372-22-5

Basic information

• Product Name: 5,5,5-TRIFLUORO-DL-LEUCINE
• Synonyms: 5,5,5-Trifluoro-DL-leucine 97%;5,5,5-Trifluoro-DL-leucine97%;5',5',5'-trifluoroleucine;(2S)-5,5,5-Trifluoro-2-amino-4-methylpentanoic acid;(2S)-5,5,5-Trifluoroleucine;5,5,5-Trifluoro-L-leucine;4,4,4-Trifluoro-2-(isothioureido-thiophen-3-yl-methyl)-3-oxo-butyricacidethylester
• CAS NO: 372-22-5
• Molecular Formula: C6H10F3NO2
• Molecular Weight: 185.15
• EINECS: -0
• Mol File: 372-22-5.mol
• Article Data: 2

Chemical Properties

• Melting Point: 273-275°C
• Boiling Point: 217.4°C at 760 mmHg
• Flash Point: 85.3°C
• Appearance: /
• Density: 1.294g/cm³
• Vapor Pressure: 0.0507mmHg at 25°C
• Refractive Index: 1.408
• PKA: pK1:2.045(+1);pK2:8.942(0) (25°C)
• BRN: 4664821
• CAS DataBase Reference: 5,5,5-TRIFLUORO-DL-LEUCINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5,5-TRIFLUORO-DL-LEUCINE(372-22-5)
• EPA Substance Registry System: 5,5,5-TRIFLUORO-DL-LEUCINE(372-22-5)

Safety Data

• Hazard Codes: T
• Statements: 22-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 2811
• HazardClass: TOXIC
• PackingGroup: III
• Hazardous Substances Data: 372-22-5(Hazardous Substances Data)

Usage

General Description

5,5,5-TRIFLUORO-DL-LEUCINE is a chemical compound with the molecular formula C6H10F3NO2. It is a derivative of the amino acid leucine, with three fluorine atoms attached to the carbon backbone. 5,5,5-TRIFLUORO-DL-LEUCINE is used as a chiral building block in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals. It has been studied for its potential use in drug design and development, particularly in the production of novel antimicrobial and antifungal agents. Due to its unique structure and properties, 5,5,5-TRIFLUORO-DL-LEUCINE has garnered interest in the scientific and industrial communities for its potential applications in the field of drug discovery and synthesis.

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

• 81328-25-8 2-phenyl-4-<2-(trifluoromethyl)propylidene>-5-oxazolone 
• 122489-87-6 N-benzoyl-5,5,5-trifluoroleucine methyl ester 
• 122489-80-9 methyl (Z)-2-benzamido-4-(trifluoromethyl)-2-pentenoate 
• 122489-87-6 N-benzoyl-5,5,5-trifluoroleucine methyl ester 
• 120097-69-0 (DL)-2-(N-acetylamino)-4-methyl-5,5,5-trifluoropentanoic acid 
• 2792-72-5 2-amino-4-methyl-5,5,5-trifluoropentanoic acid 

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.