Trimethylsilyl 2-(fluorosulfonyl)difluoroacetate Chemical Properties

Boiling point:

156 °C (lit.)

Density 

1.27 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.367(lit.)

Flash point:

80 °F

storage temp. 

2-8°C, stored under nitrogen, away from moisture

solubility 

Soluble in ether, toluene, and diglyme.

form 

clear liquid

color 

Colorless to Almost colorless

Specific Gravity

1.28

Water Solubility 

Reacts with water.

Hydrolytic Sensitivity

7: reacts slowly with moisture/water

InChI

InChI=1S/C5H9F3O4SSi/c1-14(2,3)12-4(9)5(6,7)13(8,10)11/h1-3H3

InChIKey

XHVSCKNABCCCAC-UHFFFAOYSA-N

SMILES

C(O[Si](C)(C)C)(=O)C(F)(F)S(F)(=O)=O

CAS DataBase Reference

120801-75-4(CAS DataBase Reference)

EPA Substance Registry System

Acetic acid, 2,2-difluoro-2-(fluorosulfonyl)-, trimethylsilyl ester (120801-75-4)

Safety Information

Hazard Codes 

C,F,Xi

Risk Statements 

10-34

Safety Statements 

16-26-27-36/37/39-45

RIDADR 

UN 2920 8/PG 2

WGK Germany 

2

Hazard Note 

Flammable/Corrosive

HazardClass 

8

PackingGroup 

II

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich

Trimethylsilyl 2-(fluorosulfonyl)difluoroacetate Usage And Synthesis

Physical properties

73–74 °C at 35mm Hg.

Uses

Fluoroalkylation agent. Reactant for Preparation of difluorocyclopropenes and Preparation of difluorocarbene reagents.

Uses

• Fluoroalkylation agent

• Preparation of difluorocyclopropenes
• Preparation of difluorocarbene reagents

Uses

Trimethylsilyl Fluorosulfonyldifluoroacetate is a reagent used in Synthesis of gem-Difluorocyclopropanes, Synthesis of gem-Difluorocyclopropenes, etc.

Preparation

Prepared by treatment of FO2SCF2CO2H with (CH3)3SiCl.

reaction suitability

reaction type: C-C Bond Formation

Synthesis

In this embodiment, trimethylsilyl chloride was included in the initial feed to the reactor to reduce the RSUA content in the product RSUTMS. Hexamethyldisiloxane (28.3 g, 0.174 mol) and trimethylchlorosilane (CTMS, 2.8 g, 0.0258 mol) were added to the C oscillation tube. After sealing the reaction tube, it was cooled in dry ice, evacuated and subsequently RSU (33 g, 0.183 mol) was added. The reaction tube was heated at 105°C for 6 hours to a maximum pressure of 67 psig (0.56 MPa) during the reaction. Upon completion of the reaction, the mixture was cooled to room temperature and the yellow-brown liquid product was transferred to a distillation flask. Analysis of the crude product by 1H NMR showed a conversion of about 93% based on the limiting reactant hexamethyldisiloxane.19F NMR analysis of the reaction mixture indicated that the concentration of RSUA relative to RSUTMS was about 8.6 mol%. The low-boiling components (RSU and fluorotrimethylsilane) were first removed by distillation at atmospheric pressure until the tank temperature reached 103 °C. The reaction was carried out at a pressure of 0.5 mmHg (4 mmHg). Subsequent distillation of RSUTMS at a pressure of 34 mmHg (4.5 kPa) yielded 34.6 g (0.138 mol) of product containing about 2 mole % of RSUA. the distillation product had a yield of 84% over a 6 hour reaction time. The lower RSUA content compared to Example 1 without added CTMS demonstrates the effectiveness of adding trimethylmethylsilyl chloride at the beginning of the reaction.

References

[1] Patent: US2007/270602, 2007, A1. Location in patent: Page/Page column 4

Trimethylsilyl 2-(fluorosulfonyl)difluoroacetate(120801-75-4)Related Product Information

• Butyl acetate
• Iodotrimethylsilane
• (Trifluoromethyl)trimethylsilane
• N-(Trimethylsilyl)acetamide
• tert-Butyldimethylsilyl chloride
• Methyltriethoxysilane
• Vinyl acetate
• Tocopheryl acetate
• Sodium acetate
• Dimethylbenzylcarbinyl acetate
• Bromotrimethylsilane
• Potassium Acetate
• Dichlorodimethylsilane
• Ethyl acetate
• Glatiramer acetate
• Methyltrimethoxysilane
• Methyltrichlorosilane
• Trimethylsilyl trifluoromethanesulfonate