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802794

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

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

Signal Word

Danger

Hazard Statements

H300 + H310 + H330,H314

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCS5880
MKCQ9514
MKCQ0571
MKCM8645
MKCG9719

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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.
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

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