(3S)-3-azaniumyl-3-(4-bromophenyl)propanoate

Base Information

• Chemical Name: (3S)-3-azaniumyl-3-(4-bromophenyl)propanoate
• CAS No.: 275826-36-3
• Molecular Formula: C9H10BrNO2
• Molecular Weight: 244.088
• Hs Code.: 2922499990
• Mol file: 275826-36-3.mol

Synonyms:

Chemical Property of (3S)-3-azaniumyl-3-(4-bromophenyl)propanoate

Chemical Property:

• Vapor Pressure: 2.17E-06mmHg at 25°C
• Refractive Index: 1.607
• Boiling Point: 378.1 °C at 760 mmHg
• PKA: 3.62±0.10(Predicted)
• Flash Point: 182.5 °C
• PSA: 63.32000
• Density: 1.585 g/cm³
• LogP: 2.62390
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 242.98949
• Heavy Atom Count: 13
• Complexity: 173

Purity/Quality:

98% ^*data from raw suppliers

Benzenepropanoicacid,?-amino-4-bromo-,(?S)- 96% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(CC(=O)[O-])[NH3+])Br
• Isomeric SMILES: C1=CC(=CC=C1[C@H](CC(=O)[O-])[NH3+])Br

Technology Process of (3S)-3-azaniumyl-3-(4-bromophenyl)propanoate

There total 5 articles about (3S)-3-azaniumyl-3-(4-bromophenyl)propanoate 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: 46.0%

n-propyl 3-amino-3-(4-bromophenyl)propionate → C12H16BrNO2 + (S)-3-amino-3-(4-bromophenyl)propionic acid (275826-36-3,295356-30-8)

Guidance literature:

With Amano Lipase PS; water; In tert-butyl methyl ether; for 15h; pH=8.2; optical yield given as %ee; enantioselective reaction; Enzymatic reaction;

DOI:10.1021/op200084g

Reference yield: 46.0%

3-amino-3-(4-bromophenyl)propionic acid ethyl ester (275826-32-9) → (R)-3-amino-3-(4-bromophenyl)propionic acid ethyl ester + (S)-3-amino-3-(4-bromophenyl)propionic acid (275826-36-3,295356-30-8)

Guidance literature:

With Lipase Amano PS; In phosphate buffer; pH=8.2;

DOI:10.1016/S0040-4039(00)00222-7

Reference yield:

3-amino-3-(4'-bromophenyl)propanoic acid (39773-47-2,295356-30-8) → (S)-3-amino-3-(4-bromophenyl)propionic acid (275826-36-3,295356-30-8)

Guidance literature:

Multi-step reaction with 2 steps

1: HCl

2: 46 percent / lipase Amano PS / aq. phosphate buffer / pH 8.2

With hydrogenchloride; Lipase Amano PS; In phosphate buffer; 1: Fisher esterification / 2: Hydrolysis;

DOI:10.1016/S0040-4039(00)00222-7

upstream raw materials:

3-amino-3-(4-bromophenyl)propionic acid ethyl ester

3-amino-3-(4'-bromophenyl)propanoic acid

3-amino-3-(4-bromophenyl)propionic acid methyl ester

p-bromo-DL-phenylalanine

Downstream raw materials:

(S)-3-amino-3-(4-bromophenyl)propan-1-ol

(3S)-methyl 3-amino-3-(4-bromophenyl)propionate

C₃₃H₄₀BrN₉O₁₅P₂

(S)-N-(4-pentenoyl)-β-(p-bromophenyl)-β-alanine cyanomethyl ester

Refernces

• 1、 Grayson, J. Ian,Roos, Juergen,Osswald, Steffen. "Development of a commercial process for (S)-β-phenylalanine (1)". scheme or table. p. 1201 - 1206. Retrieved 2011/12/16.
• 2、 Faulconbridge, Susan J.,Holt, Karen E.,Garcia Sevillano, Luis,Lock, Christopher J.,Tiffin, Peter D.,Tremayne, Neil,Winter, Stephen. "Preparation of enantiomerically enriched aromatic β-amino acids via enzymatic resolution". . p. 2679 - 2681. Retrieved 2007/10/03.