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

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

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

Downstream Products

• 5418-53-1 2-[3-(7-chloro-[4]quinolylamino)-propylamino]-ethanol 
• 80092-44-0 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 
• 80108-21-0 7-Chloro-10-hydroxy-1-[(E)-3-(2-hydroxy-ethylamino)-propylimino]-3-(4-trifluoromethyl-phenyl)-1,3,4,10-tetrahydro-2H-acridin-9-one 
• 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.

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