4426-11-3

Basic information

• Product Name: Cyanocyclobutane
• Synonyms: CYCLOBUTANECARBONITRILE;Cyanocyclobutane;Cyclobutyl cyanide;Cyanocyclobutane~Cyclobutyl cyanide;Cyclobutanecarbonitrile,97%;Cyclobutanecarbonitrile - C5653
• CAS NO: 4426-11-3
• Molecular Formula: C₅H₇N
• Molecular Weight: 81.12
• EINECS: 224-606-1
• Mol File: 4426-11-3.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 144-146°C
• Flash Point: 42°C
• Appearance: Colorless liquid
• Density: 0,868 g/cm3
• Refractive Index: 1.4325
• Storage Temp.: 2-8°C
• Water Solubility: Slightly soluble in water.
• BRN: 2037573
• CAS DataBase Reference: Cyanocyclobutane(CAS DataBase Reference)
• NIST Chemistry Reference: Cyanocyclobutane(4426-11-3)
• EPA Substance Registry System: Cyanocyclobutane(4426-11-3)

Safety Data

• Hazard Codes: T
• Statements: 11-20/21/22-36-25
• Safety Statements: 3/7-9-16-36/37/39-45-26
• RIDADR: 3275
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 4426-11-3(Hazardous Substances Data)

Usage

Chemical Properties

Colorless pure liquid

Uses

It is used for research or analysis use only, as pharmaceutical intermediate.

Application

Cyclobutanecarbonitrile is a highly polluting and highly toxic coating material, which has been banned in many countries in marine antifouling coatings.

InChI:InChI=1/C5H7N/c6-4-5-2-1-3-5/h5H,1-3H2

Synthetic route

δ-chlorovaleronitrile (6280-87-1) → cyclobutanecarbonitrile (4426-11-3) + 1-chloro-4,8-dicyanooctane

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.

5-bromopentan-1-nitrile (5414-21-1) → cyclobutanecarbonitrile (4426-11-3)

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;

Dimethyl-dithiocarbamic acid 1-cyano-cyclobutyl ester (61540-42-9) → cyclobutanecarbonitrile (4426-11-3)

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

isocyanate de chlorosulfonyle (1189-71-5) + Cyclobutanecarboxylic acid (3721-95-7) → cyclobutanecarbonitrile (4426-11-3)

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

δ-chlorovaleronitrile (6280-87-1) → cyclobutanecarbonitrile (4426-11-3)

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

cyclobutyl amide (1503-98-6) → cyclobutanecarbonitrile (4426-11-3)

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

1-cyanocyclobutane-1-carboxylic acid (30491-91-9) → cyclobutanecarbonitrile (4426-11-3)

1-cyanobicyclo<1.1.0>butane (16955-35-4) → cyclobutanecarbonitrile (4426-11-3) + trans-1-cyano-2-methylcyclopropane (6142-59-2, 26343-62-4, 26343-63-5, 62279-41-8, 62279-42-9)

Conditions	Yield
Yield given. Multistep reaction;

1-Benzenesulfonyl-cyclobutanecarbonitrile → cyclobutanecarbonitrile (4426-11-3)

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

sodium cyanide (143-33-9) + 1,4-dichlorobutane (110-56-5) → hexanedinitrile (111-69-3) + δ-chlorovaleronitrile (6280-87-1) + cyclobutanecarbonitrile (4426-11-3)

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

1-cyanocyclobutane-1-carboxylic acid (30491-91-9) → carbon dioxide (124-38-9) + cyclobutanecarbonitrile (4426-11-3)

Conditions	Yield
at 160℃;

Cyclobutanecarboxylic acid (3721-95-7) → cyclobutanecarbonitrile (4426-11-3)

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

cyclobutane-1,1'-dicarboxylic acid (5445-51-2) → cyclobutanecarbonitrile (4426-11-3)

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

diethyl cyclobutane-1,1-dicarboxylate (3779-29-1) → cyclobutanecarbonitrile (4426-11-3)

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

Cyclobutanecarbonyl chloride (5006-22-4) → cyclobutanecarbonitrile (4426-11-3)

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 → cyclobutanecarbonitrile (4426-11-3)

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 → cyclobutanecarbonitrile (4426-11-3)

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

tetradeuterioacetic acid (1186-52-3) + C9H14F3NO3SSi → cyclobutanecarbonitrile (4426-11-3) + C10H14(2)H3NO2Si + C10H14(2)H3NO2Si

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

N,N'-(ethane-1,2-diyl)dicyclobutanecarboxamide + acetonitrile (75-05-8) → cyclobutyl amide (1503-98-6) + cyclobutanecarbonitrile (4426-11-3)

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

cyclobutanecarbonitrile (4426-11-3) + methyl 2-amino-5-methoxybenzoate (2475-80-1) → 2-cyclobutyl-7-methoxyquinazolin-4-ol (1448676-71-8)

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

bromochlorobenzene (106-39-8) + cyclobutanecarbonitrile (4426-11-3) → 1-(4-chlorophenyl)cyclobutanecarbonitrile (28049-61-8)

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%

cyclobutanecarbonitrile (4426-11-3) + prenyl bromide (870-63-3) → 1-(3-methylbut-2-enyl)cyclobutanecarbonitrile (1228309-45-2)

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

tert-butyl 5-bromoindoline-1-carboxylate (261732-38-1) + cyclobutanecarbonitrile (4426-11-3) → C18H22N2O2

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

6-bromo-1H-indazole (79762-54-2) + cyclobutanecarbonitrile (4426-11-3) → 1-(1H-indazol-6-yl)cyclobutane-1-carbonitrile

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

p-benzyloxyphenylbromide (6793-92-6) + cyclobutanecarbonitrile (4426-11-3) → 1-(4-(benzyloxy)phenyl)cyclobutanecarbonitrile (626603-28-9)

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%

cyclobutanecarbonitrile (4426-11-3) + methyl 2-amino-4-methoxybenzoate (50413-30-4) → 2-cyclobutyl-6-methoxyquinazolin-4-ol (1448676-68-3)

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

((1,2-bis(diisopropylphosphino)ethane)NiH)2 (130777-67-2) + cyclobutanecarbonitrile (4426-11-3) → [(1,2-bis(diisopropylphosphino)ethane)Ni(η2-cyclobutyl cyanide)] (834880-39-6)

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%

2,4,6-trichloropyridine (16063-69-7) + cyclobutanecarbonitrile (4426-11-3) → 1-(2,6-dichloro-4-pyridyl)cyclobutanecarbonitrile

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

cyclobutanecarbonitrile (4426-11-3) + N,N-dibenzyl-3,5-dibromoaniline → 1,1'-(5-(dibenzylamino)-1,3-phenylene)bis(cyclobutane-1-carbonitrile)

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%

cyclobutanecarbonitrile (4426-11-3) + 2-Iodobenzyl bromide (40400-13-3) → 1-(2-iodobenzyl)cyclobutanecarbonitrile (495414-03-4)

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%

cyclobutanecarbonitrile (4426-11-3) + 2-carbomethoxyaniline (134-20-3) → 4-hydroxy-3-cyclobutylquinazoline (496867-71-1)

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

methyl 6-aminobenzo[d][1,3]dioxole-5-carboxylate (40680-63-5) + cyclobutanecarbonitrile (4426-11-3) → 6-cyclobutyl-[1,3]dioxolo[4,5-g]quinazolin-8-ol (1448676-75-2)

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

3-bromo-2-(phenylmethoxy)pyridine (52200-49-4) + cyclobutanecarbonitrile (4426-11-3) → 1-(2-(benzyloxy)pyridin-3-yl)cyclobutanecarbonitrile

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%

cyclobutanecarbonitrile (4426-11-3) + 2-fluoro-4-(trifluoromethyl) Pyridine → 1-[4-(trifluoromethyl)pyridin-2-yl]cyclobutanecarbonitrile (1432492-69-7)

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

Cyclopentyl bromide (137-43-9) + cyclobutanecarbonitrile (4426-11-3) → 1-cyclopentylcyclobutanecarbonitrile (1432492-80-2)

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%

cyclobutanecarbonitrile (4426-11-3) + allyl bromide (106-95-6) → 1-allylcyclobutanecarbonitrile

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;

Upstream product

• 1503-98-6 cyclobutyl amide 
• 5414-21-1 5-bromopentan-1-nitrile 
• 6280-87-1 δ-chlorovaleronitrile 
• 75-05-8 acetonitrile 
• 1186-52-3 tetradeuterioacetic acid 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 3721-95-7 Cyclobutanecarboxylic acid 
• 5006-22-4 Cyclobutanecarbonyl chloride 
• 3779-29-1 diethyl cyclobutane-1,1-dicarboxylate 
• 5445-51-2 cyclobutane-1,1'-dicarboxylic acid 
• 30491-91-9 1-cyanocyclobutane-1-carboxylic acid 
• 143-33-9 sodium cyanide 
• 110-56-5 1,4-dichlorobutane 
• 61540-42-9 Dimethyl-dithiocarbamic acid 1-cyano-cyclobutyl ester 

Downstream Products

• 3721-95-7 Cyclobutanecarboxylic acid 
• 4415-83-2 cyclobutylmethylamine 
• 5454-82-0 cyclobutylmethylamine hydrochloride 
• 71690-89-6 cyclobutanecarboximidamide hydrochloride 
• 874183-40-1 1-(3,4-bis(4-(trifluoromethyl)phenyl)phenyl)cyclobutane-1-carbonitrile 
• 913473-12-8 1-{4-[2-(cyclopropylmethoxy)ethyl]benzyl}cyclobutanecarbonitrile 
• 913473-28-6 1-[4-(2-hydroxyethyl)benzyl]cyclobutanecarbonitrile 
• 1382486-27-2 1-(5-bromopyridin-2-yl)cyclobutanecarboxylic acid 

Relevant articles and documents

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