646-19-5

Basic information

• Product Name: 1,7-DIAMINOHEPTANE
• Synonyms: RARECHEM AL BW 0083;HEPTAMETHYLENEDIAMINE;HEPTANEDIAMINE;1,7-DIAMINOHEPTANE;1,7-HEPTANEDIAMINE;1,7-Heptamethylenediamine;H2N(CH2)7NH2;Diaminoheptane
• CAS NO: 646-19-5
• Molecular Formula: C₇H₁₈N₂
• Molecular Weight: 130.23
• EINECS: 211-468-2
• Product Categories: alpha,omega-Alkanediamines;alpha,omega-Bifunctional Alkanes;Monofunctional & alpha,omega-Bifunctional Alkanes
• Mol File: 646-19-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 26-29 °C(lit.)
• Boiling Point: 223-225 °C(lit.)
• Flash Point: 190 °F
• Appearance: White to light yellow/Crystalline Chunks
• Density: 0,86 g/cm3
• Vapor Pressure: 0.0933mmHg at 25°C
• Refractive Index: 1.4590
• Storage Temp.: 2-8°C
• Solubility: 450g/l
• PKA: 10.95±0.10(Predicted)
• Water Solubility: Soluble in water, ethanol, acetone, ether and benzene.
• Sensitive: Air Sensitive
• BRN: 1734159
• CAS DataBase Reference: 1,7-DIAMINOHEPTANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,7-DIAMINOHEPTANE(646-19-5)
• EPA Substance Registry System: 1,7-DIAMINOHEPTANE(646-19-5)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3259 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 646-19-5(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystalline chunks

Uses

1,7-Diaminoheptane is used in the preparation of 7-amino-1-guanidinooctane and 1,7-diamino-trans-hept-3-ene, which is used as a deoxyhypusine synthase inhibitor.

InChI:InChI=1/C7H18N2/c8-6-4-2-1-3-5-7-9/h1-9H2/p+2

Synthetic route

2,2'-(heptane-1,7-diyl)bis(isoindoline-1,3-dione) (37830-03-8) → heptane-1,7-diamine (646-19-5)

Conditions	Yield
With hydrazine hydrate In ethanol at 80℃;	61%

pimelonitrile (646-20-8) → heptane-1,7-diamine (646-19-5)

Conditions	Yield
With sodium; butan-1-ol at 145℃;
With ammonia; nickel at 130 - 150℃; under 73550.8 Torr; Hydrogenation;
With ethanol; sodium
With ammonia; nickel at 90℃; under 44130.5 Torr; Hydrogenation;
With cobalt catalyst; ammonia at 120℃; under 73550.8 - 132391 Torr; Hydrogenation;

1,7-heptanedicarboxamide (1842-72-4) → heptane-1,7-diamine (646-19-5)

Conditions	Yield
With sodium hydroxide; bromine

1,6-heptadiene (3070-53-9) → heptane-1,7-diamine (646-19-5)

Conditions	Yield
With sodium hypochlorite; dimethylborane; ammonia 2.) 0 deg C, 10 min; Yield given. Multistep reaction;

2-Hept-6-enyl-1,1,1,3,3,3-hexamethyl-disilazane (131259-39-7) → heptane-1,7-diamine (646-19-5)

Conditions	Yield
With sodium hypochlorite; dimethylborane; ammonia 1.) 0 deg C, 1 h, 2.) O deg C; Yield given. Multistep reaction;

azelaic acid diamide → heptane-1,7-diamine (646-19-5)

Conditions	Yield
With sodium hypobromide

azelaic acid-diazide → heptane-1,7-diamine (646-19-5)

Conditions	Yield
With benzene at 60 - 65℃; Kochen des Reaktionsprodukts mit 20prozentig. HCl.;

1,7-dibromoheptane (4549-31-9) + toluene-4-sulfonamide (70-55-3) + aqueous-alcoholic alkaline solution → heptane-1,7-diamine (646-19-5) + heptamethyleneimine

Conditions	Yield
Erhitzen des Reaktionsprodukts mit konz.HCl im Rohr auf 160grad;

azelaic acid (123-99-9) → heptane-1,7-diamine (646-19-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: PCl5, aq. NH3 2: aq. NaOH, Br2 View Scheme

4,7-dichloroquinoline (86-98-6) + heptane-1,7-diamine (646-19-5) → N-(7-chloro-[4]quinolyl)-heptanediyldiamine (102882-13-3)

Conditions	Yield
Inert atmosphere;	100%
In pentan-1-ol at 120℃; for 16h;	80%
With N-ethyl-N,N-diisopropylamine In pentan-1-ol for 18h; Heating;	80%

heptane-1,7-diamine (646-19-5) → 1,7-diaminoheptane dihydrochloride (15536-15-9)

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; methanol for 0.166667h;	100%
With hydrogenchloride In 1,4-dioxane; methanol for 0.166667h; Schlenk technique; Inert atmosphere;	100%
With hydrogenchloride In diethyl ether
With hydrogenchloride In water at 70℃; for 1h;

1,4-dioxane-2,6-dione (4480-83-5) + heptane-1,7-diamine (646-19-5) → {[7-(2-carboxymethoxyacetylamino)heptylaminocarbonyl]methoxy}acetic acid (1383455-59-1)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃;	100%
In tetrahydrofuran at 0 - 20℃;	96%
In tetrahydrofuran at 0 - 20℃;	96%

heptane-1,7-diamine (646-19-5) + isovaleraldehyde (590-86-3) → C17H38N2 (1432473-24-9)

Conditions	Yield
With sodium tetrahydroborate In ethanol for 24h;	100%

heptane-1,7-diamine (646-19-5) + amoxicillin (26787-78-0) → C23H37N5O5S

Conditions	Yield
With sodium carbonate In water at 0 - 20℃; for 3h; pH=4; Inert atmosphere;	100%

heptane-1,7-diamine (646-19-5) + di-tert-butyl dicarbonate (24424-99-5) → N-(tert-butoxycarbonyl)-1,7-heptanediamine (99733-18-3)

Conditions	Yield
In chloroform at 0 - 20℃;	99%
In chloroform at 20℃; for 24h;	90%
In chloroform at 20℃; for 24h;	90%

heptane-1,7-diamine (646-19-5) + (rac)-gossypol (303-45-7) → 8,8'-Bis-[1-(7-amino-heptylamino)-meth-(Z)-ylidene]-1,6,1',6'-tetrahydroxy-5,5'-diisopropyl-3,3'-dimethyl-8H,8'H-[2,2']binaphthalenyl-7,7'-dione

Conditions	Yield
With acid In ethanol for 3h; Heating;	98.7%

9-chloro-1,2,3,4-tetrahydroacridine (5396-30-5) + heptane-1,7-diamine (646-19-5) → bis(7)-tacrine

Conditions	Yield
at 120℃; for 0.666667h;	98%
With indium(III) chloride In acetonitrile at 120℃; for 2h; Microwave irradiation; regioselective reaction;	88%
	55%

heptane-1,7-diamine (646-19-5) + N-{3-((E)-2-Carboxy-vinyl)-5-[3-(3,7-dimethyl-oct-6-enyloxycarbonyl)-propionylamino]-phenyl}-succinamic acid 3,7-dimethyl-oct-6-enyl ester (831179-85-2) → N-{3-{(E)-2-[7-((E)-3-{3,5-Bis-[3-(3,7-dimethyl-oct-6-enyloxycarbonyl)-propionylamino]-phenyl}-acryloylamino)-heptylcarbamoyl]-vinyl}-5-[3-(3,7-dimethyl-oct-6-enyloxycarbonyl)-propionylamino]-phenyl}-succinamic acid 3,7-dimethyl-oct-6-enyl ester

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 48h;	98%
With benzotriazole-1-yl-oxy-tris-(dimethylamino) PF6; N-ethyl-N,N-diisopropylamine In acetonitrile	98%

heptane-1,7-diamine (646-19-5) + phenyl isocyanate (103-71-9) → 3,3'-bis-phenyl(heptylene-1,7)-bisurea (52502-46-2)

Conditions	Yield
In chloroform for 1h;	98%

heptane-1,7-diamine (646-19-5) + 5-(benzyloxy)-4-chloro-6-methoxyquinazoline (120075-53-8) → N,N'-Bis-(5-benzyloxy-6-methoxy-quinazolin-4-yl)-heptane-1,7-diamine (120075-72-1)

Conditions	Yield
With triethylamine In ethanol for 24h; Ambient temperature;	97%

heptane-1,7-diamine (646-19-5) → N1,N7-di(p-toluenesulfonyl)-1,7-diaminoheptane (81505-98-8)

Conditions	Yield
	97%

heptane-1,7-diamine (646-19-5) + p-toluenesulfonyl chloride (98-59-9) → N1,N7-di(p-toluenesulfonyl)-1,7-diaminoheptane (81505-98-8)

Conditions	Yield
With potassium carbonate In water at 80℃; for 24h;	97%
With N,N'-dimethylaminopyridine; triethylamine In dichloromethane Ambient temperature;	92%
With sodium hydrogencarbonate In dichloromethane for 1h;	70%
With pyridine at 80 - 90℃;
In pyridine

n-dodecanoyl chloride (112-16-3) + heptane-1,7-diamine (646-19-5) → dodecanamide, N,N'-1,7-heptanediylbis- (195989-99-2)

Conditions	Yield
With sodium hydrogencarbonate In diethyl ether; water at 20℃; Schotten-Bauman acylation;	97%

heptane-1,7-diamine (646-19-5) + N-{3-((E)-2-Carboxy-vinyl)-5-[3-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxycarbonyl)-propionylamino]-phenyl}-succinamic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (831179-87-4) → C81H122N6O14

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h;	96%
With benzotriazole-1-yl-oxy-tris-(dimethylamino) PF6; N-ethyl-N,N-diisopropylamine In acetonitrile	96%

heptane-1,7-diamine (646-19-5) + 2-Nitrobenzenesulfonyl chloride (1694-92-4) → N,N'-bis(2-nitrobenzenesulfonyl)-1,7-heptanediamine (255383-14-3)

Conditions	Yield
With triethylamine In diethyl ether; dichloromethane	96%
With triethylamine In diethyl ether; dichloromethane	96%
With triethylamine In dichloromethane at 20℃; for 72h; Inert atmosphere;	96%

heptane-1,7-diamine (646-19-5) + boric acid (11113-50-1) → NH3(CH2)7NH3(2+)*B7O9(OH)5(2-)*H2O

Conditions	Yield
In neat (no solvent) mixt. boric acid and 1,7-diaminoheptane was heated at 80°C for 16h; product was suspended in MeOH, ppt. was filtered and dried in 60°C oven; elem. anal.;	96%
In neat (no solvent) mixt. boric acid and 1,7-diaminoheptane was heated at 120-250°C for 16 h; product was suspended in MeOH, ppt. was filtered and dried in 60°C oven; X-ray diffraction;

heptane-1,7-diamine (646-19-5) + 1,3-di(tert-butyloxycarbonyl)-2-(trifluoromethylsulfonyl)guanidine (207857-15-6) → C18H36N4O4 (342888-39-5)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 12h;	96%

heptane-1,7-diamine (646-19-5) + (1-adamantyl)methyl isocyanate (69887-12-3) → 1,1'-(heptane-1,7-diyl)bis[3-(adamantan-1-ylmethyl)urea]

Conditions	Yield
In N,N-dimethyl-formamide at 15 - 25℃; for 6h;	96%

heptane-1,7-diamine (646-19-5) + pyrene-1-aldehyde (3029-19-4) → N-[1-Pyren-1-yl-meth-(E)-ylidene]-N'-[1-pyren-1-yl-meth-(Z)-ylidene]-heptane-1,7-diamine

Conditions	Yield
In toluene for 3h; Heating;	95%

isatoic anhydride (118-48-9) + heptane-1,7-diamine (646-19-5) → 1,7-bis{(2-aminobenzoyl)amino}heptane

Conditions	Yield
In N,N-dimethyl-formamide at 50℃; for 3.5h;	95%

heptane-1,7-diamine (646-19-5) → 1,7-dinitroheptane (6848-85-7)

Conditions	Yield
With water; fluorine In dichloromethane; acetonitrile at 20℃; for 0.5h; Inert atmosphere; Flow reactor;	95%

heptane-1,7-diamine (646-19-5) + formic acid ethyl ester (109-94-4) → 1,7-Bis-formamino-heptan (70980-64-2)

Conditions	Yield
Reflux;	93%
for 5h; Reflux;
at 52℃;

heptane-1,7-diamine (646-19-5) + [PdCl(1-pyrrolidinecarbodithioato)] (849909-58-6) → [Pd2Cl2(pyrrolidine dithiocarbamate)2(1,7-diaminoheptane)] (1334597-03-3)

Conditions	Yield
In chloroform Pd compd. and ligand (2:1 molar ratio) stirred; ppt. filtered off, washed (CHCl3, pantane), dried (vac.), elem. anal.;	93%

heptane-1,7-diamine (646-19-5) + 6-Chloropurine riboside (2004-06-0) → (2R,3R,4S,5R)-2-(6-((7-aminoheptyl)amino)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

Conditions	Yield
With triethylamine In ethanol for 3h; Inert atmosphere; Reflux;	92%

heptane-1,7-diamine (646-19-5) + C23H21NO5 (1292805-59-4) → C24H34N2O2

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	92%

heptane-1,7-diamine (646-19-5) + (3-chloroadamantan-1-yl)methyl isocyanate → N,N′-(heptane-1,7-diyl)bis{N′-[(3-chloroadamantan-1-yl)methyl]urea}

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 12h;	92%

4-chloroquinoline (611-35-8) + heptane-1,7-diamine (646-19-5) → N,N'-di-quinolin-4-yl-heptane-1,7-diamine; compound with GENERIC INORGANIC NEUTRAL COMPONENT

Conditions	Yield
In pentan-1-ol for 14h; Substitution; Heating;	91%

heptane-1,7-diamine (646-19-5) + 9-chloro-7-methoxy-1,2,3,4-tetrahydroacridine (53618-65-8) → N1-(7-methoxy-1,2,3,4-tetrahydroacridin-9-yl)heptane-1,7-diamine (1432502-89-0)

Conditions	Yield
Stage #1: 9-chloro-7-methoxy-1,2,3,4-tetrahydroacridine With phenol at 80 - 90℃; Stage #2: heptane-1,7-diamine at 125 - 130℃;	91%
In phenol at 130℃; for 4h;
In pentan-1-ol for 18h; Reflux;
In phenol at 130℃; Inert atmosphere;
With sodium hydroxide; phenol at 130℃; for 4h;

heptane-1,7-diamine (646-19-5) + 2-hydroxynaphthalene-1-carbaldehyde (708-06-5) → 1,1’-[1,7-heptanediylbis(nitrilomethylidine)]bis(2-naphthol) (83849-11-0)

Conditions	Yield
In methanol at 20℃; for 0.133333h;	91%

Upstream product

• 646-20-8 pimelonitrile 
• 1842-72-4 1,7-heptanedicarboxamide 
• 4549-31-9 1,7-dibromoheptane 
• 70-55-3 toluene-4-sulfonamide 
• 37830-03-8 2,2'-(heptane-1,7-diyl)bis(isoindoline-1,3-dione) 
• 131259-39-7 2-Hept-6-enyl-1,1,1,3,3,3-hexamethyl-disilazane 
• 3070-53-9 1,6-heptadiene 
• 123-99-9 azelaic acid 

Downstream Products

• 29333-99-1 N₁,N₁,N₇,N₇-tetramethylheptane-1,7-diamine 
• 27914-72-3 Acetic acid 4-[7-(4-acetoxy-benzoylamino)-heptylcarbamoyl]-phenyl ester 
• 27906-53-2 C₃₁H₄₆N₂O₄ 
• 27914-70-1 C₂₃H₃₀N₂O₂S₂ 
• 62578-22-7 C₂₃H₂₈F₂N₂O₄ 
• 27914-34-7 C₂₃H₂₈Cl₂N₂O₄ 
• 27906-50-9 C₂₅H₃₄N₂O₄ 
• 27906-52-1 C₂₉H₄₂N₂O₄ 
• 27914-47-2 C₃₃H₃₄N₂O₄ 
• 27914-38-1 C₂₃H₂₄Cl₆N₂O₄ 
• 28031-25-6 C₂₅H₂₆Cl₂F₆N₂O₄ 
• 27890-78-4 C₂₃H₂₆F₄N₂O₄ 
• 27890-77-3 C₂₉H₄₂N₂O₄ 
• 27906-51-0 C₂₇H₃₈N₂O₄ 

Relevant articles and documents

Photochemical Decarboxylative C(sp3)-X Coupling Facilitated by Weak Interaction of N-Heterocyclic Carbene

While N-hydroxyphthalimide (NHPI) ester has emerged as a powerful reagent as an alkyl radical source for a variety of C-C bond formations, the corresponding C(sp3)-N bond formation is still in its infancy. We demonstrate herein transition-metal-free decarboxylative C(sp3)-X bond formation enabled by the photochemical activity of the NHPI ester-NaI-NHC complex, giving primary C(sp3)-(N)phth, secondary C(sp3)-I, or tertiary C(sp3)-(meta C)phth coupling products. The primary C(sp3)-(N)phth coupling offers convenient access to primary amines.

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