111-18-2

Basic information

• Product Name: N,N,N',N'-Tetramethyl-1,6-hexanediamine
• Synonyms: N,N,N',N'-teramethyl-1,6-hexamethylenediamine;N,N,N',N'-Tetramethyl-1,6-hexanediamine,99%;TMHDA;N,N,N',N'-Tetramethyl-1,6-hexanediamine, 98+%;Lupragen N500 Tetramethylhexandiamine);1,6-Bis(dimethylamino)hexane N,N,N',N'-Tetramethyl-1,6-hexanediamine;N1,N1,N6,N6-TetraMethylhexane-1,6-diaMine;N,N,N',N'-Tetramethyl-1,6-diaminohexane
• CAS NO: 111-18-2
• Molecular Formula: C₁₀H₂₄N₂
• Molecular Weight: 172.31
• EINECS: 203-842-9
• Product Categories: Miscellaneous;Amine Monomers;Monomers;Tertiary Amines
• Mol File: 111-18-2.mol
• Article Data: 13

Chemical Properties

• Melting Point: -46 °C
• Boiling Point: 209-210 °C(lit.)
• Flash Point: 165 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 0.806 g/mL at 25 °C(lit.)
• Vapor Pressure: 12.4Pa at 20℃
• Refractive Index: n20/D 1.4359(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: miscible
• PKA: 10.07±0.28(Predicted)
• Water Solubility: miscible
• CAS DataBase Reference: N,N,N',N'-Tetramethyl-1,6-hexanediamine(CAS DataBase Reference)
• NIST Chemistry Reference: N,N,N',N'-Tetramethyl-1,6-hexanediamine(111-18-2)
• EPA Substance Registry System: N,N,N',N'-Tetramethyl-1,6-hexanediamine(111-18-2)

Safety Data

• Hazard Codes: T
• Statements: 22-24-34-23/24
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3390 6.1/PG 1
• WGK Germany: 1
• RTECS: MO1370000
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 111-18-2(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to yellow liquid

Uses

N,N,N'',N''-Tetramethyl-1,6-hexanediamine is used in the synthesis of fluorene containing poly(arylene ether sulfone) as anion exchange membranes for alkaline fuel cells.

Preparation

N,N,N',N'-Tetramethyl-1,6-hexanediamine can be made from adipodinitrile and dimethylamine or from 1,6- hexanediamine and formaldehyde.

Flammability and Explosibility

Notclassified

Synthetic route

1 ,6-dibromohexane (629-03-8) + dimethyl amine (124-40-3) → N,N,N',N'-tetramethylhexamethylenediamine (111-18-2)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 24h;	100%
In chloroform at 20℃; for 24h;	100%
With sodium carbonate In ethanol; water for 24h; Heating;	98%

methanol (67-56-1) + 1,6-Hexanediamine (124-09-4) → N,N,N',N'-tetramethylhexamethylenediamine (111-18-2)

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)ruthenium(III)]; bis[2-(diphenylphosphino)phenyl] ether; lithium tert-butoxide at 100℃; for 24h;	95%
With [1,2,3,4,5-pentamethylcyclopentadiene*Ir(2,2'-bibenzimidazole)Cl]Cl; caesium carbonate at 120℃; for 12h;	78%
With TiO2 supported nano-Pd(0.8) catalyst In water at 20℃; for 15h; Inert atmosphere; Irradiation; Green chemistry;	96 %Chromat.

methanol (67-56-1) + hexanedinitrile (111-69-3) → N,N,N',N'-tetramethylhexamethylenediamine (111-18-2)

Conditions	Yield
With C22H19ClN5ORu(1+)*F6P(1-); caesium carbonate at 140℃; for 48h;	57%

1,6-Hexanediamine (124-09-4) + formaldehyd (50-00-0) + formic acid (64-18-6) → N,N,N',N'-tetramethylhexamethylenediamine (111-18-2)

Conditions	Yield
	41%

1,6-Hexanediamine (124-09-4) + formaldehyd (50-00-0) → N,N,N',N'-tetramethylhexamethylenediamine (111-18-2)

Conditions	Yield
With formic acid; water

tetra-N-methyl-hex-3-ynediyldiamine (104093-79-0) → N,N,N',N'-tetramethylhexamethylenediamine (111-18-2)

Conditions	Yield
With ethanol; nickel

tetra-N-methyl-hex-2-ynediyldiamine (104093-81-4) → N,N,N',N'-tetramethylhexamethylenediamine (111-18-2)

Conditions	Yield
With ethanol; nickel

N,N,N',N'-tetramethyladipamide (3644-93-7) → N,N,N',N'-tetramethylhexamethylenediamine (111-18-2)

Conditions	Yield
With sulfuric acid Durch elektrolytische Reduktion an einer Bleikathode.;

1,6-diiodohexane (629-09-4) + dimethyl amine (124-40-3) → N,N,N',N'-tetramethylhexamethylenediamine (111-18-2)

Conditions	Yield
With ethanol

formaldehyd (50-00-0) + N,N-dimethyl-1,6-hexanediamine (1938-58-5) → N,N,N',N'-tetramethylhexamethylenediamine (111-18-2)

Conditions	Yield
With formic acid

hexamethylene-bis-trimethylammonium hydroxide → N,N,N',N'-tetramethylhexamethylenediamine (111-18-2)

Conditions	Yield
With hydrogen sulfide; water und das hierbei enstandene Sulfid durch Destillation gespalten;

N,N-Dimethylpropargylamin (7223-38-3) → N,N,N',N'-tetramethylhexamethylenediamine (111-18-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium amide 2: Raney nickel; ethanol View Scheme

3-(Dimethylamino)propyl chloride (109-54-6) → N,N,N',N'-tetramethylhexamethylenediamine (111-18-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium amide 2: Raney nickel; ethanol View Scheme

bis(dimethylaminopropyl)manganese → manganese (7439-96-5) + N,N-dimethylaminopropane (926-63-6) + N,N,N',N'-tetramethylhexamethylenediamine (111-18-2)

Conditions	Yield
In neat (no solvent) byproducts: dimethylamine, propene; decompn. at 52°C; metal mirror obtained;;	A n/a B 0% C 0%

1,6-hexanediol (629-11-8) + dimethyl amine (124-40-3) → 6-(N,N-dimethylamino)-1-hexanol (1862-07-3) + N,N,N',N'-tetramethylhexamethylenediamine (111-18-2)

Conditions	Yield
Stage #1: 1,6-hexanediol With C39H57ClIrNP2 In 5,5-dimethyl-1,3-cyclohexadiene; ethanol at -78℃; for 0.5h; Autoclave; Inert atmosphere; Stage #2: dimethyl amine In 5,5-dimethyl-1,3-cyclohexadiene; ethanol at 150℃; under 112511 Torr; for 240h; Solvent; Reagent/catalyst; Autoclave; Inert atmosphere;

1,3-propanesultone (1120-71-4) + N,N,N',N'-tetramethylhexamethylenediamine (111-18-2) → N,N,N',N'-tetramethyl-N,N'-bis(3-sulfopropyl)-1,6-hexandiyldiammonium bis(hydrogensulfate)

Conditions	Yield
Stage #1: 1,3-propanesultone; N,N,N',N'-tetramethylhexamethylenediamine In 1,2-dichloro-ethane at 55 - 60℃; for 2.25h; Inert atmosphere; Stage #2: With sulfuric acid In water at 80℃; for 2h;	100%

N,N,N',N'-tetramethylhexamethylenediamine (111-18-2) + 2-bromo-N-hexylethanamide (5439-32-7) → C26H56N4O2(2+)*2Br(1-)

Conditions	Yield
In chloroform at 85℃; for 24h;	100%

N,N,N',N'-tetramethylhexamethylenediamine (111-18-2) + 2-Bromo-N-(n-octyl)acetamide (5326-97-6) → C30H64N4O2(2+)*2Br(1-)

Conditions	Yield
In chloroform at 85℃; for 24h;	100%

N,N,N',N'-tetramethylhexamethylenediamine (111-18-2) + 2-bromo-N-decyl-acetamide (5345-68-6) → C34H72N4O2(2+)*2Br(1-)

Conditions	Yield
In chloroform at 85℃; for 24h;	100%

N,N,N',N'-tetramethylhexamethylenediamine (111-18-2) + S-[4-(bromomethyl)phenyl] benzenecarbothioc acid (77552-03-5) → N1,N6-bis((4-benzoylthio)benzyl)-N1,N1,N6,N6-tetramethylhexane-1,6-diammonium bromide

Conditions	Yield
In acetonitrile	99%

1,3-propanesultone (1120-71-4) + N,N,N',N'-tetramethylhexamethylenediamine (111-18-2) → C13H30N2O3S (636565-15-6)

Conditions	Yield
In acetone at 20℃; for 3h;	98%

N,N,N',N'-tetramethylhexamethylenediamine (111-18-2) + 1-(4-bromobutoxy)-4-(tert-butyl)benzene (53669-73-1) → N,N'-Bis<4-(4-tert-butylphenoxy)butyldimethyl>-1,6-hexanediammonium dibromide (66264-45-7)

Conditions	Yield
In methanol	96%

N,N,N',N'-tetramethylhexamethylenediamine (111-18-2) + 2-propynyl chloride (624-65-7) → C16H30N2(2+)*2Cl(1-)

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 10h; Inert atmosphere;	96%

N,N,N',N'-tetramethylhexamethylenediamine (111-18-2) + propargyl bromide (106-96-7) → N,N,N',N'-tetramethyl-N,N'-dipropargylhexane-1,6-diammonium bromide

Conditions	Yield
In acetonitrile at 0 - 55℃; for 12h; Inert atmosphere;	96%

1,3-propanesultone (1120-71-4) + N,N,N',N'-tetramethylhexamethylenediamine (111-18-2) → N,N,N',N'-tetramethyl-1,6-hexandiyldiammonium-bis(propanesulfonate) (53055-22-4)

Conditions	Yield
In 1,2-dichloro-ethane at 55 - 60℃; for 2h; Inert atmosphere;	95%
In methanol at 30℃; for 20h;	78%

N,N,N',N'-tetramethylhexamethylenediamine (111-18-2) + 3-monochloro-1,2-propanediol (96-24-2) → 4,4,11,11-tetramethyl-4,11-diazoniatetradecane-1,2,13,14-tetrol dichloride

Conditions	Yield
In ethanol; water at 65℃; for 24h;	94%
In acetonitrile at 20℃; Reflux;	47%

N,N,N',N'-tetramethylhexamethylenediamine (111-18-2) + 2-bromo-N-(4-(hexadecyloxy)phenyl)acetamide → C58H104N4O4(2+)*2Br(1-)

Conditions	Yield
In diethyl ether at 40℃; for 72h;	94%

N,N,N',N'-tetramethylhexamethylenediamine (111-18-2) → N,N,N’,N’-tetramethylhexane-1,6-diamine dihydrochloride (1938-71-2, 19932-01-5)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; methanol for 0.166667h;	94%

N,N,N',N'-tetramethylhexamethylenediamine (111-18-2) + 4-bromo-1-(4'-methylphenoxy)butane (3257-49-6) → C32H54N2O2(2+)*2Br(1-) (87723-13-5)

Conditions	Yield
In methanol	93%

N,N,N',N'-tetramethylhexamethylenediamine (111-18-2) + 1-Bromotetradecane (112-71-0) → C24H53N2(1+)*Br(1-)

Conditions	Yield
In N,N-dimethyl-formamide at 60℃; for 30h; Inert atmosphere;	92.5%

N,N,N',N'-tetramethylhexamethylenediamine (111-18-2) + 2-bromo-N-(4-(tetradecyloxy)phenyl)acetamide → C54H96N4O4(2+)*2Br(1-)

Conditions	Yield
In diethyl ether at 40℃; for 72h;	92%

N,N,N',N'-tetramethylhexamethylenediamine (111-18-2) + methyl iodide (74-88-4) → N,N,N,N',N',N'-hexamethylhexanediammonium iodide (870-62-2)

Conditions	Yield
In acetonitrile at 20℃; Reflux;	91.5%
In acetonitrile at 40℃; for 48h;

2-chlorobenzo[d][1,3]thiazole (615-20-3) + N,N,N',N'-tetramethylhexamethylenediamine (111-18-2) → N-Benzothiazol-2-yl-N,N',N'-trimethyl-hexane-1,6-diamine (136540-14-2)

Conditions	Yield
In tetrahydrofuran at 100℃; under 6000480 Torr;	91%

4,4,4-trifluoro-1-(2-furanyl)-1,3-butanedione (326-90-9) + N,N,N',N'-tetramethylhexamethylenediamine (111-18-2) → C10H24N2*2C8H4F3O3(1-)*2H(1+)

Conditions	Yield
In acetonitrile at 25℃; for 24h;	90%

1,1,1-trifluoro-4-(2-thienyl)butane-2,4-dione (326-91-0) + N,N,N',N'-tetramethylhexamethylenediamine (111-18-2) → C10H24N2*2C8H4F3O2S(1-)*2H(1+)

Conditions	Yield
In acetonitrile at 25℃; for 24h;	90%

N,N,N',N'-tetramethylhexamethylenediamine (111-18-2) + 1,1,1,5,5,5-hexafluoroacetylacetone (1522-22-1) → C10H24N2*2C5HF6O2(1-)*2H(1+)

Conditions	Yield
In acetonitrile at 25℃; for 24h;	90%

N,N,N',N'-tetramethylhexamethylenediamine (111-18-2) + 1,4-Dichloro-2-butyne (821-10-3) → C14H28N2(2+)*2Cl(1-)

Conditions	Yield
In acetonitrile for 168h; Alkylation; Heating;	89%
In acetonitrile for 24h; Alkylation; Cyclization; Heating;	89%

N,N,N',N'-tetramethylhexamethylenediamine (111-18-2) + 2-bromo-N-(4-(octyloxy)phenyl)acetamide → C42H72N4O4(2+)*2Br(1-)

Conditions	Yield
In diethyl ether at 40℃; for 72h;	89%

N,N,N',N'-tetramethylhexamethylenediamine (111-18-2) + 2-bromo-N-(4-(decyloxy)phenyl)acetamide → C46H80N4O4(2+)*2Br(1-)

Conditions	Yield
In diethyl ether at 40℃; for 72h;	89%

N,N,N',N'-tetramethylhexamethylenediamine (111-18-2) + 2-bromo-N-(4-(dodecyloxy)phenyl)acetamide → C50H88N4O4(2+)*2Br(1-)

Conditions	Yield
In diethyl ether at 40℃; for 72h;	88%

N,N,N',N'-tetramethylhexamethylenediamine (111-18-2) + 3,5-di-tert-butylbenzyl bromide (62938-08-3) → C25H47N2(1+)*Br(1-)

Conditions	Yield
In acetonitrile at 80℃; for 10h;	88%

N,N,N',N'-tetramethylhexamethylenediamine (111-18-2) + propyl bromide (106-94-5) → N,N,N',N'-tetramethyl-N,N'-dipropyl-N,N'-hexanediyl-di-ammonium; dibromide (13112-74-8)

Conditions	Yield
In acetonitrile at 20℃; Reflux;	87%
With ethanol

6-chloro-1-hexanol (2009-83-8) + N,N,N',N'-tetramethylhexamethylenediamine (111-18-2) → N,N'-bis(6-hydroxyhexyl)-N,N,N',N'-tetramethyl-1,6-hexanediyldiammonium bromide dichloride

Conditions	Yield
at 90℃; for 24h;	86%
In acetonitrile at 20℃; Reflux;	60.1%

Upstream product

• 3644-93-7 N,N,N',N'-tetramethyladipamide 
• 629-11-8 1,6-hexanediol 
• 124-40-3 dimethyl amine 
• 67-56-1 methanol 
• 111-69-3 hexanedinitrile 
• 124-09-4 1,6-Hexanediamine 
• 109-54-6 3-(Dimethylamino)propyl chloride 
• 7223-38-3 N,N-Dimethylpropargylamin 
• 50-00-0 formaldehyd 
• 64-18-6 formic acid 
• 1938-58-5 N,N-dimethyl-1,6-hexanediamine 
• 629-09-4 1,6-diiodohexane 
• 629-03-8 1 ,6-dibromohexane 
• 104093-81-4 tetra-N-methyl-hex-2-ynediyldiamine 

Downstream Products

• 87723-14-6 C₃₀H₄₈Cl₂N₂O₂⁽²⁺⁾*2Br^(1-) 
• 88610-77-9 Ni(C₁₂H₁₄N₄(CH₃)2(C(C₆H₅)N(CH₃)(CH₂)6N(CH₃)C(C₆H₅)))⁽²⁺⁾*2PF₆^(1-)=(Ni(C₃₆H₄₈N₆))(PF₆)2 

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