4-(Trifluoromethyl)-L-phenylalanine

Base Information

• Chemical Name: 4-(Trifluoromethyl)-L-phenylalanine
• CAS No.: 114926-38-4
• Molecular Formula: C₁₀H₁₀F₃NO₂
• Molecular Weight: 233.19
• Hs Code.: 2922499990
• European Community (EC) Number: 822-926-1
• DSSTox Substance ID: DTXSID801347041
• Nikkaji Number: J329.735G
• Wikidata: Q76148935
• Mol file: 114926-38-4.mol

Synonyms:4-(trifluoromethyl)phenylalanine;tfm-Phe;tri-fluoromethyl-phenylalanine;trifluoromethyl-phenylalanine;trifluoromethylphenylalanine

Chemical Property of 4-(Trifluoromethyl)-L-phenylalanine

Chemical Property:

• Boiling Point: 311.5 °C at 760 mmHg
• PKA: 2.15±0.10(Predicted)
• Flash Point: 142.2 °C
• PSA: 63.32000
• Density: 1.364 g/cm³
• LogP: 2.36010
• Storage Temp.: Store at -15°C
• Water Solubility.: Slightly soluble in water.
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 233.06636305
• Heavy Atom Count: 16
• Complexity: 247

Purity/Quality:

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

p-Trifluoromethyl-L-phenylalanine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CC(C(=O)O)N)C(F)(F)F
• Isomeric SMILES: C1=CC(=CC=C1C[C@@H](C(=O)O)N)C(F)(F)F
• Uses: 4-fluoro-l-phenylalanine (fF), or 4-trifluoromethyl-l-phenylalanine were introduced inside the chain of peptides to enhances their antimicrobial activity..

Technology Process of 4-(Trifluoromethyl)-L-phenylalanine

There total 10 articles about 4-(Trifluoromethyl)-L-phenylalanine 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: 75.0%

diethyl 2-acetamido-2-<<4-(trifluoromethyl)phenyl>methyl>malonate (114872-59-2) → 2-acetamido-3-(4-(trifluoromethyl)phenyl)propanoic acid (82337-58-4) + (S)-4-trifluoromethylphenylalanine (3832-75-5,14091-16-8,114872-99-0,114926-38-4)

Guidance literature:

With sodium hydroxide; In acetone; Reflux;

Reference yield: 57.0%

4-(trifluoromethyl)cinnamic acid (16642-92-5,87212-84-8,2062-26-2) → (S)-4-trifluoromethylphenylalanine (3832-75-5,14091-16-8,114872-99-0,114926-38-4)

Guidance literature:

With ammonium hydroxide; borane-ammonia complex; In aq. buffer; at 37 ℃; pH=9.6; Reagent/catalyst; Enzymatic reaction;

DOI:10.1002/anie.201410670

Reference yield:

C35H30F3N3NiO3 → (S)-4-trifluoromethylphenylalanine (3832-75-5,14091-16-8,114872-99-0,114926-38-4)

Guidance literature:

C₃₅H₃₀F₃N₃NiO₃; With hydrogenchloride; In methanol; water; at 50 ℃;

With ammonium hydroxide; In water;

DOI:10.1016/j.molstruc.2020.127850

upstream raw materials:

(S)-2-amino-3-(4-(trifluoromethyl)phenyl)propanoic acid methyl ester

4-Trifluoromethylbenzaldehyde

(Z)-2-methyl-4-[4-(trifluoromethyl)benzylidene]-5(4H)-oxazolone

4-bromomethyltrifluoromethylbenzene

Downstream raw materials:

N-tert-butoxycarbonyl-L-4-trifluoromethylphenylalanine

4-(trifluoromethyl)-dl-phenylalanine

2-oxo-3-(4-(trifluoromethyl)phenyl)propanoic acid

Refernces

• 1、 Parmeggiani, Fabio,Lovelock, Sarah L.,Weise, Nicholas J.,Ahmed, Syed T.,Turner, Nicholas J.. "Synthesis of D- and L-Phenylalanine Derivatives by Phenylalanine Ammonia Lyases: A Multienzymatic Cascade Process". . p. 4608 - 4611. Retrieved 2015/04/14.
• 2、 -. "BORON CONTAINING POLYBASIC BACTERIAL EFFLUX PUMP INHIBITORS AND THERAPEUTICS USES THEREOF". . . Retrieved 2012/08/28.