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Sigma-Aldrich

DMPU-HF Reagent

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C6H13FN2O
CAS Number:
287966-55-6
Molecular Weight:
148.18
UNSPSC Code:
12352000
PubChem Substance ID:
329768755
NACRES:
NA.22

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

Related Categories

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

pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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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.
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
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

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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.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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