(1S)-1-phenylethanamine

Base Information

• Chemical Name: (1S)-1-phenylethanamine
• CAS No.: 2627-86-3
• Deprecated CAS: 137577-63-0
• Molecular Formula: C8H11N
• Molecular Weight: 121.182
• Hs Code.: 29214980
• European Community (EC) Number: 220-098-0
• UNII: 05780F90V3
• DSSTox Substance ID: DTXSID701014613
• Nikkaji Number: J45.983F
• Wikidata: Q27116451
• Metabolomics Workbench ID: 55093
• ChEMBL ID: CHEMBL282700
• Mol file: 2627-86-3.mol

Synonyms:2627-86-3;(S)-(-)-1-Phenylethylamine;(1S)-1-phenylethanamine;(S)-1-phenylethanamine;(S)-(-)-alpha-Methylbenzylamine;(S)-1-Phenylethylamine;L-1-Phenylethylamine;L-alpha-Methylbenzylamine;L(-)-alpha-Methylbenzylamine;(S)-alpha-Methylbenzenemethanamine;(s)-(-)-1-methylbenzylamine;(-)-alpha-Phenethylamine;L-(-)-1-Phenylethylamine;L-(-)-alpha-Phenylethylamine;(1S)-1-phenylethan-1-amine;1-Phenethylamine, (-)-;(S)-alpha-Methylbenzylamine;(alphaS)-alpha-methylbenzenemethanamine;CHEMBL282700;MFCD00064406;(1S)-(-)-1-Phenylethylamine;CHEBI:35321;UNII-05780F90V3;Benzenemethanamine, .alpha.-methyl-, (.alpha.S)-;EINECS 220-098-0;05780F90V3;Benzenemethanamine, alpha-methyl-, (alphaS)-;EC 220-098-0;s-(-)-alpha-phenylethylamine;(S)-alpha-methyl benzylamine;S-Alfa-Methylbenzylamine;(S)-(-)-a-methyl-benzylamine;(S)-1-phenylethan-1-amine;(S)-(-)-a-methylbenzylamine;(S)-(-)-.alpha.-Methylbenzylamine;(S)-(-)-?-Methylbenzylamine;98B;(S)-1phenylethylamine;1(S)-phenylethylamine;(-)-1-phenethylamine;L-alpha-Phenylethylamine;(S) -1phenylethylamine;(S)-1 phenylethylamine;1-(S)-phenylethylamine;(S)1-Phenyl-Ethylamine;(s)-1-phenylethyl amine;1(s)-phenyl ethyl amine;(1S)-1-phenylethylamine;(s)-(-)-phenethylamine;(S)-1-phenyl-ethylamine;(S)-1-phenylethyl-amine;(s)-(-)-phenylethylamine;(1 S)-1-phenylethanamine;(1S)-1-phenyl-ethylamine;(S)-1-(phenyl)ethylamine;(5)-alpha-methylbenzylamine;SCHEMBL42904;(S)-(-)1-phenylethylamine;(S)-1-(phenyl)-ethylamine;(S)-alpha-methyl-benzylamine;(s)-alpha-methylbenzyl amine;(S)-PEA;[(1S)-1-phenylethyl]amine;(S)-(-)-1-phenethylamine;(-)-(S)-1-penylethylamine;(S)-(-)-1-phenylethanamine;(S)-alpha methyl benzyl amine;L-(-)-alpha-methylbenzylamine;SCHEMBL4166272;(S)(-)-alpha-methylbenzylamine;(S)-(-)-1-phenyl-ethylamine;l(-)-alpha-methyl-benzyl amine;(S)-(-)-|A-Methylbenzylamine;(S)-(-)-alpha-methylbenzylamin;(s)-(-)-alpha-phenylethylamine;(S)-(?)-|A-Methylbenzylamine;(-)-(S)-alpha-methylbenzylamine;(S)-(+)-alpha-methylbenzylamine;DTXSID701014613;L-.ALPHA.-PHENYLETHYLAMINE;(S)-(-)-alpha-methyl benzylamine;S-.ALPHA.-METHYLBENZYLAMINE;STR00933;(S)-(-)- alpha -Methylbenzylamine;(S)-(-)-alpha methyl benzyl amine;(S)-(-)-alpha-methyl benzyl amine;(S)-(-)-alpha-methyl-benzyl amine;BDBM50028638;s6260;AKOS005259686;AKOS012313698;AC-8774;CS-W019840;(-)-(S)-alpha-methyl-benzenemethanamine;L-(-)-.ALPHA.-METHYLBENZYLAMINE;(S)-(-)-alpha-Methylbenzylamine, 98%;AS-14055;AM20060475;P0793;EN300-67316;D77861;.ALPHA.-METHYLBENZYLAMINE (-)-FORM [MI];J-505090;Q27116451;F0001-2350;Z1079131570;(S)-(-)-alpha-Methylbenzylamine, ChiPros(R), produced by BASF, >=99.0%;(S)-(-)-alpha-Methylbenzylamine, for chiral derivatization, >=99.0%;(S)-(-)-alpha-Methylbenzylamine, purum, >=98.0% (sum of enantiomers, GC)

Chemical Property of (1S)-1-phenylethanamine

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Vapor Pressure: 0.5 mm Hg ( 20 °C)
• Melting Point: -10 °C
• Refractive Index: 1.5260
• Boiling Point: 183 °C at 760 mmHg
• PKA: 9.04±0.10(Predicted)
• Flash Point: 75.8 °C
• PSA: 26.02000
• Density: 0.956 g/cm³
• LogP: 2.40660
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Solubility.: 42g/l
• Water Solubility.: slightly soluble
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 121.089149355
• Heavy Atom Count: 9
• Complexity: 74.6

Purity/Quality:

99.0%Min ^*data from raw suppliers

(S)-(-)-α-Methylbenzylamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,Xi
• Hazard Codes: C,Xi
• Statements: 21/22-34-35
• Safety Statements: 26-28-36/37/39-45-28A-27

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Aromatic
• Canonical SMILES: CC(C1=CC=CC=C1)N
• Isomeric SMILES: C[C@@H](C1=CC=CC=C1)N
• Uses: L-1-Phenylethylamine can be used in a one-pot, multi-component synthesis of a highly substituted, chiral pyrrole (S)-(-)-1-Phenylethylamine is utilized in a one-pot, multi-component synthesis of a highly substituted, chiral pyrrole. Used in a one-pot, multi-component synthesis of a highly substituted, chiral pyrrole.

Technology Process of (1S)-1-phenylethanamine

There total 276 articles about (1S)-1-phenylethanamine 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: 70.0%

(S)-N-acetyl-1-phenylethylamine (19144-86-6,6284-14-6) + ethylene glycol (107-21-1) → 2-hydroxyethyl acetate (542-59-6) + (S)-1-phenyl-ethylamine (2627-86-3)

Guidance literature:

(S)-N-acetyl-1-phenylethylamine; With triphenyl phosphite; chlorine; triethylamine; In dichloromethane; at -30 ℃;

ethylene glycol; In dichloromethane; at -30 - 20 ℃;

With water;

DOI:10.1021/ol048852h

Reference yield: 29.0%

ethyl 2-cyanoacetate (105-56-6) + rac-methylbenzylamine (618-36-0) → (R)-2-cyano-N-(1-phenylethyl)acetamide (1202405-40-0) + (S)-1-phenyl-ethylamine (2627-86-3) + (R)-1-phenyl-ethyl-amine (3886-69-9)

Guidance literature:

With Novozym, lipase B from Candida antarctica, recombinant, expressed in Aspergillus niger, adsorbed on acrylic resin; In tetrahydrofuran; toluene; at 25 ℃; for 24h; Reagent/catalyst; enantioselective reaction; Resolution of racemate; Enzymatic reaction;

DOI:10.1016/j.tetasy.2015.04.013

Reference yield:

C12H17NOS (842121-02-2) → 1-Phenylethanol (98-85-1,13323-81-4) + (S)-1-phenyl-ethylamine (2627-86-3) + (R)-1-phenyl-ethyl-amine (3886-69-9) + S-tert-butylsulfinimide (146374-27-8) + acetophenone (98-86-2)

Guidance literature:

C₁₂H₁₇NOS; With [RhCl₂(p-cymene)]2; ethanolamine; potassium hydroxide; In isopropyl alcohol; at 25 ℃; for 15h;

With hydrogenchloride; In methanol; optical yield given as %ee; stereoselective reaction;

DOI:10.1016/j.tetlet.2009.07.044

upstream raw materials:

1-methyl-4-nitrosobenzene

S(+)-2-phenyl-propanoic acid amide

(S)-2-Phenylpropionic acid

rac-methylbenzylamine

Downstream raw materials:

(S)-N-(4-chlorobenzylidene)-1-phenylethanamine

(S)-(-)-N-ethyl-α-methylbenzylamine

1-(1-phenyl-ethylamino)-3-thiazol-2-yloxy-propan-2-ol

Tetrahydro-3-<(1S)-phenylethyl>-2-thioxo-4H-1,3-thiazin-4-on

Refernces

Synthesis of (-)-(1′S,4aS,8aR)- and (+)-(1′S,4aR,8aS)-4a-ethyl-1-(1′-phenylethyl)-octahydroquinolin- 7-ones

10.1016/S0957-4166(01)00391-3

The study in the provided scholarly article focuses on the synthesis of specific octahydroquinolin-7-ones, which are compounds derived from aspidosperma alkaloids and are important in asymmetric synthesis. The researchers synthesized the enamine (?)-(1’S)-5-ethyl-1-(1’-phenylethyl)-1,2,3,4-tetrahydropyridine 4 and used it to create (?)-(1’S,4aS,8aR)- and (+)-(1’S,4aR,8aS)-4a-ethyl-1-(1’-phenylethyl)-octahydroquinolin-7-ones 5 and 6. Key chemicals used in the study include (?)-(S)-1-phenylethylamine, 4-formyl-hexanoic acid methyl ester, LiAlH4/THF for reduction, and methyl vinyl ketone (MVK) in the presence of KOH/18-crown-6/methanol. These chemicals served various purposes, such as starting materials for the synthesis, a reducing agent, and reagents for the condensation reaction to form the desired octahydroquinolin-7-ones. The study also reports an X-ray study of compound 6, which confirmed the cis-fused ring structure and absolute configurations of the stereogenic centers. The purpose of these chemical syntheses was to explore the applications of 3,4-dihydro-1H-pyridin-2-ones in asymmetric synthesis and to prepare compounds 5 and 6 with specific stereochemistries.

Heat-set gels and egg-like vesicles using two component gel system based on chiral calix[4]arenes

10.1039/b713548c

The research focuses on the development of heat-set gels and egg-like vesicles using a two-component gel system based on chiral calix[4]arenes. The purpose of this study was to demonstrate the formation of these structures enantioselectively with D-2,3-dibenzoyltartaric acid in cyclohexane, marking the first instance of heat-set gels resulting from the interaction differences between two-component gelators. The researchers synthesized chiral calix[4]arene diamine 1 with long tertiary alkyl groups at the upper rim and S-1-phenylethylamine groups at the lower rim, which, when combined with 2,3-dibenzoyltartaric acid 2, could form heat-set gels and vesicles. The study concluded that the diameter of the vesicles could be controlled by altering the length of the alkyl groups, and that the size of the vesicles decreased with an increase in the length of these groups. This finding not only provides a new approach to heat-set gels but also has potential applications in thermoresponsive materials. The key chemicals used in this process include chiral calix[4]arenes with specific alkyl groups, D-2,3-dibenzoyltartaric acid, and cyclohexane as the solvent.

Asymmetric reduction with 5-deazaflavin. II. Synthesis of some chiral 5-deazaflavin derivatives

10.1248/cpb.38.312

The research focuses on the development of functional biomimetic coenzyme models, specifically the synthesis of chiral 5-deazaflavin derivatives. The purpose of this study was to prepare new types of chiral deazaflavin derivatives that could effectively discriminate the enantiotopic faces of carbonyls in asymmetric reduction reactions, potentially serving as models for enzymatic systems. The researchers synthesized 5-deazaflavin derivatives with chiral substituents at the C(6) position and a chiral tertiary asymmetric carbon center at C(5). They used various chemicals in the process, including 8-chloro derivative, chiral primary amines such as (+)-dehydroabietylamine and (S)-(-)-phenylethylamine, dicyclohexylcarbodimide (DCC), and N-(tert-butoxycarbonyl)-L-valine.

Novel chiral 1,5-diaza-3,7-diphosphacyclooctane ligands and their transition metal complexes

10.1039/b300754e

The research focuses on the synthesis and application of novel chiral 1,5-diaza-3,7-diphosphacyclooctane ligands and their transition metal complexes. The key chemicals involved in this research include bis(hydroxymethyl)phenylphosphine and (R)- or (S)-α-methylbenzylamine, which were used to synthesize the chiral bisphosphine ligands 1,5-(R,R)- and 1,5-(S,S)-bis(α-methylbenzyl)-3,7-diphenyl-1,5-diaza-3,7-diphosphacyclooctane (1r and 1s). These ligands were then reacted with [MCl2(cod)] (M = Pt, Pd; cod = 1,5-cyclooctadiene) and [{ReBr(CO)3(thf)}2] to form various chiral chelate complexes of PtII (2r, 3r, and 3s), PdII (4s, 5s), and ReI (6r). The synthesized compounds were characterized using multinuclear NMR (1H, 13C, 31P) and IR spectroscopy. Additionally, compound 1s was utilized to create a palladium catalyst for the copolymerization of carbon monoxide and norbornadiene, with the resulting copolymers being characterized by GPC, 1H and 13C NMR spectroscopy, and elemental analysis.

Asymmetric Michael reaction: novel efficient access to chiral β-ketophosphonates

10.1016/j.tetasy.2007.02.023

The research investigates the asymmetric Michael reaction to develop a method for synthesizing chiral b-ketophosphonates, which are valuable precursors for b-amino and b-hydroxy-phosphonates and have biological significance. The study focuses on using chiral b-enaminophosphonates derived from (S)-1-phenylethylamine and various electrophilic alkenes to achieve b,b-disubstituted ketophosphonates with high enantioselectivity and good yields. Key chemicals involved include the non-commercial b-ketophosphonate precursors 3a–3d, which were synthesized through a series of reactions involving hydrazones, Arbuzov reactions, and deprotection steps. The enaminophosphonates 4a–4d were then reacted with Michael acceptors such as phenylvinylsulfone and methyl acrylate. The study concludes that the asymmetric Michael reaction on acyclic enaminophosphonate compounds with non-substituted Michael acceptors is feasible, yielding chiral b-ketophosphonates with high enantiomeric excesses, similar to acyclic enaminoester derivatives. The introduction of dibenzyl- or diphenyl-phosphonate groups, however, decreased reactivity and enantioselectivity compared to diethylphosphonate groups. The absolute configurations of the adducts were determined using vibrational circular dichroism (VCD) due to challenges in obtaining single-crystal samples for X-ray analysis. Future work aims to extend this reaction to substituted Michael acceptors.