19614-67-6

Basic information

• Product Name: N-(2,3-epoxypropyl)-N-ethylaniline
• Synonyms: N-(2,3-epoxypropyl)-N-ethylaniline;N-Ethyl-N-phenyloxiranemethanamine;Einecs 243-185-5
• CAS NO: 19614-67-6
• Molecular Formula: C₁₁H₁₅NO
• Molecular Weight: 177.2429
• EINECS: 243-185-5
• Mol File: 19614-67-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 274.7°Cat760mmHg
• Flash Point: 80.7°C
• Appearance: /
• Density: 1.079g/cm³
• Vapor Pressure: 0.00533mmHg at 25°C
• Refractive Index: 1.571
• CAS DataBase Reference: N-(2,3-epoxypropyl)-N-ethylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2,3-epoxypropyl)-N-ethylaniline(19614-67-6)
• EPA Substance Registry System: N-(2,3-epoxypropyl)-N-ethylaniline(19614-67-6)

Safety Data

• Hazardous Substances Data: 19614-67-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H15NO/c1-2-12(8-11-9-13-11)10-6-4-3-5-7-10/h3-7,11H,2,8-9H2,1H3

Upstream product

• 103-69-5 N-ethyl-N-phenylamine 
• 106-89-8 epichlorohydrin 
• 71176-56-2 1-chloro-3-(N-ethyl-N-phenylamino)propan-2-ol 

Downstream Products

• 1258220-58-4 3-(N-ethyl-N-phenylamino)-1-(piperidin-1-yl)propan-2-ol 
• 947394-05-0 3-(N-ethyl-N-phenylamino)-1-morpholinopropan-2-ol 
• 1258220-59-5 3-(N-ethyl-N-phenylamino)-1-(4-methylpiperazin-1-yl)propan-2-ol 
• 1258220-64-2 1-[3-(N-ethylanilino)prop-1-enyl]peridin-2(1H)-one 
• 1258220-60-8 3-(5,5-dimethylhydantoin-3-yl)-1-(N-ethylanilino)propan-2-ol 
• 1258220-61-9 3-(2-hydroxyethylamino)-1-(N-ethylanilino)propan-2-ol 
• 7030-62-8 1,3-bis(N-ethylanilino)propan-2-ol 
• 1258220-63-1 3-[N,N-bis(2-hydroxyethyl)amino]-1-(N-ethylanilino)propan-2-ol 
• 1258220-62-0 3-(2-hydroxypropylamino)-1-(N-ethylanilino)propan-2-ol 
• 1309922-48-2 1-(N-ethyl-N-phenylamino)-3-thiocyanatopropan-2-yl acetate 
• 1455432-83-3 3,3'-{[biphenyl-4,4'-diylbis(methylene)]bis(sulfanediyl)}bis{1-[ethyl(phenyl)amino]propan-2-ol} 
• 1455432-81-1 3,3'-{[4,4'-oxybis(4,1-phenylene)bis(methylene)]bis(sulfanediyl)}bis{1-[ethyl(phenyl)amino]-propan-2-ol} 
• 1455432-78-6 3,3'-{[4,4'-methylenebis(4,1-phenylene)bis(-methylene)]bis(sulfanediyl)}bis{1-[ethyl(phenyl)amino]-propan-2-ol} 
• 1310582-01-4 3-(N-ethyl-N-phenylamino)-1-(adenine-9-yl)propane-2-ol 

Relevant articles and documents

Simple synthesis of β-acetoxy thiocyanates from oxiranes

A convenient and simple method for the preparation of previously unknown β-acetoxy thiocyanates by regioselective ring opening of the corresponding oxiranes with thiocyanate anion followed by acetylation is described. The shorter reaction times, better yields of the products, and easy workup are the advantages of this methodology.

Synthesis, Src kinase inhibitory and anticancer activities of 1-substituted 3-(N-alkyl-N-phenylamino)propane-2-ols

A series of 3-(N-alkyl-N-phenylamino)propan-2-ol derivatives were synthesized from epichlorohydrine in a multi-step strategy and were evaluated as Src kinase inhibitors. First, epoxy ring opening of epichlorohydrine was carried out in the presence of N-alkylanilines to yield 3-(N-alkyl-N-phenylamino)-1-chloro-propan-2-ol derivatives using Ca(OTf)2 as catalyst based on our previous studies [1]. Second, ring closure was performed under basic conditions to afford N-epoxymethyl N-alkylaniline derivatives. Finally, the epoxide ring opening with four different secondary amines and three nucleobases afforded the final products, i.e., a series of β-amino alcohols. All compounds were screened for their inhibitory activity against Src kinase and anticancer activity on human breast carcinoma cells, BT-20 cell line. Among all compounds, 3-N-methyl-N-phenylamino-1-(pyrrolidin-1-yl)propan-2-ol (13b) exhibited the highest inhibitory potency (IC50 = 66.1 μM) against Src kinase. Structure-activity relationship studies suggested that the incorporation of bulky groups at position 1 and N-substitution with groups larger than methyl moiety, reduced the inhibitory potency of the compound significantly. Compounds 3-(N-ethyl-N-phenylamino-)-1-(4-methylpiperazin-1-yl)propan-2-ol (14c) and 3-(N-ethyl-N-phenylamino)-1-(thymine-1-yl)propan-2-ol (17) were found to inhibit the growth of breast carcinoma cells by approximately 45-49% at concentration of 50 μM.