2-amino-3-(6-chloro-1H-indol-3-yl)propanoic acid

Base Information

• Chemical Name: 2-amino-3-(6-chloro-1H-indol-3-yl)propanoic acid
• CAS No.: 17808-21-8
• Molecular Formula: C11H11 Cl N2 O2
• Molecular Weight: 238.67
• Hs Code.: 2933990090
• UNII: TC49834B5D
• DSSTox Substance ID: DTXSID70939030
• Metabolomics Workbench ID: 46102
• Mol file: 17808-21-8.mol

Synonyms:6-chlorotryptophan;6-chlorotryptophan, (DL)-isomer;6-chlorotryptophan, (R)-isomer

Chemical Property of 2-amino-3-(6-chloro-1H-indol-3-yl)propanoic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 264-265°C
• Boiling Point: 476.906oC at 760 mmHg
• Flash Point: 242.224oC
• PSA: 79.11000
• Density: 1.475g/cm3
• LogP: 2.47600
• Storage Temp.: Refrigerator
• Solubility.: Aqueous Acid (Slightly), Methanol (Slightly)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 238.0509053
• Heavy Atom Count: 16
• Complexity: 275

Purity/Quality:

99%, ^*data from raw suppliers

6-Chloro-DL-tryptophan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1Cl)NC=C2CC(C(=O)O)N
• Uses: 6-Chloro-D,L-tryptophan (cas# 17808-21-8) is a compound useful in organic synthesis.

Technology Process of 2-amino-3-(6-chloro-1H-indol-3-yl)propanoic acid

There total 9 articles about 2-amino-3-(6-chloro-1H-indol-3-yl)propanoic 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:

1-Acetyl-4-(2-amino-4-chlorophenyl)-2,3-dihydro-1H-pyrrole-2,2-dicarboxylic acid diethylester → 6-chloro-tryptophan (17808-21-8,17808-35-4)

Guidance literature:

With sodium hydroxide; aqueous HBr; In water;

Reference yield:

(6-chloro-indol-3-ylmethyl)-formylamino-malonic acid diethyl ester (1076199-98-8) → 6-chloro-tryptophan (17808-21-8,17808-35-4)

Guidance literature:

With sodium hydroxide; anschliessend Erhitzen des Reaktionsgemisches mit Essigsaeure;

DOI:10.1039/jr9550003499

Reference yield:

6-chloroindole (17422-33-2) → 6-chloro-tryptophan (17808-21-8,17808-35-4)

Guidance literature:

Multi-step reaction with 5 steps

1: aq. AcOH / 20 °C

2: NaOH / toluene / Heating

3: aq. NaOH / tetrahydrofuran / 20 °C

4: AcOH / Heating

5: aq. HCl / Heating

With hydrogenchloride; sodium hydroxide; acetic acid; In tetrahydrofuran; toluene;

DOI:10.1016/j.bmcl.2005.07.077

upstream raw materials:

(6-chloro-indol-3-ylmethyl)-formylamino-malonic acid diethyl ester

N-Formyl-6-chlortryptophan

6-chloroindole

1-(6-chloro-1H-indol-3-yl)-N,N-dimethylmethanamine

Downstream raw materials:

D-6-chlorotryptophan

Refernces

• 1、 Teng, Xin,Degterev, Alexei,Jagtap, Prakash,Xing, Xuechao,Choi, Sungwoon,Denu, Regine,Yuan, Junying,Cuny, Gregory D.. "Structure-activity relationship study of novel necroptosis inhibitors". . p. 5039 - 5044. Retrieved 2007/10/03.