4461-39-6

Basic information

• Product Name: N-(2-Hydroxyethyl)-1,3-propanediamine
• Synonyms: N-(2-HYDROXYETHYL)-1,3-DIAMINOPROPANE;N-(2-HYDROXYETHYL)-1,3-PROPANEDIAMINE;N-(2-HYDROXYETHYL)-PROPANEDIAMINE-1,3;N-(2-HYDROXYETHYL)TRIMETHYLENEDIAMINE;2-HYDROXYETHYLAMINO PROPYLAMINE;2-(3-AMINOPROPYLAMINO)ETHANOL;HEAPA;N-(2-Hydroxyethyl)propan-1,3-diamine
• CAS NO: 4461-39-6
• Molecular Formula: C₅H₁₄N₂O
• Molecular Weight: 118.18
• EINECS: 224-718-0
• Product Categories: Hydroxyethylamines
• Mol File: 4461-39-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 15-19 °C
• Boiling Point: 250-252 °C(lit.)
• Flash Point: 152 °C
• Appearance: clear liquid
• Density: 1.007 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.00648mmHg at 25°C
• Refractive Index: n20/D 1.486
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 14.79±0.10(Predicted)
• Water Solubility: miscible
• BRN: 1734412
• CAS DataBase Reference: N-(2-Hydroxyethyl)-1,3-propanediamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-Hydroxyethyl)-1,3-propanediamine(4461-39-6)
• EPA Substance Registry System: N-(2-Hydroxyethyl)-1,3-propanediamine(4461-39-6)

Safety Data

• Hazard Codes: C
• Statements: 34-37-35
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2735 8/PG 3
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 4461-39-6(Hazardous Substances Data)

Usage

Chemical Properties

clear liquid

Uses

Curing epoxy resins.

InChI:InChI=1/C5H14N2O/c6-2-1-3-7-4-5-8/h7-8H,1-6H2/p+2

Synthetic route

3-<(2-hydroxyethyl)amino>propionitrile (33759-44-3) → 2-[(3-aminopropyl)amino]ethanol (4461-39-6)

Conditions	Yield
With rhodium(III) oxide; gold oxide; hydrogen at 82 - 83℃; under 15001.5 Torr; for 18h; Pressure;	98.2%
With ethanol; ammonia; nickel at 120℃; under 66195.7 Torr; Hydrogenation;

oxirane (75-21-8) + Trimethylenediamine (109-76-2) → 2-[(3-aminopropyl)amino]ethanol (4461-39-6) + N,N'-bis(2-hydroxyethyl)-1,3-propanediamine (10563-27-6)

Conditions	Yield
In methanol at 0℃;	A 60% B 20%

azetidine (503-29-7) + ethanolamine (141-43-5) → 2-[(3-aminopropyl)amino]ethanol (4461-39-6)

Conditions	Yield
With perchloric acid at 25℃; Rate constant; Thermodynamic data; E(a), ΔS(excit.);

2-[(3-aminopropyl)amino]ethanol (4461-39-6) + 9,10-Dihydroxy-2,3-dihydro-anthracene-1,4-dione (17648-03-2) → 1,4-bis({3-[(2-hydroxyethyl)amino]-propyl}amino)-9,10-dihydroanthracene-9,10-dione (65271-79-6)

Conditions	Yield
Stage #1: 2-[(3-aminopropyl)amino]ethanol; 9,10-Dihydroxy-2,3-dihydro-anthracene-1,4-dione In acetonitrile at 50℃; for 1h; Inert atmosphere; Stage #2: With air at 50℃; for 1h;	99%

2-[(3-aminopropyl)amino]ethanol (4461-39-6) → dibromohydrate du N-(bromoethyl-2)diamino-1,3 propane (23545-42-8)

Conditions	Yield
Stage #1: 2-[(3-aminopropyl)amino]ethanol With hydrogen bromide In sulfolane at 90 - 119℃; Stage #2: With phosphorus tribromide In sulfolane at 120℃; for 1h; Product distribution / selectivity;	96%

2-[(3-aminopropyl)amino]ethanol (4461-39-6) → 2-(3-aminopropylamino)ethyl bromide (55159-49-4)

Conditions	Yield
Stage #1: 2-[(3-aminopropyl)amino]ethanol With hydrogen bromide In ethanol at 13 - 15℃; for 2h; Stage #2: In methanol for 1h; Time; Reflux;	91%

2-[(3-aminopropyl)amino]ethanol (4461-39-6) → piperazine (110-85-0)

Conditions	Yield
With phosphorus pentachloride In tetrachloromethane at 30 - 60℃; for 20h; Inert atmosphere;	90%

2-[(3-aminopropyl)amino]ethanol (4461-39-6) + methyl 1-(2-fluorophenylmethyl)-1H-indazole-3-carboxylate → 1-(2-fluoro-benzyl)-1H-indazole-3-carboxylic acid [3-(2-hydroxy-ethylamino)-propyl]-amide

Conditions	Yield
at 20℃; for 96h;	85%

2-[(3-aminopropyl)amino]ethanol (4461-39-6) + 3-chloro-8,9-methylenedioxyindeno[1,2-c]isochromene-5,12-dione → 3-chloro-5,6-dihydro-6-(3-((2-hydroxyethyl)amino)-propyl)-8,9-methylenedioxy-5,11-dioxo-11H-indeno[1,2-c]isoquinoline

Conditions	Yield
In chloroform for 22h; Reflux; Inert atmosphere;	84%

7-chloro-3-(3,4-dichlorophenyl)-3,4-dihydro-10-hydroxy-1,9(2H,10H)-acridinedione (75618-33-6) + 2-[(3-aminopropyl)amino]ethanol (4461-39-6) → 7-Chloro-3-(3,4-dichloro-phenyl)-10-hydroxy-1-[(E)-3-(2-hydroxy-ethylamino)-propylimino]-1,3,4,10-tetrahydro-2H-acridin-9-one (80092-44-0)

Conditions	Yield
In ethanol for 1.5h; Heating;	83%

carbon disulfide (75-15-0) + 2-[(3-aminopropyl)amino]ethanol (4461-39-6) + 3-Benzyloxybenzaldehyde (1700-37-4) + copper(II) acetate monohydrate (6046-93-1) → C40H46CuN4O4S4

Conditions	Yield
Stage #1: 2-[(3-aminopropyl)amino]ethanol; 3-Benzyloxybenzaldehyde With carbon disulfide In methanol at 20℃; for 2h; Stage #2: carbon disulfide In methanol for 0.666667h; Stage #3: copper(II) acetate monohydrate In methanol for 4h;	81%

2-[(3-aminopropyl)amino]ethanol (4461-39-6) + 3-fluoro-8,9-methylenedioxyindeno[1,2-c]isochromene-5,12-dione → 3-fluoro-5,6-dihydro-6-(3-(2-hydroxyethyl)amino)-8,9-methylenedioxy-5,11-dioxo-11H-indeno[1,2-c]isoquinoline

Conditions	Yield
In chloroform for 3.5h; Reflux; Inert atmosphere;	76%

2-[(3-aminopropyl)amino]ethanol (4461-39-6) + di-tert-butyl dicarbonate (24424-99-5) → (3-tert-BOCamino-propyl)-(2-hydroxy-ethyl)-carbamic acid tert-butyl ester (162339-83-5)

Conditions	Yield
In dichloromethane at 20℃;	71%

4-chloro-2-(4-methoxyphenyl)-pyrimido[5,4-c]cinnoline (874903-60-3) + 2-[(3-aminopropyl)amino]ethanol (4461-39-6) → 2-[(3-[2-(4-methoxyphenyl)-pyrimido[5,4-c]cinnolin-4-yl]aminopropyl)amino]ethanol

Conditions	Yield
In ethanol for 0.333333h; Heating;	68%

2-[(3-aminopropyl)amino]ethanol (4461-39-6) + 2-(3-cyanobenzyloxy)-4-(2-methyl-(1,1’-diphenyl)-3-yl-methoxyl)benzaldehyde → 3-[[2-[1-(2-hydroxyethyl)-5,6-dihydro-4H-pyrimidin-2-yl]-5-((2-methyl-3-phenylphenyl)methoxy)phenoxy]methyl]benzonitrile hydrochloride

Conditions	Yield
Stage #1: 2-[(3-aminopropyl)amino]ethanol; 2-(3-cyanobenzyloxy)-4-(2-methyl-(1,1’-diphenyl)-3-yl-methoxyl)benzaldehyde With iodine; potassium carbonate In tert-butyl alcohol at 70℃; for 3h; Stage #2: With hydrogenchloride In water; acetonitrile for 0.333333h;	67%

2-[(3-aminopropyl)amino]ethanol (4461-39-6) + 2-oxopropanal (78-98-8) → 2-hydroxy-2-methylhexahydropyrimidino[1,2-c]morpholine

Conditions	Yield
In water for 12h; Ambient temperature;	66%

2-[(3-aminopropyl)amino]ethanol (4461-39-6) + benzyl chloroformate (501-53-1) → {3-[Benzyloxycarbonyl-(2-hydroxy-ethyl)-amino]-propyl}-carbamic acid benzyl ester (142253-82-5)

Conditions	Yield
With sodium hydroxide at 0 - 20℃; for 25h;	64%

2-[(3-aminopropyl)amino]ethanol (4461-39-6) + AF 1311TS (41354-03-4) → 1-benzyl-1H-indazole-3-carboxylic acid [3-(2-hydroxy-ethylamino)-propyl]-amide

Conditions	Yield
Stage #1: AF 1311TS With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 2-[(3-aminopropyl)amino]ethanol In N,N-dimethyl-formamide at 20℃; for 24h;	64%

5-(biphenyl-4-yl)-1,3,4-oxadiazole-2-carboxylic acid ethyl ester (858100-01-3) + 2-[(3-aminopropyl)amino]ethanol (4461-39-6) → 5-biphenyl-4-yl-[1,3,4]oxadiazole-2-carboxylic acid [3-(2-hydroxy-ethylamino)-propyl]-amide

Conditions	Yield
In dichloromethane at 20℃;	63%

copper(II) perchlorate hexahydrate + 2-[(3-aminopropyl)amino]ethanol (4461-39-6) → Cu4(C5H13N2O)4(4+)*4ClO4(1-)*H2O = [Cu4(C5H13N2O)4](ClO4)4*H2O

Conditions	Yield
In methanol; water pH 8;	60%

2-[(3-aminopropyl)amino]ethanol (4461-39-6) + 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (58632-95-4) → (3-tert-BOCamino-propyl)-(2-hydroxy-ethyl)-carbamic acid tert-butyl ester (162339-83-5)

Conditions	Yield
In tetrahydrofuran for 12h; Ambient temperature;	58%

2-[(3-aminopropyl)amino]ethanol (4461-39-6) + 1-(3-chlorophenylmethyl)-1H-indazole-3-carboxylic acid (50264-61-4) → 1-(3-chloro-benzyl)-1H-indazole-3-carboxylic acid [3-(2-hydroxy-ethylamino)-propyl]-amide

Conditions	Yield
Stage #1: 1-(3-chlorophenylmethyl)-1H-indazole-3-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 2-[(3-aminopropyl)amino]ethanol In N,N-dimethyl-formamide at 20℃; for 24h;	58%

4-chloro-2-phenyl-pyrimido[5,4-c]cinnoline (874903-59-0) + 2-[(3-aminopropyl)amino]ethanol (4461-39-6) → 2-[(3-[2-phenyl-pyrimido[5,4-c]cinnolin-4-yl]aminopropyl)-amino]ethanol

Conditions	Yield
In ethanol for 0.333333h; Heating;	57%

3-(biphenyl-4-yl)-1,2,4-oxadiazole-5-carboxylic acid ethyl ester (40019-23-6) + 2-[(3-aminopropyl)amino]ethanol (4461-39-6) → 3-biphenyl-4-yl-[1,2,4]oxadiazole-5-carboxylic acid [3-(2-hydroxy-ethylamino)-propyl]-amide

Conditions	Yield
In dichloromethane at 20℃;	56%

3-(4-trifluoromethylphenyl)-7-chloro-10-hydroxy-3,4-dihydroacridine-1,9(2H,10H)-dione (53966-34-0) + 2-[(3-aminopropyl)amino]ethanol (4461-39-6) → 7-Chloro-10-hydroxy-1-[(E)-3-(2-hydroxy-ethylamino)-propylimino]-3-(4-trifluoromethyl-phenyl)-1,3,4,10-tetrahydro-2H-acridin-9-one (80108-21-0)

Conditions	Yield
In benzene for 2h; Heating;	53%

2-[(3-aminopropyl)amino]ethanol (4461-39-6) + (1S,3'S,5'S)-N-(2-cyclohexyl-1-(3-isopropyl-2-oxo-2,3,4,5-tetrahydrofuran-5-yl)ethyl)-(1S)-(1-((4-(methoxymethoxy)piperidin-1-yl)carbonyl)-2-phenylethyl)-L-norleucinamide (161316-40-1) → (2S,4S,5S)-5-{(S)-2-[(S)-1-Benzyl-2-(4-methoxymethoxy-piperidin-1-yl)-2-oxo-ethylamino]-hexanoylamino}-6-cyclohexyl-4-hydroxy-2-isopropyl-hexanoic acid [3-(2-hydroxy-ethylamino)-propyl]-amide

Conditions	Yield
With acetic acid at 85℃; for 24h;	52%

2-[(3-aminopropyl)amino]ethanol (4461-39-6) + 1-(2-chlorophenylmethyl)-1H-indazole-3-carboxylic acid (50264-60-3) → 1-(2-chloro-benzyl)-1H-indazole-3-carboxylic acid [3-(2-hydroxy-ethylamino)-propyl]-amide

Conditions	Yield
Stage #1: 1-(2-chlorophenylmethyl)-1H-indazole-3-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 2-[(3-aminopropyl)amino]ethanol In N,N-dimethyl-formamide at 20℃; for 24h;	44%

Glyoxal (131543-46-9) + 2-[(3-aminopropyl)amino]ethanol (4461-39-6) → 7,15-dioxa-4,8,12,16-tetraazaperhydroperylene + 2-hydroxyhexahydropyrimidino<1,2-c>morpholine

Conditions	Yield
In water Ambient temperature;	A 11% B 38%

4-chloro-2-(2-furyl)-pyrimido[5,4-c]cinnoline (874903-63-6) + 2-[(3-aminopropyl)amino]ethanol (4461-39-6) → 2-[(3-[(2-furyl)pyrimido[5,4-c]cinnolin-4-yl]aminopropyl)amino]ethanol

Conditions	Yield
In ethanol for 0.333333h; Heating;	36%

2-[(3-aminopropyl)amino]ethanol (4461-39-6) + N-(1-Methyl-5-nitro-1H-imidazol-2-yl)-formimidic acid ethyl ester (86151-52-2) → C15H22N10O5 (86151-40-8)

Conditions	Yield
In benzene Heating;	30%

2-[(3-aminopropyl)amino]ethanol (4461-39-6) + urea (57-13-6) → 1-(2-hydroxyethyl)tetrahydropyrimidin-2(1H)-one (53386-63-3)

Conditions	Yield
In neat (no solvent) at 130℃; for 10h; Sealed tube;	14%

Upstream product

• 75-21-8 oxirane 
• 109-76-2 Trimethylenediamine 
• 503-29-7 azetidine 
• 141-43-5 ethanolamine 
• 33759-44-3 3-<(2-hydroxyethyl)amino>propionitrile 

Downstream Products

• 142253-82-5 {3-[Benzyloxycarbonyl-(2-hydroxy-ethyl)-amino]-propyl}-carbamic acid benzyl ester 
• 110-85-0 piperazine 
• 65271-79-6 1,4-bis({3-[(2-hydroxyethyl)amino]-propyl}amino)-9,10-dihydroanthracene-9,10-dione 
• 1350814-40-2 N-(5-chloro-2-hydroxyphenyl)-N'-[3-(2-hydroxyethylamino)propyl]oxamide 
• 23545-42-8 dibromohydrate du N-(bromoethyl-2)diamino-1,3 propane 
• 5769-35-7 N,N'-di-p-toluenesulfonylhomopiperazine 
• 5451-44-5 N,N'-Di(phenylsulphonyl)hexahydro-1,4-diazepin 
• 124821-30-3 3-(2-Hydroxy-ethyl)-tetrahydro-pyrimidine-1-carboxylic acid phenylamide 

Relevant articles and documents

Synthetic method of amifostine

The invention discloses a synthetic method of amifostine. The method includes the following steps that 1, a compound shown in the formula (IV) reacts with hydrogen in the presence of rhodium oxide, gold oxide and raney nickel to obtain a compound shown in formula (III); 2, the compound shown in formula (III) reacts with hydrogen bromide in a mixed solvent formed by water and C1-5 alcohol solventsto obtain a compound shown in the formula (II) at 0-20 DEG C; 3, the compound shown in formula (II) reacts with sodium thiophosphate to obtain amifostine shown in the formula (I). Through the method,high-yield and high-purity products can be obtained, the process is simple, and the method is suitable for industrial production.

NUCLEOPHILIC CLEAVAGE AND FORMATION OF SATURATED HETEROCYCLES. XII. REACTIVITY OF SMALL HETEROCYCLES TOWARD AMINOLYSIS AND HYDROLYSIS

The cleavage of four-membered saturated heterocycles proceeds via a more product-like transition state than that of three-membered rings.General acid catalysis is characteristic of oxygen heterocycles, but in the case of nitrogen heterocycles catalysis is specific.The reactivity of amines in the cleavage of azetidines is linearly dependent on their pKa values, primary and secondary amines comprising separate reaction series.