diethyl(1,1,2,3,3,3-hexafluoropropyl)amine

• ChemBase ID: 94916
• Molecular Formular: C7H11F6N
• Molecular Mass: 223.1593592
• Monoisotopic Mass: 223.07956868
• SMILES: N(CC)(CC)C(F)(F)C(C(F)(F)F)F
• Canonical SMILES: CCN(C(C(C(F)(F)F)F)(F)F)CC
• InChI: InChI=1S/C7H11F6N/c1-3-14(4-2)7(12,13)5(8)6(9,10)11/h5H,3-4H2,1-2H3
• InChIKey: BNTFCVMJHBNJAR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diethyl(1,1,2,3,3,3-hexafluoropropyl)amine
• IUPAC Traditional name: diethyl(1,1,2,3,3,3-hexafluoropropyl)amine
• Synonyms: Ishikawa's Reagent; N,N-Diethyl-1,1,2,3,3,3-hexafluoropropylamine 97%; N,N-Diethyl-1,1,2,3,3,3-hexafluoropropylamine, 40-50% in diglyme; N,N-Diethyl-1,1,2,3,3,3-hexafluoropropylamine; Ishikawa's Reagent; Ishikawa’s Reagent; N,N-Diethyl-1,1,2,3,3,3-hexafluoropropylamine; 石川试剂; Ishikawa 试剂; N,N-二乙基-1,1,2,3,3,3-六氟丙胺

Database IDs

• CAS Number: 309-88-6
• MDL Number: MFCD00054683
• PubChem SID: 162081570; 24880211
• PubChem CID: 136149

CALCULATED PROPERTIES

• Acid pKa: 15.528426
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.9677773
• LogD (pH = 7.4): 2.9677773
• Log P: 2.9677773
• Molar Refractivity: 39.7709 cm^3
• Polarizability: 14.381502 Å^3
• Polar Surface Area: 3.24 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 56-57 °C(lit.); 56-57°C/58mm; 56-57°C/58mm
• Flash Point: 104 °F; 14°C(57°F); 40 °C
• Density: 1.23; 1.230; 1.230 g/mL at 25 °C(lit.)
• Refractive Index: 1.3500; n20/D 1.3460(lit.)

Safety Information

• Storage Warning: Corrosive
• European Hazard Symbols: Corrosive (C); Flammable (F)
• UN Number: 2920; UN2924
• German water hazard class: 3
• Hazard Class: 3; 8
• Packing Group: 2; II
• Risk Statements: 10-34; 11-34
• Safety Statements: 16-26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H314-H318; H226-H314
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 2920 8/PG 2

Product Information

• Purity: 90+%
• Linear Formula: CF3CHFCF2N(C2H5)2

DETAILS

Apollo Scientific Ltd - PC2567

Active fluorinating agent see: Ishikawa, Bull. Chem.Soc. Jpn., 1979, 52, 3377

Sigma Aldrich - 564990

Application
Demonstrates utility in fluorination.7
Displays the ability to insert a fluoro(trifluoromethyl) methylene moiety in unsaturated alcohols.
Reactant for:
• Friedel-Crafts type arylation of hydrofluorocarbons1
• Microbial hydroxylation of antibiotics2
• Electrochemical fluorination of trialkylamines and tetraalkylammonium salts3
• Fluorination of pyrethroides4Reactant for synthesis of:
• γ-Hydroxy-α-fluoro-α-trifluoromethylcarboxamide5
• Florfenicol and thiamphenicol6
Packaging
25 g in glass bottle
General description
GC analysis includes Et2NCF=CFCF3 (two isomers), both of which are active fluorinating agents.

REFERENCES

• For use in conversion, in ether or THF, of alcohols to alkyl fluorides, see: Bull. Chem. Soc. Jpn., 52, 3377 (1979); J. Fluorine Chem., 31, 135 (1986); 38, 243 (1988). Addition of NaF as a scavenger of the HF liberated in the reaction gives improved results: J. Fluorine Chem., 23, 383 (1983). Carboxylic acids are converted to acyl fluorides: Bull. Chem. Soc. Jpn., 52, 3377 (1979).
• A mixture of N,N-Diethyl-1,1,2,3,3,3-hexafluoropropylamine and N,N-Diethyl-1,2,3,3,3-pentafluoropropenamine, both of which are active fluorinating agents.