| Identification | Back Directory | [Name]
TriMethyl(broModifluoroMethyl)silane | [CAS]
115262-01-6 | [Synonyms]
(Bromodifluoromethyl)
Difluorobromomethylsilane
TriMethyl(broModifluoroMethyl)silane
(BroModifluoroMethyl)triMethylsilane
Bromodifluoro(trimethylsilyl)methane
Silane, (bromodifluoromethyl)trimethyl-
(Bromodifluoromethyl)trimethylsilane 98%
Trimethyl(bromodifluoromethyl)silane 97%
(Bromodifluoromethyl)trimethylsilane >
TriMethyl(broModifluoroMethyl)silane ISO 9001：2015 REACH | [EINECS(EC#)]
806-938-4 | [Molecular Formula]
C4H9BrF2Si | [MDL Number]
MFCD18641931 | [MOL File]
115262-01-6.mol | [Molecular Weight]
203.101 |
| Chemical Properties | Back Directory | [Boiling point ]
108°C(lit.) | [density ]
1.306 | [refractive index ]
n/D1.407 | [Fp ]
46℃ | [storage temp. ]
-20°C | [form ]
liquid | [color ]
clear | [InChI]
InChI=1S/C4H9BrF2Si/c1-8(2,3)4(5,6)7/h1-3H3 | [InChIKey]
WDZVWBWAUSUTTO-UHFFFAOYSA-N | [SMILES]
[Si](C(Br)(F)F)(C)(C)C | [CAS DataBase Reference]
115262-01-6 |
| Hazard Information | Back Directory | [Chemical Properties]
Colorless transparent liquid, initial boiling point 108℃, relative density 1.31 g/cm3. | [Uses]
Novel difluorocarbene source for the efficient difluoromethylenation of alkenes/alkynes and difluoromethylation of O-, S-, and N-nucleophiles. | [Application]
- TriMethyl(broModifluoroMethyl)silane commonly can be used as a source for generating difluorocarbene, it is a general reagent with broad synthetic utility.
- Can generate difluorocarbene under neutral/acidic/basic conditions in the presence/absence of water at low/high temperatures.
- Can be used to prepare gem-difluorocyclopropan(e)nes, O-, S-, N-, and P-difluoromethylated compounds
| [Reactions]
(1) Difluoromethylenation of TMSCN.
Ref. J. Org. Chem. 2012, 77, 5850?5855.
(2) Difluoromethylenation of benzyl and alkylzinc halides.
Ref. Org. Lett. 2013, 15, 917 – 919.
(3) Fluorination aminocarbonylation of aldehydes
Ref. Angew. Chem. Int. Ed. 2022, e202115467
| [General Description]
(Bromodifluoromethyl)trimethylsilane (TMSCF2Br) is commonly used as a source to generate dilfluorocarbene. TMSCF3 (Ruppert–Prakash reagent) and BBr3 undergoes fast halogen–exchange reaction to form MSCF2Br. | [Synthesis]
A flask equipped with a reflux condenser was filled with NaBr (10.8 g, 105 mmol), 30% aqueous H2O2 solution (14.2 g, 125 mmol) and water (7
mL). The mixture was cooled in an ice/water bath and concentrated sulfuric acid (6.7 mL, 125 mmol) was added dropw | [References]
[1]Angewandte Chemie International Edition.DOI :10.1002/anie.202283811
[2]The Journal of Organic Chemistry.DOI :10.1021/acs.orglett.2c02899
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