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915807

Sigma-Aldrich

Difluoromethyltriphenylphosphonium bromide

≥95.0%

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About This Item

Empirical Formula (Hill Notation):
C19H16BrF2P
CAS Number:
58310-28-4
Molecular Weight:
393.20

Assay

≥95.0%

form

solid

storage temp.

2-8°C

InChI

1S/C19H16F2P.BrH/c20-19(21)22(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18;/h1-15,19H;1H/q+1;/p-1

InChI key

WNPMJTVOWUTTSY-UHFFFAOYSA-M

Application

When irradiated with visible light, difluoromethyltriphenylphosphonium bromide generates a difluoromethyl radical, which has been shown to react with alkenes, enamides, and thiols to give the difluoromethylated product.

Product can be used with our line of photoreactors: Including Penn PhD (Z744035) & SynLED 2.0 (Z744080)

Other Notes

Visible-Light-Induced Hydrodifluoromethylation of Alkenes with Bromodifluoromethylphosphonium Bromide

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Danger

Hazard Classifications

Acute Tox. 3 Oral - Acute Tox. 4 Dermal - Aquatic Chronic 2 - Eye Dam. 1 - Skin Irrit. 2

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

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Qing-Yu Lin et al.
Angewandte Chemie (International ed. in English), 55(4), 1479-1483 (2015-12-17)
Bromodifluoromethylphosphonium bromide was solely used as the precursor of difluorocarbene. Herein, an unprecedented visible-light-induced hydrodifluoromethylation of alkenes with bromodifluoromethylphosphonium bromide using H2O and THF as hydrogen sources for the synthesis of difluoromethylated alkanes is described. This difluoromethylation is characterized by
Niklas B Heine et al.
Organic letters, 19(15), 4150-4153 (2017-07-21)
A method for facile difluoromethylation of various thiols using (difluoromethyl)triphenylphosphonium bromide under mild reaction conditions is presented. The transformation proceeds in the absence of any transition metal using a bench-stable and readily accessible phosphonium salt. Deuterium labeling experiments and cyclic

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