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Sigma-Aldrich

Dibromodifluoromethane

≥95.0% (GC)

Synonym(s):

Carbon dibromide difluoride, Difluorodibromomethane

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About This Item

Empirical Formula (Hill Notation):
CBr2F2
CAS Number:
75-61-6
Molecular Weight:
209.82
Beilstein:
1732515
EC Number:
200-885-5
MDL number:
MFCD00000367
UNSPSC Code:
12352100
PubChem Substance ID:
57649084
NACRES:
NA.22

vapor density

7.24 (vs air)

vapor pressure

12.79 psi ( 20 °C)

Assay

≥95.0% (GC)

form

liquid

refractive index

n20/D 1.398 (lit.)
n20/D 1.398

bp

22-23 °C (lit.)

mp

−142-−141 °C (lit.)

density

2.297 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

FC(F)(Br)Br

InChI

1S/CBr2F2/c2-1(3,4)5

InChI key

AZSZCFSOHXEJQE-UHFFFAOYSA-N

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General description

The photolysis products of dibromodifluoromethane were characterized by matrix isolation infrared and UV/Visible spectroscopy. Free radical addition of dibromodifluoromethane with fluoroolefins has been reported. Dibromodifluoromethane reacts with hydrocarbon olefins to yield 1,3-dibromo-1,1-difluoroalkene. Sulfinatodehalogenation reagent promoted addition reaction of difluorodibromomethane with alkenes, alkynes and cyclic enol ethers has been described.

Application

  • Synthesis of 3‑Fluoropyrazoles via Radical-Polar Crossover Photoinduced Cyclization: This study highlights the use of dibromodifluoromethane (CF2Br2) for the synthesis of valuable difluorinated and monofluorinated compounds through a novel photoinduced cyclization process (MA Reed, ND Patil, Synfacts, 2023).

Other Notes

Reagent for the Wittig olefination of carbonyl compounds to difluoromethylene and fluoromethylene derivatives; Precursor of difluorocarbene

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335,H420

Hazard Classifications

Eye Irrit. 2 - Ozone 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Free Radical Additions Involving Fluorine Compounds. I. The Addition of Dibromodifluoromethane to Hydrocarbon Olefins.
Tarrant P and Lovelace AM.
Journal of the American Chemical Society, 76(13), 3466-3468 (1954)
Free Radical Additions Involving Fluorine Compounds. IV. The Addition of Dibromodifluoromethane to Some Fluoroolefins1.
Tarrant P, et al.
Journal of the American Chemical Society, 77(10), 2783-2787 (1955)
H.P. Fritz et al.
Zeitschrift fur Naturforschung, B: Chemical Sciences, 86, 1375-1375 (1981)
Lisa George et al.
The Journal of chemical physics, 132(8), 084503-084503 (2010-03-03)
The photolysis products of dibromodifluoromethane (CF(2)Br(2)) were characterized by matrix isolation infrared and UV/Visible spectroscopy, supported by ab initio calculations. Photolysis at wavelengths of 240 and 266 nm of CF(2)Br(2):Ar samples (approximately 1:5000) held at approximately 5 K yielded iso-CF(2)Br(2)
S. Hayaski et al.
Chemistry Letters (Jpn), 983-983 (1979)
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