n-[(1s)-1-Phenylethyl]acetamide

Base Information

• Chemical Name: n-[(1s)-1-Phenylethyl]acetamide
• CAS No.: 19144-86-6
• Molecular Formula: C10H13 N O
• Molecular Weight: 163.219
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID60940776
• Nikkaji Number: J51.673B
• Wikidata: Q74417972
• Mol file: 19144-86-6.mol

Synonyms:19144-86-6;n-[(1s)-1-phenylethyl]acetamide;(S)-N-(1-phenylethyl)acetamide;(S)-(-)-N-Acetyl-1-methylbenzylamine;Acetamide, N-[(1S)-1-phenylethyl]-;SCHEMBL640385;(s)-n-acetyl-1-phenylethylamine;(S)-N-acetyl 1-phenylethylamine;DTXSID60940776;(S)-n-acetyl-1-methylbenzylamine;CHEBI:141109;PAVMRYVMZLANOQ-QMMMGPOBSA-N;N-(1-Phenylethyl)ethanimidic acid;N-(1S)-1-phenyl-ethyl-acetamide;AKOS017382522;(-)-(s)-N-(1-phenylethyl)acetamide;GS-0414;A813490

Chemical Property of n-[(1s)-1-Phenylethyl]acetamide

Chemical Property:

• Vapor Pressure: 0.000196mmHg at 25°C
• Melting Point: 102-103 °C
• Refractive Index: 1.5400 (estimate)
• Boiling Point: 327.9°Cat760mmHg
• PKA: 15?+-.0.46(Predicted)
• Flash Point: 192.2°C
• PSA: 29.10000
• Density: 1.007g/cm³
• LogP: 2.27460
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 163.099714038
• Heavy Atom Count: 12
• Complexity: 150

Purity/Quality:

98%min ^*data from raw suppliers

(S)-(-)-N-ACETYL-1-METHYLBENZYLAMINE 95.00% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC=CC=C1)NC(=O)C
• Isomeric SMILES: C[C@@H](C1=CC=CC=C1)NC(=O)C

Technology Process of n-[(1s)-1-Phenylethyl]acetamide

There total 75 articles about n-[(1s)-1-Phenylethyl]acetamide 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: 100.0%

N-(1-phenylvinyl)acetamide (57957-24-1) → (S)-N-acetyl-1-phenylethylamine (19144-86-6,6284-14-6)

Guidance literature:

With (S)-diBr-SIPHOS; hydrogen; rhodium(I)-bis(1,5-cyclooctadiene) tetrafluoroborate; In toluene; at 0 ℃; for 30h; under 38000 Torr;

DOI:10.1016/j.tetasy.2003.08.017

Reference yield: 99.0%

(S)-1-phenyl-ethylamine (2627-86-3) + acetonitrile (75-05-8,26809-02-9) → (S)-N-acetyl-1-phenylethylamine (19144-86-6,6284-14-6)

Guidance literature:

With aluminum oxide; at 200 ℃; for 0.45h; under 37503.8 Torr; Sonication; Green chemistry;

DOI:10.3390/molecules25081985

Reference yield: 96.0%

(S)-N-(1-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl))acetamide → (S)-N-acetyl-1-phenylethylamine (19144-86-6,6284-14-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In toluene; at 10 - 30 ℃; for 3h;

upstream raw materials:

(S)-1-phenyl-ethylamine

acetic anhydride

1-ethoxyvinyl acetate

(S)-2,3,3-Trimethyl-4-oxo-2-phenyl-azetidine-1-carboxylic acid ((S)-1-phenyl-ethyl)-amide

Downstream raw materials:

(S)-N-[1-(4-nitrophenyl)ethyl]acetamide

(S)-1-(p-nitrophenyl)ethylamine

(S)-(-)-α-methylbenzylamine hydrochloride

(S)-1-phenyl-ethylamine

Refernces

• 1、 Satyanarayana, Tummanapalli,Kagan, Henri B.. "Amplification of the enantiomeric excess of a compound in kinetic resolution by a racemic reagent". . p. 6415 - 6422. Retrieved 2007.
• 2、 De Los Santos, Zeus A.,Wolf, Christian. "Chiroptical Asymmetric Reaction Screening via Multicomponent Self-Assembly". . p. 13517 - 13520. Retrieved 2016.
• 3、 Zhu, Guoxin,Zhang, Xumu. "Asymmetric Rh-catalyzed hydrogenation of enamides with a chiral 1,4- bisphosphine bearing diphenylphosphino groups". . p. 9590 - 9593. Retrieved 1998.
• 4、 Jiang, Xiao-Bin,Van Den Berg,Minnaard, Adriaan J.,Feringa, Ben L.,De Vries, Johannes G.. "The application of monodentate secondary phosphine oxide ligands in rhodium- and iridium-catalyzed asymmetric hydrogenation". . p. 2223 - 2229. Retrieved 2004.
• 5、 Wassenaar, Jeroen,Reek, Joost N. H.. "Asymmetric hydrogenation of enamides, α-enol and α-enamido ester phosphonates catalyzed by IndolPhos-Rh complexes". . p. 8403 - 8406. Retrieved 2009.
• 6、 Dahment, Stefan,Braese, Stefan. "The asymmetric dialkylzinc addition to imines catalyzed by [2.2]paracyclophane-based N,O-ligands". . p. 5940 - 5941. Retrieved 2002.
• 7、 Hirose, Takuji,Begum, Muksana,Sadequl Islam,Taniguchi, Kayoko,Yasutake, Mikio. "Resolution of α-methylbenzylamine via diastereomeric salt formation using the naturally based reagent N-tosyl-(S)-phenylalanine together with a solvent switch technique". . p. 1641 - 1646. Retrieved 2008.
• 8、 Erre, Giulia,Enthaler, Stephan,Junge, Kathrin,Addis, Daniele,Beller, Matthias. "Iridium-catalysed asymmetric hydrogenation of enamides in the presence of 3,3-substituted h8-phosphoramidites". . p. 1437 - 1441. Retrieved 2009.
• 9、 Wzorek, Alicja,Sato, Azusa,Drabowicz, J?zef,Soloshonok, Vadim A.,Klika, Karel D.. "Enantiomeric enrichments via the self-disproportionation of enantiomers (SDE) by achiral, gravity-driven column chromatography: A case study using N-(1-phenylethyl)acetamide for optimizing the enantiomerically pure yield and magnitude of the SDE". . p. 1147 - 1159. Retrieved 2015.
• 10、 -. "Chiral ferrocene phosphine-indole aminophosphine ligand as well as preparation method and application thereof". Paragraph 0048-0049. . Retrieved 2021/05/22.