7617-74-5

Basic information

• Product Name: 3-Lauryloxypropyl-1-amine
• Synonyms: 3-(dodecyloxy)-1-propanamin;3-LAURYLOXYPROPYL-1-AMINE 98%;3-lauryloxypropanamine;3-(Dodecyloxy)-1-propanamine;3-Dodecyloxy-1-propanamine;Dodecyl 3-aminopropyl ether;3-Lauryloxypropyl-1-amine,98%;3-Lauryloxypropyl-1-amine3-n-Dodecyloxy-1-aminopropane
• CAS NO: 7617-74-5
• Molecular Formula: C₁₅H₃₃NO
• Molecular Weight: 243.43
• EINECS: 231-528-1
• Product Categories: Pharmaceutical Raw Materials
• Mol File: 7617-74-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 13 °C
• Boiling Point: 315 °C
• Flash Point: 165 °C
• Appearance: /
• Density: 0.845
• Vapor Pressure: 0.000114mmHg at 25°C
• Refractive Index: 1.4455-1.4485
• Storage Temp.: 2-8°C
• Water Solubility: <0.1 g/L (20℃)
• CAS DataBase Reference: 3-Lauryloxypropyl-1-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Lauryloxypropyl-1-amine(7617-74-5)
• EPA Substance Registry System: 3-Lauryloxypropyl-1-amine(7617-74-5)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34-22-36/37/38
• Safety Statements: 45-37/39-26-36/37/39
• RIDADR: 2735
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 7617-74-5(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to light yellow liquid

InChI:InChI=1/C15H33NO/c1-2-3-4-5-6-7-8-9-10-11-14-17-15-12-13-16/h2-16H2,1H3

Synthetic route

1-(3-azidopropoxy)dodecane (1380680-79-4) → 3-(dodecyloxy)-1-propylamine (7617-74-5)

Conditions	Yield
Stage #1: 1-(3-azidopropoxy)dodecane With triphenylphosphine In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: With water In tetrahydrofuran at 20℃; for 28h;	57%

3-dodecyloxy-propionitrile (56637-94-6) → 3-(dodecyloxy)-1-propylamine (7617-74-5)

Conditions	Yield
With hydrogen; Ni(Raney)
With sodium hydroxide; hydrogen; Raney type Ni-Mo-Al catalyst R-239 In water at 70℃; under 7500.75 Torr;
With hydrogen; Ni-diatomaceous earth catalyst at 180℃; under 11251.1 Torr;
With hydrogen; Raney type Ni-Mo-Al catalyst R-239 In water at 150℃; under 7500.75 Torr;
With lithium hydroxide; hydrogen; Raney type Co-Al catalyst R-400 In water at 150℃; under 11251.1 Torr;

1-dodecyl alcohol (112-53-8) → 3-(dodecyloxy)-1-propylamine (7617-74-5)

Conditions	Yield
Multi-step reaction with 2 steps 2: hydrogen / Ni(Raney) View Scheme

1-dodecylbromide (143-15-7) → 3-(dodecyloxy)-1-propylamine (7617-74-5)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide; oil / 0.17 h / 0 - 20 °C 1.2: 4 h / 95 °C 2.1: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 3 h / 90 °C 3.1: triphenylphosphine / tetrahydrofuran / 0.17 h / 20 °C 3.2: 28 h / 20 °C View Scheme

2-(dodecyloxy)methyl-1-ethanol (84337-56-4) → 3-(dodecyloxy)-1-propylamine (7617-74-5)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 3 h / 90 °C 2.1: triphenylphosphine / tetrahydrofuran / 0.17 h / 20 °C 2.2: 28 h / 20 °C View Scheme

3-(dodecyloxy)-1-propylamine (7617-74-5) + 1,3,5-trichloro-2,4,6-triazine (108-77-0) → C48H96N6O3

Conditions	Yield
Stage #1: 3-(dodecyloxy)-1-propylamine; 1,3,5-trichloro-2,4,6-triazine In toluene at 30℃; for 0.5h; Stage #2: With sodium hydroxide In water; toluene for 8h; Heating / reflux;	90%

3-(dodecyloxy)-1-propylamine (7617-74-5) + 2-ethyl-hexyl glycidyl ether (2461-15-6) → poly(2-ethylhexyl glycidyl ether-co-3-(dodecyloxy)-1-propylamine)

Conditions	Yield
at 60 - 120℃; for 10.6667h;	85%

3-(dodecyloxy)-1-propylamine (7617-74-5) + 4,6-dichloro-1,3,5-triazin-2-amine (933-20-0) → N,N-bis(dodecyloxypropyl)melamine

Conditions	Yield
With sodium hydroxide for 14h; Heating;	74%

3-(dodecyloxy)-1-propylamine (7617-74-5) + perylene-3,4,9,10-tetracarboxylic acid 3,4:9,10-dianhydride (128-69-8) → N,N'-bis(3-(n-dodecyloxy)-n-propyl)-3,4:9,10-perylene tetracarboxylic diimide (1300055-82-6)

Conditions	Yield
With 1H-imidazole at 160℃; for 4h; Inert atmosphere;	70%

3-(dodecyloxy)-1-propylamine (7617-74-5) + Boc-Glu (2419-94-5) → C40H79N3O6

Conditions	Yield
With diethyl cyanophosphonate; triethylamine In tetrahydrofuran at 0 - 20℃; for 72h;	60.2%

3-(dodecyloxy)-1-propylamine (7617-74-5) + formaldehyde hydrazone (6629-91-0) + orthoformic acid triethyl ester (122-51-0) → 4-(3-lauryloxy)propyl-1,2,4-triazol (674802-60-9)

Conditions	Yield
Stage #1: formaldehyde hydrazone; orthoformic acid triethyl ester In methanol for 3h; Heating; Stage #2: 3-(dodecyloxy)-1-propylamine In methanol for 10h; Heating;	52%

3-(dodecyloxy)-1-propylamine (7617-74-5) → 5-t-butyl-4-chloromethyl-2-{4-(3-dodecyloxypropyl)carbamoyl-2-nitrophenyl}-4-isoxazolin-3-one (118938-17-3)

Conditions	Yield
With thionyl chloride; triethylamine In chloroform	52%

3-(dodecyloxy)-1-propylamine (7617-74-5) + 2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) → N-(3-Dodecyloxy-propyl)-[1,3,5]triazine-2,4,6-triamine

Conditions	Yield
With sodium hydroxide for 48h; Heating;	44%

3-(dodecyloxy)-1-propylamine (7617-74-5) + 4-chloromethyl-5-methyl-2-(4-carboxy-2-nitrophenyl)-4-isoxazolin-3-one (118937-97-6) → 4-chloromethyl-5-methyl-2-{4-(3-dodecyloxypropyl)carbamoyl-2-nitrophenyl}-4-isoxazolin-3-one (118938-06-0)

Conditions	Yield
With thionyl chloride; triethylamine In N-methyl-acetamide; chloroform; ethyl acetate	35.6%

3-(dodecyloxy)-1-propylamine (7617-74-5) + bis-N,N-(2-chloroethyl)-2-methoxyaniline (1207-00-7) → 1-(3-dodecyloxy-propyl)-4-(2-methoxy-phenyl)-piperazine (116283-15-9)

Conditions	Yield
With ethanol

2,2'-dithiodibenzoic acid dichloride (19602-82-5) + 3-(dodecyloxy)-1-propylamine (7617-74-5) → 2-(3-dodecyloxy-propyl)-benzo[d]isothiazol-3-one (4299-15-4)

Conditions	Yield
(i) Cl2, CCl4, (ii) /BRN= 1098965/; Multistep reaction;

3,5-diallyl-[1,3,5]oxadiazinane-2,4,6-trione (36020-15-2) + 3-(dodecyloxy)-1-propylamine (7617-74-5) → 1,3-Diallyl-5-<3-dodecyloxy-propyl>-biuret (36020-04-9)

Conditions	Yield
In benzene Heating;

3-(dodecyloxy)-1-propylamine (7617-74-5) + ethyl 2-mercaptoethyl carbonate (5628-96-6) → 2-(4-Oxa-hexadecylamino)-aethanthiol (20613-24-5)

Conditions	Yield
In toluene Heating;

3-(dodecyloxy)-1-propylamine (7617-74-5) + 3,5-dimethyl-1,3,5-oxadiazane-2,4,6-trione (36209-52-6) → C19H39N3O3 (54144-67-1)

Conditions	Yield
With triethylamine In acetonitrile

3-(dodecyloxy)-1-propylamine (7617-74-5) + p-toluenesulfonyl chloride (98-59-9) → N-<3-Lauryloxy-propyl>-p-toluolsulfonamid (909-88-6)

Conditions	Yield
With pyridine

3-(dodecyloxy)-1-propylamine (7617-74-5) + acetone (67-64-1) → 2-(3-Lauryloxy-propyl-amino)-propyl-(2)-phosphonigsaeure (17316-69-7)

Conditions	Yield
With hypophosphorous acid

3-(dodecyloxy)-1-propylamine (7617-74-5) + 2-bromoethanol (540-51-2) → 2-(3-Dodecyloxy-propylamino)-ethanol

Conditions	Yield
In ethanol Heating;

Dimethyl oxalate (553-90-2) + 3-(dodecyloxy)-1-propylamine (7617-74-5) → N,N'-Bis-(3-dodecyloxy-propyl)-oxalamide (132867-45-9)

3-(dodecyloxy)-1-propylamine (7617-74-5) + <2-hydroxy-ethyl>-cyanamide (?) → N-(3-dodecyloxy-propyl)-N'-(2-hydroxy-ethyl)-guanidine; acetate

Conditions	Yield
at 120℃;

3-(dodecyloxy)-1-propylamine (7617-74-5) → N,N'-Bis-(3-dodecyloxy-propyl)-ethane-1,2-diamine (132867-38-0)

Conditions	Yield
Multi-step reaction with 2 steps 2: LiAlH4 / tetrahydrofuran View Scheme

3-(dodecyloxy)-1-propylamine (7617-74-5) → 2-(3-Lauryloxy-propylamino)-propyl-(2)-phosphonigsaeure-methylester (17316-89-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: H3PO2 2: methanol; diethyl ether View Scheme

3-(dodecyloxy)-1-propylamine (7617-74-5) → N-Nitroso-N-<3-lauryloxy-propyl>-p-toluolsulfonamid

Conditions	Yield
Multi-step reaction with 2 steps 1: Py 2: NaNO2 View Scheme

3-(dodecyloxy)-1-propylamine (7617-74-5) + 2-ethyl-hexyl glycidyl ether (2461-15-6) → C37H77NO5

3-(dodecyloxy)-1-propylamine (7617-74-5) + dodecyl glycidyl ether (2461-18-9) → C45H93NO5

3-(dodecyloxy)-1-propylamine (7617-74-5) + acetaldehyde (75-07-0) → diethyl-(3-dodecyloxy-propyl)-amine

Conditions	Yield
With hydrogen; Pd/Al2O3 at 130℃; under 15001.5 Torr; for 10.5h;

3-(dodecyloxy)-1-propylamine (7617-74-5) + formaldehyd (50-00-0) → N,N-dimethyl-N-[3-(dodecyloxy)propyl] amine (17517-02-1)

Conditions	Yield
With hydrogen; Pd/Al2O3 In water at 110℃; under 75007.5 Torr; for 7h;

Upstream product

• 56637-94-6 3-dodecyloxy-propionitrile 
• 112-53-8 1-dodecyl alcohol 
• 1380680-79-4 1-(3-azidopropoxy)dodecane 
• 143-15-7 1-dodecylbromide 
• 84337-56-4 2-(dodecyloxy)methyl-1-ethanol 

Downstream Products

• 116283-15-9 1-(3-dodecyloxy-propyl)-4-(2-methoxy-phenyl)-piperazine 
• 674802-60-9 4-(3-lauryloxy)propyl-1,2,4-triazol 
• 118938-17-3 5-t-butyl-4-chloromethyl-2-{4-(3-dodecyloxypropyl)carbamoyl-2-nitrophenyl}-4-isoxazolin-3-one 
• 118938-06-0 4-chloromethyl-5-methyl-2-{4-(3-dodecyloxypropyl)carbamoyl-2-nitrophenyl}-4-isoxazolin-3-one 

Relevant articles and documents

Lipophilic amines as potent inhibitors of N-acylethanolamine-hydrolyzing acid amidase

N-Acylethanolamines (NAEs) including N-arachidonoylethanolamine (anandamide) and N-palmitoylethanolamine are endogenous lipid mediators. These molecules are degraded to the corresponding fatty acids and ethanolamine by fatty acid amide hydrolase (FAAH) or NAE-hydrolyzing acid amidase (NAAA). Lipophilic amines, especially pentadecylamine (2c) and tridecyl 2-aminoacetate (11b), were found to exhibit potent NAAA inhibitory activities (IC50 = 5.7 and 11.8 μM), with much weaker effects on FAAH. These simple structures would provide a scaffold for further improvement in NAAA inhibitory activity.

Aldose epimerization by Ni(II): effect of ether-containig alkylenediamine ligands

Several N-substituted ethylenediamine (en) Ni(II) derivatives containing ether linkages were prepared in order to study the effect of ligand structure on C-2 epimerization of aldohexoses.The reagent consisted of a Ni(II)-alkyenediamine derivative in methanol.The presence of ether linkages in the ligand increased the solubilty of the complexes, and resulted in an increase in the rate of epimerization.Epimerization occured rapidly under mild conditions, and the same equilibrium point was reached regardless of whether the reaction was started from glucose or mannose.Among the ligands studied, N,N'-dialkylethylenediamine was the most effective in C-2 epimerization.