3-(3-Benzothienyl)-D-alanine

Base Information

• Chemical Name: 3-(3-Benzothienyl)-D-alanine
• CAS No.: 111139-55-0
• Molecular Formula: C₁₁H₁₁NO₂S
• Molecular Weight: 221.28
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID90357535
• Nikkaji Number: J2.185.256B
• Wikidata: Q72439990
• Mol file: 111139-55-0.mol

Synonyms:3-(3-Benzothienyl)-D-alanine;111139-55-0;(2R)-2-amino-3-(1-benzothiophen-3-yl)propanoic acid;D-3-BENZOTHIENYLALANINE;(R)-2-Amino-3(benzo[b]thiophen-3-yl)-propionic acid;(R)-2-amino-3-(benzo[b]thiophen-3-yl)propanoic acid;(2R)-2-azanyl-3-(1-benzothiophen-3-yl)propanoic acid;3-benzothienyl-d-alanine;H-beta-(3-Benzothienyl)-D-Ala-OH;Benzothiophene-L-Alanine;d-3-benzothienyl-alanine;H-D-Ala(3-Bzt)-OH;(R)-2-Amino-3-(benzo[b]thiophen-3-yl)propionic acid;SCHEMBL1421072;DTXSID90357535;H--(3-Benzothienyl)-D-Ala-OH;72120-71-9;MFCD00079683;AKOS016843039;AC-5883;PS-12173;CS-0156020;F12293;EN300-5462720;A802300;J-002528;D-3-BenZothienylalanine (H-D-Ala(benZothiophen-3-yl)-OH);EXR

Chemical Property of 3-(3-Benzothienyl)-D-alanine

Chemical Property:

• Vapor Pressure: 1.09E-07mmHg at 25°C
• Melting Point: 143-145 °C(lit.)
• Refractive Index: 1.692
• Boiling Point: 416.66 °C at 760 mmHg
• PKA: 2.23±0.10(Predicted)
• Flash Point: 205.789 °C
• PSA: 91.56000
• Density: 1.374 g/cm³
• LogP: 2.55600
• Storage Temp.: Store at RT.
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 221.05104977
• Heavy Atom Count: 15
• Complexity: 247

Purity/Quality:

98.50% ^*data from raw suppliers

3-Benzothienyl-D-alanine 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CS2)CC(C(=O)O)N
• Isomeric SMILES: C1=CC=C2C(=C1)C(=CS2)C[C@H](C(=O)O)N
• Uses: D-3-Benzothienylalanine is a useful intermediate used in the preparation of enantiopure L-benzofuranyl- and L-benzothienyl alanines.

Technology Process of 3-(3-Benzothienyl)-D-alanine

There total 3 articles about 3-(3-Benzothienyl)-D-alanine 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:

(R)-α-acetamido-β-<1>benzothiophene-3-ylpropionic acid (144125-23-5) → (R)-2-amino-3-<1>benzothiophene-3-ylpropionic acid (111139-55-0)

Guidance literature:

With methanesulfonic acid; at 100 ℃; for 7h;

DOI:10.1021/jm00075a006

Reference yield:

α-acetamido-β-<1>benzothiophene-3-ylpropionic acid (63024-19-1) → (R)-2-amino-3-<1>benzothiophene-3-ylpropionic acid (111139-55-0)

Guidance literature:

Multi-step reaction with 2 steps

2: 400 g / 5N CH₃SO₃H / 7 h / 100 °C

With methanesulfonic acid;

DOI:10.1021/jm00075a006

Reference yield:

(R)-α-amino-3-[1]benzothiophene-3-ylpropionic acid (1956-23-6) → benzothiophene-3-acrylic acid (5381-29-3) + (R)-2-amino-3-<1>benzothiophene-3-ylpropionic acid (111139-55-0)

Guidance literature:

With phenylalanine ammonia-lyase; In various solvent(s); at 30 ℃; pH=8.8; Enzyme kinetics;

DOI:10.1002/chem.200501034

upstream raw materials:

(R)-α-acetamido-β-<1>benzothiophene-3-ylpropionic acid

(R)-α-amino-3-[1]benzothiophene-3-ylpropionic acid

α-acetamido-β-<1>benzothiophene-3-ylpropionic acid

Refernces

• 1、 Paizs, Csaba,Katona, Adrian,Retey, Janos. "The interaction of heteroaryl-acrylates and alanines with phenylalanine ammonia-lyase from parsley". . p. 2739 - 2744. Retrieved 2008/02/03.