2792-72-5

Basic information

• Product Name: 5,5,5-TRIFLUORO-DL-LEUCINE
• Synonyms: (+/-)2-AMINO-4-(TRIFLUOROMETHYL)PENTANOIC ACID;5,5,5-TRIFLUORO-DL-LEUCINE;5,5,5-TRIFLUORO-DL-LEUCINE, 97% MIN.;2-amino-5,5,5-trifluoro-4-methylpentanoic acid;2-amino-5,5,5-trifluoro-4-methyl-valeric acid;2-azanyl-5,5,5-trifluoro-4-methyl-pentanoic acid
• CAS NO: 2792-72-5
• Molecular Formula: C₆H₁₀F₃NO₂
• Molecular Weight: 185.14
• Mol File: 2792-72-5.mol
• Article Data: 2

Chemical Properties

• Melting Point: 273 °C
• Boiling Point: 217.4 °C at 760 mmHg
• Flash Point: 85.3 °C
• Appearance: /
• Density: 1.294 g/cm³
• Vapor Pressure: 0.0507mmHg at 25°C
• Refractive Index: 1.408
• PKA: 2.27±0.21(Predicted)
• CAS DataBase Reference: 5,5,5-TRIFLUORO-DL-LEUCINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5,5-TRIFLUORO-DL-LEUCINE(2792-72-5)
• EPA Substance Registry System: 5,5,5-TRIFLUORO-DL-LEUCINE(2792-72-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 2792-72-5(Hazardous Substances Data)

Usage

Description

5,5,5-TRIFLUORO-DL-LEUCINE, with the CAS number 2792-72-5, is a leucine derivative in which one of its methyl groups is replaced by a trifluoromethyl. This modification gives it unique properties that make it useful in various applications.

Uses

Used in Pharmaceutical Industry:
5,5,5-TRIFLUORO-DL-LEUCINE is used as an inhibitor for tumor cell invasion, helping to prevent the spread of cancer cells within the body. Its application in this area is crucial for the development of treatments aimed at controlling cancer progression.
Used in Medical Industry:
5,5,5-TRIFLUORO-DL-LEUCINE is used to combat bacterial infections, providing an alternative treatment option for various bacterial diseases. Its effectiveness in this regard contributes to the broader fight against antibiotic resistance.
Used in Biotechnology Industry:
5,5,5-TRIFLUORO-DL-LEUCINE is used as a stabilizing agent for variants of bacterial glucose-binding proteins. This application allows for the development of more reliable and sensitive biosensors to monitor blood glucose levels, which is particularly important for managing diabetes and other related conditions.

InChI:InChI=1/C6H10F3NO2/c1-3(6(7,8)9)2-4(10)5(11)12/h3-4H,2,10H2,1H3,(H,11,12)

Upstream product

• 120097-69-0 (DL)-2-(N-acetylamino)-4-methyl-5,5,5-trifluoropentanoic acid 
• 122489-80-9 methyl (Z)-2-benzamido-4-(trifluoromethyl)-2-pentenoate 
• 81328-25-8 2-phenyl-4-<2-(trifluoromethyl)propylidene>-5-oxazolone 
• 122489-87-6 N-benzoyl-5,5,5-trifluoroleucine methyl ester 
• 122489-87-6 N-benzoyl-5,5,5-trifluoroleucine methyl ester 

Downstream Products

• 372-22-5 (R)-2-Amino-5,5,5-trifluoro-4-methyl-pentanoic acid 
• 409333-67-1 2-(tert-butoxycarbonylamino)-5,5,5-trifluoro-4-methylpentanoic acid 
• 409333-67-1 N-(t-Boc)-(2S,4S),(2S,4R)-5,5,5-trifluoroleucine 

Relevant articles and documents

New and Effective Routes to Fluoro Analogues of Aliphatic and Aromatic Amino Acids

New and efficient syntheses of 4,4,4-trifluorovaline (1), 5,5,5-trifluoronorvaline (2), 5,5,5-trifluoroleucine (5), 6,6,6-trifluoronorleucine (6), 4,5,6,7-tetrafluorotryptophan (25), and α-(trifluoromethyl)-β-alanine are studied.Trifluorovaline (1) and trifluoronorvaline (2) are synthesized through amidocarbonylation of 2-(trifluoromethyl)propanal (2-TFMPA) and 3-(trifluoromethyl)propanal (3-TFMPA), respectively, followed by hydrolysis.Trifluoroleucine (5) and trifluoronorleucine (6) are synthesized by using modified Erlenmeyer's azlactone method from 2-TFMPA and 3-TFMPA, respectively. (S)- and (R)-trifluoronorvalines and trifluoronorleucines with high enantiomeric purities (95-100percent ee) are obtained through enzymatic optical resolution of N-acetyltrifluoronorvaline (4) and N-acetyltrifluoronorleucine (17) with the use of a porcine kidney acylase I.Optically active trifluoronorleucine is also obtained via the asymmetric hydrogenation of (Z)-N-benzoyldehydrotrifluoroleucine ethyl ester (10a-Z) with a chiral rhodium catalyst, ClO4, followed by hydrolysis.Unexpectedly high diastereoselectivities (80-87percent ee) are observed in the hydrogenation of (Z)-N-benzoyldehydrotrifluoroleucine ethyl ester (11b) and (Z)-N-benzoyl-4-(pentafluorophenyl)dehydronorvaline (14-Z) over palladium/carbon. 4,5,6,7-Tetrafluorotryptophan (25) and 4,5,6,7-tetrahydrotryptamine (30) are synthesized from 3-formyl-4,5,6,7-tetrafluoroindole (22a) in 51percent (four steps) and 83percent (two steps) overall yields, respectively. 4,5,6,7-Tetrafluoroindoleacetic acid (28) is obtained from 1-acetyl-3-(acetoxymethyl)-4,5,6,7-tetrafluoroindole (23a) in four steps in 65percent overall yield.The 3-formyl- and 1-acetyl-3-(acetoxymethyl)tetrafluoroindoles (22a, 23a) are prepared through selenium dioxide oxidation of 1-acyl-3-methyl-4,5,6,7-tetrafluoroindole (21), which is obtained via the cyclization of a Schiff base of 2-(pentafluorophenyl)propanal (2-PFPPA), in good yields.