azetidine
Trimethylenediamine
A
bis(3-aminopropyl)amine
B
N-γ-aminopropyltrimethyleneimine
Conditions | Yield |
---|---|
palladium at 170℃; | A 84% B 1% |
palladium Product distribution; |
Conditions | Yield |
---|---|
With sodium hydroxide; hydrogen; nickel In ethanol under 2068.6 Torr; | 81% |
With sodium hydroxide; sodium tetrahydroborate; nickel In methanol at 50℃; for 0.5h; | 80% |
With sodium-potassium alloy; butan-1-ol | |
With ammonia; nickel at 90 - 125℃; under 36775.4 - 183877 Torr; Hydrogenation; |
bis(3-aminopropyl)amine
Conditions | Yield |
---|---|
With nitrogen(II) oxide In acetonitrile | 55% |
Conditions | Yield |
---|---|
With ethanol; ammonia; water |
Conditions | Yield |
---|---|
With ammonia |
N1-(cyanoethyl)-1,3-propanediamine
bis(3-aminopropyl)amine
Conditions | Yield |
---|---|
With ammonia; hydrogen; nickel In ethanol |
3,3',3''-nitrilotripropanamide
A
bis(3-aminopropyl)amine
B
Tris(3-aminopropyl)amine
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride |
N-γ-aminopropyltrimethyleneimine
bis(3-aminopropyl)amine
Conditions | Yield |
---|---|
With ammonia at 120℃; Rate constant; Thermodynamic data; ΔH(excit.), ΔS(excit.);; | |
With ammonium hydroxide at 50℃; Rate constant; Thermodynamic data; E(a); |
Conditions | Yield |
---|---|
With ammonium hydroxide at 50℃; Rate constant; Thermodynamic data; E(a); |
trimethyleneglycol
A
bis(3-aminopropyl)amine
B
propan-1-ol
C
Trimethylenediamine
D
propan-1-ol-3-amine
Conditions | Yield |
---|---|
With ammonia; hydrogen; carbon monoxide at 210℃; under 101258 Torr; Product distribution; Further Variations:; Catalysts; Temperatures; Pressures; amination; |
ammonia
1,3-dibromo-propane
A
bis(3-aminopropyl)amine
B
Trimethylenediamine
Conditions | Yield |
---|---|
at 25℃; |
bis(3-aminopropyl)amine
Conditions | Yield |
---|---|
With ammonia |
3,3'-Iminodipropionitrile
ammonia
A
bis(3-aminopropyl)amine
B
Tris(3-aminopropyl)amine
C
Trimethylenediamine
Conditions | Yield |
---|---|
at 90 - 125℃; unter Druck; |
Trimethylenediamine
A
bis(3-aminopropyl)amine
B
N,N'-bis-(3-aminopropyl)-1,3-propanediamine
C
N-(3-aminopropyl)-N'-<3-<(3-aminopropyl)amino>propyl>propane-1,3-diamine
Conditions | Yield |
---|---|
With hydrogen at 100 - 200℃; under 0 - 15001.5 Torr; Product distribution / selectivity; |
bis-(3-amino-propyl)-carbamic acid tert-butyl ester
bis(3-aminopropyl)amine
Conditions | Yield |
---|---|
With trifluoroacetic acid at 20℃; Inert atmosphere; |
ethylenediamine
Trimethylenediamine
A
bis(3-aminopropyl)amine
B
tripropylene-tetramine
C
N-(2-Aminoethyl)-1,3-propanediamine
Conditions | Yield |
---|---|
With hydrogen; Ni and Re on Al2O3/SiO2 at 130 - 135℃; under 8517.48 Torr; for 6h; Autoclave; |
dipropylenetriamine NONOate
A
bis(3-aminopropyl)amine
B
nitrogen(II) oxide
Conditions | Yield |
---|---|
With perchloric acid In water at 25℃; pH=< 2; Kinetics; pH-value; |
bis(3-aminopropyl)amine
phthalic anhydride
N,N-bis(phthalimidopropyl)amine
Conditions | Yield |
---|---|
In acetic acid for 1h; Heating; | 100% |
99% | |
With acetic acid for 2h; Reflux; | 98% |
bis(3-aminopropyl)amine
ethyl trifluoroacetate,
N-[3-(trifluoroacetamido)propyl]-N'-trifluoroacetyl-1,3-diaminopropane
Conditions | Yield |
---|---|
In ethanol for 60h; Acylation; | 100% |
In acetonitrile at 20℃; for 15h; | 100% |
In tetrahydrofuran Acylation; Heating; | 99% |
(3α,5β)-3,24-bis(3-bromophenoxy)cholane
bis(3-aminopropyl)amine
Conditions | Yield |
---|---|
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane Heating; | 100% |
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; [Pd(dibenzylideneacetone)2] In 1,4-dioxane for 5h; Heating; | 90 % Spectr. |
bis(3-aminopropyl)amine
2,2-dimethyltetrahydro-[1,3]dithiol[4,5-c]furan
C20H33N3O6S4
Conditions | Yield |
---|---|
In dichloromethane at 0 - 20℃; for 1h; | 100% |
bis(3-aminopropyl)amine
tris(dimethylamino)borane
1,8,10,9-Triazoboradecalin
Conditions | Yield |
---|---|
100% | |
In benzene byproducts: dimethylamine; reflux, 1h; | 75% |
In benzene byproducts: dimethylamine; reflux, 1h; | 75% |
bis(3-aminopropyl)amine
acrylonitrile
3-[{3-[{3-[bis-(2-cyanoethyl)amino]propyl}-(2-cyanoethyl)amino]propyl}-(2-cyanoethyl)amino]propionitrile
Conditions | Yield |
---|---|
at 20℃; for 120h; Michael condensation; | 100% |
In water at 20 - 110℃; Inert atmosphere; | 63% |
Conditions | Yield |
---|---|
at 20℃; under 750075 Torr; for 16h; neat (no solvent); | 100% |
Conditions | Yield |
---|---|
Stage #1: 2-methyl-2-(methyltellanyl)propanoic acid With 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: bis(3-aminopropyl)amine In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
Stage #1: 2,6-Pyridinedicarboxaldehyde; zinc perchlorate In methanol at 25℃; for 1.5h; Stage #2: bis(3-aminopropyl)amine In methanol at 25℃; for 12h; | 100% |
pyridine-2-carbaldehyde
bis(3-aminopropyl)amine
N-pyridin-2-ylmethyl-N'-{3-[(pyridin-2-ylmethyl)amino]propyl}propane-1,3-diamine
Conditions | Yield |
---|---|
Stage #1: pyridine-2-carbaldehyde; bis(3-aminopropyl)amine With acetic acid; zinc In methanol at 70 - 80℃; for 4.5h; Stage #2: With hydrogenchloride In methanol at 20℃; Stage #3: With sodium hydroxide In water | 99% |
bis(3-aminopropyl)amine
2-acetyldimedone
N1,N9-bis-1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl-norspermidine
Conditions | Yield |
---|---|
In ethanol for 2h; Heating; | 99% |
bis(3-aminopropyl)amine
2-bromonaphthalene
N1-(3-aminopropyl)-N3-(naphthalen-2-yl)propane-1,3-diamine
Conditions | Yield |
---|---|
With copper(l) iodide; caesium carbonate; rac-Pro-OH In acetonitrile for 24h; Ullmann reaction; Inert atmosphere; Reflux; regioselective reaction; | 99% |
With copper(l) iodide; caesium carbonate; L-proline In acetonitrile Inert atmosphere; Reflux; | 90% |
bis(3-aminopropyl)amine
1,2-bis(4-tert-butyl-2,6-diformylphenylsulfanyl)ethane
C38H64N6S2
Conditions | Yield |
---|---|
Stage #1: bis(3-aminopropyl)amine; 1,2-bis(4-tert-butyl-2,6-diformylphenylsulfanyl)ethane In ethanol; dichloromethane at 0 - 20℃; for 23h; Stage #2: With sodium tetrahydroborate In ethanol at 20℃; for 4h; | 99% |
bis(3-aminopropyl)amine
tetradecane-1,14-diol dimesylate
Conditions | Yield |
---|---|
In acetonitrile for 4h; Heating; | 98% |
1-(benzyloxy)-6-(2-thioxothiazolidine-3-carbonyl)pyridin-2(1H)-one
bis(3-aminopropyl)amine
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; | 98% |
With triethylamine In dichloromethane at 20℃; for 6h; | 98% |
bis(3-aminopropyl)amine
benzyl chloroformate
[3-(3-benzyloxycarbonylaminopropylamino)propyl]carbamic acid benzyl ester
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 10℃; Temperature; Reagent/catalyst; Solvent; | 97.1% |
Conditions | Yield |
---|---|
In water; acetonitrile Heating; | 97% |
In water; acetonitrile for 4h; Reflux; | 97% |
93% | |
With water In acetonitrile for 3h; Heating / reflux; |
bis(3-aminopropyl)amine
p-toluenesulfonyl chloride
1,5,9-Tritosyl-1,5,9-triazanonane
Conditions | Yield |
---|---|
With sodium hydroxide In diethyl ether; water Heating / reflux; | 96.5% |
With potassium carbonate In water at 60℃; for 3h; | 95% |
With sodium hydroxide In dichloromethane at 20℃; for 3h; | 90% |
bis(3-aminopropyl)amine
pivalaldehyde
1,1'-carbonyldiimidazole
bis[3-(t-butoxycarbonylamino)propyl]amine
Conditions | Yield |
---|---|
Stage #1: pivalaldehyde; 1,1'-carbonyldiimidazole With potassium hydroxide In toluene at 60℃; for 3h; Stage #2: bis(3-aminopropyl)amine In toluene at 60℃; for 3h; Further stages.; | 96% |
bis(3-aminopropyl)amine
1,7-di-(5-norbornen-2-yl)-4-heptanone
Conditions | Yield |
---|---|
With hydrogenchloride; sodium borohydrid In water; isopropyl alcohol; toluene | 96% |
With hydrogenchloride; sodium borohydrid In water; isopropyl alcohol; toluene | 96% |
bis(3-aminopropyl)amine
molybdenum hexacarbonyl
fac-[(H2N(CH2)3NH(CH2)3NH2)Mo(CO)3]
Conditions | Yield |
---|---|
In dibutyl ether N2-atmosphere; slight excess metal carbonyl, refluxing for 2 h (returning sublimed hexacarbonyl into reaction vessel); cooling to room temp., collection of ppt., washing (hexane), drying (vac., 50°C); | 96% |
bis(3-aminopropyl)amine
N,N-diethyl-3-iodobenzamide
3,3'-[3,3'-azanediyl-bis(propane-3,1-diyl)bis(azanediyl)]bis(N,N-diethylbenzamide)
Conditions | Yield |
---|---|
With copper(l) iodide; caesium carbonate; rac-Pro-OH In propiononitrile for 24h; Ullmann reaction; Inert atmosphere; Reflux; regioselective reaction; | 96% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 0℃; for 5h; | 95% |
In tetrahydrofuran at -5℃; for 24h; | 70% |
Conditions | Yield |
---|---|
With sodium t-butanolate; 1,1'-bis-(diphenylphosphino)ferrocene; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane Substitution; Amination; Heating; | 95% |
With 1,3-bis(diphenylphosphino)ferrocene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In 1,4-dioxane for 30h; Heating; | 95% |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium t-butanolate In 1,4-dioxane for 20h; Heating; | 64% |
Conditions | Yield |
---|---|
In toluene at 20℃; for 1h; | 95% |
bis(3-aminopropyl)amine
(di(3-aminopropyl)amine)trichloro cobalt(III)
Conditions | Yield |
---|---|
In isopropyl alcohol refluxing a mixt. of the Co-compd. and the amine for 0.5 h; pptn. after cooling, filtering off, washing with EtOH and acetone, air-drying; | 95% |
bis(3-aminopropyl)amine
Conditions | Yield |
---|---|
In water Cu(ClO4)2*6H2O was dissolved in water, ligand was added with stirring, soln. of NaN3 in water was added, stirred for 0.5 h; crystd. for 1 w; elem. anal.; | 95% |
bis(3-aminopropyl)amine
sodium tetraphenyl borate
salicylaldehyde
acetonitrile
Conditions | Yield |
---|---|
With C5H5N In methanol salicylaldehyde and 3,3'-diaminodipropylamine mixed in MeOH, Fe salt in MeOH added, C5H5N added, stirred for 1 h, Na salt added; pptd. for hours, filtered, washed (Et2O), dried at room temp., recrystd.(MeCN); elem. anal.; | 95% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 23℃; for 2h; | 95% |
bis(3-aminopropyl)amine
tert-butyl 1H-imidazole-1-carboxylate
bis[3-(t-butoxycarbonylamino)propyl]amine
Conditions | Yield |
---|---|
In toluene at 60℃; for 18h; | 95% |
In tetrahydrofuran at 20℃; Reflux; | 80% |
at 60℃; for 4h; | 66% |
Molecular Formula: C6H17N3
Molar mass: 131.22 g/mol
EINECS: 200-261-2
Density: 0.912 g/cm3
Flash Point: 118.3 °C
Index of Refraction: 1.475
Boiling Point: 242.1 °C at 760 mmHg
Vapour Pressure: 0.0346 mmHg at 25°C
Appearance: Colourless to yellow liquid
Stable:Air and light sensitive. Combustible. Incompatible with oxidizing agents
Structure of Aminobis(propylamine) (56-18-8):
XLogP3-AA: -1.4
H-Bond Donor: 3
H-Bond Acceptor: 3
Systematic Name: N-(3-aminopropyl)propane-1,3-diamine
SMILES: NCCCNCCCN
InChI: InChI=1/C6H17N3/c7-3-1-5-9-6-2-4-8/h9H,1-8H2
InChIKey: OTBHHUPVCYLGQO-UHFFFAOYAG
Std. InChI: InChI=1S/C6H17N3/c7-3-1-5-9-6-2-4-8/h9H,1-8H2
Std. InChIKey: OTBHHUPVCYLGQO-UHFFFAOYSA-N
Aminobis(propylamine) (56-18-8) can be used to make soaps, dyes, and pharmaceuticals.
1. | skn-rbt 470 mg open MOD | UCDS** Union Carbide Data Sheet. (Industrial Medicine and Toxicology Dept., Union Carbide Corp., 270 Park Ave., New York, NY 10017) 6/13/68 . | ||
2. | eye-rbt 47 mg SEV | UCDS** Union Carbide Data Sheet. (Industrial Medicine and Toxicology Dept., Union Carbide Corp., 270 Park Ave., New York, NY 10017) 6/13/68 . | ||
3. | orl-rat LD50:738 mg/kg | ZHYGAM Zeitschrift fuer die Gesamte Hygiene und Ihre Grenzgebiete. 20 (1974),393. | ||
4. | orl-mus LD50:435 mg/kg | ZHYGAM Zeitschrift fuer die Gesamte Hygiene und Ihre Grenzgebiete. 20 (1974),393. | ||
5. | orl-rbt LD50:210 mg/kg | ZHYGAM Zeitschrift fuer die Gesamte Hygiene und Ihre Grenzgebiete. 20 (1974),393. | ||
6. | skn-rbt LDLo:110 mg/kg | AIHAAP American Industrial Hygiene Association Journal. 23 (1962),95. |
Carcinogenicity of Aminobis(propylamine) (56-18-8) hasn't been listed as a carcinogen by NTP, IARC,ACGIH, or CA Prop 65.You can see actual entry in RTECS for complete information.
Reported in EPA TSCA Inventory.
Poison by skin contact. Moderately toxic by ingestion. A skin and severe eye irritant. When heated to decomposition it emits toxic fumes of NOx. An explosive.
DOT Classification: 8; Label: Corrosive
Aminobis(propylamine) (56-18-8) also can be called 3,3'-Iminobispropylamine ; Dipropylenetriamine ; N,N-di(3-aminopropyl)amine ; N-(3-Aminopropyl)-1,3-propanediamine ; 1,3-Propanediamine, N- (3-aminopropyl)- ; 3,3'-azanediyldi(propanamine) ; N-(3-aminopropyl)propane-1,3-diamine ; Bis(3-aminopropyl)amine and Norspermidine .It is hazardous,so the first aid measures and others should be known.Such as: When on the skin: first,should flush skin with plenty of water immediatelyfor at least 15 minutes while removing contaminated clothing. Secondly,Get shoesmedical aid . Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids.Then get medical aid soon.While ,it's Inhaled: Remove from exposure and move to fresh air immediately.Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product : Wash mouth out with water,and get medical aid immediately.Notes to physician: Treat supportively and symptomatically.
In addition, Aminobis(propylamine) (56-18-8) absorbs moisture or water from the air, and can be stable under normal temperature and pressure conditions.It is not compatible with strong oxidizing agents, acids, acid chlorides, acid anhydrides, chloroformates, and you must not take it with incompatible materials and not be exposured to moist air or water.And also prevent it to broken down into hazardous decomposition products: oxides of nitrogen, carbon dioxide, carbon monoxide.
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