5-Bromo-DL-tryptophan

Base Information

• Chemical Name: 5-Bromo-DL-tryptophan
• CAS No.: 6548-09-0
• Molecular Formula: C11H11BrN2O2
• Molecular Weight: 283.125
• Hs Code.: 29339980
• European Community (EC) Number: 229-464-4
• NSC Number: 88149
• DSSTox Substance ID: DTXSID90863904
• Nikkaji Number: J268.727E
• Metabolomics Workbench ID: 78528
• ChEMBL ID: CHEMBL513050
• Mol file: 6548-09-0.mol

Synonyms:5-bromotryptophan;5-bromotryptophan, (L)-isomer;5-BrTrp

Chemical Property of 5-Bromo-DL-tryptophan

Chemical Property:

• Appearance/Colour: Off-white to light beige fine crystalline powder
• Vapor Pressure: 1.19E-10mmHg at 25°C
• Melting Point: 264 °C (dec.)(lit.)
• Refractive Index: 1.718
• Boiling Point: 495.8 °C at 760 mmHg
• Flash Point: 253.7 °C
• PSA: 79.11000
• Density: 1.704 g/cm³
• LogP: 2.58510
• Storage Temp.: 2-8°C
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 282.00039
• Heavy Atom Count: 16
• Complexity: 275

Purity/Quality:

99% ^*data from raw suppliers

5-Bromo-DL-tryptophan 99% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=C(C=C1Br)C(=CN2)CC(C(=O)O)N

Technology Process of 5-Bromo-DL-tryptophan

There total 35 articles about 5-Bromo-DL-tryptophan 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%

2-amino-3-(5-bromo-1H-indol-3-yl)propionic acid ethyl ester hydrochloride → 5-bromo-DL-tryptophan (6548-09-0)

Guidance literature:

With sodium hydroxide; In methanol; for 15h; Ambient temperature;

Reference yield: 94.0%

Nα-acetyl-5-bromo-D,L-tryptophan (75816-15-8) → 5-bromo-DL-tryptophan (6548-09-0,25197-99-3,93299-40-2) + Nα-acetyl-5-bromo-D-tryptophan (75816-16-9)

Guidance literature:

With borate buffer; cobalt(II) chloride; at 37 ℃; for 48h; pH=8.0; Enzymatic reaction;

DOI:10.1016/j.tetlet.2008.02.120

Reference yield: 75.0%

C11H9BrN4O2 → 5-bromo-DL-tryptophan (6548-09-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 8h; under 760.051 Torr;

upstream raw materials:

(5-bromo-indol-3-ylmethyl)-formylamino-malonic acid diethyl ester

2-Acetylamino-2-(1-benzenesulfonyl-5-bromo-1H-indol-3-ylmethyl)-malonic acid diethyl ester

5-bromo-3-methyl-1H-indole

5-bromo-3-methyl-1H-indole-2-carboxylic acid ethyl ester

Downstream raw materials:

5-(4-methoxyphenyl)-L-tryptophan

5-(4-trifluoromethylphenyl)-L-tryptophan

5-(4-carboxyphenyl)-L-tryptophan

N-t-butoxycarbonyl-5-bromotryptophan

Refernces

• 1、 Schnepel, Christian,Dodero, Veronica I.,Sewald, Norbert. "Novel Arylindigoids by Late-Stage Derivatization of Biocatalytically Synthesized Dibromoindigo". supporting information. p. 5404 - 5411. Retrieved 2021/03/03.
• 2、 Zlatopolskiy, Boris D.,Zischler, Johannes,Sch?fer, Dominique,Urusova, Elizaveta A.,Guliyev, Mehrab,Bannykh, Olesia,Endepols, Heike,Neumaier, Bernd. "Discovery of 7-[18F]Fluorotryptophan as a Novel Positron Emission Tomography (PET) Probe for the Visualization of Tryptophan Metabolism in Vivo". . p. 189 - 206. Retrieved 2018/02/10.