L-Phenylalaninol

Base Information

• Chemical Name: L-Phenylalaninol
• CAS No.: 3182-95-4
• Molecular Formula: C9H13NO
• Molecular Weight: 151.208
• Hs Code.: 29221980
• European Community (EC) Number: 221-674-4
• UNII: 9GE9QOP0ET
• DSSTox Substance ID: DTXSID001025528
• Nikkaji Number: J50.948E
• Wikidata: Q27081711
• Metabolomics Workbench ID: 148929
• ChEMBL ID: CHEMBL1235287
• Mol file: 3182-95-4.mol

Synonyms:(S)-2-amino-3-phenyl-1-propanol;phenylalaninol;phenylalaninol hydrobromide;phenylalaninol, (R)-isomer;phenylalaninol, (S)-isomer

Chemical Property of L-Phenylalaninol

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.0004mmHg at 25°C
• Melting Point: 92-94 °C(lit.)
• Refractive Index: -24.5 ° (C=5, EtOH)
• Boiling Point: 303.8 °C at 760 mmHg
• PKA: 12.85±0.10(Predicted)
• Flash Point: 137.5 °C
• PSA: 46.25000
• Density: 1.077 g/cm³
• LogP: 1.24900
• Storage Temp.: -15°C
• Sensitive.: Air Sensitive
• Solubility.: Soluble in chloroform, ethyl acetate, ethanol and methanol.
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 151.099714038
• Heavy Atom Count: 11
• Complexity: 99.7

Purity/Quality:

99% ^*data from raw suppliers

L-Phenylglycinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45-24/25-27

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(CO)N
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H](CO)N
• Uses: Enantiomer of L-Phenylalaninol, an inhibitor of intestinal Phenylalanine absorption. Inhibits the intestinal absorption of Phenylalanine, making it a prospective treatment for phenylketonuria. antiulcer

Technology Process of L-Phenylalaninol

There total 83 articles about L-Phenylalaninol 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%

Phenylalanine (150-30-1,25191-15-5,658-69-5,67675-33-6) → rac-phenylalaninol (1795-98-8,3182-95-4,5267-64-1,16088-07-6)

Guidance literature:

With sodium tetrahydroborate; iodine;

DOI:10.1002/cctc.202000597

Reference yield: 80.0%

ethyl 2-(hydroxyimino)-3-phenylpropanoate (6943-96-0,70564-52-2,70564-53-3) → rac-phenylalaninol (1795-98-8,3182-95-4,5267-64-1,16088-07-6)

Guidance literature:

With sodium tetrahydroborate; iodine; In tetrahydrofuran; for 4h; Heating;

DOI:10.1055/s-2003-41046

Reference yield: 77.0%

Phenylalanine (150-30-1,25191-15-5,658-69-5,67675-33-6) + dimethyl sulfide borane (13292-87-0) → rac-phenylalaninol (1795-98-8,3182-95-4,5267-64-1,16088-07-6)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water;

upstream raw materials:

ethyl N-acetyl-DL-phenylalaninate

Z-β-ethoxycarbonyl-β-nitrostyrene

phenylalanine ethyl ester

acetic acid-(β-nitro-cinnamyl ester)

Downstream raw materials:

(S)-(-)-2-Amino-1-(2-methoxyethoxyethoxy)-3-phenylpropan

(4S)-4-benzyl-2-(2-thienyl)-1,3-oxazoline

(S)-N,N'-bis<1-(hydroxymethyl)-2-phenylethyl>ethanediamide

2-methyl-3-carbonylaminopyridine

Refernces

• 1、 Cui, Zhihao,Du, Da-Ming. "Enantioselective Synthesis of β-Hydrazino Alcohols Using Alcohols and N-Boc-Hydrazine as Substrates". . p. 5616 - 5619. Retrieved 2016.
• 2、 Gao, Chunyou,Xiao, Xiuzheng,Mao, Dongsen,Lu, Guanzhong. "Preparation of L-phenylalaninol with high ee selectivity by catalytic hydrogenation of L-phenylalaninate over Cu/ZnO/Al2O3 catalyst". . p. 1056 - 1062. Retrieved 2013.
• 3、 Vo, Lanchi,Ciula, James,Gooding, Owen W.. "Chemical development on the chiral auxiliary (S)-4-(phenylmethyl)-2-oxazolidinone utilizing automated synthesis and DoE". . p. 514 - 520. Retrieved 2003.
• 4、 Du, Yi-Dan,Chen, Bi-Hong,Shu, Wei. "Direct Access to Primary Amines from Alkenes by Selective Metal-Free Hydroamination". supporting information. p. 9875 - 9880. Retrieved 2021/03/29.
• 5、 Tian, Yingying,Kunz, Doris. "Nucleophilic RhI Catalyzed Selective Isomerization of Terminal Aziridines to Enamides". . p. 4272 - 4275. Retrieved 2020/07/04.