543-82-8

Basic information

• Product Name: 2-AMINO-6-METHYLHEPTANE
• Synonyms: 1,5-dimethyl-hexylamin;2-Heptanamine, 6-methyl-;2-Heptylamine, 6-methyl-;2-Isooctylamine;2-Methyl-6-aminoheptane;2-Metil-6-amino-eptano;6-Amino-2-methylheptane;6-methyl-2-heptanamin
• CAS NO: 543-82-8
• Molecular Formula: C₈H₁₉N
• Molecular Weight: 129.24
• EINECS: 208-851-1
• Product Categories: Amines;Building Blocks;C8;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Aliphatics;Inhibitors;Intermediates;Fine chemicals
• Mol File: 543-82-8.mol

Chemical Properties

• Melting Point: 25°C
• Boiling Point: 154-156 °C(lit.)
• Flash Point: 120 °F
• Appearance: /Liquid
• Density: 0.767 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.09mmHg at 25°C
• Refractive Index: n20/D 1.422(lit.)
• Storage Temp.: Flammables area
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: pKa 10.28 ± 0.1(H2O,t =25±0.2,I<0.001) (Uncertain)
• Stability: Hygroscopic
• Merck: 14,6757
• BRN: 1209250
• CAS DataBase Reference: 2-AMINO-6-METHYLHEPTANE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-6-METHYLHEPTANE(543-82-8)
• EPA Substance Registry System: 2-AMINO-6-METHYLHEPTANE(543-82-8)

Safety Data

• Hazard Codes: Xn
• Statements: 10-22-36/37/38
• Safety Statements: 26-36/37/39-37/39-16
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• RTECS: MQ4840000
• F: 10-34
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 543-82-8(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-AMINO-6-METHYLHEPTANE is used as a building block for the synthesis of n-type photoconductors, specifically N,N′-bis(1,5-dimethylhexyl)-3,4:9,10-perylenebis(dicarbox-imide) (PDHEP). This application is due to its ability to contribute to the development of advanced materials with specific electronic properties.
Used in Pharmaceutical Industry:
2-AMINO-6-METHYLHEPTANE serves as a reagent in the synthesis of substituted pyrrolidones through reductive amination of levulinic acid using a supported platinum catalyst. This process is essential for the production of various pharmaceutical compounds with potential therapeutic applications.
Used in Organic Chemistry:
As a nucleophilic amine, 2-AMINO-6-METHYLHEPTANE is involved in the synthesis of unsymmetrical sulfamides by reacting with sulfamic acid salts and triphenylphosphine ditriflate. This reaction is crucial for the creation of novel chemical entities with potential applications in various fields.

Preparation

1,5-Dimethylhexylamine was synthesized from 6-methyl-2-heptanone ([928-68-7]) by amination and catalytic hydrogenation.

InChI:InChI=1/C8H19N/c1-7(2)5-4-6-8(3)9/h7-8H,4-6,9H2,1-3H3/p+1/t8-/m0/s1

Synthetic route

ammonium formate (540-69-2) + 6-methylheptan-2-one (928-68-7) → 1,5-dimethylhexylamine (543-82-8)

Conditions	Yield
at 180 - 185℃; Kochen des Reaktionsprodukts mit konz.HCl;

6-methylheptan-2-one (928-68-7) → 1,5-dimethylhexylamine (543-82-8)

Conditions	Yield
With ethanol; ammonia; nickel Hydrogenation.unter Druck;

6-methylheptan-2-one (928-68-7) → 1,5-dimethylhexylamine (543-82-8) + bis-(1,5-dimethyl-hexyl)-amine (101440-18-0)

Conditions	Yield
With hydrazine hydrate anschliessend mit Methanol, wss. Ammoniak und aktiviertem Aluminium;

2-methyl-heptanone-(6)-oxime → 1,5-dimethylhexylamine (543-82-8)

Conditions	Yield
With nickel Hydrogenation;
With ethanol; sodium

(R)-6-methylheptan-2-amine (70419-11-3) → 1,5-dimethylhexylamine (543-82-8)

Conditions	Yield
With 2,2,2-trifluoroethanethiol In tetrahydrofuran; 3-methylpentan-3-ol at 22 - 24℃; for 2h; Photolysis;

6-Methyl-hept-5-en-2-on (110-93-0) → 1,5-dimethylhexylamine (543-82-8) + 6-methylhept-5-en-2-ol (4630-06-2, 1569-60-4) + 6-methylhept-5-en-2-amine (22462-79-9)

Conditions	Yield
With ammonia; hydrogen In tert-butyl alcohol at 120℃; for 24h; Autoclave; High pressure;	A 5 %Chromat. B 73 %Chromat. C 15 %Chromat.

1,5-dimethylhexylamine (543-82-8) + bis(1H-benzo[d][1,2,3]triazol-1-yl)methanethione (4314-19-6) → benzotriazole-1-carbothioic acid (1,5-dimethylhexyl)amide (690634-05-0)

Conditions	Yield
In dichloromethane at 20℃; for 18h;	99%
In dichloromethane at 20℃; for 18h;	87%

1,5-dimethylhexylamine (543-82-8) + N-tert-butoxycarbonyl-L-leucine (13139-15-6) → L-Leucin-(+)-1,5-dimethylhexylamid (13532-69-9)

Conditions	Yield
Stage #1: N-tert-butoxycarbonyl-L-leucine With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at -15℃; for 0.333333h; Stage #2: 1,5-dimethylhexylamine In tetrahydrofuran at -15 - 20℃; for 8h; Stage #3: With trifluoroacetic acid In dichloromethane for 5h;	98%

1,5-dimethylhexylamine (543-82-8) + N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → C17H28N2O

Conditions	Yield
Stage #1: N-tert-butoxycarbonyl-L-phenylalanine With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at -15℃; for 0.333333h; Stage #2: 1,5-dimethylhexylamine In tetrahydrofuran at -15 - 20℃; for 8h; Stage #3: With trifluoroacetic acid In dichloromethane for 5h;	97%

1,5-dimethylhexylamine (543-82-8) + pyroglutamic acid sodium salt (54571-67-4) → C13H25N2O3(1-)*Na(1+) (1311195-36-4)

Conditions	Yield
at 140℃; for 5h;	94%

succinic acid anhydride (108-30-5) + 1,5-dimethylhexylamine (543-82-8) → 4-[(6-methylheptan-2-yl)amino]-4-oxobutanoic acid (897522-18-8)

Conditions	Yield
In acetone at 20℃; Inert atmosphere;	93%

1,5-dimethylhexylamine (543-82-8) + methyl 3,4,6-tri-O-acetyl-2-deoxy-2-(4-nitrophenoxycarbonylamino)-β-D-glucopyranoside (130539-23-0) → methyl 3,4,6-tri-O-acetyl-2-deoxy-2-<3-(1,5-dimethylhexyl)ureido>-β-D-glucopyranoside (130539-31-0)

Conditions	Yield
In dichloromethane Ambient temperature;	92%

1,5-dimethylhexylamine (543-82-8) + p-benzyloxybenzaldehyde (4397-53-9) → N-(4-(benzyloxy)benzyl)-6-methylheptan-2-amine

Conditions	Yield
With sodium tris(acetoxy)borohydride In tetrahydrofuran for 12h; Inert atmosphere;	92%

formaldehyd (50-00-0) + 1,5-dimethylhexylamine (543-82-8) → N,N',N''-tris(1,5-dimethylhexyl)-1,3,5-triazacyclohexane

Conditions	Yield
In toluene for 0.5h; Heating;	91%

1,5-dimethylhexylamine (543-82-8) + 4-phenoxy benzaldehyde (67-36-7) → 6-methyl-N-(4-phenoxybenzyl)heptan-2-amine

Conditions	Yield
With sodium tris(acetoxy)borohydride In tetrahydrofuran for 12h; Inert atmosphere;	91%

1,5-dimethylhexylamine (543-82-8) + 3-Aminophenylboronic acid (30418-59-8) + 3-bromo-4-chloropyrazolo<3,4-d>pyrimidine (90914-41-3) → [3-(3-amino-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]-(1,5-dimethyl-hexyl)-amine

Conditions	Yield
Stage #1: 1,5-dimethylhexylamine; 3-bromo-4-chloropyrazolo<3,4-d>pyrimidine With acetic acid In 1,4-dioxane at 150℃; for 0.166667h; microwave irradiation; Stage #2: 3-Aminophenylboronic acid With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane at 180℃; for 0.166667h; Suzuki coupling; microwave irradiation;	90%

1,5-dimethylhexylamine (543-82-8) + (E)-2-hydroxy-2-methyl-5-phenylpent-4-en-3-one (63677-96-3) → N-(6-methylheptan-2-yl)-3-phenylpropanamide (885902-84-1)

Conditions	Yield
With 1,2,4-Triazole; C6H10N3O2S(1+)*Cl(1-); N-ethyl-N,N-diisopropylamine In dichloromethane at 40℃; for 3h;	90%

1,5-dimethylhexylamine (543-82-8) + N-tert-butoxycarbonyl-D-cyclohexylalanine (127095-92-5) → tert-butyl N-[(1R)-1-(cyclohexylmethyl)-2-(1,5-dimethylhexylamino)-2-oxoethyl]carbamate

Conditions	Yield
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 10 - 20℃; for 4h;	86%

1,5-dimethylhexylamine (543-82-8) + (±)-3-(1-phenylethoxy)benzaldehyde → (±)-6-methyl-N-(3-(1-phenylethoxy)benzyl)heptan-2-amine

Conditions	Yield
With sodium tris(acetoxy)borohydride In tetrahydrofuran for 12h; Inert atmosphere;	85%

1,5-dimethylhexylamine (543-82-8) + N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → C22H36N2O3

Conditions	Yield
Stage #1: N-tert-butoxycarbonyl-L-phenylalanine With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at -15℃; for 0.333333h; Stage #2: 1,5-dimethylhexylamine In tetrahydrofuran at -15 - 20℃; for 8h;	85%

1,5-dimethylhexylamine (543-82-8) + (±)-4-(1-phenylethoxy)benzaldehyde → (±)-6-methyl-N-(4-(1-phenylethoxy)benzyl)heptan-2-amine

Conditions	Yield
With sodium tris(acetoxy)borohydride In tetrahydrofuran for 12h; Inert atmosphere;	83%

1,5-dimethylhexylamine (543-82-8) + 2,4-Toluene diisocyanate (584-84-9) → 1,5-dimethylhexyl-3-[3-(3-(1,5-dimethylhexyl)ureido)-4-methylphenyl]urea

Conditions	Yield
In dichloromethane for 24h;	82%

1,5-dimethylhexylamine (543-82-8) + C26H24N6O12S2 → C42H58N8O10S2

Conditions	Yield
Stage #1: C26H24N6O12S2 With thionyl chloride In chloroform; N,N-dimethyl-formamide at 50℃; for 5h; Stage #2: 1,5-dimethylhexylamine With triethylamine In chloroform; N,N-dimethyl-formamide at 20℃;	82%

1,5-dimethylhexylamine (543-82-8) + 2-chloro-5-fluoronicotinic acid (38186-88-8) → 2-[(1,5-dimethylhexyl)amino]-5-fluoronicotinic acid (1038827-24-5)

Conditions	Yield
Stage #1: 1,5-dimethylhexylamine; 2-chloro-5-fluoronicotinic acid With copper; potassium carbonate; copper(I) bromide In N,N-dimethyl-formamide at 120℃; for 2h; Stage #2: With hydrogenchloride; water	81%

1,5-dimethylhexylamine (543-82-8) + diisopropylamine (108-18-9) → 6-methyl-N-(1-methylethyl)-2-heptanamine (13946-02-6)

Conditions	Yield
With μ-diiodo-di((η5-pentamethylcyclopentadienyl)(iodo)iridium) In 5,5-dimethyl-1,3-cyclohexadiene at 155℃; for 10h; Inert atmosphere;	80%

1,5-dimethylhexylamine (543-82-8) + (2-(4-chlorophenyl)cyclopropyl)(4-fluorophenyl)methanone → (2-(4-chlorophenyl)cyclopropyl)(4-(6-methylheptan-2-ylamino)phenyl)methanone

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100 - 120℃; Inert atmosphere;	80%

phthalic anhydride (85-44-9) + 1,5-dimethylhexylamine (543-82-8) → N-phthaloyl-6-methylheptan-2-amine

Conditions	Yield
In toluene for 5h; Reflux;	80%

1,5-dimethylhexylamine (543-82-8) + 4-bromo-1,8-naphthalenedicarboxylic anhydride (81-86-7) → 6-bromo-2-(1,5-dimethylhexyl)benzo[de]isoquinoline-1,3-dione

Conditions	Yield
In ethanol for 24h; Reflux;	80%

1,5-dimethylhexylamine (543-82-8) + C30H26N8O10S2 → C46H60N10O8S2 + C38H43N9O9S2

Conditions	Yield
Stage #1: C30H26N8O10S2 With thionyl chloride In chloroform; N,N-dimethyl-formamide at 20 - 50℃; for 5h; Stage #2: 1,5-dimethylhexylamine With triethylamine In chloroform; N,N-dimethyl-formamide at 20℃;	A 80% B n/a

1,5-dimethylhexylamine (543-82-8) + N-tert-butoxycarbonyl-L-leucine (13139-15-6) → C19H38N2O3

Conditions	Yield
Stage #1: N-tert-butoxycarbonyl-L-leucine With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at -15℃; for 0.333333h; Stage #2: 1,5-dimethylhexylamine In tetrahydrofuran at -15 - 20℃; for 8h;	78%

1,5-dimethylhexylamine (543-82-8) + levulinic acid (123-76-2) → C13H25NO

Conditions	Yield
With hydrogen In neat (no solvent) at 100℃; under 2250.23 Torr; for 20h;	77%

1,5-dimethylhexylamine (543-82-8) + triethylammonium N-tert-butylsulfamate → N-tert-butyl-N'-(6-methylhept-2-yl)sulfamide

Conditions	Yield
Stage #1: triethylammonium N-tert-butylsulfamate With trifluoromethylsulfonic anhydride; Triphenylphosphine oxide In dichloromethane at 0℃; for 0.25h; Inert atmosphere; Stage #2: With triethylamine In dichloromethane at -78℃; for 0.25h; Inert atmosphere; Stage #3: 1,5-dimethylhexylamine In dichloromethane at -78 - 22℃; Inert atmosphere;	77%

1,5-dimethylhexylamine (543-82-8) + p-acetylaminobenzenesulfonyl chloride (121-60-8) → N-[4-(1,5-dimethyl-hexylsulfamoyl)-phenyl]-acetamide

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 6h; Substitution;	76%
With dmap; triethylamine In dichloromethane at 5 - 20℃; for 6.21h;

1,5-dimethylhexylamine (543-82-8) + methyl 3-methoxypropionate (3852-09-3) → (R)-3-methoxy-N-(6-methylheptan-2-yl) propanamide (1322805-10-6)

Conditions	Yield
With Candida antarctica lipase B; Octanethiol; [Ir(2-phenylpyridine)2(4,4′-di-tert-butyl-2,2′-bipyridine)](PF6) In acetonitrile at 38℃; for 48h; Schlenk technique; Molecular sieve; Inert atmosphere; Irradiation; Enzymatic reaction; enantioselective reaction;	74%

1,3-propanesultone (1120-71-4) + 1,5-dimethylhexylamine (543-82-8) → 3-(1,5-dimethyl-hexylamino)-1-propanesulfonic acid

Conditions	Yield
In acetone; toluene at 20℃; Heating / reflux;	72%

1,5-dimethylhexylamine (543-82-8) + benzaldehyde (100-52-7) → (±)-N-benzyl-6-methylheptan-2-amine

Conditions	Yield
With sodium tris(acetoxy)borohydride In tetrahydrofuran for 12h; Inert atmosphere;	71%
Stage #1: 1,5-dimethylhexylamine; benzaldehyde In methanol for 3h; Stage #2: With sodium sulfate In methanol for 0.166667h; Stage #3: With methanol; sodium tetrahydroborate for 4h;	51%

Upstream product

• 540-69-2 ammonium formate 
• 928-68-7 6-methylheptan-2-one 
• 70419-11-3 (R)-6-methylheptan-2-amine 
• 110-93-0 6-Methyl-hept-5-en-2-on 

Downstream Products

• 502-59-0 octamylamine 
• 30121-80-3 4-{[(E)-1,5-Dimethyl-hexylimino]-methyl}-2-ethoxy-phenol 
• 15332-58-8 Bis-(2-chloro-ethyl)-(4-{[(E)-1,5-dimethyl-hexylimino]-methyl}-3-methyl-phenyl)-amine 
• 30121-85-8 (1,5-Dimethyl-hexyl)-[2-[1-phenyl-meth-(E)-ylidene]-oct-(E)-ylidene]-amine 
• 30121-81-4 (1,5-Dimethyl-hexyl)-[2-phenyl-eth-(E)-ylidene]-amine 
• 30121-74-5 (1,5-Dimethyl-hexyl)-[1-(4-nitro-phenyl)-meth-(E)-ylidene]-amine 
• 30121-77-8 N-(4-{[(E)-1,5-Dimethyl-hexylimino]-methyl}-phenyl)-acetamide 
• 30121-68-7 (1,5-Dimethyl-hexyl)-[1-phenyl-meth-(E)-ylidene]-amine 
• 30121-69-8 4-{[(E)-1,5-Dimethyl-hexylimino]-methyl}-phenol 
• 30121-71-2 (1,5-Dimethyl-hexyl)-[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-amine 
• 30121-72-3 2-{[(E)-1,5-Dimethyl-hexylimino]-methyl}-phenol 
• 30121-78-9 4-{[(E)-1,5-Dimethyl-hexylimino]-methyl}-2-methoxy-phenol 
• 30121-75-6 [1-(2,5-Dimethoxy-phenyl)-meth-(E)-ylidene]-(1,5-dimethyl-hexyl)-amine 
• 30121-84-7 (1,5-Dimethyl-hexyl)-[2-[1-phenyl-meth-(E)-ylidene]-hept-(E)-ylidene]-amine 

Relevant articles and documents

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