143-23-7

Basic information

• Product Name: BIS(HEXAMETHYLENE)TRIAMINE
• Synonyms: TIMTEC-BB SBB006597;BIS(6-AMINOHEXYL)AMINE;BIS(HEXAMETHYLENE)TRIAMINE;6,6'-IMINODIHEXYLAMINE;7-Azatridecan-1,-diamin;6,6μ-Iminodihexylamine, Bis(6-aminohexyl)amine;6,6'-Iminobis(1-hexanamine);6,6'-Iminodi(1-hexanamine)
• CAS NO: 143-23-7
• Molecular Formula: C₁₂H₂₉N₃
• Molecular Weight: 215.38
• EINECS: 205-593-1
• Product Categories: Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Polyamines
• Mol File: 143-23-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 33-36 °C(lit.)
• Boiling Point: 163-165 °C4 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.85 g/mL at 20 °C(lit.)
• Vapor Pressure: <0.01 mm Hg ( 25 °C)
• Refractive Index: n20/D 1.49(lit.)
• Storage Temp.: 2-8°C
• Solubility: soluble in Methanol
• PKA: 10.94±0.10(Predicted)
• Water Solubility: 437g/L at 20℃
• Stability: Stable. Protect from moisture - store under inert gas. Incompatible with strong oxidizing agents, carbon monoxide, carbon dioxid
• BRN: 2323517
• CAS DataBase Reference: BIS(HEXAMETHYLENE)TRIAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: BIS(HEXAMETHYLENE)TRIAMINE(143-23-7)
• EPA Substance Registry System: BIS(HEXAMETHYLENE)TRIAMINE(143-23-7)

Safety Data

• Hazard Codes: C
• Statements: 22-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3259 8/PG 2
• WGK Germany: 1
• RTECS: MO1186250
• F: 3-10-34
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 143-23-7(Hazardous Substances Data)

Usage

Chemical Properties

light beige solid

General Description

A colorless crystalline or flaked solid. Corrosive. Irritating to skin and eyes. May be toxic by ingestion. Used to make plastics.

Air & Water Reactions

Very soluble in water.

Reactivity Profile

BIS(HEXAMETHYLENE)TRIAMINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides.

Health Hazard

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C12H29N3/c13-9-5-1-3-7-11-15-12-8-4-2-6-10-14/h15H,1-14H2/p+3

Synthetic route

8-(2-(trimethylsilyl)ethanesulfonyl)-1,8,15-triazapentadecane (652130-77-3) → 1,8,15-triazapentadecane (143-23-7)

Conditions	Yield
With cesium fluoride In N,N-dimethyl-formamide at 100℃;	46%

N1,N13-diacetyl-1,13-diamino-7-azatridecane (500309-42-2) → 1,8,15-triazapentadecane (143-23-7)

Conditions	Yield
With hydrogenchloride for 2h; Heating; Yield given;

1,6-Hexanediamine (124-09-4) → 1,8,15-triazapentadecane (143-23-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 78 percent / 24 h / 100 °C 2: Raney Ni / benzene / 7 h / Heating 3: 2N HCl / 2 h / Heating View Scheme
Multi-step reaction with 2 steps 1: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr 2: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr View Scheme

mono-N-acetylhexamethylenediamine (49631-88-1) → 1,8,15-triazapentadecane (143-23-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: Raney Ni / benzene / 7 h / Heating 2: 2N HCl / 2 h / Heating View Scheme

6-amino-1-hexanol (4048-33-3) → hexamethylene imine (111-49-9) + 1,6-Hexanediamine (124-09-4) + 6-(azepan-1-yl)hexan-1-amine (21920-79-6) + 1,8,15-triazapentadecane (143-23-7)

Conditions	Yield
With ammonia; hydrogen In tert-butyl alcohol at 220℃; under 120012 Torr; for 6h;	A 33 %Chromat. B 20.7 %Chromat. C n/a D n/a

6-amino-1-hexanol (4048-33-3) → 1,6-Hexanediamine (124-09-4) + 1,8,15-triazapentadecane (143-23-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr 2: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr View Scheme

6-amino-1-hexanol (4048-33-3) → hexamethylene imine (111-49-9) + 6-(azepan-1-yl)hexan-1-amine (21920-79-6) + 1,8,15-triazapentadecane (143-23-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr 2: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr View Scheme

6-amino-1-hexanol (4048-33-3) → 1,8,15-triazapentadecane (143-23-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr 2: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr 3: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr View Scheme

6-amino-1-hexanol (4048-33-3) → 6-(azepan-1-yl)hexan-1-amine (21920-79-6) + 1,8,15-triazapentadecane (143-23-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr 2: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr 3: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr View Scheme

1,6-Hexanediamine (124-09-4) → hexamethylene imine (111-49-9) + 6-(azepan-1-yl)hexan-1-amine (21920-79-6) + 1,8,15-triazapentadecane (143-23-7)

Conditions	Yield
With ammonia; hydrogen In tert-butyl alcohol at 220℃; under 120012 Torr; for 6h;

hexamethylene imine (111-49-9) → 1,6-Hexanediamine (124-09-4) + 6-(azepan-1-yl)hexan-1-amine (21920-79-6) + 1,8,15-triazapentadecane (143-23-7)

Conditions	Yield
With ammonia; hydrogen In tert-butyl alcohol at 220℃; under 120012 Torr; for 6h;

1,6-hexanediol (629-11-8) → hexamethylene imine (111-49-9) + 1,6-Hexanediamine (124-09-4) + 6-(azepan-1-yl)hexan-1-amine (21920-79-6) + 1,8,15-triazapentadecane (143-23-7)

Conditions	Yield
With ammonia; hydrogen In tert-butyl alcohol at 220℃; under 120012 Torr; for 4.5h; Kinetics; Temperature; Pressure; Time;	A 31.9 %Chromat. B 38.4 %Chromat. C n/a D n/a

1,6-hexanediol (629-11-8) → 1,6-Hexanediamine (124-09-4) + 1,8,15-triazapentadecane (143-23-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen; ammonia; / tert-butyl alcohol / 4.5 h / 220 °C / 120012 Torr 2: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr View Scheme
Multi-step reaction with 2 steps 1: hydrogen; ammonia; / tert-butyl alcohol / 4.5 h / 220 °C / 120012 Torr 2: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr View Scheme
Multi-step reaction with 2 steps 1: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr 2: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr View Scheme
Multi-step reaction with 3 steps 1: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr 2: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr 3: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr View Scheme

1,6-hexanediol (629-11-8) → hexamethylene imine (111-49-9) + 6-(azepan-1-yl)hexan-1-amine (21920-79-6) + 1,8,15-triazapentadecane (143-23-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen; ammonia; / tert-butyl alcohol / 4.5 h / 220 °C / 120012 Torr 2: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr View Scheme
Multi-step reaction with 2 steps 1: hydrogen; ammonia; / tert-butyl alcohol / 4.5 h / 220 °C / 120012 Torr 2: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr View Scheme
Multi-step reaction with 2 steps 1: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr 2: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr View Scheme
Multi-step reaction with 2 steps 1: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr 2: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr View Scheme
Multi-step reaction with 3 steps 1: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr 2: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr 3: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr View Scheme

1,6-hexanediol (629-11-8) → 1,8,15-triazapentadecane (143-23-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogen; ammonia; / tert-butyl alcohol / 4.5 h / 220 °C / 120012 Torr 2: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr 3: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr View Scheme
Multi-step reaction with 3 steps 1: hydrogen; ammonia; / tert-butyl alcohol / 4.5 h / 220 °C / 120012 Torr 2: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr 3: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr View Scheme
Multi-step reaction with 3 steps 1: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr 2: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr 3: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr View Scheme
Multi-step reaction with 4 steps 1: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr 2: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr 3: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr 4: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr View Scheme

1,6-hexanediol (629-11-8) → 6-(azepan-1-yl)hexan-1-amine (21920-79-6) + 1,8,15-triazapentadecane (143-23-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogen; ammonia; / tert-butyl alcohol / 4.5 h / 220 °C / 120012 Torr 2: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr 3: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr View Scheme
Multi-step reaction with 3 steps 1: hydrogen; ammonia; / tert-butyl alcohol / 4.5 h / 220 °C / 120012 Torr 2: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr 3: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr View Scheme
Multi-step reaction with 3 steps 1: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr 2: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr 3: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr View Scheme
Multi-step reaction with 4 steps 1: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr 2: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr 3: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr 4: hydrogen; ammonia; / tert-butyl alcohol / 6 h / 220 °C / 120012 Torr View Scheme

hexanedinitrile (111-69-3) → hexamethylene imine (111-49-9) + 1,6-Hexanediamine (124-09-4) + di(5-cyanopentyl)-amine + 1-amino-5-cyanopentane (2432-74-8) + 1,8,15-triazapentadecane (143-23-7)

Conditions	Yield
With 1-butyl-3-methylimidazolium hydroxide; hydrogen In ethanol at 349.84℃; under 15001.5 Torr; for 6h; Reagent/catalyst; Temperature; Pressure; Time; Flow reactor; Sealed tube; Inert atmosphere; Ionic liquid;

1,8,15-triazapentadecane (143-23-7) + p-toluenesulfonyl chloride (98-59-9) → N,N',N"-tritosyl-7-aza-tridecanetriamine (187839-67-4)

Conditions	Yield
With potassium carbonate In water at 70℃; for 24h;	98%

1,8,15-triazapentadecane (143-23-7) + 1-[(2-oxazepan-1-yl)carbonyl]azepan-2-one (19494-73-6) → C26H47N5O4

Conditions	Yield
	95%
In toluene at 80℃; for 20h; Inert atmosphere;	80%
In toluene at 60℃;
In 5,5-dimethyl-1,3-cyclohexadiene at 80℃; for 8h; Inert atmosphere;

cobalt pivalate + chromium(III) fluoride tetrahydrate + 1,8,15-triazapentadecane (143-23-7) + Trimethylacetic acid (75-98-9) → [H2N((CH2)6NHCOtBu)2][Cr(III)7Co(II)F8(pivalate)16]

Conditions	Yield
With ((CH3)3CCO)2O In further solvent(s) heating mixt. of 1 equiv. of triamine deriv., 5 equiv. of chromium compd., 1 equiv. of cobalt compd. and 6 equiv. of pivalic anhydride in pivalic acid at 160°C for 30 h;	92%

chromium(III) fluoride tetrahydrate + [Ni2(μ-OH2)(μ-trimethylacetate)2(trimethylacetate)2(trimethylacetic acid)4] + 1,8,15-triazapentadecane (143-23-7) + Trimethylacetic acid (75-98-9) → [H2N((CH2)6NHCOtBu)2][Cr(III)7Ni(II)F8(pivalate)16]

Conditions	Yield
With ((CH3)3CCO)2O In further solvent(s) heating mixt. of 1 equiv. of triamine deriv., 5 equiv. of chromium compd., 1 equiv. of nickel compd. and 6 equiv. of pivalic anhydride in pivalic acid at 160°C for 30 h;	92%

di-tert-butyl dicarbonate (24424-99-5) + 1,8,15-triazapentadecane (143-23-7) → di-tert-butyl (((tert-butoxycarbonyl)azanediyl)bis(hexane-6,1-diyl))dicarbamate (187839-71-0)

Conditions	Yield
In methanol for 12h;	91%
In dichloromethane for 12h;	82%

7-chloro-4-bromo-quinoline (98519-65-4) + 1,8,15-triazapentadecane (143-23-7) → N1-(7-chloroquinolin-4-yl)-N6-(6-((7-chloroquinolin-4-yl)amino)hexyl)-hexane-1,6-diamine

Conditions	Yield
With potassium phosphate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane; water at 120℃; for 14h; Sealed tube; Inert atmosphere;	90%

1,8,15-triazapentadecane (143-23-7) + N-allyl isothiocyanate (57-06-7) → C24H44N6S3

Conditions	Yield
In tetrahydrofuran at 20℃; for 1h; Cooling with ice;	86%

1,8,15-triazapentadecane (143-23-7) + methyl iodide (74-88-4) → 2,2,9,9,16,16-hexamethyl-2,9,16-triazoniaheptadecane triiodide

Conditions	Yield
With 1,2,2,6,6-pentamethylpiperidine In N,N-dimethyl-formamide at 20℃;	85%

2,2,2-trichloro-1-(4-chloro-1H-pyrrol-2-yl)ethan-1-one (72652-31-4) + 1,8,15-triazapentadecane (143-23-7) → N,N'-(azanediylbis(hexane-6',1'-diyl))bis(4-chloro-1H-pyrrole- 2-carboxamide)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 18h; Inert atmosphere;	84%

manganese carbonate * 2 H2O + chromium(III) fluoride tetrahydrate + 1,8,15-triazapentadecane (143-23-7) + Trimethylacetic acid (75-98-9) → [H2N((CH2)6NHCOtBu)2][Cr(III)7Mn(II)F8(pivalate)16]

Conditions	Yield
With ((CH3)3CCO)2O In further solvent(s) heating mixt. of 1 equiv. of triamine deriv., 5 equiv. of chromium compd., 1 equiv. of manganese compd. and 6 equiv. of pivalic anhydride in pivalic acid at 160°C for 30 h;	81%

1,8,15-triazapentadecane (143-23-7) + Glyoxilic acid (298-12-4) → [6-(6-amino-hexylamino)-hexylamino]-acetic acid (454466-23-0)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol at 20℃;	80%

tert-butyl {[(tert-butoxycarbonyl)imino](1H-pyrazol-1-yl)methyl}(ethyl)carbamate + 1,8,15-triazapentadecane (143-23-7) → tert‐butyl N‐({[6‐({6‐[({[(tert‐butoxy)carbonyl](ethyl)amino}({[(tert‐butoxy)carbonyl]imino})methyl)amino]hexyl}amino)hexyl]amino}({[(tert‐butoxy)carbonyl]imino})methyl)‐N‐ethylcarbamate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; methanol at 20℃; for 16h;	80%

1,8,15-triazapentadecane (143-23-7) + N,N′-di-boc-N-crotyl-1H-pyrazole-1-carboxamidine → C27H53N5O4

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In methanol; acetonitrile at 50℃; for 5h;	79%

1,8,15-triazapentadecane (143-23-7) + Deoxycholic acid (83-44-3) → (4R,4'R)-N,N'-(azanediylbis(hexane-6,1-diyl))bis(4-((3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanamide)

Conditions	Yield
Stage #1: 1,8,15-triazapentadecane; Deoxycholic acid With benzotriazol-1-ol; triethylamine In N,N-dimethyl-formamide at 0℃; for 0.166667h; Inert atmosphere; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 25℃; for 24h; Inert atmosphere;	79%

4,5-dibromopyrrol-2-yl trichloromethyl ketone (50371-52-3) + 1,8,15-triazapentadecane (143-23-7) → N,N'-(azanediylbis(hexane-6',1'-diyl))bis(4,5-dibromo-1H-pyrrole-2-carboxamide)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 18h; Inert atmosphere;	78%
In tetrahydrofuran at 19℃; for 36h;	68%

1,8,15-triazapentadecane (143-23-7) + trityl chloride (76-83-5) → N-trityl-N'-[6-(trityl-amino)-hexyl]-hexane-1,6-diamine

Conditions	Yield
With triethylamine In chloroform	75%

zinc(II) hydroxide carbonate + chromium(III) fluoride tetrahydrate + 1,8,15-triazapentadecane (143-23-7) + Trimethylacetic acid (75-98-9) → [H2N((CH2)6NHCOtBu)2][Cr(III)7Zn(II)F8(pivalate)16]

Conditions	Yield
With ((CH3)3CCO)2O In further solvent(s) heating mixt. of 1 equiv. of triamine deriv., 5 equiv. of chromium compd., 1 equiv. of zinc compd. and 6 equiv. of pivalic anhydride in pivalic acid at 160°C for 30 h;	75%

1,8,15-triazapentadecane (143-23-7) + N,N'-bis-Boc-S-methyl-isothiourea (322474-21-5) → tert‐butyl N‐[({6‐[(6‐aminohexyl)amino]hexyl}amino)({[(tert‐butoxy)carbonyl]amino})methylidene]carbamate

Conditions	Yield
In tetrahydrofuran; methanol at 50℃; for 16h;	74%

1,8,15-triazapentadecane (143-23-7) + cholic acid (81-25-4) → (4R,4'R)-N,N'-(azanediylbis(hexane-6,1-diyl))bis(4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanamide)

Conditions	Yield
Stage #1: 1,8,15-triazapentadecane; cholic acid With benzotriazol-1-ol; triethylamine In N,N-dimethyl-formamide at 0℃; for 0.166667h; Inert atmosphere; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 25℃; for 24h; Inert atmosphere;	72%

S-methylisothiourea hemisulphate + 1,8,15-triazapentadecane (143-23-7) → 1,1‘-(azanediylbis(hexane-6,1-diyl))diguanidine (13516-25-1)

Conditions	Yield
In ethanol; water at 20℃; for 16h;	71%
With hydrogen bromide; acetic acid In ethanol; water at 20℃; for 16h;	71%

1,6-Hexanediamine (124-09-4) + hexan-1-amine (111-26-2) + 1,8,15-triazapentadecane (143-23-7) → hexamethylene imine (111-49-9)

Conditions	Yield
	70%

1,8,15-triazapentadecane (143-23-7) + tert-butyl (((tert-butoxycarbonyl)imino)(1H-pyrazol-1-yl)methyl)(cyclopropylmethyl)carbamate → tert‐butyl N‐({[6‐({6‐[({[(tert‐butoxy)carbonyl](cyclopropylmethyl)amino}({[(tert‐butoxy)carbonyl]imino})methyl)amino]hexyl}amino)hexyl]amino}({[(tert‐butoxy)carbonyl]imino})methyl)‐N‐(cyclopropylmethyl)carbamate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; methanol at 20℃; for 16h;	69%

di-tert-butyl dicarbonate (24424-99-5) + 1,8,15-triazapentadecane (143-23-7) → N1-Boc-N6-(6-(Boc-amino)hexyl)hexane-1,6-diamine (86536-93-8)

Conditions	Yield
In methanol at -80℃; for 1h;	68%

malachite + chromium(III) fluoride tetrahydrate + 1,8,15-triazapentadecane (143-23-7) + Trimethylacetic acid (75-98-9) → [H2N((CH2)6NHCOtBu)2][Cr(III)7Cu(II)F8(pivalate)16]

Conditions	Yield
With ((CH3)3CCO)2O In further solvent(s) heating mixt. of 1 equiv. of triamine deriv., 5 equiv. of chromium compd., 1 equiv. of copper compd. and 6 equiv. of pivalic anhydride in pivalic acid at 160°C for 30 h;	64%

1,8,15-triazapentadecane (143-23-7) + cholic acid (81-25-4) → (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-N,N-bis(6-((R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3,7,12-trihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanamido)hexyl)pentanamide

Conditions	Yield
Stage #1: 1,8,15-triazapentadecane; cholic acid With benzotriazol-1-ol; triethylamine In N,N-dimethyl-formamide at 0℃; for 0.166667h; Inert atmosphere; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 25℃; for 24h; Inert atmosphere;	62%

1,8,15-triazapentadecane (143-23-7) + benzaldehyde (100-52-7) → N1-benzyl-N6-(6-(benzylamino)hexyl)hexane-1,6-diamine (1135274-04-2)

Conditions	Yield
Stage #1: 1,8,15-triazapentadecane; benzaldehyde In isopropyl alcohol at 0 - 20℃; for 2h; Stage #2: With hydrogen; palladium 10% on activated carbon In isopropyl alcohol under 1500.15 Torr; for 16h;	61%

2,6-bis-tert-butoxycarbonylamino-hexanoic acid (2483-46-7, 65360-27-2, 119962-72-0) + 1,8,15-triazapentadecane (143-23-7) → N1-(Boc-Lys-Boc)-N6-[{6-(Boc-Lys-Boc)amido}hexyl]hexane-1,6-diamine

Conditions	Yield
Stage #1: 2,6-bis-tert-butoxycarbonylamino-hexanoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 0℃; Stage #2: 1,8,15-triazapentadecane In dichloromethane; N,N-dimethyl-formamide for 48h;	60%

1,8,15-triazapentadecane (143-23-7) + tert-butyl (((tert-butoxycarbonyl)imino)(1H-pyrazol-1-yl)methyl)(cyclopropylmethyl)carbamate → C27H53N5O4

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In methanol; acetonitrile at 50℃; for 5h;	57%

C27H33NO5S (1135274-06-4) + 1,8,15-triazapentadecane (143-23-7) → C69H101N3O12S3 (1135274-08-6)

Conditions	Yield
In isopropyl alcohol for 16h; Heating / reflux;	52%

Upstream product

• 500309-42-2 N¹,N¹³-diacetyl-1,13-diamino-7-azatridecane 
• 111-69-3 hexanedinitrile 
• 49631-88-1 mono-N-acetylhexamethylenediamine 
• 124-09-4 1,6-Hexanediamine 
• 652130-77-3 8-(2-(trimethylsilyl)ethanesulfonyl)-1,8,15-triazapentadecane 
• 629-11-8 1,6-hexanediol 
• 111-49-9 hexamethylene imine 
• 4048-33-3 6-amino-1-hexanol 

Downstream Products

• 187839-67-4 N,N',N-tritosyl-7-aza-tridecanetriamine 
• 1135274-04-2 N₁-benzyl-N₆-(6-(benzylamino)hexyl)hexane-1,6-diamine 
• 1135274-08-6 C₆₉H₁₀₁N₃O₁₂S₃ 
• 111-49-9 hexamethylene imine 
• 187839-72-1 2-Allyloxymethyl-4,11,18-tris-(toluene-4-sulfonyl)-1-oxa-4,11,18-triaza-cyclohenicosane 
• 187839-64-1 1,8,15-Tris-(toluene-4-sulfonyl)-1,8,15-triaza-cyclohenicosane 
• 454466-25-2 [(2,3-diacetoxy-benzoyl)-(6-{(2,3-diacetoxy-benzoyl)-[6-(2,3-diacetoxy-benzoylamino)-hexyl]-amino}-hexyl)-amino]-acetic acid benzyl ester 
• 212777-21-4 [(2,3-bis-methoxycarbonyloxy-benzoyl)-(6-{(2,3-bis-methoxycarbonyloxy-benzoyl)-[6-(8-methoxycarbonyloxy-2,4-dioxo-4H-benzo[e][1,3]oxazin-3-yl)-hexyl]-amino}-hexyl)-amino]-acetic acid 
• 454466-02-5 [(2,3-diacetoxy-benzoyl)-(6-{(2,3-diacetoxy-benzoyl)-[6-(2,3-diacetoxy-benzoylamino)-hexyl]-amino}-hexyl)-amino]-acetic acid 
• 212777-50-9 [6-(6-amino-hexylamino)-hexylamino]-acetic acid benzyl ester 
• 869531-65-7 (5-{bis-[6-(3-{bis-[6-(2,2,2-trifluoro-acetylamino)-hexyl]-carbamoyl}-propionylamino)-hexyl]-carbamoyl}-pentyl)-carbamic acid benzyl ester 
• 869531-57-7 (5-{bis-[6-(2,2,2-trifluoro-acetylamino)-hexyl]-carbamoyl}-pentyl)-carbamic acid benzyl ester 

Relevant articles and documents

Functionalized multi-walled carbon nanotubes supported Ni-based catalysts for adiponitrile selective hydrogenation to 6-aminohexanenitrile and 1,6-hexanediamine: Switching selectivity with [Bmim]OH

Functionalized multi-walled carbon nanotubes supported nickel-based catalysts were prepared and applied in adiponitrile (ADN) hydrogenation. The characterization results show that different functional groups such as NH2– COOH– OH– on MWCNTs surface can effectively act on metal ions by electrostatic attractions and chemical interactions so as to provide nucleation sites, and N species in MWCNTs can act as active sites for Ni deposition due to the strong electronic interactions between N species and Ni so as to promote ultra-small Ni nanoparticles formation, decrease NiO reduction activation energy, increase zero-valent Ni amounts as well as Ni nanoparticles dispersion. Furthermore, the doped N increases the lewis basicity, which favors the formation of primary amine of 6-aminohexanenitrile (ACN) and 1,6-hexanediamine (HDA). Moreover, the basic ionic liquid [Bmim]OH may switch the selectivity by inhibiting nucleophilic addition of the primary amine to the α-carbon of aldimine via the stabilization of –NH2 groups in the amino-imine intermediates so as to impede by-products formation. In addition, the mechanism for ADN hydrogenation in [Bmim]OH was studied by density functional theory calculations. Under optimized conditions, it gives 97.80% total selectivity to ACN and HDA at 95.34% ADN conversion over Ni/N-MWCNTs-800 in the presence of [Bmim]OH.

A practical method for building linear and cyclic triamines from (2-trimethylsilyl)ethanesulfonamides (SES-amides)

SES-chloride has been obtained in higher yield and purity by improving Weinreb's original procedure, allowing efficient access to the primary SES-amide. Linear triamines can be built conveniently from the SES-amide in high yields, with the potential for orthogonal protection. The modified Richman-Atkins cyclisation of SES-amides allows access to novel biologically interesting triazamacrocycles with combinations of three-, four-, five- and six-carbon bridges within the ring. Purification of the free macrocyclic amines by distillation greatly simplifies the workup, increasing the practicability of multi-gram scale synthesis. Although CsF sometimes provided undesirably low yields in the deprotection step, alternative fluoride sources were found to be unsuitable for the deprotection of SES-triazamacrocycles.

Decolorization of polyalkylene polyamines

A process for decolorizing polyalkylene polyamines, which comprises contacting one or more polyalkylene polyamines having an average molecular weight of greater than about 200 and less than about 1000 with carbon at a temperature greater than or equal to about 100° C. and less than or equal to about 300° C. under conditions effective to reduce the color rating of the one or more polyalkylene polyamines.