4415-83-2

Basic information

• Product Name: Cyclobutylmethylamine
• Synonyms: Cyclobutylmethylamine;Aminomethylcyclobutane;1-Cyclobutylmethylamine;cyclobutylmethanamine hydrochloride;cyclobutylMethanaMine
• CAS NO: 4415-83-2
• Molecular Formula: C₅H₁₁N
• Molecular Weight: 85.15
• Mol File: 4415-83-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 90.6 °C at 760 mmHg
• Flash Point: 2.1 °C
• Appearance: /
• Density: 0.889 g/cm³
• Vapor Pressure: 55.9mmHg at 25°C
• Refractive Index: 1.469
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 10.50±0.29(Predicted)
• CAS DataBase Reference: Cyclobutylmethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclobutylmethylamine(4415-83-2)
• EPA Substance Registry System: Cyclobutylmethylamine(4415-83-2)

Safety Data

• Hazardous Substances Data: 4415-83-2(Hazardous Substances Data)

Usage

General Description

Cyclobutylmethylamine is a chemical compound with the molecular formula C5H11N. It is a colorless liquid with a strong amine odor and is not found naturally in the environment. Cyclobutylmethylamine is mainly used as an intermediate in the production of pharmaceuticals and agrochemicals. It is also utilized in the synthesis of other organic compounds. The physical and chemical properties of cyclobutylmethylamine make it suitable for a variety of applications in the chemical industry. However, it is important to handle this compound with care due to its potential hazards, including its irritant and flammable properties.

InChI:InChI=1/C5H11N/c6-4-5-2-1-3-5/h5H,1-4,6H2

Synthetic route

cyclobutanecarbonitrile (4426-11-3) → cyclobutylmethylamine (4415-83-2)

Conditions	Yield
With hydrogenchloride; palladium on activated charcoal Hydrogenation;
With ethanol; sodium
With borane-THF In tetrahydrofuran Heating;
Stage #1: cyclobutanecarbonitrile With borane In tetrahydrofuran for 17h; Heating / reflux; Stage #2: With hydrogenchloride In tetrahydrofuran; methanol for 2h; Heating / reflux;
Stage #1: cyclobutanecarbonitrile With hydrogen; acetic acid; platinum(IV) oxide In ethanol under 2689.24 Torr; for 18h; Stage #2: With sodium hydroxide In diethyl ether; water

2-aza-bicyclo[2.2.0]hex-5-ene (59501-58-5) → cyclobutylmethylamine (4415-83-2)

Conditions	Yield
(reduction);

cyclobutyl amide (1503-98-6) → cyclobutylmethylamine (4415-83-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: P2O5 / durch Destillation 2: sodium; alcohol View Scheme

cyclobutylmethylamine (4415-83-2) + C15H17NO3 → 1-butyl-3-{[(cyclobutylmethyl)amino]methylidene}-8-methylquinoline-2,4(1H,3H)-dione

Conditions	Yield
With acetic anhydride Reflux;	94.6%

carbon disulfide (75-15-0) + cyclobutylmethylamine (4415-83-2) + methyl N-(chloroacetyl)carbamate (13558-70-8) → 3-(cyclobutylmethyl)-2-thioxothiazolidin-4-one

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 0.166667h;	93%

cyclobutylmethylamine (4415-83-2) + methyl 6-methoxy-3-[({4-[(methylsulfanyl)methyl]-naphthalen-1-yl}carbonyl)amino]pyridine-2-carboxylate (1416989-68-8) → N-(cyclobutylmethyl)-6-methoxy-3-({4-[(methylthio)methyl]-1-naphthoyl}amino)-pyridine-2-carboxamide (1430228-61-7)

Conditions	Yield
With pyridine; dmap In N,N-dimethyl-formamide at 80℃; for 3h;	89%

methyl 6-methoxy-3-{[4-(1H-1,2,3-triazol-1-ylmethyl)-1-naphthoyl]amino}-pyridine-2-carboxylate (870971-20-3) + cyclobutylmethylamine (4415-83-2) → 6-methoxy-N-(tetrahydro-2H-pyran-4-ylmethyl)-3-{[4-(lH-1,2,3-triazol-1-ylmethyl)-1-naphthoyl]amino}pyridine-2-carboxamide

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 3.83333h;	87%
In N,N-dimethyl-formamide at 80℃; for 0.666667h;	87%

2,4-dichloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (950661-87-7) + cyclobutylmethylamine (4415-83-2) → C18H26ClN5OSi

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol at 80℃; for 12h;	85.5%

2-(1-naphthalenyl)-1H-pyrido[3,2-d][1,3]oxazin-4-one (870762-08-6) + cyclobutylmethylamine (4415-83-2) → N-(cyclobutylmethyl)-3-[(1-naphthalenylcarbonyl)amino]-2-pyridinecarboxamide

Conditions	Yield
In methanol; DMF (N,N-dimethyl-formamide) at 20℃; for 18h;	83%
In methanol; DMF (N,N-dimethyl-formamide) at 20℃; for 18h;	83%
In methanol; N,N-dimethyl-formamide at 0 - 20℃; for 18h;	160 mg

cyclobutylmethylamine (4415-83-2) + 3-amino-pyridine-2-carboxylic acid (1462-86-8) → 3-amino-N-(cyclobutylmethyl)pyridine-2-carboxamide (870970-70-0)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In methanol; DMF (N,N-dimethyl-formamide) at 20℃; for 24h;	82%
Stage #1: 3-amino-pyridine-2-carboxylic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.25h; Stage #2: cyclobutylmethylamine at 20℃; for 1h;	71%
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1 - 2h;	28%

methyl 6-methoxy-3-[(quinolin-4-ylcarbonyl)amino]pyridine-2-carboxylate + cyclobutylmethylamine (4415-83-2) → N-{2-[(cyclobutylmethyl)carbamoyl]-4-methoxyphenyl}quinoline-4-carboxamide

Conditions	Yield
In N,N-dimethyl-formamide at 80 - 100℃; for 3 - 6h;	80%
In N,N-dimethyl-formamide at 80℃; for 5h;	80%

N-(4-fluoro-3-nitro-phenyl)-N-methyl-acetamide (849351-09-3) + cyclobutylmethylamine (4415-83-2) → N-{4-[(cyclobutylmethyl)amino]-3-nitrophenyl}-N-methylacetamide (849351-82-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide); diethyl ether at 0 - 20℃;	77%
With N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide) at 0 - 20℃;	77%

cyclobutylmethylamine (4415-83-2) + Ethyl oxalyl chloride (4755-77-5) → ethyl 2-(cyclobutylmethylamino)-2-oxoacetate

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 0.25h;	77%

5-amino-4,6-dichloropyridimine (5413-85-4) + cyclobutylmethylamine (4415-83-2) → 6-Chloro-N4-cyclobutylmethyl-pyrimidine-4,5-diamine (195252-61-0)

Conditions	Yield
With triethylamine In butan-1-ol for 16h; Heating;	75%

carbon dioxide (124-38-9) + cyclobutylmethylamine (4415-83-2) + alkyl 2-benzylacrylate → C9H15NO

Conditions	Yield
With Quinuclidine; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate In toluene at 40℃; under 760.051 Torr; Irradiation; regioselective reaction;	75%

2-azido-5-bromobenzaldehyde (1001621-59-5) + ethyl-2-fluoroacetoacetate (1522-41-4) + cyclobutylmethylamine (4415-83-2) → ethyl 6-bromo-4-((cyclobutylmethyl)amino)-2-methylquinoline-3-carboxylate

Conditions	Yield
With triphenylphosphine In acetonitrile at 100℃; for 12h;	75%

cyclobutylmethylamine (4415-83-2) + meta-aminobenzoic acid (99-05-8) → 3-amino-N-(cyclobutylmethyl)benzamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	72%

cyclobutylmethylamine (4415-83-2) + N-(tert-butyloxycarbonyl)-L-tyrosyl-D-alanylglycine (64410-47-5, 79225-08-4) → Boc-Tyr(OH)-D-Ala-Gly-(aminomethyl)cyclobutane (74814-33-8)

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 0 - 25℃; for 52h;	71%

4-[(S)-4-tert-butoxycarbonyl-2-({5-[2-((S)-2-carboxy-pyrrolidin-1-yl)-2-oxoethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}amino)butyryl]piperazine-1-carboxylic acid ethyl ester (1163790-69-9) + cyclobutylmethylamine (4415-83-2) → 4-{(S)-4-carboxy-2-[(5-{2-[(S)-2-(cyclobutylmethyl-carbamoyl)-pyrrolidin-1-yl]-2-oxo-ethoxy}-1-phenyl-1H-pyrazole-3-carbonyl)-amino]-butyryl}-piperazine-1-carboxylic acid ethyl ester (1163790-88-2)

Conditions

Yield

Stage #1: 4-[(S)-4-tert-butoxycarbonyl-2-({5-[2-((S)-2-carboxy-pyrrolidin-1-yl)-2-oxoethoxy]-1-phenyl-1H-pyrazole-3-carbonyl}amino)butyryl]piperazine-1-carboxylic acid ethyl ester With benzotriazol-1-ol; 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.333333h; Stage #2: cyclobutylmethylamine In N,N-dimethyl-formamide for 12h; Stage #3: With trifluoroacetic acid In dichloromethane for 12h;

67%

methyl 3-({[4-(1H-1,2,3-triazol-1-ylmethyl)naphthalen-1-yl]-carbonyl}amino)pyrazine-2-carboxylate (870970-77-7) + cyclobutylmethylamine (4415-83-2) → C24H23N7O2

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 0.666667h;	66%

2-bromo-1,4-naphthoquinone (2065-37-4) + cyclobutylmethylamine (4415-83-2) → 2-((cyclobutylmethyl)amino)naphthalene-1,4-dione

Conditions	Yield
In ethanol at 20℃;	57%

cyclobutylmethylamine (4415-83-2) + ethyl 3-(5-(cis-3-isopropyl-4-oxo-3,4,4a,5,8,8a-hexahydrophthalazin-1-yl)-2-methoxyphenyl)propiolate → N-(cyclobutylmethyl)-3-(5-(cis-3-isopropyl-4-oxo-3,4,4a,5,8,-8a-hexahydrophthalazin-1-yl)-2-methoxyphenyl)propiolamide

Conditions	Yield
With trimethylaluminum; triethylamine hydrochloride; potassium carbonate In dichloromethane at 20℃; Inert atmosphere;	52%

cyclobutylmethylamine (4415-83-2) + C8H11FO3 + 2-azidobenzaldehyde (16714-25-3) → ethyl 4-((cyclobutylmethyl)amino)-2-cyclopropylquinoline-3-carboxylate

Conditions	Yield
With triphenylphosphine In acetonitrile at 100℃; for 12h;	51%

6-chloronicotinylaldehyde (23100-12-1) + cyclobutylmethylamine (4415-83-2) → [(6-chloropyridin-3-yl)methyl](cyclobutylmethyl)amine

Conditions	Yield
Stage #1: 6-chloronicotinylaldehyde; cyclobutylmethylamine With magnesium sulfate In 1,2-dichloro-ethane at 20℃; for 1.5h; Stage #2: With sodium tetrahydroborate In methanol; 1,2-dichloro-ethane at 20 - 40℃; for 23.5h;	46%

cyclobutylmethylamine (4415-83-2) + (2S,3R)-2-(5-(tert-butoxycarbonyl)-1-oxo-2,5-diazaspiro[3.4]octan-2-yl)-3-hydroxybutanoic acid (1621435-15-1) → tert-butyl 2-((2S,3R)-1-((cyclobutylmethyl)amino)-3-hydroxy-1-oxobutan-2-yl)-1-oxo-2,5-diazaspiro[3.4]octane-5-carboxylate (1621435-64-0)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 16h;	41.5%

cyclobutylmethylamine (4415-83-2) + 2-[(4-oxo-2-thioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-1-yl)methyl]benzaldehyde → 1-(2-{[(cyclobutylmethyl)amino]methyl}benzyl)-2-thioxo-1,2,3,5-tetrahydro-4H-pyrrolo[3,2-d]pyrimidin-4-one

Conditions	Yield
Stage #1: cyclobutylmethylamine; 2-[(4-oxo-2-thioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-1-yl)methyl]benzaldehyde With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one for 1h; Stage #2: With sodium tetrahydroborate In 1-methyl-pyrrolidin-2-one at 20℃; for 0.5h;	38%

cyclobutylmethylamine (4415-83-2) + 2-[[4-(1-tetrahydropyran-2-ylindazol-4-yl)imidazol-1-yl]methyl]imidazo[1,2-a]pyridine-6-carbaldehyde → N-(cyclobutylmethyl)-1-[2-[[4-(1-tetrahydropyran-2-ylindazol-4-yl)imidazol-1-yl]methyl]imidazo[1,2-a]pyridin-6-yl]methanamine

Conditions	Yield
With 1,1,1,3',3',3'-hexafluoro-propanol at 20℃; for 1.5h;	27%

di-tert-butyl dicarbonate (24424-99-5) + cyclobutylmethylamine (4415-83-2) + methyl 4-[1-({6-formylimidazo[1,2-a]pyridin-2-yl}methyl)-1H-1,2,3-triazol-4-yl]-1-(oxan-2-yl)-1H-indazole-6-carboxylate → methyl 4-[1-[[6-[[tert-butoxycarbonyl(cyclobutylmethyl)amino]methyl]imidazo[1,2-a]pyridin-2-yl]methyl]triazol-4-yl]-1-tetrahydropyran-2-yl-indazole-6-carboxylate

Conditions	Yield
Stage #1: cyclobutylmethylamine; methyl 4-[1-({6-formylimidazo[1,2-a]pyridin-2-yl}methyl)-1H-1,2,3-triazol-4-yl]-1-(oxan-2-yl)-1H-indazole-6-carboxylate With 1,1,1,3',3',3'-hexafluoro-propanol at 20℃; for 2h; Stage #2: di-tert-butyl dicarbonate In methanol at 20℃; for 18.5h;	26%

cyclobutylmethylamine (4415-83-2) + C15H10F2N4O3S2 (1383563-60-7) → C20H19F2N5O2S2 (1436388-64-5)

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 100℃; for 0.5h; Microwave irradiation;	24%

cyclobutylmethylamine (4415-83-2) + 3-[(quinolin-8-ylcarbonyl)amino]pyridine-2-carboxylate (1416989-74-6) → C21H20N4O2 (1416989-55-3)

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 21h;	14%

cyclobutylmethylamine (4415-83-2) + 6-fluoro-8-hydroxy-4-oxo-4H-chromene-2-carboxylic acid → N-(cycIobutylmethyl)-6-fluoro-8-hydroxy-4-oxo-4H-chromene-2-carboxamide

Conditions	Yield
Stage #1: 6-fluoro-8-hydroxy-4-oxo-4H-chromene-2-carboxylic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran for 1h; Stage #2: cyclobutylmethylamine With triethylamine In tetrahydrofuran at 20℃;	12%

cyclobutylmethylamine (4415-83-2) → methylidenecyclobutane (1120-56-5)

Conditions	Yield
With cis-nitrous acid

Upstream product

• 1503-98-6 cyclobutyl amide 
• 59501-58-5 2-aza-bicyclo[2.2.0]hex-5-ene 
• 4426-11-3 cyclobutanecarbonitrile 

Downstream Products

• 1095118-07-2 C₁₁H₁₄N₂O₂ 
• 1237714-91-8 4-((cyclobutylmethylamino)methyl)-N-((1R,3S)-3-hydroxycyclohexyl)-5-(4-(trifluoromethyl)phenyl)isoxazole-3-carboxamide 

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