5397-31-9

Basic information

• Product Name: 2-Ethylhexyloxypropylamine
• Synonyms: 2-Ethylhexyloxypropy;FENTAMINE OPA-8EH;3-Aminopropyl 2-Ethylhexyl Ether 3-Aminopropyl Octyl Ether n-Propanolamine 2-Ethylhexyl Ether;3-(2-Ethyl-n-hexyloxy)propylaMine, 97%;ethylhexyloxypropylaMine;3-((2-ethylhexyl)oxy)-propylamin;3-[(2-ethylhexyl)oxy]-1-propanamin;3-[(2-ethylhexyl)oxy]-1-Propanamine
• CAS NO: 5397-31-9
• Molecular Formula: C₁₁H₂₅NO
• Molecular Weight: 187.32
• EINECS: 226-420-6
• Product Categories: Industrial/Fine Chemicals;Amines;C11 to C38;Nitrogen Compounds
• Mol File: 5397-31-9.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 152 °C13 mm Hg(lit.)
• Flash Point: 217 °F
• Appearance: Colorless liquid
• Density: 0.848 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.063mmHg at 25°C
• Refractive Index: n20/D 1.438(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 15g/l
• PKA: 9.76±0.10(Predicted)
• Explosive Limit: 1-4.7%(V)
• Water Solubility: 0.1-0.5 g/100 mL at 20.5 ºC
• CAS DataBase Reference: 2-Ethylhexyloxypropylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Ethylhexyloxypropylamine(5397-31-9)
• EPA Substance Registry System: 2-Ethylhexyloxypropylamine(5397-31-9)

Safety Data

• Hazard Codes: T
• Statements: 22-24-34-52
• Safety Statements: 26-27-36-45
• RIDADR: UN 2922 8/PG 3
• WGK Germany: 3
• RTECS: UI2820000
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 5397-31-9(Hazardous Substances Data)

Usage

General Description

Colorless liquid.

Air & Water Reactions

Slightly soluble in water.

Reactivity Profile

2-Ethylhexyloxypropylamine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Health Hazard

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Flash point for 2-Ethylhexyloxypropylamine is >93 C (>200 F). 2-Ethylhexyloxypropylamine is combustible.

InChI:InChI=1/C11H25NO/c1-4-7-8-11(6-3)10-13-12-9-5-2/h11-12H,4-10H2,1-3H3

Synthetic route

3-(2-ethyl-hexyloxy)-propionitrile (10213-75-9) → 3-(2-ethylhexoxy)propylamine (5397-31-9)

Conditions	Yield
With ammonia; nickel at 60 - 100℃; under 51485.6 Torr; Hydrogenation;

2-ethyl-hexyl glycidyl ether (2461-15-6) + 3-(2-ethylhexoxy)propylamine (5397-31-9) → C33H69NO5

Conditions	Yield
at 60 - 120℃; for 10.67h;	98%

3-(2-ethylhexoxy)propylamine (5397-31-9) + triphenylsulfonium trifluoromethanesulfonate (66003-78-9) → N-(3-((2-ethylhexyl)oxy)propyl)-N-phenylaniline

Conditions	Yield
With potassium tert-butylate In toluene at 80℃; for 24h; Inert atmosphere; Sealed tube; Glovebox;	98%

3-(2-ethylhexoxy)propylamine (5397-31-9) → 3-(2-ethyl-hexyloxy)-propionitrile (10213-75-9)

Conditions	Yield
With nickel(II) sulphate; sodium hydroxide; dipotassium peroxodisulfate In dichloromethane for 24h; Ambient temperature;	96%
With sodium hypochlorite In ethanol for 0.25h; Ambient temperature;	67%
With oxygen; RuHAP In toluene at 110℃; for 24h;	94 % Chromat.

3-(2-ethylhexoxy)propylamine (5397-31-9) + 4-bromo-1,8-naphthalenedicarboxylic anhydride (81-86-7) → C23H28BrNO3

Conditions	Yield
In ethanol at 50℃; for 8h;	95.6%

3-(2-ethylhexoxy)propylamine (5397-31-9) + 2,6-dichloro-4-methylnicotinonitrile (875-35-4) → C29H52N4O2 (861395-95-1)

Conditions	Yield
In water at 120℃; for 4h;	93.2%

3-(2-ethylhexoxy)propylamine (5397-31-9) + 4,4-dimethyl pyroglutamine acid → C18H36N2O4 (1311195-37-5)

Conditions	Yield
In methanol at 70℃; for 3h;	93%

3-(2-ethylhexoxy)propylamine (5397-31-9) + 4-bromo-1,8-naphthalenedicarboxylic anhydride (81-86-7) → C34H52N2O4

Conditions	Yield
at 120℃; for 8h;	75.6%

3-(2-ethylhexoxy)propylamine (5397-31-9) + 1,7-dibromoperylene-3,4,9,10-tetracarboxylic dianhydride (118129-60-5) → C46H52Br2N2O6 (1444106-92-6)

Conditions	Yield
With butyric acid In 1-methyl-pyrrolidin-2-one at 150℃; for 24h; Inert atmosphere;	70%
In 1-methyl-pyrrolidin-2-one; acetic acid at 150℃; for 24h; Inert atmosphere;	70%

3-(2-ethylhexoxy)propylamine (5397-31-9) + triphenylsulfonium trifluoromethanesulfonate (66003-78-9) → N-(3-((2-ethylhexyl)oxy)propyl)aniline

Conditions	Yield
With potassium tert-butylate In toluene at 80℃; for 28h; Glovebox; Inert atmosphere; Sealed tube;	65%

3-(2-ethylhexoxy)propylamine (5397-31-9) + trifluoromethyl trifluoromethanesulfonate (3582-05-6) → 1,3-bis(3-((2-ethylhexyl)oxy)propyl)urea

Conditions	Yield
In acetonitrile at 20℃; for 1h; Sealed tube;	64%

3-(2-ethylhexoxy)propylamine (5397-31-9) + methyloxirane (75-56-9, 16033-71-9) → [3-(2-ethyl-hexyloxy)-propyl]-bis-(2-hydroxy-propyl)-amine

Conditions	Yield
With water

3-(2-ethylhexoxy)propylamine (5397-31-9) + N-(4-chloro-2-fluorophenyl)-3,4,5,6-tetrahydroisophthalimide (61714-45-2) → Cyclohex-1-ene-1,2-dicarboxylic acid 1-[(4-chloro-2-fluoro-phenyl)-amide] 2-{[3-(2-ethyl-hexyloxy)-propyl]-amide} (71416-85-8)

2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + 3-(2-ethylhexoxy)propylamine (5397-31-9) → N-[3-(2-Ethyl-hexyloxy)-propyl]-[1,3,5]triazine-2,4,6-triamine

Conditions	Yield
With sodium hydroxide for 48h; Heating;

C31H38F3N5O4 + 3-(2-ethylhexoxy)propylamine (5397-31-9) + nickel dichloride → C42H62F3N6NiO5(2+)

Conditions	Yield
With ammonia In tert-Amyl alcohol; water; toluene at 60℃; pH=8.0 - 9;

3-(2-ethylhexoxy)propylamine (5397-31-9) + 1,4,5,8-naphthalenetetracarboxylic dianhydride (81-30-1) → C25H27NO6 (866142-25-8)

Conditions	Yield
In N,N-dimethyl-formamide for 6.75h; Heating / reflux;

Upstream product

• 10213-75-9 3-(2-ethyl-hexyloxy)-propionitrile 

Downstream Products

• 71416-85-8 Cyclohex-1-ene-1,2-dicarboxylic acid 1-[(4-chloro-2-fluoro-phenyl)-amide] 2-{[3-(2-ethyl-hexyloxy)-propyl]-amide} 
• 10213-75-9 3-(2-ethyl-hexyloxy)-propionitrile