802794

DMPU-HF Reagent

• Synonym(s): DMPU-HF Complex (HF 65% w/w)
• Empirical Formula (Hill Notation): C₆H₁₃FN₂O
• CAS Number: 287966-55-6
• Molecular Weight: 148.18
• UNSPSC Code: 12352000
• PubChem Substance ID: 329768755
• NACRES: NA.22

Properties

• form: liquid
• Quality Level: 100
• storage temp.: 2-8°C
• SMILES string: F/O=C1N(C)CCCN\1C
• InChI: 1S/C6H12FN2O/c1-8-4-3-5-9(2)6(8)10-7/h3-5H2,1-2H3
• InChI key: ZTQIVQDBIIEDTI-UHFFFAOYSA-N

Description

Application

DMPU-HF Reagent is a nucleophilic fluorination reagent that can be used:       

• To prepare fluoroalkenes and gem-difluoromethlylene from substituted alkynes in the presence of an Au-JohnPhos complex as a catalyst.      
• To synthesize substituted 4-fluorotetrahydropyrans and 4-fluoropiperidines from homoallylic alcohol/amine with aldehyde via fluoro-Prins reaction.       
• In the bromofluorination of alkenes in the presence of N-bromosuccinimide to yield corresponding bromofluoro compounds.

DMPU-HF, like TREAT-HF and Olah′s Reagent, is a convenient way of utilizing Hydrogen Fluoride as a fluorination reagent. However, unlike TREAT-HF and Olah′s Reagent, DMPU-HF is more tolerant of transition metals due to the reduced basicity of DMPU, compared to Triethylamine and Pyridine. Hammond and coworkers display its compatibility in transition-metal catalysis in gold-catalyzed mono- and difluoroination of alkynes.

Other Notes

Designer HF-Based Fluorination Reagent: Highly Regioselective Synthesis of Fluoroalkenes and gem-Difluoromethylene Compounds from Alkynes

Safety Information

• Pictograms: GHS05,GHS06
• Signal Word: Danger
• Hazard Statements: H300 + H310 + H330 - H314
• Precautionary Statements: P280 - P301 + P310 + P330 - P301 + P330 + P331 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 1 Inhalation - Acute Tox. 2 Dermal - Acute Tox. 2 Oral - Skin Corr. 1A
• Storage Class Code: 6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable