646-24-2

Usage

Uses

1,9-DIAMINONONANE is used as an organic intermediate for the synthesis of various chemical compounds and materials. Its presence in the molecular structure allows for the formation of amide, urea, and other functional groups, which are essential in the production of polymers, pharmaceuticals, and agrochemicals.
Used in Food Industry:
1,9-DIAMINONONANE is used as a detection agent for spermine and spermidine by matrix-assisted laser desorption/ionization combined with time-of-flight mass spectrometry (MALDI-TOF MS). These polyamines are essential for cell growth, proliferation, and differentiation, and their levels can be used as indicators of food quality and freshness.
Used in Pharmaceutical Industry:
1,9-DIAMINONONANE is used as a tool for the identification of apoptosis-related proteins by nano-flow ultra-performance liquid chromatography tandem mass-spectrometry (UPLC-MS/MS) after treatment with spermine and spermidine. Apoptosis is a crucial process in the regulation of cell death, and understanding its mechanisms can lead to the development of new therapeutic strategies for various diseases.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C9H22N2/c10-8-6-4-2-1-3-5-7-9-11/h1-11H2/p+2

Synthetic route

1,11-undecanediamide (73154-82-2) → 1.9-diaminononane (646-24-2)

Conditions	Yield
With sodium hypochlorite; sodium hydroxide In 1,4-dioxane at 10 - 75℃; for 3h; pH=10 - 11; pH-value; Solvent;	92%
Stage #1: 1,11-undecanediamide With sodium hypochlorite; sodium hydroxide Stage #2: With water In 1,4-dioxane at 45 - 75℃; for 1h; Solvent;	14.9 g

nonanedinitrile (1675-69-0) → 1.9-diaminononane (646-24-2)

Conditions	Yield
With ammonia; hydrogen; sodium hydroxide; Raney nickel In water at 130℃; under 22502.3 Torr; for 6h; Product distribution / selectivity; Autoclave;	88%
With ammonia; nickel at 100℃; Hydrogenation;
With ethanol; sodium

2,2"-(nonane-1,9-diyl)bis(isoindole-1,3-dione) (37830-04-9) → 1.9-diaminononane (646-24-2)

Conditions	Yield
With hydrazine hydrate In ethanol Reflux;	44%

diethyl ether (60-29-7) + nonanedinitrile (1675-69-0) → 1.9-diaminononane (646-24-2)

Conditions	Yield
With lithium aluminium tetrahydride

azelaic acid (123-99-9) → 1.9-diaminononane (646-24-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: NH3, H3PO4 2: Na, K, MeOH View Scheme

1,9-Nonanediol (3937-56-2) → 1.9-diaminononane (646-24-2) + 9-amino-1-nonanol

Conditions	Yield
With ammonia; chlorocarbonylhydrido[4,5-bis(dicyclohexylphosphinomethyl)acridine]ruthenium(II) In tetrahydrofuran at 150℃; under 11251.1 Torr; for 24h; Autoclave; Inert atmosphere;
With ammonia; (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); 1,1,1-tris(diethylphosphinomethyl)ethane In 1,3,5-trimethyl-benzene at 155℃; under 10501.1 Torr; for 24h; Product distribution / selectivity; Autoclave;
With ammonia; (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In 1,3,5-trimethyl-benzene at 155℃; under 10501.1 Torr; for 24h; Product distribution / selectivity; Inert atmosphere;

undecanedioic acid (1852-04-6) → 1.9-diaminononane (646-24-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: thionyl chloride / 1.5 h / Reflux 2.1: ammonia / methanol / 1 h / 40 °C 3.1: sodium hypochlorite; sodium hydroxide 3.2: 1 h / 45 - 75 °C View Scheme

2,8-dicyano-2,7-diene-1,9-sebacic acid → 1.9-diaminononane (646-24-2)

Conditions	Yield
Stage #1: 2,8-dicyano-2,7-diene-1,9-sebacic acid With triethylamine for 5h; Reflux; Stage #2: With hydrogen; sodium hydroxide In methanol at 25 - 75℃; under 22502.3 - 26252.6 Torr; for 4.5h; Autoclave; Further stages;	71.5 g

lactobionic acid (96-82-2, 534-41-8, 534-42-9, 51267-45-9, 58459-39-5, 69728-97-8) + 1.9-diaminononane (646-24-2) → 1,9-dilactobionamidononane

Conditions	Yield
In methanol for 24h; Heating;	100%

1.9-diaminononane (646-24-2) → 1,9-diaminononane dihydrochloride (16822-47-2, 68192-89-2)

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

1.9-diaminononane (646-24-2) + isovaleraldehyde (590-86-3) → C19H42N2 (1432473-22-7)

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

1.9-diaminononane (646-24-2) + 1,3-di(tert-butyloxycarbonyl)-2-(trifluoromethylsulfonyl)guanidine (207857-15-6) → C20H40N4O4 (1137830-47-7)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 12h;	98%

1.9-diaminononane (646-24-2) + carbonic acid dimethyl ester (616-38-6) → N,N'-nonanediyl-bis-carbamic acid dimethyl ester

Conditions	Yield
lipase from Candida antarctica In toluene at 70℃; for 48h; Product distribution / selectivity;	98%

2-(1,3,6,8-tetraoxo-1,3,6,8-tetrahydro-2-oxa-7-aza-pyren-7-yl)-3-tritylsulfanyl-propionic acid + 1.9-diaminononane (646-24-2) → C81H64N4O12S2 (1412450-92-0)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 40 - 140℃; for 0.25h; Microwave irradiation; Sonication;	96%

1.9-diaminononane (646-24-2) + formic acid ethyl ester (109-94-4) → 1,9-Bis-formamino-nonan

Conditions	Yield
Reflux;	96%
at 52℃;

1.9-diaminononane (646-24-2) + 2,5-di-iodo-1,1,1,6,6,6-hexafluoro-3,4-diazahexa-2,4-diene (88579-78-6) → 2,20-di-iodo-1,1,1,21,21,21-hexafluoro-5,17-bis(trifluoromethyl)-3,4,6,16,18,19-hexa-azauneicosa-2,4,17,19-tetraene

Conditions	Yield
In diethyl ether for 16h; Ambient temperature;	95%

n-dodecanoyl chloride (112-16-3) + 1.9-diaminononane (646-24-2) → N,N'-1,9-nonanediylbis-dodecanamide

Conditions	Yield
With sodium hydrogencarbonate In diethyl ether; water at 20℃; Schotten-Bauman acylation;	95%
With sodium hydrogencarbonate In diethyl ether; water at 0 - 20℃; for 8h;	70%

1.9-diaminononane (646-24-2) + p-toluenesulfonyl chloride (98-59-9) → N1,N9-di(p-toluenesulfonyl)-1,9-diaminononane (83492-50-6)

Conditions	Yield
With N,N'-dimethylaminopyridine; triethylamine In dichloromethane Ambient temperature;	94%
With pyridine at 80 - 90℃;

9-chloro-1,2,3,4-tetrahydroacridine (5396-30-5) + 1.9-diaminononane (646-24-2) → N-9'-(1',2',3',4'-tetrahydroacridinyl)-1,9-diaminononane (249290-20-8)

Conditions	Yield
In pentan-1-ol at 160℃; for 18h; Condensation;	94%
With sodium iodide; phenol at 180℃; for 2h;	68%
In pentan-1-ol for 18h; Heating;

1.9-diaminononane (646-24-2) + 4-chloro-2-methylquinoline (4295-06-1) → N,N'-di-4-quinaldinyl-1,9-diaminononane bis-hydrochloride (31892-52-1)

Conditions	Yield
In pentan-1-ol for 14h; Substitution; Heating;	93%

1.9-diaminononane (646-24-2) + Cholest-4-en-3-one (601-57-0) → 3α-(9-aminononyl)amino-4-cholestene + 3β-(9-aminononyl)amino-4-cholestene (1021952-47-5)

Conditions	Yield
Stage #1: 1.9-diaminononane; Cholest-4-en-3-one With titanium(IV) isopropylate In methanol at 20℃; for 12h; Stage #2: With sodium tetrahydroborate In methanol at -78℃; for 2h; Further stages.;	A n/a B 93%

1.9-diaminononane (646-24-2) + 6-[2,3-difluoro-4-[4-(trans-4-pentylcyclohexyl)phenyl]phenyloxy]hexanoic acid (1154761-94-0) → N,N'-bis[6-[2,3-difluoro-4-[4-(trans-4-pentylcyclohexyl)phenyl]phenyloxy]hexanoyl]-1,9-diaminononane (1154761-90-6)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 5h; Inert atmosphere;	93%

1.9-diaminononane (646-24-2) + acrylonitrile (107-13-1) → 3-(9-[(2-cyanoethyl)amino]nonylamino)propanenitrile (35514-03-5)

Conditions	Yield
In ethanol at 20℃; for 20h; Michael addition;	92%

1.9-diaminononane (646-24-2) + D-Glucono-1,5-lactone (90-80-2) → 1,9-digluconamidononane

Conditions	Yield
In methanol for 24h; Ambient temperature;	91%

1.9-diaminononane (646-24-2) + Cbz-sarcosine 2,4,5-trichlorophenyl ester → 1,9-bis(Cbz-sarcosylamino)nonane (335627-65-1)

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane for 168h;	91%

1.9-diaminononane (646-24-2) + geldanmycin (30562-34-6) → C65H94N6O16

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 0.5h;	91%

N-methoxycarbonylmaleimide (55750-48-6) + 1.9-diaminononane (646-24-2) → N,N'-Nonamethylendimaleinimid (38460-50-3)

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran for 3h; Ambient temperature;	90%

4-chloroquinoline (611-35-8) + 1.9-diaminononane (646-24-2) → N,N'-di-quinolin-4-yl-nonane-1,9-diamine; compound with GENERIC INORGANIC NEUTRAL COMPONENT

Conditions	Yield
In pentan-1-ol Substitution; Heating;	90%

1.9-diaminononane (646-24-2) + Nα-lauroyl-L-nitroarginine → C45H88N12O8

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In dichloromethane	90%

1.9-diaminononane (646-24-2) + pentadecanyl isocyanate (39633-51-7) → 1-pentadecyl-3-[9-(3-pentadecylureido)nonyl]urea

Conditions	Yield
In toluene for 2h;	90%

1.9-diaminononane (646-24-2) + 3-(triethoxypropyl) isocyanate (24801-88-5) → 1,9-bis[(triethoxysilyl)propylureido]nonane

Conditions	Yield
In dichloromethane at 20℃; for 12h;	90%

gallium oxyhydroxide + 1.9-diaminononane (646-24-2) + phosphoric acid (86119-84-8, 7664-38-2) + hydrogen fluoride (7664-39-3) → 9Ga(3+)*9PO4(3-)*2OH(1-)*3F(1-)*2NH3(CH2)9NH3(2+)*3H2O*H(1+)=Ga9(PO4)9(OH)2F3(H2O)*2NH3(CH2)9NH3*H3O*H2O

Conditions	Yield
With tri-n-propylamine In water High Pressure; hydrothermal synthesis at pH 3-4 by heating at 180°C for 3 d; filtered, washed with water, dried at room temp.; elem. anal.;	90%

2,5-Dihydroxybenzaldehyde (1194-98-5) + 1.9-diaminononane (646-24-2) + zinc diacetate (557-34-6) → 2,2'-(1,9-nonanediylbisnitrilomethylidine)bis(4-hydroxyphenolato)zinc(II) (1416548-29-2)

Conditions	Yield
In methanol at 50℃;	88%

1.9-diaminononane (646-24-2) + 1-tosyl-3,4,4-trimethyl-Δ2-imidazolinium iodide (71254-91-6) → (Z)-1,3-Diaza-cyclododec-1-ene; hydriodide (71255-01-1)

Conditions	Yield
In acetonitrile Heating;	87%

1.9-diaminononane (646-24-2) + p-cyanobenzenesulfonyl chloride (49584-26-1) → 1,9-bis(-4-cyanobenzenesulfonamidoamido)nonane (862252-25-3)

Conditions	Yield
With triethylamine In DMF (N,N-dimethyl-formamide) at 0℃; for 4h;	87%
With triethylamine In DMF (N,N-dimethyl-formamide) for 4h;	87%

1.9-diaminononane (646-24-2) + Z-Lys(Boc)-OH (2389-60-8) → C47H74N6O10 (1029802-56-9)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	87%

Upstream product

• 60-29-7 diethyl ether 
• 1675-69-0 nonanedinitrile 
• 123-99-9 azelaic acid 
• 3937-56-2 1,9-Nonanediol 
• 1852-04-6 undecanedioic acid 
• 73154-82-2 1,11-undecanediamide 
• 37830-04-9 2,2-(nonane-1,9-diyl)bis(isoindole-1,3-dione) 

Downstream Products

• 67232-08-0 (1E,9E)-2,2'-[nonane-1,9-diylbis(nitrilomethylidyne)]diphenol 
• 27890-79-5 C₂₅H₂₈F₆N₂O₄ 
• 27906-49-6 C₂₅H₃₄N₂O₄ 
• 510754-90-2 (9-amino-nonyl)-carbamic acid tert-butyl ester 
• 104807-19-4 {5-[9-(6-Benzyloxycarbonylamino-hexanoylamino)-nonylcarbamoyl]-pentyl}-carbamic acid benzyl ester 
• 54897-77-7 N,N'-Bis-(2,4-dinitro-phenyl)-nonane-1,9-diamine 
• 83492-50-6 N¹,N⁹-di(p-toluenesulfonyl)-1,9-diaminononane 

Relevant academic research and scientific papers

Synthesis method of 1,9-diaminononane

The invention relates to a synthesis method of 1,9-diaminononane. The synthesis method comprises the following steps: 1) in the presence of an acid catalyst or an alkali catalyst, carrying out a condensation reaction on 1,5-glutaraldehyde with cyanoacetic acid or cyanoacetate to generate an intermediate A; 2) in the presence of no catalyst or in the presence of an inorganic base catalyst or an organic amine catalyst, directly carrying out a decarboxylation reaction on the intermediate A, or carrying out a decarboxylation reaction after hydrolysis to obtain an intermediate B; and 3) in the presence of a hydrogenation reduction catalyst, carrying out a hydrogenation reaction on the intermediate B to generate the final product 1,9-diaminononane.

High-carbon alkane diamine, and preparation method and application thereof

The invention relates to the field of high-carbon alkane diamine preparation, and discloses high-carbon alkane diamine, and a preparation method and application thereof. The preparation method of thehigh-carbon alkane diamine disclosed by the invention is characterized in that the structure of the high-carbon alkane diamine is as shown in the formula NH2-(CH2)m-NH2; the method comprises the following steps: (1) under amideation reaction conditions, reacting high-carbon alkane diacid which is as shown in the formula COOH-(CH2)n-COOH with an ammonia-containing compound to obtain high-carbon chain diamide which is as shown in the formula CONH2-(CH2)n-CONH2; (2) under an alkaline condition, enabling the high-carbon chain diamide which is as shown in the formula CONH2-(CH2)n-CONH2 to perform rearrangement degradation in the existence of water, sodium hypochlorite and/or sodium hypobromite to obtain the high-carbon alkane diamine which is as shown in the formula NH2-(CH2)m-NH2, wherein n=11to 15, and m=9 to 13. The method provided by the invention is a safe, convenient, simple and feasible preparation method for the high-carbon alkane diamine.

Synthetic method of 1,9-diaminononane

The invention provides a synthetic method of 1,9-diaminononane. The method comprises the following steps: firstly, carrying out condensation reaction on undecanoic acid and transforming the undecanoicacid into a derivative of the undecanoic acid; then carrying out ammoniation to generate undecendiamide, and then carrying out Hofmann rearrangement reaction to generate a target product 1,9-diaminononane. The method disclosed by the invention has the advantages that raw materials are inexpensive and easily obtained and have a sufficient supply, and high-temperature and high-pressure reaction conditions are not involved, and a production process has more security. Compared with an abroad production technology, the synthetic method disclosed by the invention has the advantages of less side reaction, high purity of the product, less reaction steps and low requirement on equipment. Compared with a production process reported by domestic companies, the synthetic method has the advantages of less three wastes, and meanwhile, hydrogenation reaction is not involved, and the synthetic method has higher reaction security.

A new kind of acetylcholine esterase inhibitors and its preparation method and application (by machine translation)

The present invention provides a novel acetyl choline esterase inhibitor and its preparation method and application, in particular, the invention discloses a formula A shown with double AChE binding site of substituted acridine compound, and its preparation method and as acetylcholinesterase inhibitors. The preparation of the novel compounds of this invention demonstrate good inhibit acetylcholine esterase role, can be used as a preparation for treating and preventing HAMER (AD) application value. (by machine translation)

METHOD FOR PRODUCING ALKANOL AMINES BY HOMOGENEOUSLY CATALYZED ALCOHOL AMINATION

PROBLEM TO BE SOLVED: To provide a method for producing alkanol amines by alcohol amination of diols using ammonia under elimination of water. SOLUTION: The invention relates to a method for producing alkanol amines which comprise a primary amino group (-NH2) and a hydroxyl group (-OH), by alcohol amination of diols comprising two hydroxyl groups (-OH) using ammonia under elimination of water. The reaction is homogeneously catalyzed in the presence of at least one complex catalyst which contains at least one element selected from groups 8, 9 and 10 of the periodic table and at least one donor ligand. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPO&INPIT

The preparation obtained by homogeneous catalysis mellow amination method of the primary amine

The invention relates to a method for producing primary amines comprising at least one functional group of formula (-CH2-NH2), by alcohol amination of educts which comprise at least one functional group of formula (-CH2-OH), using ammonia, and elimination of water. The homogeneously catalyzed alcohol amination is carried out in the presence of at least one complex catalyst which contains at least one element selected from the groups 8 and 9 of the periodic table and at least one phosphorus donor ligand of general formula (I).

· Uniform catalyst by using alcohol aminosilicone di-, tri-and a method of manufacturing a polyphenylenepolyamine

The invention relates to a method for producing primary amines, which contain at least one functional group of the formula (-CH2-NH2) and at least one further primary amino group, by the alcohol amination of reactants, which contain at least one functional group of the formula (-CH2-OH) and at least one further functional group (-X), wherein (-X) is selected from hydroxyl groups and primary amino groups, using ammonia with removal of water, wherein the reaction is carried out in a homogeneously catalyzed manner in the presence of at least one complex catalyst containing at least one element selected from groups 8, 9 and 10 of the periodic table and at least one donor ligand.

PROCESS FOR PREPARING DI-, TRI- AND POLYAMINES BY HOMOGENEOUSLY CATALYZED ALCOHOL AMINATION

Process for preparing primary amines which have at least one functional group of the formula (—CH2—NH2) and at least one further primary amino group by alcohol amination of starting materials having at least one functional group of the formula (—CH2—OH) and at least one further functional group (—X), where (—X) is selected from among hydroxyl groups and primary amino groups, by means of ammonia with elimination of water, wherein the reaction is carried out homogeneously catalyzed in the presence of at least one complex catalyst comprising at least one element selected from groups 8, 9 and 10 of the Periodic Table and also at least one donor ligand.

PROCESS FOR PREPARING ALKANOLAMINES BY HOMOGENEOUSLY CATALYZED ALCOHOL AMINATION

Process for preparing alkanolamines which have a primary amino group (—NH2) and a hydroxyl group (—OH) by alcohol amination of diols having two hydroxyl groups (—OH) by means of ammonia with elimination of water, wherein the reaction is carried out homogeneously catalyzed in the presence of at least one complex catalyst comprising at least one element selected from groups 8, 9 and 10 of the Periodic Table and also at least one donor ligand.

PROCESS FOR THE PREPARATION OF PRIMARY AMINES BY HOMOGENEOUSLY CATALYZED ALCOHOL AMINATION

Process for the preparation of primary amines which have at least one functional group of the formula (—CH2—NH2) by alcohol amination of starting materials which have at least one functional group of the formula (—CH2—OH), with ammonia, with the elimination of water, where the alcohol amination is carried out under homogeneous catalysis in the presence of at least one complex catalyst which comprises at least one element selected from groups 8 and 9 of the Periodic Table of the Elements, and also at least one phosphorus donor ligand of the general formula (I).