(2S)-2-azaniumyl-3-(5-bromo-1H-indol-3-yl)propanoate

Base Information

• Chemical Name: (2S)-2-azaniumyl-3-(5-bromo-1H-indol-3-yl)propanoate
• CAS No.: 25197-99-3
• Molecular Formula: C₁₁H₁₁BrN₂O₂
• Molecular Weight: 283.125
• Hs Code.: 2933998090
• Mol file: 25197-99-3.mol

Synonyms:

Chemical Property of (2S)-2-azaniumyl-3-(5-bromo-1H-indol-3-yl)propanoate

Chemical Property:

• 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.: Sealed in dry,Room Temperature
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 282.00039
• Heavy Atom Count: 16
• Complexity: 269

Purity/Quality:

99% ^*data from raw suppliers

5-BROMO-L-TRYPTOPHAN 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1Br)C(=CN2)CC(C(=O)[O-])[NH3+]
• Isomeric SMILES: C1=CC2=C(C=C1Br)C(=CN2)C[C@@H](C(=O)[O-])[NH3+]

Technology Process of (2S)-2-azaniumyl-3-(5-bromo-1H-indol-3-yl)propanoate

There total 23 articles about (2S)-2-azaniumyl-3-(5-bromo-1H-indol-3-yl)propanoate 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: 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: 70.0%

5-bromo-L-tryptophan methyl ester (93299-38-8,93299-39-9) → 5-bromo-L-tryptophan (6548-09-0,25197-99-3,93299-40-2)

Guidance literature:

With sodium hydroxide; In methanol;

Reference yield: 53.0%

5-bromo-D-tryptophan methyl ester (93299-38-8,93299-39-9) → 5-bromo-L-tryptophan (6548-09-0,25197-99-3,93299-40-2)

Guidance literature:

With sodium hydroxide; In methanol; Ambient temperature;

upstream raw materials:

N^α-acetyl-5-bromo-D,L-tryptophan

5-bromo-1H-indole

L-serin

5-bromo-3-<2-acetamido-2,2-bis(ethoxycarbonyl)ethyl>indole

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.