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HomeProduct name list(Difluoromethyl)trimethylsilane

(Difluoromethyl)trimethylsilane

  • CAS NO.:65864-64-4
  • Empirical Formula: C4H10F2Si
  • Molecular Weight: 124.2
  • MDL number: MFCD19381658
  • EINECS: 804-145-8
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-04-15 18:41:30
(Difluoromethyl)trimethylsilane Structural

What is (Difluoromethyl)trimethylsilane?

Description

A direct nucleophilic difluoromethylation reagent. The nucleophilic activation of the silicon center with Lewis base initiators allows transfer of the difluoromethyl moiety to electrophiles such as aldehydes, ketones, and aldimines. The copper-mediated difluoromethylation of halides using TMSCF2H tolerates amine, ether, amide, ester, aromatic bromide, and protected alcohol functionalities in aryl iodides and occurs in high yield and stereoselectivity with vinyl iodides.

The Uses of (Difluoromethyl)trimethylsilane

(Difluoromethyl)trimethylsilane, can be used for difluoromethylation of carbonyl compounds. Difluromethylated compounds are very useful in materials science and medicinal and agricultural chemistry.

What are the applications of Application

Difluoromethyl)trimethylsilane is a fluorination reagent

Reactions

(1) Direct bromination to prepare TMSCF2Br.
Direct bromination to prepare TMSCF2Br.
(2) Difluoromethylation of aldehydes and ketones.
Difluoromethylation of aldehydes and ketones.
(3) Difluoromethylation of aldimines.
Difluoromethylation of aldimines.
(4) Difluoromethylation of aryl and vinyl iodides.
Difluoromethylation of aryl and vinyl iodides.

References

[1] MIKHAIL D. KOSOBOKOV. Difluoro(trimethylsilyl)acetonitrile: Synthesis and Fluoroalkylation Reactions[J]. The Journal of Organic Chemistry, 2012, 77 13: 5850-5855. DOI:10.1021/jo301094b.
[2] YANCHUAN ZHAO. Efficient and Direct Nucleophilic Difluoromethylation of Carbonyl Compounds and Imines with Me3SiCF2H at Ambient or Low Temperature[J]. Organic Letters, 2011, 13 19: 5342-5345. DOI:10.1021/ol202208b.
[3] PATRICK S. FIER  John F H. Copper-Mediated Difluoromethylation of Aryl and Vinyl Iodides[J]. Journal of the American Chemical Society, 2012, 134 12: 5524-5527. DOI:10.1021/ja301013h.

Properties of (Difluoromethyl)trimethylsilane

Boiling point: 52°C(lit.)
Density  0.877±0.06 g/cm3(Predicted)
refractive index  1.3560-1.3600
Flash point: -17℃
storage temp.  Keep in dark place,Inert atmosphere,2-8°C
form  clear liquid
color  Colorless to Almost colorless
Specific Gravity 0.91
Hydrolytic Sensitivity 4: no reaction with water under neutral conditions
BRN  2423974
CAS DataBase Reference 65864-64-4

Safety information for (Difluoromethyl)trimethylsilane

Signal word Danger
Pictogram(s)
ghs
Flame
Flammables
GHS02
GHS Hazard Statements H225:Flammable liquids
Precautionary Statement Codes P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

Computed Descriptors for (Difluoromethyl)trimethylsilane

InChIKey OOKFLLNDYNWCHK-UHFFFAOYSA-N

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