5,5,5-Trifluoroleucine

HCID 259832CAS 2792-72-5

Substructure search Find similar structures

Basic information

Standard SMILES: CC(CC(N)C(=O)O)C(F)(F)F
InChIKey: XFGVJLGVINCWDP-UHFFFAOYSA-N
Molecular formula: C6H10F3NO2
Average molar mass: 185.14 g/mol
Monoisotopic mass: 185.06636322

Overview

5,5,5-trifluoroleucine is a leucine derivative in which one of its methyl groups is replaced by trifluoromethyl. It is an organofluorine compound, a leucine derivative and a non-proteinogenic alpha-amino acid. It is functionally related to a leucine.

Names & identifiers

Preferred name: 5,5,5-Trifluoroleucine
IUPAC: 2-amino-5,5,5-trifluoro-4-methylpentanoic acid
English name: 5,5,5-Trifluoro-DL-leucine
Molecular formula: C6H10F3NO2
Molecular weight: 185.14

Names & synonyms

2792-72-55,5,5-TrifluoroleucineTrifluoroleucine5',5',5'-TrifluoroleucineDL-5',5',5'-TrifluoroleucineCHEBI:78014DTXSID3013467435',5',5'-Trifluoro-DL-leucineRefChem:100736DTXCID408597565,5,5-Trifluoro-DL-leucine2-amino-5,5,5-trifluoro-4-methylpentanoic acid

Show more names

5,5,5-TRIFLUORO-DL-LEUCINE USP/EP/BP5,5,5-TRIFLUORO-DL-LEUCINE, 97% MIN.2-amino-5,5,5-trifluoro-4-methyl-valeric acid(+/-)2-AMINO-4-(TRIFLUOROMETHYL)PENTANOIC ACID2-azanyl-5,5,5-trifluoro-4-methyl-pentanoic acid

372-22-5Leucine, 5,5,5-trifluoro-MFCD00039528Norvaline, 5,5,5-trifluoro-4-methyl-, DL-DL-Leucine, 5,5,5-trifluoro-Leucine, 5,5,5-trifluoro-, DL-SCHEMBL188081NSC90440

Database identifiers

CAS: 2792-72-5、372-22-5
PubChem CID: 259832
DTXSID: DTXSID301346743
ChEBI: CHEBI:78014
EC Number: 634-772-0、670-536-3
Nikkaji: J1.531.847C

Properties

Computed structural properties

XLogP: -0.9
Topological polar surface area: 63.3 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 6
Rotatable bonds: 3
Heavy atoms: 12
Formal charge: 0
Complexity: 169

Physicochemical properties

Melting point: 273 °C · 273 °C
Boiling point: 217.4 · 217.4±40.0 °C(Predicted)
Density: 1.294 · 1.294±0.06 g/cm3(Predicted)
pka: 2.27 · 2.27±0.21(Predicted)
form: powder
color: White
Major Application: peptide synthesis
InChI: 1S/C6H10F3NO2/c1-3(6(7,8)9)2-4(10)5(11)12/h3-4H,2,10H2,1H3,(H,11,12)
InChIKey: XFGVJLGVINCWDP-UHFFFAOYSA-N
SMILES: CC(CC(N)C(O)=O)C(F)(F)F
CAS DataBase Reference: 2792 · 2792-72-5(CAS DataBase Reference)
UNSPSC Code: 12352209 · 12352209
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
target organs: Respiratory system
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26
WGK Germany: 3 · 3
HS Code: 2922498590 · 2922498590
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 41 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

Hazard information

Hazard Classes and Categories · 2 items

Skin Irrit. 2 (100%)

Acute Tox. 4 (100%)

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
hs_code: 2922498590
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H315-H319-H335
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P264-P271-P280-P302+P352-P305+P351+P338

Chemistry & industry

Applications · 1 item

Uses5,5,5-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.