7-Chlorotryptophan

Base Information

• Chemical Name: 7-Chlorotryptophan
• CAS No.: 153-97-9
• Molecular Formula: C11H11ClN2O2
• Molecular Weight: 238.674
• Hs Code.: 2933990090
• Nikkaji Number: J3.045.467G
• Wikidata: Q27124250
• Mol file: 153-97-9.mol

Synonyms:7-chlorotryptophan

Chemical Property of 7-Chlorotryptophan

Chemical Property:

• Vapor Pressure: 6.66E-10mmHg at 25°C
• Refractive Index: 1.701
• Boiling Point: 476.9 °C at 760mmHg
• Flash Point: 242.2 °C
• PSA: 79.11000
• Density: 1.474 g/cm³
• LogP: 2.47600
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: -0.4
• 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

2-Amino-3-(7-chloro-1H-indol-3-yl)propanoicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C(=C1)Cl)NC=C2CC(C(=O)O)N

Technology Process of 7-Chlorotryptophan

There total 31 articles about 7-Chlorotryptophan 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%

(S)-N-acetyl-7'-chlorotryptophan (852391-55-0) → 7-chloro-L-tryptophan (153-97-9,73945-46-7,75102-74-8)

Guidance literature:

With hydrogenchloride; for 6h; Heating;

DOI:10.1016/j.bmcl.2005.07.077

Reference yield: 99.0%

7-chloro-1H-indole (53924-05-3) + L-serin (56-45-1,83245-15-2) → 7-chloro-L-tryptophan (153-97-9,73945-46-7,75102-74-8)

Guidance literature:

With Pf₀A₉ enzyme; In aq. phosphate buffer; water; dimethyl sulfoxide; at 75 ℃; for 12h; pH=8; Enzymatic reaction;

DOI:10.1021/jacs.7b05007

Reference yield: 96.0%

N-Acetyl-7-chlor-DL-tryptophan (77290-47-2) → 7-chloro-D/L-tryptophan (153-97-9)

Guidance literature:

With sodium hydroxide; In water; for 15h; Heating;

upstream raw materials:

N-Acetyl-7-chlor-DL-tryptophan

2-(7-Chloro-1H-indol-3-ylmethyl)-2-formylamino-malonic acid diethyl ester

7-chloro-1H-indole

7-chloro-N,N-dimethyl-1H-indole-3-methanamine

Downstream raw materials:

7-chloro-L-tryptophan

7-Chlor-D-tryptophan

7-phenyl-L-tryptophan

2-(7-chloro-1H-indol-3-yl)ethanamine

Refernces

• 1、 Poor, Catherine B.,Andorfer, Mary C.,Lewis, Jared C.. "Improving the stability and catalyst lifetime of the halogenase RebH by directed evolution". . p. 1286 - 1289. Retrieved 2014.
• 2、 Payne, James T.,Andorfer, Mary C.,Lewis, Jared C.. "Regioselective arene halogenation using the FAD-dependent halogenase RebH". . p. 5271 - 5274. Retrieved 2013.
• 3、 Flecks, Silvana,Patallo, Eugenio P.,Zhu, Xiaofeng,Ernyei, Aliz J.,Seifert, Gotthard,Schneider, Alexander,Dong, Changjiang,Naismith, James H.,Van Pee, Karl-Heinz. "New insights into the mechanism of enzymatic chlorination of tryptophan". . p. 9533 - 9536. Retrieved 2008.
• 4、 Yu, Jinhai,Li, Jing,Gao, Xia,Zeng, Shuiyun,Zhang, Hongjuan,Liu, Junzhong,Jiao, Qingcai. "Dynamic Kinetic Resolution for Asymmetric Synthesis of L-Noncanonical Amino Acids from D-Ser Using Tryptophan Synthase and Alanine Racemase". . p. 6618 - 6625. Retrieved 2019/11/03.