167993-21-7

Basic information

• Product Name: BOC-L-2-Trifluoromethylphe
• Synonyms: BOC-L-PHE(2-TRIFLUOROMETHYL)-OH;BOC-L-PHE(2-CF3)-OH;BOC-PHE(2-CF 3)-OH;BOC-L-2-TRIFLUOROMETHYLPHE;BOC-L-2-TRIFLUOROMETHYLPHENYLALANINE;BOC-2-(TRIFLUOROMETHYL)-L-PHENYLALANINE;(S)-2-TERT-BUTOXYCARBONYLAMINO-3-(2-TRIFLUOROMETHYL-PHENYL)-PROPIONIC ACID;tert-butoxycarbonyl-l-2-trifluoromethylphenylalanine
• CAS NO: 167993-21-7
• Molecular Formula: C₁₅H₁₈F₃NO₄
• Molecular Weight: 333.3
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;Amino Acid Derivatives;a-amino
• Mol File: 167993-21-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 421.8 °C at 760 mmHg
• Flash Point: 208.9 °C
• Appearance: /
• Density: 1.271 g/cm³
• Vapor Pressure: 7.2E-08mmHg at 25°C
• Refractive Index: 1.487
• Storage Temp.: Store at -15°C
• PKA: 3.76±0.11(Predicted)
• CAS DataBase Reference: BOC-L-2-Trifluoromethylphe(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-L-2-Trifluoromethylphe(167993-21-7)
• EPA Substance Registry System: BOC-L-2-Trifluoromethylphe(167993-21-7)

Safety Data

• Hazard Codes: Xi
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 167993-21-7(Hazardous Substances Data)

Usage

General Description

BOC-L-2-Trifluoromethylphe, also known as BOC-L-2-(Trifluoromethyl)Phenylalanine, is an amino acid derivative used in peptide synthesis. It's known for its particularity of having a trifluoromethyl group, which can increase the molecule's metabolic stability and make it more lipophilic. It is a synthesized product, largely used in the pharmaceutical industry for drug design and development. As an advanced building block, it is a key component in medicinal chemistry and chemical biology fields.

InChI:InChI=1/C15H18F3NO4/c1-14(2,3)23-13(22)19-11(12(20)21)8-9-6-4-5-7-10(9)15(16,17)18/h4-7,11H,8H2,1-3H3,(H,19,22)(H,20,21)/t11-/m1/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 130930-49-3 (2S)-2-amino-3-[2-(trifluoromethyl)phenyl]propanoic acid 

Downstream Products

• 1044851-57-1 1,1-dimethylethyl ((1S)-2-hydroxy-1-{[2-(trifluoromethyl)phenyl]methyl}ethyl)carbamate 
• 1044851-60-6 1,1-dimethylethyl ((1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-{[2-(trifluoromethyl)phenyl]methyl}ethyl)carbamate 
• 1044851-55-9 2-{(2S)-2-amino-3-[2-(trifluoromethyl)phenyl]propyl}-1H-isoindole-1,3(2H)-dione hydrochloride 
• 1067613-55-1 4-(4-chloro-1-methyl-1H-pyrazol-5-yl)-N-((1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-{[2-(trifluoromethyl)phenyl]methyl}ethyl)-3-fluorobenzamide 
• 1067613-73-3 3-bromo-N-((1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-{[2-(trifluoromethyl)phenyl]methyl}ethyl)-4-(1-methyl-1H-pyrazol-5-yl)benzamide 
• 1067613-99-3 N-((1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-{[2-(trifluoromethyl)phenyl]methyl}ethyl)-4-(1-methyl-1H-1,2,4-triazol-5-yl)benzamide 
• 1067613-95-9 N-((1S)-2-amino-1-{[2-(trifluoromethyl)phenyl]methyl}ethyl)-4-(1-methyl-1H-1,2,4-triazol-5-yl)benzamide 
• 1067612-56-9 5-bromo-N-((1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-{[2-(trifluoromethyl)phenyl]methyl}ethyl)-2-pyridinecarboxamide 
• 1067612-59-2 1,1-dimethylethyl {(2S)-2-{[(5-bromo-2-pyridinyl)carbonyl]amino}-3-[2-(trifluoromethyl)phenyl]propyl}carbamate 
• 1067612-62-7 C₁₆H₁₅BrF₃N₃O 
• 1067612-65-0 1,1-dimethylethyl {(2S)-2-({[5-(1-methyl-1H-pyrazol-5-yl)-2-pyridinyl]carbonyl}amino)-3-[2-(trifluoromethyl)phenyl]propyl}carbamate 
• 1067613-16-4 N-((1S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-{[2-(trifluoromethyl)phenyl]methyl}ethyl)-3-fluoro-4-(1-methyl-1H-pyrazol-5-yl)benzamide 

Relevant articles and documents

2H-1,2,3-Triazole-Based Dipeptidyl Nitriles: Potent, Selective, and Trypanocidal Rhodesain Inhibitors by Structure-Based Design

Macrocyclic inhibitors of rhodesain (RD), a parasitic cysteine protease and drug target for the treatment of human African trypanosomiasis, have shown low metabolic stability at the macrocyclic ether bridge. A series of acyclic dipeptidyl nitriles was developed using structure-based design (PDB ID: 6EX8). The selectivity against the closely related cysteine protease human cathepsin L (hCatL) was substantially improved, up to 507-fold. In the S2 pocket, 3,4-dichlorophenylalanine residues provided high trypanocidal activities. In the S3 pocket, aromatic residues provided enhanced selectivity against hCatL. RD inhibition (Ki values) and in vitro cell-growth of Trypanosoma brucei rhodesiense (IC50 values) were measured in the nanomolar range. Triazole-based ligands, obtained by a safe, gram-scale flow production of ethyl 1H-1,2,3-triazole-4-carboxylate, showed excellent metabolic stability in human liver microsomes and in vivo half-lives of up to 1.53 h in mice. When orally administered to infected mice, parasitaemia was reduced but without complete removal of the parasites.