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802794

Sigma-Aldrich

DMPU-HF Reagent

Synonyme(s) :

DMPU-HF Complex (HF 65% w/w)

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About This Item

Formule empirique (notation de Hill):
C6H13FN2O
Numéro CAS:
287966-55-6
Poids moléculaire :
148.18
Code UNSPSC :
12352000
ID de substance PubChem :
329768755
Nomenclature NACRES :
NA.22

Forme

liquid

Niveau de qualité

100

Température de stockage

2-8°C

Chaîne SMILES 

F/O=C1N(C)CCCN\1C

InChI

1S/C6H12FN2O/c1-8-4-3-5-9(2)6(8)10-7/h3-5H2,1-2H3

Clé InChI

ZTQIVQDBIIEDTI-UHFFFAOYSA-N

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.

Autres remarques

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

Pictogrammes

Skull and crossbonesCorrosion
GHS06,GHS05

Mention d'avertissement

Danger

Mentions de danger

H300 + H310 + H330,H314

Classification des risques

Acute Tox. 1 Inhalation - Acute Tox. 2 Dermal - Acute Tox. 2 Oral - Skin Corr. 1A

Code de la classe de stockage

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Consulter la Bibliothèque de documents

Shengzong Liang et al.
Journal of fluorine chemistry, 203, 136-139 (2018-02-13)
Bromofluorination reactions were performed by treating of a variety of unsaturated compounds with N-bromosuccinimide (NBS) and DMPU/HF as the fluorinating reagent. The DMPU/HF complex showed to be an efficient fluorinating reagent to convert alkenes into their corresponding bromofluoro compounds. It
Otome E Okoromoba et al.
Organic letters, 17(16), 3975-3977 (2015-08-12)
DMPU/HF (HF content 65 wt %/wt) is an ideal nucleophilic fluorination reagent for the diastereoselective synthesis of substituted 4-fluorotetrahydropyrans and 4-fluoropiperidines via a fluoro-Prins reaction. When compared to classical nucleophilic fluorination reagents like pyridine/HF, DMPU/HF gives both higher yields and
Otome E Okoromoba et al.
Journal of the American Chemical Society, 136(41), 14381-14384 (2014-09-27)
Hydrogen fluoride (HF) and selected nonbasic and weakly coordinating (toward cationic metal) hydrogen-bond acceptors (e.g., DMPU) can form stable complexes through hydrogen bonding. The DMPU/HF complex is a new nucleophilic fluorination reagent that has high acidity and is compatible with

Contenu apparenté

Hammond Group – Professor Product Portal

The research of the Hammond-Xu Group is focused on the understanding of novel interactions between organic and organometallic compounds from the perspective of physical organic chemistry.

Xu Group – Professor Product Portal

The research of the Hammond-Xu Group is focused on the understanding of novel interactions between organic and organometallic compounds from the perspective of physical organic chemistry.

Notre équipe de scientifiques dispose d'une expérience dans tous les secteurs de la recherche, notamment en sciences de la vie, science des matériaux, synthèse chimique, chromatographie, analyse et dans de nombreux autres domaines..

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