(S)-Amino-(1H-indol-3-YL)-acetic acid

Base Information

• Chemical Name: (S)-Amino-(1H-indol-3-YL)-acetic acid
• CAS No.: 630392-83-5
• Molecular Formula: C10H10N2O2
• Molecular Weight: 190.202
• DSSTox Substance ID: DTXSID00363561
• Nikkaji Number: J2.553.205H
• Mol file: 630392-83-5.mol

Synonyms:630392-83-5;(S)-AMINO-(1H-INDOL-3-YL)-ACETIC ACID;(2S)-2-amino-2-(1H-indol-3-yl)acetic acid;(S)-2-AMINO-2-(1H-INDOL-3-YL)ACETIC ACID;MFCD06858424;SCHEMBL10079616;DTXSID00363561;(S)-2-(1H-Indole-3-yl)glycine;(2S)-Amino(1H-indol-3-yl)acetic acid;(S)-AMINO-(1H-INDOL-3-YL)-ACETICACID;(S)-2-AMINO-2-(1H-INDOL-3-YL)ACETICACID;(S)-2-Amino-2-(1H-indol-3-yl)acetic acid (H-L-nTrp-OH)

Chemical Property of (S)-Amino-(1H-indol-3-YL)-acetic acid

Chemical Property:

• Vapor Pressure: 1.82E-08mmHg at 25°C
• Refractive Index: 1.726
• Boiling Point: 438.6°C at 760 mmHg
• Flash Point: 219°C
• PSA: 79.11000
• Density: 1.422g/cm³
• LogP: 1.95260
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 190.074227566
• Heavy Atom Count: 14
• Complexity: 232

Purity/Quality:

98%min ^*data from raw suppliers

(S)-2-Amino-2-(1H-indol-3-yl)aceticacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)C(C(=O)O)N
• Isomeric SMILES: C1=CC=C2C(=C1)C(=CN2)[C@@H](C(=O)O)N

Technology Process of (S)-Amino-(1H-indol-3-YL)-acetic acid

There total 7 articles about (S)-Amino-(1H-indol-3-YL)-acetic acid 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: 98.0%

3-indolylglycine ethyl ester (1031436-76-6) → (S)-2-amino-2-(1H-indol-3-yl)acetic acid (630392-83-5)

Guidance literature:

With sodium trimethylsilanolate; In tetrahydrofuran; at 20 ℃; for 2.5h;

Reference yield: 93.0%

C35H30N4NiO3 → (S)-2-amino-2-(1H-indol-3-yl)acetic acid (630392-83-5)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; methanol; water; at 20 ℃; for 6h;

DOI:10.1039/c3cc38908a

Reference yield: 80.0%

(S)-2-(1H-indol-3-yl)-2-(((R)-1-phenylethyl)amino)acetic acid → (S)-2-amino-2-(1H-indol-3-yl)acetic acid (630392-83-5)

Guidance literature:

With palladium 10% on activated carbon; triethylammonium formate; In methanol; at 25 ℃; for 24h; stereoselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.201900814

upstream raw materials:

3-indolylglycine ethyl ester

indole

Downstream raw materials:

C₂₀H₁₄N₂O₄

Refernces

• 1、 Lin, Daizong,Wang, Jiang,Zhang, Xu,Zhou, Shengbin,Lian, Jie,Jiang, Hualiang,Liu, Hong. "Highly diastereoselective synthesis of 3-indolylglycines via an asymmetric oxidative heterocoupling reaction of a chiral nickel(ii) complex and indoles". supporting information. p. 2575 - 2577. Retrieved 2013/04/23.
• 2、 Wanner, Martin J.,Hauwert, Peter,Schoemaker, Hans E.,De Gelder, Rene,Van Maarseveen, Jan H.,Hiemstra, Henk. "Synthesis of enantiopure (S)-indolylglycine by organocatalyzed Friedel-Crafts alkylation of indole". . p. 180 - 185. Retrieved 2008/09/18.