28292-43-5

Basic information

• Product Name: 2-AMINO-5-METHYLHEXANE
• Synonyms: 2-METHYL-5-HEXYLAMINE;2-AMINO-5-METHYLHEXANE;1,4-DIMETHYLPENTYLAMINE;1,4-DIMETHYL-AMYLAMINE;5-METHYL-2-HEXYLAMINE;1,4-dimethyl-pentylamin;5-Amino-2-methylhexane;5-methyl-2-hexanamin
• CAS NO: 28292-43-5
• Molecular Formula: C₇H₁₇N
• Molecular Weight: 115.22
• EINECS: 248-941-8
• Mol File: 28292-43-5.mol
• Article Data: 2

Chemical Properties

• Melting Point: -19°C (estimate)
• Boiling Point: 128-129 °C(lit.)
• Flash Point: 28°C
• Appearance: /
• Density: 0.760 g/mL at 20 °C(lit.)
• Vapor Pressure: 8.02mmHg at 25°C
• Refractive Index: n20/D 1.416
• PKA: 10.98±0.35(Predicted)
• BRN: 1731716
• CAS DataBase Reference: 2-AMINO-5-METHYLHEXANE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-5-METHYLHEXANE(28292-43-5)
• EPA Substance Registry System: 2-AMINO-5-METHYLHEXANE(28292-43-5)

Safety Data

• Hazard Codes: C
• Statements: 10-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2734 8/PG 2
• WGK Germany: 3
• RTECS: SC0875000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 28292-43-5(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Oil

Uses

2-Amino-5-methylhexane is an aliphatic amine used in the preparation of pyridines and other cyclic nitrogen based compounds for use ranging from antiparasitics to calcium channel inhibitors.

InChI:InChI=1/C7H17N/c1-6(2)4-5-7(3)8/h6-7H,4-5,8H2,1-3H3/p+1/t7-/m0/s1

Synthetic route

bis-(1,4-dimethyl-pentylidene)-hydrazine (60372-16-9) → 2-amino-5-methylhexane (28292-43-5) + bis-(1,4-dimethyl-pentyl)-amine (145659-67-2)

Conditions	Yield
With nickel at 190 - 200℃; Hydrogenation;

5-Methyl-2-hexanone (110-12-3) → 2-amino-5-methylhexane (28292-43-5)

N-(5-methyl-2-hexyl)phthalimide → 2-amino-5-methylhexane (28292-43-5)

Conditions	Yield
With hydrazine hydrate In ethanol hydrazinolysis; Heating;

5-methylhexan-2-ol (627-59-8) → 2-amino-5-methylhexane (28292-43-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 65 percent / PPh3; diethyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C 2: N2H4*H2O / ethanol / Heating View Scheme

4-Methylpentanoic acid (646-07-1) → 2-amino-5-methylhexane (28292-43-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: thorium oxide 2: aqueous alcoholic NaOH-solution; hydrazine hydrate 3: nickel / 190 - 200 °C / Hydrogenation View Scheme

2-amino-5-methylhexane (28292-43-5) + 4-methoxy-phenyl-sulphonyl chloride (98-68-0) → 4-methoxy-N-(5-methylhexan-2-yl)benzenesulfonamide

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 12h;	90%

2-amino-5-methylhexane (28292-43-5) + allylsulfonyl chloride (14418-84-9) → N-(5-methylhexan-2-yl)prop-2-ene-1-sulfonamide

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 3h;	83%

2-amino-5-methylhexane (28292-43-5) + dibenzoyl peroxide (94-36-0) → O-benzoyl-N-(5-methylhexan-2-yl)hydroxylamine

Conditions	Yield
Stage #1: dibenzoyl peroxide With caesium carbonate In dichloromethane at 23℃; for 2h; Stage #2: 2-amino-5-methylhexane In dichloromethane at 23℃; for 14h;	82%

2-amino-5-methylhexane (28292-43-5) → bis-(1,4-dimethyl-pentyl)-amine (145659-67-2)

Conditions	Yield
With chlorohydridocarbonylbis(tricyclohexylphosphine)ruthenium(II) In toluene at 120℃; for 24h; Schlenk technique; Inert atmosphere;	80%

2-amino-5-methylhexane (28292-43-5) + monofluoroacetyl chloride (359-06-8) → N-(1,4-Dimethyl-pentyl)-2-fluoro-acetamide

Conditions	Yield
With potassium hydroxide In diethyl ether at 5 - 15℃; for 5h;	75%

2-amino-5-methylhexane (28292-43-5) + trifluoroacetic anhydride

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 12h; Inert atmosphere; Cooling with ice;	75%

phthalic anhydride + 2-amino-5-methylhexane (28292-43-5) → N-(5-methyl-2-hexyl)phthalimide

Conditions	Yield
In toluene for 5h; Reflux;	70%

2-amino-5-methylhexane (28292-43-5) + boron trifluoride diethyl etherate (109-63-7) → trifluoro(1,4-dimethylpentylamino)borate

Conditions	Yield
In dichloromethane at 0℃; for 1.5h; Inert atmosphere;	63%

1,3-propanesultone (1120-71-4) + 2-amino-5-methylhexane (28292-43-5) → 3-(1,4-dimethyl-pentylamino)-1-propanesulfonic acid

Conditions	Yield
In acetone; toluene at 20℃; Heating / reflux;	60%

2-amino-5-methylhexane (28292-43-5) → 2-methyl 5-nitrohexane (135498-84-9)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In 1,2-dichloro-ethane at 83℃; for 3h;	59%
With 3-chloro-benzenecarboperoxoic acid In 1,2-dichloro-ethane for 3h; Heating;	59%

2-amino-5-methylhexane (28292-43-5) + 4-methoxy-benzoyl chloride (100-07-2) → 4-methoxy-N-(5-methylhexan-2-yl)benzamide

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 4h; Inert atmosphere;	55%

2-amino-5-methylhexane (28292-43-5) + benzoic acid anhydride (93-97-0) + 3-Methyl-2,4-pentanedione (815-57-6) → (R,Z)-3-methyl-4-((5-methylhexan-2-yl)amino)pent-3-en-2-one + (S)-N-(5-methylhexan-2-yl)benzamide + (S,Z)-3-methyl-4-((5-methylhexan-2-yl)amino)pent-3-en-2-one

Conditions	Yield
Stage #1: 2-amino-5-methylhexane; 3-Methyl-2,4-pentanedione With C74H89O4P In diethyl ether at -78 - -5℃; for 20h; Inert atmosphere; Molecular sieve; Resolution of racemate; Stage #2: benzoic acid anhydride With triethylamine In diethyl ether at 20℃; for 0.5h; Inert atmosphere;	A 41% B 46% C n/a

2-amino-5-methylhexane (28292-43-5) + 4,7-dihydro-1,3-dimethyl-4-oxo-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid (1057670-29-7, 57862-43-8) → 4,7-dihydro-1,3-dimethyl-N-(5-methylhexan-2-yl)-4-oxo-1H-pyrazolo[3,4-b]pyridine-5-carboxamide (1421702-73-9)

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 20℃; for 16.1667h;	25%

2-amino-5-methylhexane (28292-43-5) → sodium 1-(5-methyl-2-hexylamino)diazen-1-ium-1,2-diolate

Conditions	Yield
Stage #1: 2-amino-5-methylhexane With nitrogen(II) oxide In diethyl ether at -80℃; under 2068.65 Torr; Inert atmosphere; Stage #2: With sodium methylate In methanol for 0.0833333h;	15%

2-amino-5-methylhexane (28292-43-5) + 1-Chloro-3,4-dimethyl-2,6-dinitrobenzene (40318-32-9) → (3,4-Dimethyl-2,6-dinitro-phenyl)-(1,4-dimethyl-pentyl)-amine (40318-40-9)

Conditions	Yield
In toluene Heating;

2-amino-5-methylhexane (28292-43-5) + N-benzyloxycarbonyl-L-leucine hydrazide (4703-53-1, 39978-36-4, 42384-22-5) → L-Leucin-(+)-1,4-dimethylpentylamid (13532-68-8)

Conditions	Yield
(i), (ii) (hydrogenation); Multistep reaction;

2-amino-5-methylhexane (28292-43-5) + 3α-hydroxy-11β-chloroacetoxy-5α-pregnan-20-one (64510-61-8) → (1,4-Dimethyl-pentylamino)-acetic acid (3R,5S,8S,9S,10S,11S,13S,14S,17S)-17-acetyl-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-11-yl ester (64509-79-1)

Conditions	Yield
With sodium iodide In ethanol for 72h;

2-amino-5-methylhexane (28292-43-5) → (1,4-Dimethyl-pentyl)-sulfamic acid

Conditions	Yield
With chlorosulfonic acid; triethylamine In chloroform

2-amino-5-methylhexane (28292-43-5) → (R)-5-methylhexan-2-amine (24110-97-2)

2-amino-5-methylhexane (28292-43-5) + 4-chloropyridine-3-sulphonamide (33263-43-3) → 4-(1,4-Dimethyl-pentylamino)-pyridine-3-sulfonic acid amide (76254-96-1)

Conditions	Yield
at 80 - 100℃;

2-amino-5-methylhexane (28292-43-5) + acetonitrile (75-05-8) → N-(2-(5-amino-2-methylhexyl))acetamide

Conditions	Yield
With tetrafluoroboric acid; methyltrifluoromethyldioxirane; sodium carbonate Yield given. Multistep reaction;

2-amino-5-methylhexane (28292-43-5) + 3-(4-methyl-6-dimethylaminopyridin-3-yl)-2,5-dimethyl-7-chloropyrazolo[1,5-a]pyrimidine (195055-65-3)

Conditions	Yield
In acetonitrile Heating;	44 mg

+ 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonyl chloride → 5-(4-chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-1H-pyrazole-3-carboxylic acid (1,4-dimethyl-pentyl)-amide

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2h;

2-amino-5-methylhexane (28292-43-5) + 2-chloro-6-methyl-5-nitro-3H-pyrimidin-4-one (65224-66-0) → C12H20N4O3 (937364-89-1)

Conditions	Yield
In chloroform Heating;

2-amino-5-methylhexane (28292-43-5) → Z-2-(2,5-dimethyl hexen-1-yl) 3-nitroimidazo<1,2-a>pyridine (135921-66-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 59 percent / m-chloroperbenzoic acid / 1,2-dichloro-ethane / 3 h / Heating View Scheme

2-amino-5-methylhexane (28292-43-5) → E-2-(2,5-dimethyl hexen-1-yl) 3-nitroimidazo<1,2-a>pyridine (135921-65-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 59 percent / m-chloroperbenzoic acid / 1,2-dichloro-ethane / 3 h / Heating View Scheme

Upstream product

• 646-07-1 4-Methylpentanoic acid 
• 627-59-8 5-methylhexan-2-ol 
• 110-12-3 5-Methyl-2-hexanone 
• 60372-16-9 bis-(1,4-dimethyl-pentylidene)-hydrazine 

Downstream Products

• 40318-40-9 (3,4-Dimethyl-2,6-dinitro-phenyl)-(1,4-dimethyl-pentyl)-amine 
• 27298-98-2 (S)-1-(4-methylphenyl)ethylamine 
• 586-70-9 (R)-4'-methyl-1-phenylethylamine 
• 6496-48-6 2,2,5-trimethylpyrrolidine 
• 110-12-3 5-Methyl-2-hexanone 

Relevant articles and documents

Biochemical and Structural Characterization of an (R)-Selective Transaminase in the Asymmetric Synthesis of Chiral Hydroxy Amines

An (R)-selective transaminase RbTA with excellent stereoselectivity (>99% ee) in the asymmetric amination of hydroxy ketones was identified. Biochemical characterization showed that RbTA exhibited the highest activity toward 4-hydroxy-2-butanone among reported enzymes, and that it has broad substrate specificity, including for aliphatic, aromatic, and alicyclic ketones. Crystallization of RbTA were performed, as were molecular docking and mutagenesis studies. Residue Tyr125 plays a key role in substrate recognition by forming a hydrogen bond with hydroxy ketone. The applicability of the enzyme was determined in preparative-scale synthesis of (R)-3-amino-1-butanol, demonstrating the potential of RbTA as a green biocatalyst for production of value-added chiral hydroxy amines. This study provides an efficient tool for enzymatic synthesis of chiral hydroxy amines, as well as structural insight into substrate recognition by transaminases in the asymmetric amination of hydroxy ketones. (Figure presented.).