
With phosphorus pentoxide at 255℃; for 1h; Temperature;

: 30491-91-9
1-cyanocyclobutane-1-carboxylic acid

: 4426-11-3
cyclobutanecarbonitrile

: 16955-35-4
1-cyanobicyclo<1.1.0>butane

A: 4426-11-3
cyclobutanecarbonitrile

: 6142-59-2, 26343-62-4, 26343-63-5, 62279-41-8, 62279-42-9
trans-1-cyano-2-methylcyclopropane

Conditions

Conditions	Yield
Yield given. Multistep reaction;

: 1-Benzenesulfonyl-cyclobutanecarbonitrile

: 4426-11-3
cyclobutanecarbonitrile

Conditions

Conditions	Yield
With magnesium; mercury dichloride In tetrahydrofuran; methanol for 2h; 0 deg C to r.t.;

: 143-33-9
sodium cyanide

: 110-56-5
1,4-dichlorobutane

A: 111-69-3
hexanedinitrile

B: 6280-87-1
δ-chlorovaleronitrile

C: 4426-11-3
cyclobutanecarbonitrile

Conditions

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide In tetrahydrofuran for 3h; Heating; Yield given. Yields of byproduct given;

...Expand

: 30491-91-9
1-cyanocyclobutane-1-carboxylic acid

A: 124-38-9
carbon dioxide

B: 4426-11-3
cyclobutanecarbonitrile

Conditions

Conditions	Yield
at 160℃;

: 3721-95-7
Cyclobutanecarboxylic acid

: 4426-11-3
cyclobutanecarbonitrile

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: SOCl2 2: NH4OH 3: P2O5 View Scheme
Multi-step reaction with 3 steps 1: SOCl2 2: aq. NH3 3: P2O5 View Scheme
Multi-step reaction with 2 steps 1: ammonia / 0.5 h / 130 °C 2: phosphorus pentoxide / 1 h / 255 °C View Scheme

: 5445-51-2
cyclobutane-1,1'-dicarboxylic acid

: 4426-11-3
cyclobutanecarbonitrile

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: Heating 2: SOCl2 3: NH4OH 4: P2O5 View Scheme

: 3779-29-1
diethyl cyclobutane-1,1-dicarboxylate

: 4426-11-3
cyclobutanecarbonitrile

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: H3O+ 2: Heating 3: SOCl2 4: NH4OH 5: P2O5 View Scheme

: 5006-22-4
Cyclobutanecarbonyl chloride

: 4426-11-3
cyclobutanecarbonitrile

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NH4OH 2: P2O5 View Scheme
Multi-step reaction with 2 steps 1: aq. NH3 2: P2O5 View Scheme

: C9H15NO2Si

: 4426-11-3
cyclobutanecarbonitrile

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: lithium borohydride / diethyl ether / 5.75 h / 20 °C / Inert atmosphere 2: 2,6-dimethylpyridine / dichloromethane / -10 - 20 °C 3: 2,6-dimethylpyridine / 20 °C View Scheme

: 1-(cyano)-2-(trimethylsilyl)cyclopropylmethanol

: 4426-11-3
cyclobutanecarbonitrile

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 2,6-dimethylpyridine / dichloromethane / -10 - 20 °C 2: 2,6-dimethylpyridine / 20 °C View Scheme

: 1186-52-3
tetradeuterioacetic acid

: C9H14F3NO3SSi

A: 4426-11-3
cyclobutanecarbonitrile

: C10H14(2)H3NO2Si

C: C10H14(2)H3NO2Si

Conditions

Conditions	Yield
With 2,6-dimethylpyridine at 20℃; Kinetics;	A 47 %Spectr. B 46 %Spectr. C 7 %Spectr.

...Expand

: N,N'-(ethane-1,2-diyl)dicyclobutanecarboxamide

: 75-05-8
acetonitrile

A: 1503-98-6
cyclobutyl amide

B: 4426-11-3
cyclobutanecarbonitrile

Conditions

Conditions	Yield
With lithium perchlorate at 40℃; for 0.5h; Electrolysis;

...Expand

: 4426-11-3
cyclobutanecarbonitrile

: 2475-80-1
methyl 2-amino-5-methoxybenzoate

: 1448676-71-8
2-cyclobutyl-7-methoxyquinazolin-4-ol

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 100℃; for 15h; Inert atmosphere;	98%

: 106-39-8
bromochlorobenzene

: 4426-11-3
cyclobutanecarbonitrile

: 28049-61-8
1-(4-chlorophenyl)cyclobutanecarbonitrile

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; lithium hexamethyldisilazane In tetrahydrofuran at 80℃; for 3h; Inert atmosphere;	96%

: 4426-11-3
cyclobutanecarbonitrile

: 870-63-3
prenyl bromide

: 1228309-45-2
1-(3-methylbut-2-enyl)cyclobutanecarbonitrile

Conditions

Conditions	Yield
With n-butyllithium; ammonium chloride; diisopropylamine In tetrahydrofuran	95%

: 261732-38-1
tert-butyl 5-bromoindoline-1-carboxylate

: 4426-11-3
cyclobutanecarbonitrile

: C18H22N2O2

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); lithium hexamethyldisilazane; nixantphos In tetrahydrofuran at 80℃; for 18h;	95%

: 79762-54-2
6-bromo-1H-indazole

: 4426-11-3
cyclobutanecarbonitrile

: 1-(1H-indazol-6-yl)cyclobutane-1-carbonitrile

Conditions

Conditions	Yield
With N-Xantphos Pd G4; lithium hexamethyldisilazane In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere; Sealed tube;	91%

: 6793-92-6
p-benzyloxyphenylbromide

: 4426-11-3
cyclobutanecarbonitrile

: 626603-28-9
1-(4-(benzyloxy)phenyl)cyclobutanecarbonitrile

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; lithium hexamethyldisilazane In tetrahydrofuran at 80℃; for 3h; Inert atmosphere;	80%

: 4426-11-3
cyclobutanecarbonitrile

: 50413-30-4
methyl 2-amino-4-methoxybenzoate

: 1448676-68-3
2-cyclobutyl-6-methoxyquinazolin-4-ol

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 100℃; for 15h; Inert atmosphere;	79%

: 130777-67-2
((1,2-bis(diisopropylphosphino)ethane)NiH)2

: 4426-11-3
cyclobutanecarbonitrile

: 834880-39-6
[(1,2-bis(diisopropylphosphino)ethane)Ni(η2-cyclobutyl cyanide)]

Conditions

Conditions	Yield
In tetrahydrofuran byproducts: H2; under N2 atm. ((dippe)NiH)2 and cyclobutyl cyanide in THF were mixed at room temp. and stirred for 15 min; solvent was evapd., residue was recrystd. from hexane (cold dry ice - acetone bath) and dried in vacuo for 2 h; elem. anal.;	76%

: 16063-69-7
2,4,6-trichloropyridine

: 4426-11-3
cyclobutanecarbonitrile

: 1-(2,6-dichloro-4-pyridyl)cyclobutanecarbonitrile

Conditions

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;	76%

: 4426-11-3
cyclobutanecarbonitrile

: N,N-dibenzyl-3,5-dibromoaniline

: 1,1'-(5-(dibenzylamino)-1,3-phenylene)bis(cyclobutane-1-carbonitrile)

Conditions

Conditions	Yield
Stage #1: cyclobutanecarbonitrile; N,N-dibenzyl-3,5-dibromoaniline With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In tetrahydrofuran for 0.25h; Inert atmosphere; Stage #2: With lithium hexamethyldisilazane In tetrahydrofuran at 80℃; for 1.5h;	75%

: 4426-11-3
cyclobutanecarbonitrile

: 40400-13-3
2-Iodobenzyl bromide

: 495414-03-4
1-(2-iodobenzyl)cyclobutanecarbonitrile

Conditions

Conditions	Yield
Stage #1: cyclobutanecarbonitrile With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: 2-Iodobenzyl bromide In tetrahydrofuran; hexane at -78 - 20℃; Further stages.;	74%

: 4426-11-3
cyclobutanecarbonitrile

: 134-20-3
2-carbomethoxyaniline

: 496867-71-1
4-hydroxy-3-cyclobutylquinazoline

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 100℃; for 15h; Inert atmosphere;	73%

: 40680-63-5
methyl 6-aminobenzo[d][1,3]dioxole-5-carboxylate

: 4426-11-3
cyclobutanecarbonitrile

: 1448676-75-2
6-cyclobutyl-[1,3]dioxolo[4,5-g]quinazolin-8-ol

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 100℃; for 15h; Inert atmosphere;	71%

: 52200-49-4
3-bromo-2-(phenylmethoxy)pyridine

: 4426-11-3
cyclobutanecarbonitrile

: 1-(2-(benzyloxy)pyridin-3-yl)cyclobutanecarbonitrile

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; lithium hexamethyldisilazane In tetrahydrofuran at 80℃; for 3h; Inert atmosphere;	71%

: 4426-11-3
cyclobutanecarbonitrile

: 2-fluoro-4-(trifluoromethyl) Pyridine

: 1432492-69-7
1-[4-(trifluoromethyl)pyridin-2-yl]cyclobutanecarbonitrile

Conditions

Conditions	Yield
With potassium hexamethylsilazane In toluene at 20℃; for 72h;	64.8%
With potassium hexamethylsilazane In toluene at 20℃; for 72h;	64.8%

: 137-43-9
Cyclopentyl bromide

: 4426-11-3
cyclobutanecarbonitrile

: 1432492-80-2
1-cyclopentylcyclobutanecarbonitrile

Conditions

Conditions	Yield
Stage #1: cyclobutanecarbonitrile With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.666667h; Stage #2: Cyclopentyl bromide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 3h;	62.3%
Stage #1: cyclobutanecarbonitrile With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.666667h; Stage #2: Cyclopentyl bromide With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran at 20℃; for 3h;	62.3%

: 4426-11-3
cyclobutanecarbonitrile

: 106-95-6
allyl bromide

: 1-allylcyclobutanecarbonitrile

Conditions

Conditions	Yield
Stage #1: cyclobutanecarbonitrile With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.833333h; Inert atmosphere; Stage #2: allyl bromide In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;	61%
Stage #1: cyclobutanecarbonitrile With lithium diisopropyl amide In tetrahydrofuran at -78 - 0℃; for 1h; Inert atmosphere; Stage #2: allyl bromide In tetrahydrofuran at -78 - 20℃; Inert atmosphere;

Cyanocyclobutane Chemical Properties

Molecular Structure of Cyanocyclobutane (CAS NO.4426-11-3):

IUPAC Name: Cyclobutanecarbonitrile
Canonical SMILES: C1CC(C1)C#N
InChI: InChI=1S/C5H7N/c6-4-5-2-1-3-5/h5H,1-3H2
InChIKey: GFBLFDSCAKHHGX-UHFFFAOYSA-N
Molecular Weight: 81.11578 [g/mol]
Molecular Formula: C₅H₇N
XLogP3-AA: 1
H-Bond Donor: 0
H-Bond Acceptor: 1
EINECS: 224-606-1
Index of Refraction: 1.446
Molar Refractivity: 23.06 cm³
Molar Volume: 86.4 cm³
Surface Tension: 33.4 dyne/cm
Density: 0.93 g/cm³
Flash Point: 44.3 °C
Enthalpy of Vaporization: 36.88 kJ/mol
Boiling Point: 156.1 °C at 760 mmHg
Vapour Pressure: 2.93 mmHg at 25 °C

Cyanocyclobutane Safety Profile

Safety Information of Cyanocyclobutane (CAS NO.4426-11-3):
Risk Statements: 11-20/21/22
R11:Highly flammable.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 3/7-9-16-36/37/39
S3:Keep in a cool place.
S7:Keep container tightly closed.
S9:Keep container in a well-ventilated place.
S16:Keep away from sources of ignition.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
RIDADR: 3275
HazardClass: 6.1
PackingGroup: II

Cyanocyclobutane Specification

Cyanocyclobutane (CAS NO.4426-11-3), its Synonyms are Cyclobutanecarbonitrile ; Cyclobutyl cyanide .

Product Name

Cyanocyclobutane

Synthetic route

Cyanocyclobutane Chemical Properties

Cyanocyclobutane Safety Profile

Cyanocyclobutane Specification

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