5,5,5-TRIFLUORO-DL-LEUCINE

Base Information

• Chemical Name: 5,5,5-TRIFLUORO-DL-LEUCINE
• CAS No.: 2792-72-5
• Deprecated CAS: 110941-57-6,343328-85-8,372-22-5
• Molecular Formula: C6H10F3NO2
• Molecular Weight: 185.146
• Hs Code.: 2922499990
• European Community (EC) Number: 634-772-0,670-536-3
• NSC Number: 90440
• DSSTox Substance ID: DTXSID301346743
• Nikkaji Number: J1.531.847C
• Wikidata: Q27147586
• Mol file: 2792-72-5.mol

Synonyms:DL-Leucine,5,5,5-trifluoro-;Leucine, 5,5,5-trifluoro-, DL- (8CI);5,5,5-Trifluoro-DL-leucine;5,5,5-Trifluoroleucine;5',5',5'-Trifluoroleucine;DL-5,5,5-Trifluoroleucine;DL-5',5',5'-Trifluoroleucine;NSC 90440;Norvaline,5,5,5-trifluoro-4-methyl-, DL-;

Chemical Property of 5,5,5-TRIFLUORO-DL-LEUCINE

Chemical Property:

• Vapor Pressure: 0.0507mmHg at 25°C
• Melting Point: 273 °C
• Refractive Index: 1.408
• Boiling Point: 217.4 °C at 760 mmHg
• PKA: 2.27±0.21(Predicted)
• Flash Point: 85.3 °C
• PSA: 63.32000
• Density: 1.294 g/cm³
• LogP: 1.68710
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 185.06636305
• Heavy Atom Count: 12
• Complexity: 169

Purity/Quality:

99%, ^*data from raw suppliers

5,5,5-Trifluoro-DL-leucine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(CC(C(=O)O)N)C(F)(F)F
• Uses: 5,5,5-Trifluoro-DL-leucine (CAS# 2792-72-5) can be used to inhibit tumor cell invasion, as well as for bacterial infections. It can also be used to stabilize variants of bacterial glucose-binding proteins to use as biosensors to monitor blood glucose levels.

Technology Process of 5,5,5-TRIFLUORO-DL-LEUCINE

There total 10 articles about 5,5,5-TRIFLUORO-DL-LEUCINE 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: 94.0%

(DL)-2-(N-acetylamino)-4-methyl-5,5,5-trifluoropentanoic acid (120097-69-0) → (R)-2-Amino-5,5,5-trifluoro-4-methyl-pentanoic acid (372-22-5,2792-72-5,25367-71-9,96037-91-1,96037-92-2,109719-08-6,109719-09-7,122565-32-6,122565-33-7)

Guidance literature:

DOI:10.1016/S0040-4020(01)86044-0

Reference yield:

2-phenyl-4-<2-(trifluoromethyl)propylidene>-5-oxazolone (81328-25-8,81619-00-3) → 5,5,5-trifluoroleucine (372-22-5,2792-72-5,25367-71-9,96037-91-1,96037-92-2,109719-08-6,109719-09-7,122565-32-6,122565-33-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 79 percent / triethylamine / 2 h / Heating

2: H₂ / 5percent Pd/C / methanol / 48 h / Ambient temperature

3: 6N HCl / 24 h / Heating

With hydrogenchloride; hydrogen; triethylamine; palladium on activated charcoal; In methanol;

DOI:10.1021/jo00280a014

Reference yield:

2-phenyl-4-<2-(trifluoromethyl)propylidene>-5-oxazolone (81328-25-8,81619-00-3) → 5,5,5-trifluoroleucine (372-22-5,2792-72-5,25367-71-9,96037-91-1,96037-92-2,109719-08-6,109719-09-7,122565-32-6,122565-33-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 79 percent / triethylamine / 2 h / Heating

2: H₂ / 5percent Pd/C / methanol / 48 h / Ambient temperature

3: 6N HCl / 24 h / Heating

With hydrogenchloride; hydrogen; triethylamine; palladium on activated charcoal; In methanol;

DOI:10.1021/jo00280a014

upstream raw materials:

2-phenyl-4-<2-(trifluoromethyl)propylidene>-5-oxazolone

N-benzoyl-5,5,5-trifluoroleucine methyl ester

methyl (Z)-2-benzamido-4-(trifluoromethyl)-2-pentenoate

N-benzoyl-5,5,5-trifluoroleucine methyl ester

Downstream raw materials:

(R)-2-Amino-5,5,5-trifluoro-4-methyl-pentanoic acid

2-(tert-butoxycarbonylamino)-5,5,5-trifluoro-4-methylpentanoic acid

N-(t-Boc)-(2S,4S),(2S,4R)-5,5,5-trifluoroleucine

Refernces

• 1、 Tsushima,Kawada,Ishihara,Uchida,Shiratori,Higaki,Hirata. "Fluorine-ocntaining amino acids and their derivatives. 7.1 Synthesis and antitumor activity α- and γ-substituted methotrexate analogs". . p. 5375 - 5387. Retrieved 2007/10/02.