5-Fluorotryptophan

Base Information

• Chemical Name: 5-Fluorotryptophan
• CAS No.: 154-08-5
• Molecular Formula: C11H11FN2O2
• Molecular Weight: 222.219
• Hs Code.: 29339900
• European Community (EC) Number: 205-822-5
• NSC Number: 9363
• UNII: 5IC9663SHW
• DSSTox Substance ID: DTXSID20870489
• Nikkaji Number: J2.700.658B
• Wikidata: Q27147445
• Mol file: 154-08-5.mol

Synonyms:5-fluoro-(beta-11C)tryptophan;5-fluoro-L-tryptophan;5-fluorotryptophan;5-fluorotryptophan, (DL)-isomer;5-fluorotryptophan, (L)-isomer;5-fluorotryptophan, 18F-labeled;5-fluorotryptophan, 18F-labeled, (L)-isomer;L-5-fluorotryptophan

Chemical Property of 5-Fluorotryptophan

Chemical Property:

• Appearance/Colour: light beige powder
• Vapor Pressure: 6.54E-09mmHg at 25°C
• Melting Point: 265 °C (dec.)(lit.)
• Refractive Index: 1.673
• Boiling Point: 450.71 °C at 760 mmHg
• PKA: 2.21±0.10(Predicted)
• Flash Point: 226.382 °C
• PSA: 79.11000
• Density: 1.442 g/cm³
• LogP: 1.96170
• Storage Temp.: 2-8°C
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 222.08045576
• Heavy Atom Count: 16
• Complexity: 275

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Fluoro-DL-tryptophan ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1F)C(=CN2)CC(C(=O)O)N
• Uses: A metabolic antagonist of tryptophan

Technology Process of 5-Fluorotryptophan

There total 9 articles about 5-Fluorotryptophan 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: 84.0%

ethyl 2-amino-3-(5-fluoro-1H-indol-3-yl)propanoate (154170-01-1) → DL-5-fluorotryptophan (154-08-5,343-91-9,97749-24-1)

Guidance literature:

With potassium hydroxide; In methanol; water;

DOI:10.1074/jbc.M116.741561

Reference yield:

acetylamino-(5-fluoro-indol-3-ylmethyl)-malonic acid (363-37-1) → DL-5-fluorotryptophan (154-08-5,343-91-9,97749-24-1)

Guidance literature:

With water; anschliessend Erhitzen des Reaktionsgemisches auf 200grad;

DOI:10.1021/ja01161a523

Reference yield:

acetylamino-(5-fluoro-indol-3-ylmethyl)-malonic acid diethyl ester (428-79-5) → DL-5-fluorotryptophan (154-08-5,343-91-9,97749-24-1)

Guidance literature:

Multi-step reaction with 2 steps

1: aqueous NaOH

2: H₂O / anschliessend Erhitzen des Reaktionsgemisches auf 200grad

With sodium hydroxide; water;

DOI:10.1021/ja01161a523

upstream raw materials:

acetylamino-(5-fluoro-indol-3-ylmethyl)-malonic acid

acetylamino-(5-fluoro-indol-3-ylmethyl)-malonic acid diethyl ester

acetylamino-[3-(4-fluoro-phenylhydrazono)-propyl]-malonic acid diethyl ester

3-dimethylaminomethyl-5-fluoroindole

Downstream raw materials:

D-5-fluorotryptophan

2-((tert-butoxycarbonyl)amino)-3-(5-fluoro-1H-indol-3-yl)propanoic acid

C₃₇H₃₃FN₆O₇

C₃₆H₃₁FN₆O₇

Refernces