2-(TRIMETHYLSILYL)PHENYL TRIFLUOROMETHANESULFONATE Chemical Properties

Boiling point:

70 °C/2 mmHg (lit.)

Density 

1.229 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.456(lit.)

Flash point:

205 °F

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

clear liquid

color 

Colorless to Light yellow

Specific Gravity

1.229

Hydrolytic Sensitivity

7: reacts slowly with moisture/water

InChI

InChI=1S/C10H13F3O3SSi/c1-18(2,3)9-7-5-4-6-8(9)16-17(14,15)10(11,12)13/h4-7H,1-3H3

InChIKey

XBHPFCIWRHJDCP-UHFFFAOYSA-N

SMILES

C(F)(F)(F)S(OC1=CC=CC=C1[Si](C)(C)C)(=O)=O

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-27-36/37/39-45

RIDADR 

UN 3265 8/PG 2

WGK Germany 

3

HazardClass 

8

PackingGroup 

Ⅱ

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich

2-(TRIMETHYLSILYL)PHENYL TRIFLUOROMETHANESULFONATE Usage And Synthesis

Chemical Properties

The chemical properties of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate are mainly derived from the trifluoromethanesulfonyl and trimethylsilyl groups in its structure. As a strongly acidic leaving group, trifluoromethanesulfonyl is easily dissociated in reactions to form stable fluoride ions and trifluoromethanesulfonyl cations. This property makes it exhibit excellent catalytic performance in catalyzing esterification, etherification, condensation and other reactions. Meanwhile, the trimethylsilyl group, as a stable substituent, not only enhances the stability of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate, but also provides the possibility of its wide application in organic synthesis.

Physical properties

bp 70 °C/2 mmHg; d 1.229 g mL?1

Uses

2-(Trimethylsilyl)phenyl trifluoromethanesulfonate may be used to generate benzyne under mild conditions of simple fluoride treatment at room temperature.

Uses

2-(Trimethylsilyl)phenyl Triflate is a useful reagent applied in reactions of Polycyclic Arenes, Heteroatom Arylation,Heteroarenes and Benzannulated Heterocycles, Carbon Arylations, etc.

General Description

2-(Trimethylsilyl)phenyl trifluoromethanesulfonate is an important ortho-benzyne precursor in aryne chemistry.

Synthesis

(1) In a 10 L glass reactor, after argon displacement, 6 L of dichloromethane and 1 kg of 2-(trimethylsilyl)phenol (compound III) were added and mixed thoroughly. (2) The reaction system was cooled to -10 to -15 °C using a dry ice-ethanol bath, and 550 g of pyridine was added slowly and dropwise, and the reaction was exothermic and accompanied by the generation of white fumes. (3) Maintain the internal temperature below -10°C and slowly add 1.8 kg of trifluoromethanesulfonic anhydride dropwise. (4) After the dropwise addition, the reaction was carried out at -5 to 0°C for 5 to 6 hours. (5) After confirming the complete consumption of Compound III by GC monitoring, the reaction system was cooled to below 0°C, and the reaction was quenched by slow dropwise addition of 1.5L of 1N hydrochloric acid solution, taking care to control the exotherm. (6) After quenching and stirring, static layering, the organic phase was washed with 2L of saturated sodium bicarbonate solution and 2L of saturated sodium chloride solution, 100g of anhydrous magnesium sulfate drying, filtration and concentration under reduced pressure, to obtain 1.5kg of brown transparent liquid 2-(trimethylmethylsilyl)phenyl trifluoromethanesulfonate (Compound IV). (7) 1.5kg of crude compound IV was transferred to a 2L distillation flask and distilled under reduced pressure. Under 1.0 kPa vacuum, the bath temperature was 91~105°C, boiling point 49~76°C, the pre-fraction F1 (65 g) was collected; the bath temperature was 108~110°C, boiling point 76~79°C, the main fraction F2 (1.32 kg, GC purity 98.7%) was collected; the distillation was stopped and the residue F3 (85 g).

References

[1] Synthesis, 2010, # 6, p. 911 - 913
[2] Organic and Biomolecular Chemistry, 2016, vol. 14, # 25, p. 6079 - 6087
[3] Patent: CN107325120, 2017, A. Location in patent: Paragraph 0039; 0040; 0041; 0042; 0043; 0044; 0045-0052

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