646-19-5

Usage

Uses

Used in Pharmaceutical Industry:
1,7-Diaminoheptane is used as a key intermediate in the synthesis of 7-amino-1-guanidinooctane, which is a precursor for the development of therapeutic agents. 1,7-DIAMINOHEPTANE has potential applications in the treatment of various medical conditions, including cardiovascular diseases and neurological disorders.
Used in Biochemical Research:
1,7-Diaminoheptane is also used in the preparation of 1,7-diamino-trans-hept-3-ene, which serves as a deoxyhypusine synthase inhibitor. Deoxyhypusine synthase is an enzyme involved in the post-translational modification of proteins, and its inhibition can help researchers study the role of this enzyme in various biological processes and diseases.

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 
• 3070-53-9 1,6-heptadiene 
• 131259-39-7 2-Hept-6-enyl-1,1,1,3,3,3-hexamethyl-disilazane 
• 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) 
• 123-99-9 azelaic acid 

Downstream Products

• 29333-99-1 N₁,N₁,N₇,N₇-tetramethylheptane-1,7-diamine 
• 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 
• 28031-26-7 C₂₇H₃₄N₂O₄ 

Relevant academic research and scientific papers

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.

Functionalized Photoreactive Compounds

The present invention concerns functionalized photoreactive compounds of formula (I), that are particularly useful in materials for the alignment of liquid crystals. Due to the adjunction of an electron withdrawing group to specific molecular systems bearing an unsaturation directly attached to two unsaturated ring systems, exceptionally high photosensitivities, excellent alignment properties as well as good mechanical robustness could be achieved in materials comprising said functionalized photoreactive compounds of the invention.

Hydroboration/Amination of N-Trimethylsilyl Protected Olefinic Amines and Diolefins: Synthesis of Isomerically Pure Diamines

N-Trimethylsilyl protected olefinic amines and terminal diolefins were hydroborated with dimethylborane and the resulting organoboranes were treated with in situ generated chloramine or chloralkylamines to produce isomerically pure diamines or N-substituted diamines in good yields.

Silicone containing bis-thioether aromatic amines

A silicone containing bis-thioether aromatic amine has a chemical structure wherein an aromatic nucleus at each end of the chemical radical is chemically bonded to the remainder of the chemical radical by either sulfur, sulfoxide or sulfone.