646-24-2

Basic information

• Product Name: 1,9-DIAMINONONANE
• Synonyms: RARECHEM AL BW 0086;NONAMETHYLENEDIAMINE;1,9-NONANEDIAMINE;1,9-DIAMINONONANE;1,9-Diaminonane;1,9-Nonamethylenediamine;Diaminononane;1,9-Diaminononane,98%
• CAS NO: 646-24-2
• Molecular Formula: C₉H₂₂N₂
• Molecular Weight: 158.28
• EINECS: 211-470-3
• Product Categories: alpha,omega-Alkanediamines;alpha,omega-Bifunctional Alkanes;Monofunctional & alpha,omega-Bifunctional Alkanes
• Mol File: 646-24-2.mol
• Article Data: 14

Chemical Properties

• Melting Point: 35-37 °C(lit.)
• Boiling Point: 258-259 °C756 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: White to slightly yellow low melting solid
• Density: 0.8215 (estimate)
• Vapor Pressure: 0.0135mmHg at 25°C
• Refractive Index: 1.4686 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 10.97±0.10(Predicted)
• Water Solubility: Soluble in water.
• Sensitive: Air Sensitive
• BRN: 1737533
• CAS DataBase Reference: 1,9-DIAMINONONANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,9-DIAMINONONANE(646-24-2)
• EPA Substance Registry System: 1,9-DIAMINONONANE(646-24-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 3259 8/PG 2
• WGK Germany: 3
• F: 10-21
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 646-24-2(Hazardous Substances Data)

Usage

Uses

1,9-Diaminononane is used as an organic intermediate. It is also used to detect spermine and spermidine by matrix-assisted laser desorption/ionization combined with time-of-flight mass spectrometry ( MALDI-TOF MS) in foods and 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.

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 
• 73154-82-2 1,11-undecanediamide 
• 1852-04-6 undecanedioic acid 
• 37830-04-9 2,2-(nonane-1,9-diyl)bis(isoindole-1,3-dione) 
• 3937-56-2 1,9-Nonanediol 
• 123-99-9 azelaic acid 

Downstream Products

• 67232-08-0 (1E,9E)-2,2'-[nonane-1,9-diylbis(nitrilomethylidyne)]diphenol 
• 27906-49-6 C₂₅H₃₄N₂O₄ 
• 54897-77-7 N,N'-Bis-(2,4-dinitro-phenyl)-nonane-1,9-diamine 
• 335627-65-1 1,9-bis(Cbz-sarcosylamino)nonane 
• 910543-88-3 tert-butyl [9-(1-phenethylpiperidin-4-ylamino)nonyl]carbamate 
• 910543-97-4 tert-butyl {9-[(1-phenethylpiperidin-4-yl)propionylamino]nonyl}carbamate 
• 910544-25-1 N-[9-(N²,N³-bis(tert-butoxycarbonyl)guanidino)nonyl]-N-(1-phenethylpiperidin-4-yl)propanamide 
• 120590-16-1 N,N'-bis(9-bromononyl)-N,N'-di-p-toluenesulfonyl-1,9-nonanediamine 
• 130945-17-4 N,N'-bis(9-hydroxynonyl)-N,N'-di-p-toluenesulfonyl-1,9-nonanediamine 
• 130945-13-0 N,N'-bis<9-(2-tetrahydropyranyloxy)nonyl>-N,N'-di-p-toluenesulfonyl-1,9-nonanediamine 
• 130945-21-0 N,N'-di-p-toluenesulfonyl-N,N'-bis<9-(p-toluenesulfonyloxy)nonyl>-1,9-nonanediamine 
• 120590-12-7 1,11,21,31-tetra-p-toluenesulfonyltetraazacyclotetracontane 

Relevant articles and documents

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.

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.

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