(S)-(-)-N-Benzyl-1-phenylethylamine

Base Information

• Chemical Name: (S)-(-)-N-Benzyl-1-phenylethylamine
• CAS No.: 17480-69-2
• Molecular Formula: C15H17N
• Molecular Weight: 211.307
• Hs Code.: 29214990
• DSSTox Substance ID: DTXSID90361450
• Nikkaji Number: J1.005.042A
• Wikidata: Q72442646
• Mol file: 17480-69-2.mol

Synonyms:(aS)-a-Methyl-N-(phenylmethyl)benzenemethanamine;N-Benzyl((S)-1-phenylethyl)amine;Benzenemethanamine,a-methyl-N-(phenylmethyl)-, (S)-;Dibenzylamine, a-methyl-,(-)- (8CI);(-)-N-Benzyl-1-phenylethylamine;(1S)-N-(1-Phenylethyl)benzylamine;(1S)-N-Benzyl-1-phenylethylamine;(Benzyl)((1S)-1-phenylethyl)amine;

Chemical Property of (S)-(-)-N-Benzyl-1-phenylethylamine

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Vapor Pressure: 0.000727mmHg at 25°C
• Refractive Index: n20/D 1.563(lit.)
• Boiling Point: 309.3 °C at 760 mmHg
• PKA: 8.79±0.19(Predicted)
• Flash Point: 140.6 °C
• PSA: 12.03000
• Density: 1.01 g/cm³
• LogP: 3.92830
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Sensitive.: Air Sensitive
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 211.136099547
• Heavy Atom Count: 16
• Complexity: 178

Purity/Quality:

98% ^*data from raw suppliers

(S)-(-)-N-Benzyl-α-methylbenzylamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C1=CC=CC=C1)NCC2=CC=CC=C2
• Isomeric SMILES: C[C@@H](C1=CC=CC=C1)NCC2=CC=CC=C2
• Uses: (S)-(?)-N-Benzyl-α-methylbenzylamine can be used:In one of the key synthetic steps for the preparation of a cardioprotective drug named CP-060S.To prepare (1S,2S,3S,5R)-tert-butyl 3-[benzyl((S)-1-phenylethyl)amino]-6,6-dimethylbicyclo[3.1.1]heptane-2-carboxylate, an intermediate used to synthesize pinane-based β- and γ-amino acids.To prepare urea derivatives as potent antimicrobial agents.

Technology Process of (S)-(-)-N-Benzyl-1-phenylethylamine

There total 139 articles about (S)-(-)-N-Benzyl-1-phenylethylamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

rac-methylbenzylamine (618-36-0) + benzyl alcohol (100-51-6,185532-71-2) → N-benzyl-1-phenylethylamine (3193-62-2,17480-69-2,19302-20-6,38235-77-7)

Guidance literature:

With μ-diiodo-di((η5-pentamethylcyclopentadienyl)(iodo)iridium); In water; at 115 ℃; for 10h; Inert atmosphere;

DOI:10.1039/b923083a

Reference yield: 92.0%

N-benzylidene-α-methylbenzylamine (17480-71-6,56941-77-6,62696-51-9,69350-13-6,89103-76-4,98393-39-6,3129-98-4) → N-benzyl-1-phenylethylamine (3193-62-2,17480-69-2,19302-20-6,38235-77-7)

Guidance literature:

With zinc(II) tetrahydroborate; silica gel; In tetrahydrofuran; for 10h; Ambient temperature;

DOI:10.1021/jo961736a

Reference yield: 39.0%

N-(1-phenylethyl)-N-(prop-2-yn-1-yl)amine (56862-34-1) + phenyllithium (591-51-5) → N-benzyl-1-phenylethylamine (3193-62-2,17480-69-2,19302-20-6,38235-77-7) + dilithium acetylide (1070-75-3)

Guidance literature:

N-(1-phenylethyl)-N-(prop-2-yn-1-yl)amine; phenyllithium; at 20 ℃;

With methanol;

DOI:10.1021/acs.organomet.8b00047

upstream raw materials:

(R)-1-phenyl-ethyl-amine

benzyl chloride

rac-methylbenzylamine

acetophenone

Downstream raw materials:

(R)-N-benzyl-1-phenylethylamine

rac-methylbenzylamine

tert-butyl (3S,αS)-3-(N-benzyl-N-α-methylbenzylamino)-7-[[(4-methylphenyl)sulfonyl]oxy]heptanoate

tert-butyl (3R,αS)-3-(3,4-methylenedioxyphenyl)-3-(N-benzyl-N-α-methylbenzylamino)propanoate

Refernces

• 1、 Tani, Kazuhide,Onouchi, Jun-ichiro,Yamagata, Tsuneaki,Kataoka, Yasutaka. "Iridium(I)-Catalyzed Asymmetric Hydrogenation of Prochiral Imines; Protic Amines as Catalyst Improvers". . p. 955 - 956. Retrieved 1995.
• 2、 Huckabee, Brian K.,Lin, Sechoing,Smith, Traci L.,Stuk, Timothy L.. "A practical synthesis of enantiomerically pure N-benzyl-α-methyl benzylamine". . p. 594 - 595. Retrieved 2000.
• 3、 Guiu, Ester,Mu?oz, Bianca,Castillón, Sergio,Claver, Carmen. "Iridium-Catalyzed Enantioselective Hydrogenation of Imines with Xylose Diphosphite and Diphosphinite Ligands". . p. 169 - 171. Retrieved 2003.
• 4、 Blanc, Catherine,Agbossou-Niedercorn, Francine,Nowogrocki, Guy. "Efficient enantioselective hydrogenation of arylimines using aminophosphine-oxazoline iridium catalysts". . p. 2159 - 2163. Retrieved 2004.
• 5、 Tillack, Annegret,Hollmann, Dirk,Michalik, Dirk,Beller, Matthias. "A novel ruthenium-catalyzed amination of primary and secondary alcohols". . p. 8881 - 8885. Retrieved 2006.
• 6、 Ireland, Tania,Fontanet, Fran?ois,Tchao, Guen-Gnanh. "Identification of new catalysts for the asymmetric reduction of imines into chiral amines with polymethylhydrosiloxane using high-throughput screening". . p. 4383 - 4387. Retrieved 2004.
• 7、 Cobley, Christopher J.,Henschke, Julian P.. "Enantioselective Hydrogenation of Imines Using a Diverse Library of Ruthenium Dichloride(diphosphine)(diamine) Precatalysts". . p. 195 - 201. Retrieved 2003.
• 8、 Kozio?, Anna E.,W?odarczyk, Adam. "Prolinol as a Chiral Auxiliary in Organophosphorus Chemistry". . p. 1931 - 1941. Retrieved 2021/04/06.
• 9、 Bestvater, Brian P.,Clarke, Joshua J.,Crudden, Cathleen M.,DeJesus, Joseph F.,Devaraj, Karthik,Eisenberger, Patrick,Kojima, Ryoto. "Hydrosilylation and Mukaiyama aldol-type reaction of quinolines and hydrosilylation of imines catalyzed by a mesoionic carbene-stabilized borenium ion". . p. 6786 - 6791. Retrieved 2021/08/20.