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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)

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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)
Addition reactions of dibromodifluoromethane promoted by sulfinatodehalogenation reagents.
Wu F-H, et al.
Journal of Fluorine Chemistry, 80(2), 91-94 (1996)
S. Hayaski et al.
Chemistry Letters (Jpn), 983-983 (1979)
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)
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