40571-47-9

Basic information

• Product Name: 1-METHYL-CYCLOBUTYLAMINE
• Synonyms: 1-METHYL-CYCLOBUTYLAMINE;CYCLOBUTANAMINE, 1-METHYL-;(1-methylcyclobutyl)amine(SALTDATA: HCl);1-MethylcyclobutanaMine;1-Methyl-1-cyclobutylamine
• CAS NO: 40571-47-9
• Molecular Formula: C₅H₁₁N
• Molecular Weight: 85.15
• EINECS: 1312995-182-4
• Mol File: 40571-47-9.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 93℃
• Flash Point: -9℃
• Appearance: /
• Density: 0.878
• CAS DataBase Reference: 1-METHYL-CYCLOBUTYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYL-CYCLOBUTYLAMINE(40571-47-9)
• EPA Substance Registry System: 1-METHYL-CYCLOBUTYLAMINE(40571-47-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• HazardClass: IRRITANT
• Hazardous Substances Data: 40571-47-9(Hazardous Substances Data)

Usage

Description

1-Methyl-cyclobutylamine is an organic compound with the molecular formula C5H11N. It is a derivative of cyclobutylamine, featuring a methyl group attached to the cyclobutane ring. 1-Methyl-cyclobutylamine is known for its reactivity in various chemical reactions, making it a valuable component in the synthesis of different organic molecules.

Uses

1-Methyl-cyclobutylamine is used as a reagent in the field of organic chemistry for acid-catalyzed rearrangement reactions. It serves as a key intermediate in the synthesis of various complex organic molecules, particularly those with cyclobutane rings. The expression is: 1-Methyl-cyclobutylamine is used as a reagent for acid-catalyzed rearrangement because of its reactivity and ability to form diverse organic molecules.
Used in Organic Chemistry:
1-Methyl-cyclobutylamine is used as a reagent for Ritter reactions, which are a type of chemical reaction involving the conversion of a nitrile to an amide using an alcohol and a strong acid. 1-Methyl-cyclobutylamine's unique structure allows it to participate in these reactions, leading to the formation of valuable synthetic products. The expression is: Used in Organic Chemistry, 1-Methyl-cyclobutylamine is used as a reagent for Ritter reactions due to its compatibility with the reaction conditions and its role in producing amide products.

Synthetic route

1-methylcyclobutanol (20117-47-9) + potassium cyanide (151-50-8) → 1-methyl-1-cyclobutylamine (40571-47-9)

Conditions	Yield
With dibutyl ether; sulfuric acid und Erhitzen des Reaktionsprodukts mit wss. HCl;

methylidenecyclobutane (1120-56-5) + sodium cyanide (143-33-9) → 1-methyl-1-cyclobutylamine (40571-47-9)

Conditions	Yield
(i) AcOH, aq. H2SO4, (ii) aq. NaOH; Multistep reaction;

methylidenecyclobutane (1120-56-5) + acetonitrile (75-05-8) → 1-methyl-1-cyclobutylamine (40571-47-9)

Conditions	Yield
(i) AcOH, aq. H2SO4, (ii) aq. KOH, ethane-1,2-diol; Multistep reaction;

2-amino-4-methyl-thiophene-3-carboxylic acid ethyl ester (43088-42-2) + 1-methyl-1-cyclobutylamine (40571-47-9) + 1,1'-carbonyldiimidazole (530-62-1) → ethyl 4-methyl-2-{[(1-methylcyclobutyl)carbamoyl]amino}thiophene-3-carboxylate

Conditions	Yield
Stage #1: 2-amino-4-methyl-thiophene-3-carboxylic acid ethyl ester; 1,1'-carbonyldiimidazole With triethylamine In dichloromethane at 20℃; for 48h; Stage #2: 1-methylcyclobutan-1-amine In dichloromethane at 20℃; for 1h;	97%

3,4-dichlorobenzenesulphonyl chloride (98-31-7) + 1-methyl-1-cyclobutylamine (40571-47-9) → 3,4-dichloro-N-(1-methylcyclobutyl)benzenesulfonamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 23℃; for 16h; Inert atmosphere;	86%

4-phenyl-1,3-oxazole (20662-89-9) + 1-methyl-1-cyclobutylamine (40571-47-9) → 1-(1-methylcyclobutyl)-4-phenyl-1H-imidazole (1552273-92-3)

Conditions	Yield
With trifluoroacetic acid In 1,2-dichloro-benzene at 200℃; for 3h; Microwave irradiation;	80%

3-(3-(cyclopropanecarboxamido)isoquinolin-7-yl)-4-methylbenzoic acid (1382848-07-8) + 1-methyl-1-cyclobutylamine (40571-47-9) → 3-(3-(cyclopropanecarboxamido)isoquinolin-7-yl)-4-methyl-N-(1-methylcyclobutyl)benzamide (1382845-06-8)

Conditions	Yield
With dmap; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 50℃; for 15h;	78%

tert-butyl 4-((2-chloro-5-nitropyrimidin-4-yl)amino)piperidine-1-carboxylate (1124330-16-0) + 1-methyl-1-cyclobutylamine (40571-47-9) → tert-butyl 4-((2-((1-methylcyclobutyl)amino)-5-nitropyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 20℃; for 4h;	61%

1-methyl-1-cyclobutylamine (40571-47-9) + (1s,4s)-4-((2-chloro-5-nitropyrimidin-4-yl)amino)cyclohexane-1-carboxamide → (1s,4s)-4-((2-((1-methylcyclobutyl)amino)-5-nitropyrimidin-4-yl)amino)cyclohexane-1-carboxamide

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 60℃; for 4h;	51%

1-methyl-1-cyclobutylamine (40571-47-9) + (2R)-2-{4-[(2-methylpentyl)oxy]phenyl}-2-[(2S)-2-phenylpropanamido]acetic acid → (2S)-N-((1R)-2-((1-methylcyclobutyl)amino)-1-(4-((2-methylpentyl)oxy)phenyl)-2-oxoethyl)-2-phenylpropanamide

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 0 - 20℃; Inert atmosphere;	48%

5-phenyloxazole (1006-68-4) + 1-methyl-1-cyclobutylamine (40571-47-9) → 1-(1-methylcyclobutyl)-5-phenyl-1H-imidazole (1552273-91-2)

Conditions	Yield
With trifluoroacetic acid In 1,2-dichloro-benzene at 200℃; for 14h; Microwave irradiation;	36%

cis {3-(3-chloro-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl}(morpholin-4-yl)methanone + 1-methyl-1-cyclobutylamine (40571-47-9) → cis (3-{3-[(1-methylcyclobutyl)amino]-1,2,4-oxadiazol-5-yl}-5-[4-(trifluoromethyl)phenyl]piperidin-1-yl)(morpholin-4-yl)methanone

Conditions	Yield
In ethanol at 80 - 100℃; for 36h; Microwave irradiation;	24%

1-methyl-1-cyclobutylamine (40571-47-9) + 2,4-dichloro-alpha(elhoxymethlene)-5-fluoro-beta-oxo-benzene propanoic acid ethyl ester (86483-52-5) → (Z)-2-(2,4-Dichloro-5-fluoro-benzoyl)-3-(1-methyl-cyclobutylamino)-acrylic acid ethyl ester (118539-53-0)

Conditions	Yield
In ethanol Ambient temperature;

1-methyl-1-cyclobutylamine (40571-47-9) → 7-Chloro-6-fluoro-1-(1-methyl-cyclobutyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Conditions	Yield
Multi-step reaction with 3 steps 1: ethanol / Ambient temperature 2: NaH / dioxane / 1.) r.t., 30 min, 2.) reflux, 2.5 h 3: KOH / H2O / 1.5 h / Heating View Scheme

1-methyl-1-cyclobutylamine (40571-47-9) → 7-Chloro-6-fluoro-1-(1-methyl-cyclobutyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol / Ambient temperature 2: NaH / dioxane / 1.) r.t., 30 min, 2.) reflux, 2.5 h View Scheme

1-methyl-1-cyclobutylamine (40571-47-9) → 6-Fluoro-1-(1-methyl-cyclobutyl)-4-oxo-7-piperazin-1-yl-1,4-dihydro-quinoline-3-carboxylic acid (118539-35-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: ethanol / Ambient temperature 2: NaH / dioxane / 1.) r.t., 30 min, 2.) reflux, 2.5 h 3: KOH / H2O / 1.5 h / Heating 4: 30 percent / pyridine / 18 h / Heating View Scheme

1-methyl-1-cyclobutylamine (40571-47-9) + hexanal (66-25-1) → C11H21N

Conditions	Yield
In dichloromethane Dehydrating agent; Inert atmosphere;
With magnesium sulfate In dichloromethane for 1h;

4-amino-8-bromo-cinnoline-3-carboxylic acid sulfate + 1-methyl-1-cyclobutylamine (40571-47-9) → C14H15BrN4O (1309764-50-8)

Conditions	Yield
Stage #1: 4-amino-8-bromo-cinnoline-3-carboxylic acid sulfate With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 0 - 20℃; for 2.25h; Stage #2: 1-methylcyclobutan-1-amine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃;

4-amino-8-bromo-cinnoline-3-carboxylic acid sulfate + 1-methyl-1-cyclobutylamine (40571-47-9) → C22H24N4O3 (1309764-24-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 2.25 h / 0 - 20 °C 1.2: 0 - 20 °C 2.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,2-dimethoxyethane; ethanol; water / 90 °C View Scheme

1-methyl-1-cyclobutylamine (40571-47-9) → C14H15BrN4O (1309764-50-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 20 °C 2.1: hydrogenchloride; acetic acid; sodium nitrite / water / 0 - 5 °C 2.2: -5 - 0 °C 3.1: aluminum (III) chloride / toluene / 70 - 90 °C View Scheme

1-methyl-1-cyclobutylamine (40571-47-9) → C14H15BrN4O

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 20 °C 2.1: hydrogenchloride; acetic acid; sodium nitrite / water / 0 - 5 °C 2.2: -5 - 0 °C View Scheme

1-methyl-1-cyclobutylamine (40571-47-9) → C22H24N4O3 (1309764-24-6)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 20 °C 2.1: hydrogenchloride; acetic acid; sodium nitrite / water / 0 - 5 °C 2.2: -5 - 0 °C 3.1: aluminum (III) chloride / toluene / 70 - 90 °C 4.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / 1,2-dimethoxyethane; ethanol; water / 90 °C View Scheme

1-methyl-1-cyclobutylamine (40571-47-9) + ethyl 2-cyanoacetate (105-56-6) → C8H12N2O

Conditions	Yield
at 20℃;

1-(2,4-dimethoxybenzyl)-10-formyl-4-hydroxy-9-methyl-2-oxo-1,2,5,6,7,9-hexahydropyrido[3',2':6,7]cyclohepta[1,2-f]-indole-3-carboxylic acid + 1-methyl-1-cyclobutylamine (40571-47-9) → C33H37N3O6*C2HF3O2

Conditions	Yield
Stage #1: 1-(2,4-dimethoxybenzyl)-10-formyl-4-hydroxy-9-methyl-2-oxo-1,2,5,6,7,9-hexahydropyrido[3',2':6,7]cyclohepta[1,2-f]-indole-3-carboxylic acid; 1-methylcyclobutan-1-amine With acetic acid In 1,2-dichloro-ethane at 20℃; Stage #2: With sodium triacetoxyborohydride at 20℃; Stage #3: With trifluoroacetic acid In methanol	100.9 mg

1-(2,4-dimethoxybenzyl)-10-formyl-4-hydroxy-9-methyl-2-oxo-1,2,5,6,7,9-hexahydropyrido[3',2':6,7]cyclohepta[1,2-f]-indole-3-carboxylic acid + 1-methyl-1-cyclobutylamine (40571-47-9) → 4-hydroxy-9-methyl-10-(((1-methylcyclobutyl)amino)methyl)-2-oxo-1,2,5,6,7,9-hexahydropyrido[3',2':6,7]cyclohepta[1,2-f]indole-3-carboxylic acid hydrochloride

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid / 1,2-dichloro-ethane / 1 h / 20 °C 2: chlorotriisopropylsilane; trifluoroacetic acid / 1 h / 65 °C View Scheme

1-(2,4-dimethoxybenzyl)-10-formyl-4-hydroxy-9-methyl-2-oxo-1,2,5,6,7,9-hexahydropyrido[3',2':6,7]cyclohepta[1,2-f]-indole-3-carboxylic acid + 1-methyl-1-cyclobutylamine (40571-47-9) → C33H37N3O6

Conditions	Yield
Stage #1: 1-(2,4-dimethoxybenzyl)-10-formyl-4-hydroxy-9-methyl-2-oxo-1,2,5,6,7,9-hexahydropyrido[3',2':6,7]cyclohepta[1,2-f]-indole-3-carboxylic acid; 1-methylcyclobutan-1-amine With acetic acid In 1,2-dichloro-ethane at 20℃; for 1h; Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane

1-(2,4-dimethoxvbenzvl)-10-formyl-4-hydroxy-9-methyl-2-oxo-2,5,6,9-tetrahydro-1H-pyrido[2',3':4,5]oxepino[3,2-f]indole-3-carboxylic acid + 1-methyl-1-cyclobutylamine (40571-47-9) → 4-hydroxy-9-methyl-10-(((1-methylcyclobutyl)amino)methyl)-2-oxo-2,5,6,9-tetrahydro-1H-pyrido[2',3':4,5]oxepino[3,2-f]indole-3-carboxylic acid hydrochloride

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid / 1,2-dichloro-ethane / 1 h / 20 °C 2: chlorotriisopropylsilane; trifluoroacetic acid / 1 h / 65 °C View Scheme

1-(2,4-dimethoxvbenzvl)-10-formyl-4-hydroxy-9-methyl-2-oxo-2,5,6,9-tetrahydro-1H-pyrido[2',3':4,5]oxepino[3,2-f]indole-3-carboxylic acid + 1-methyl-1-cyclobutylamine (40571-47-9) → C32H35N3O7

Conditions	Yield
Stage #1: 1-(2,4-dimethoxvbenzvl)-10-formyl-4-hydroxy-9-methyl-2-oxo-2,5,6,9-tetrahydro-1H-pyrido[2',3':4,5]oxepino[3,2-f]indole-3-carboxylic acid; 1-methylcyclobutan-1-amine With acetic acid In 1,2-dichloro-ethane at 20℃; for 1h; Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane

1-methyl-1-cyclobutylamine (40571-47-9) + hexanal (66-25-1) → N-[(5Z)-4-butyl-2-(1-methylcyclobutyl)-isothiazol-5(2H)-ylidene]-5-chloro-2-methoxybenzamide (1075241-57-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: magnesium sulfate / dichloromethane / 1 h 2.1: tetrahydrofuran / 1 h 2.2: 1 h / 20 °C View Scheme

1-methyl-1-cyclobutylamine (40571-47-9) → N-((2S,3S)-3-amino-2-hydroxy-3-phenylpropyl)-3,4-dichloro-N-(1-methylcyclobutyl)benzenesulfonamide

Conditions	Yield
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 23 °C / Inert atmosphere 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / isopropyl alcohol / 16 h / Inert atmosphere; Heating 3: trimethylphosphane / water; tetrahydrofuran / 3 h / 23 °C / Inert atmosphere View Scheme

Upstream product

• 20117-47-9 1-methylcyclobutanol 
• 151-50-8 potassium cyanide 
• 1120-56-5 methylidenecyclobutane 
• 143-33-9 sodium cyanide 
• 75-05-8 acetonitrile 

Downstream Products

• 1382845-06-8 3-(3-(cyclopropanecarboxamido)isoquinolin-7-yl)-4-methyl-N-(1-methylcyclobutyl)benzamide 
• 1075241-57-4 N-[(5Z)-4-butyl-2-(1-methylcyclobutyl)-isothiazol-5(2H)-ylidene]-5-chloro-2-methoxybenzamide 
• 1552273-92-3 1-(1-methylcyclobutyl)-4-phenyl-1H-imidazole 
• 1552273-91-2 1-(1-methylcyclobutyl)-5-phenyl-1H-imidazole 
• 1309764-24-6 C₂₂H₂₄N₄O₃ 
• 118539-53-0 (Z)-2-(2,4-Dichloro-5-fluoro-benzoyl)-3-(1-methyl-cyclobutylamino)-acrylic acid ethyl ester