ChemicalBook CAS DataBase List 81290-20-2

81290-20-2

Name	(Trifluoromethyl)trimethylsilane
CAS	81290-20-2
Molecular Formula	C4H9F3Si
MDL Number	MFCD00145454
Molecular Weight	142.19
MOL File	81290-20-2.mol

Synonyms

RUPPERT'S REAGENT TFMTMS TMS-CF3 (TRIFLUOROMETHYL)TRIMETHYLSILANE (TRIMETHYLSILYL)TRIFLUOROMETHANE TRIMETHYL(TRIFLUOROMETHYL)SILANE TTMS (Trifluoromethyl)-trimethylsilan Ruppert's (Trifluoromethyl)trimethylsilane 0.5M solution in THF TRIMETHYL(TRIFLUOROMETHYL)SILANE, 0.5M S OLUTION IN TETRAHYDROFURAN Trimethyl(trifluoromethyl)silane solution (Trifluoromethyl)trimethylsilane, 99%+ Ruppertreagent Trifluoromethyltrimethylsilane0.5MinTHF Trifluoromethyltrimethylsilane,min.97% (Trifluoromethyl)trimethylsilane 0.5M solution in THF 98% (Trifluoromethyl)trimethylsilane0.5MsolutioninTHF98% (trifluromethyl)trimethylsilane (Trifluoromethyl)trimethylsilane [Trifluoromethylating Reagent]

Chemical Properties

Appearance	clear colorless solution
Boiling point	54-55 °C (lit.)
density	0.962 g/mL at 20 °C(lit.)
vapor pressure	10.98 psi ( 55 °C)
refractive index	n20/D 1.386
Fp	14 °F
storage temp.	2-8°C
solubility	sol THF, ether, CH2Cl2.
form	Liquid
color	Clear colorless
Specific Gravity	0.962
Water Solubility	Soluble in alcohol, THF, ether, dichloromethane, aromatic and aliphatic hydrocarbons. Soluble in water(with white smokes).
Hydrolytic Sensitivity	4: no reaction with water under neutral conditions
Sensitive	Moisture Sensitive
Merck	9683
BRN	4241868
Exposure limits	ACGIH: TWA 50 ppm; STEL 100 ppm (Skin) OSHA: TWA 200 ppm(590 mg/m3) NIOSH: IDLH 2000 ppm; TWA 200 ppm(590 mg/m3); STEL 250 ppm(735 mg/m3)
Stability:	Volatile
InChI	1S/C4H9F3Si/c1-8(2,3)4(5,6)7/h1-3H3
InChIKey	MWKJTNBSKNUMFN-UHFFFAOYSA-N
SMILES	C[Si](C)(C)C(F)(F)F
CAS DataBase Reference	81290-20-2(CAS DataBase Reference)

Safety Data

Symbol(GHS)	GHS02
Signal word	Danger
Hazard statements	H225-H261
Precautionary statements	P210-P223-P231+P232-P233-P240-P241
Hazard Codes	F,Xi,Xn
Risk Statements	R11:Highly Flammable. R36/37:Irritating to eyes and respiratory system . R19:May form explosive peroxides. R36/37/38:Irritating to eyes, respiratory system and skin . R22:Harmful if swallowed. less more
Safety Statements	S16:Keep away from sources of ignition-No smoking . S33:Take precautionary measures against static discharges . S39:Wear eye/face protection . S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S36:Wear suitable protective clothing . S29:Do not empty into drains . less more
RIDADR	UN 1993 3/PG 2
WGK Germany	3
F	10-21
Hazard Note	Flammable
TSCA	No
REACH Registrations	Active
HazardClass	3
PackingGroup	II
HS Code	29319099
Storage Class	4.3 - Hazardous materials which set free flammable gases upon contact with water
Hazard Classifications	Flam. Liq. 2 Water-react 2

Raw materials And Preparation Products

Hazard Information

Chemical Properties

clear colorless solution

Physical properties

bp 54–55 °C; d20 0.963 g cm?3

Uses

Nucleophilic addition of the trifluoromethyl group to aldehydes and ketones.1

Uses

Nucleophilic trifluoromethylating reagent.

Uses

Silicon-based fluorinating reagents for the efficient trifluoromethylation of carbonyls and ethylene diamines. Precursors used for metal-mediated trifluoromethylation of aromatic, heteroaromatic, vinyl substrates, etc.

Preparation

(Trifluoromethyl)trimethylsilane is prepared from trimethylsilyl chloride and bromotrifluoromethane in the presence of a phosphorus(III) reagent that serves as a halogen acceptor.

General Description

Trimethyl(trifluoromethyl)silane (TMSCF₃) is also called as Ruppert-Prakash fluorination reagent. It is extensively used for the synthesis of trifluoromethyl-containing compounds.

reaction suitability

reaction type: C-C Bond Formation

Toxicology

(Trifluoromethyl)trimethylsilane is classified as toxic and requires careful handling and safety protocols to minimize human exposure. Prolonged or repeated exposure can lead to various health problems such as skin, eye, and respiratory irritation.

Synthesis

75-77-4

75-46-7

81290-20-2

160 g of anhydrous toluene and 19.5 g (0.5 mol) of potassium metal were added to a 1000 mL three-necked flask and the apparatus was protected by argon. The temperature was raised to 55 °C, followed by the dropwise addition of a mixture of 104 g (1 mol) styrene and 161 g (1 mol) hexamethyldisilazane over about 30 minutes. The reaction was maintained for 2 hours until the potassium metal was completely dissolved and then cooled to room temperature to obtain a reaction solution. The reaction solution was cooled to -85 °C and maintained for 20 minutes. 81 g (0.75 mol) of trimethylchlorosilane was slowly added dropwise. Subsequently, trifluoromethane was passed into the reaction system and stopped when 35 g (0.5 mol) of trifluoromethane was passed. The reaction mixture was kept at -85°C for 1 hour and then slowly warmed up to room temperature. The reaction mixture was washed twice with water to ensure that all solids were dissolved and left to stratify. The organic layer was separated and distilled to give a final 64 g (88% yield) of trifluoromethyltrimethylsilane.

Purification Methods

Purify it by distilling it from trap to trap in a vacuum of 20mm using a bath at 45o and Dry-ice/Me2CO bath for the trap. The liquid in the trap is then washed with ice cold H2O (3x), the top layer is collected, dried (Na2SO4), and the liquid is decanted and fractionated through a helices-packed column at atmospheric pressure. 1H, 1 3C, 1 9F, and 2 9Si NMR can be used for assessing the purity of fractions. [Ruppert et al. Tetrahedron Lett 25 2195 1984, Krishnamurti et al. J Org Chem 56 984 199, Beilstein 4 IV 3892.]

References

[1] Patent: CN106117258, 2016, A. Location in patent: Paragraph 0024; 0025; 0026; 0027; 0028; 0029-0035
[2] Science, 2012, vol. 338, # 6112, p. 1324 - 1327
[3] Patent: US2014/66640, 2014, A1. Location in patent: Paragraph 0057
[4] Patent: WO2017/223406, 2017, A1. Location in patent: Paragraph 00157; 00159; 00160

Spectrum Detail

Well-known Reagent Company Product Information

Supplier

Aite (Zhejiang) Supply Chain Management Co., Ltd

Telephone15553101207 18615619105

Websitehttp://www.atgyl.cn/index.php

Qi-Chem Co., Ltd.

Telephone0411-88165951 13601035838

Websitehttp://www.qi-chem.com/

Meryer (Shanghai) Chemical Technology Co., Ltd.

Telephone4006356688 18621169109

Websitehttp://www.x-labseek.com/

Shanghai Furui Fine Chemicals Co., Ltd.

Telephone021-36041048 13361903612

Websitehttp://www.shf2chem.com/

TCI (Shanghai) Development Co., Ltd.

Telephone021-67121386

Websitehttps://www.tcichemicals.com/CN/zh/

Yangzhou modier Electronic Materials Co., Ltd

Telephone13918702962 13761402923

Websitehttp://www.modeltemol.com/

Jinan Jiecheng Biotechnology Co., LTD

Telephone 18669572301

Website

Shanghai Zhen Li Biological Technology Co., Ltd

Telephone021-16621358918; 18516310516;16621358918;13045646768

Websitehttps://www.chemicalbook.com/ShowSupplierProductsList30395/0_EN.htm

Shandong Ruihua Fluoride Industry Co., Ltd

Telephone530-6233885-001 05306238006

Websitehttp://www.rhfuye.com/about/id/1.html

Tianjin Zhongxin Chemtech Co., Ltd.

Telephone022-66880623

Websitehttp://www.tjzxchem.com

J & K SCIENTIFIC LTD.

Telephone18210857532 18210857532

Websitehttps://www.jkchemical.com

Alfa Aesar

Telephone400-6106006

Websitehttp://chemicals.thermofisher.cn

ShangHai DEMO Chemical Co.,Ltd

Telephone400-021-7337 2355568890

Websitehttp://www.demochem.com

Beijing HwrkChemical Technology Co., Ltd

Telephone89508211 18501085097

Websitehttp://www.hwrkchemical.com

Energy Chemical

Telephone021-021-58432009 400-005-6266

Websitehttp://www.energy-chemical.com

Beijing Ouhe Technology Co., Ltd

Telephone13552068683 13522913783

Websitehttp://www.ouhetech.cn/

JinYan Chemicals(ShangHai) Co.,Ltd.

Telephone13817811078

Websitehttp://www.jingyan-chemical.com/

Shanghai Sinch Parmaceuticals Tech. Co. Ltd.

Telephone+86-21-54098501

Websitehttp://www.sinch.com.cn/

1of4

Related Products

Send Inquriy