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SKU

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Availability

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T106616-5g

Available within 4-8 weeks(?)

$9.90

T106616-10g

10g

Available within 4-8 weeks(?)

$13.90

T106616-25g

25g

Available within 4-8 weeks(?)

$20.90

T106616-50g

50g

Available within 4-8 weeks(?)

$39.90

T106616-100g

100g

Available within 4-8 weeks(?)

$75.90

T106616-250g

250g

Available within 4-8 weeks(?)

$180.90

T106616-500g

500g

Available within 4-8 weeks(?)

$325.90

Basic Description

Synonyms	TMSOTf \| CS-B0886 \| Methanesulfonic acid, trifluoro-, trimethylsilyl ester \| AKOS005063796 \| J-525112 \| MFCD00000406 \| trimethylsilyl trifluoromethansulfonate \| trimethylsilyl-trifluoromethansulfonate \| Trimethylsilyl triflate \| trimethylsilyltrifluoromet
Specifications & Purity	≥98%
Storage Temp	Store at 2-8°C,Argon charged
Shipped In	Wet ice
Product Description	Trimethylsilyl trifluoromethanesulfonate is a strong Lewis acid catalyst and efficient silylating agent. Usually used in a Dieckmann-like cyclization of ester-imides and diesters,and also used to prepare difluoroboron triflate etherate a powerful Lewis acid especially in acetonitrile solvent. Allyl reaction of acetal to form high allyl ether； Synthesis of 1, 2-trans glycosides；Alcohol is converted to ester; The aminomethylation reaction between enolsilyl ether and aminomethyl alkyl ether; Glycosylation of (+)-4-demethoxyanthracyclinone

Names and Identifiers

IUPAC Name	trimethylsilyl trifluoromethanesulfonate
INCHI	InChI=1S/C4H9F3O3SSi/c1-12(2,3)10-11(8,9)4(5,6)7/h1-3H3
InChi Key	FTVLMFQEYACZNP-UHFFFAOYSA-N
Canonical SMILES	C[Si](C)(C)OS(=O)(=O)C(F)(F)F
Isomeric SMILES	C[Si](C)(C)OS(=O)(=O)C(F)(F)F
WGK Germany	3
PubChem CID	65367
UN Number	2920
Packing Group	II
Molecular Weight	222.26
Beilstein	1868911
Reaxy-Rn	1868911

Certificates

Certificate of Analysis(COA)

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Find and download the COA for your product by matching the lot number on the packaging.

21 results found

Lot Number	Certificate Type	Date	Item
G2416629	Certificate of Analysis	Jul 08, 2024	T106616
G2416630	Certificate of Analysis	Jul 08, 2024	T106616
G2416631	Certificate of Analysis	Jul 08, 2024	T106616
G2416632	Certificate of Analysis	Jul 08, 2024	T106616
G2416633	Certificate of Analysis	Jul 08, 2024	T106616
K2327461	Certificate of Analysis	Nov 16, 2023	T106616
K2327460	Certificate of Analysis	Nov 16, 2023	T106616
K2327459	Certificate of Analysis	Nov 16, 2023	T106616
K2327458	Certificate of Analysis	Nov 16, 2023	T106616
J2126576	Certificate of Analysis	Aug 16, 2023	T106616
J2126578	Certificate of Analysis	Aug 16, 2023	T106616
G2122296	Certificate of Analysis	Apr 18, 2023	T106616
G2122295	Certificate of Analysis	Apr 18, 2023	T106616
K22301222	Certificate of Analysis	Nov 16, 2022	T106616
K22301223	Certificate of Analysis	Nov 16, 2022	T106616
K22301255	Certificate of Analysis	Nov 16, 2022	T106616
K22301309	Certificate of Analysis	Nov 16, 2022	T106616
K2303221	Certificate of Analysis	Nov 16, 2022	T106616
I2322127	Certificate of Analysis	Nov 16, 2022	T106616
A2111226	Certificate of Analysis	Nov 14, 2022	T106616
A2111227	Certificate of Analysis	Nov 14, 2022	T106616

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Chemical and Physical Properties

Solubility	Miscible with aliphatic, aromatic hydrocarbons, haloalkanes and ethers. Immiscible with water.
Sensitivity	Moisture & Air sensitive.
Refractive Index	1.36-1.362
Flash Point(°F)	77 °F
Flash Point(°C)	25℃
Boil Point(°C)	140°C

Safety and Hazards(GHS)

Pictogram(s)	GHS05, GHS02
Signal	Danger
Hazard Statements	H314:Causes severe skin burns and eye damage H226:Flammable liquid and vapor
Precautionary Statements	P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do - continue rinsing. P280:Wear protective gloves/protective clothing/eye protection/face protection. P370+P378:In case of fire: Use ... to extinguish. P210:Keep away from heat, hot surface, sparks, open flames and other ignition sources. - No smoking. P310:Immediately call a POISON CENTER or doctor/physician. P321:Specific treatment (see ... on this label). P405:Store locked up. P501:Dispose of contents/container to ... P233:Keep container tightly closed. P240:Ground/bond container and receiving equipment. P264:Wash hands [and …] thoroughly after handling. P403+P235:Store in a well-ventilated place. Keep cool. P260:Do not breathe dust/fume/gas/mist/vapors/spray. P303+P361+P353:IF ON SKIN (or hair): Take off Immediately all contaminated clothing. Rinse SKIN with water [or shower]. P241:Use explosion-proof [electrical/ventilating/lighting/.../] equipment. P301+P330+P331:IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P304+P340:IF INHALED: Remove person to fresh air and keep comfortable for breathing. P363:Wash contaminated clothing before reuse. P242:Use only non-sparking tools. P243:Take precautionary measures against static discharge.
WGK Germany	3
Reaxy-Rn	1868911
Class	3(8)
Merck Index	9719
RIDADR	UN 2920 3(8) / PGII

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Citations of This Product

1. Xiaoyan Zhang, Yufei Ren, Juyan Zhang, Xiangkun Wu, Chunhai Yi, Lan Zhang, Suitao Qi. (2022) Synergistic Effect of TMSPi and FEC in Regulating the Electrode/Electrolyte Interfaces in Nickel-Rich Lithium Metal Batteries. ACS Applied Materials & Interfaces, 14 (9): (11517–11527). [PMID:35195414]
2. Jing-Fang Shi, Ping Wu, Xiao-Li Cheng, Xiao-Yi Wei, Zi-Hua Jiang. (2020) Synthesis and Cytotoxic Property of Annonaceous Acetogenin Glycoconjugates. Drug Design Development and Therapy, [PMID:33235438]

References

1. O J Plante,E R Palmacci,R B Andrade,P H Seeberger. (2001-09-27) Oligosaccharide synthesis with glycosyl phosphate and dithiophosphate triesters as glycosylating agents.. Journal of the American Chemical Society, 123 ((39)): (9545-9554). [PMID:11572674]
2. Renate M van Well,Tiina S Kärkkäinen,K P Ravindranathan Kartha,Robert A Field. (2006-05-16) Contrasting reactivity of thioglucoside and selenoglucoside donors towards promoters: implications for glycosylation stereocontrol.. Carbohydrate research, 341 ((10)): (1391-1397). [PMID:16697999]
3. Yuwen Li,Guo Wei,Biao Yu. (2006-09-19) Aryl C-glycosylation of phenols with glycosyl trifluoroacetimidates.. Carbohydrate research, 341 ((16)): (2717-2722). [PMID:16978594]
4. Miriam Romero,Luís Hernández,Leticia Quintero,Fernando Sartillo-Piscil. (2006-11-08) Nucleophilic substitution at the anomeric position of 1,2-O-isopropylidenefuranose derivatives. A novel stereoselective synthesis of cyclic phosphates analogous to cAMP.. Carbohydrate research, 341 ((18)): (2883-2890). [PMID:17087924]
5. Donald Craig,N Paul King,David M Mountford. (2007-02-28) Silyl-modified Bellus-Claisen rearrangement.. Chemical communications (Cambridge, England), ((10)(10)): (1077-1079). [PMID:17325811]
6. Kevin W C Poon,Kimberly M Lovell,Kendra N Dresner,Apurba Datta. (2007-12-14) Trimethylsilyl trifluoromethanesulfonate (TMSOTf) assisted facile deprotection of N,O-acetonides.. The Journal of organic chemistry, 73 ((2)): (752-755). [PMID:18076188]
7. Christopher G Nasveschuk,Tomislav Rovis. (2007-12-20) A diastereoselective ring contraction of 1,3-dioxepins to 2,3,4-trisubstituted and tetrasubstituted tetrahydrofurans.. The Journal of organic chemistry, 73 ((2)): (612-617). [PMID:18088144]
8. Cheng-Chung Wang,Suvarn S Kulkarni,Jinq-Chyi Lee,Shun-Yuan Luo,Shang-Cheng Hung. (2008-01-15) Regioselective one-pot protection of glucose.. Nature protocols, 3 ((1)): (97-113). [PMID:18193026]
9. Firoz A Jaipuri,Beatrice Y M Collet,Nicola L Pohl. (2008-01-19) Synthesis and quantitative evaluation of Glycero-D-manno-heptose binding to concanavalin A by fluorous-tag assistance.. Angewandte Chemie (International ed. in English), 47 ((9)): (1707-1710). [PMID:18203223]
10. C Wade Downey,Miles W Johnson,Kathryn J Tracy. (2008-03-14) One-pot enol silane formation-Mukaiyama aldol-type addition to dimethyl acetals mediated by TMSOTf.. The Journal of organic chemistry, 73 ((8)): (3299-3302). [PMID:18335962]
11. Jean-Louis Brochu,Michael Prakesch,Gary D Enright,Donald M Leek,Prabhat Arya. (2008-04-19) Reagent-based, modular, tandem Michael approach for obtaining different indoline alkaloid-inspired polycyclic architectures.. Journal of combinatorial chemistry, 10 ((3)): (405-420). [PMID:18419163]
12. Ravindra T Dere,Yingxi Wang,Xiangming Zhu. (2008-06-06) A direct and stereospecific approach to the synthesis of alpha-glycosyl thiols.. Organic & biomolecular chemistry, 6 ((12)): (2061-2063). [PMID:18528566]
13. Vishal Kumar Rajput,Balaram Mukhopadhyay. (2008-08-05) Concise synthesis of a pentasaccharide related to the anti-leishmanial triterpenoid saponin isolated from Maesa balansae.. The Journal of organic chemistry, 73 ((17)): (6924-6927). [PMID:18672936]
14. Izabella Jastrzebska,Leszek Siergiejczyk,Aneta M Tomkiel,Zofia Urbańczyk-Lipkowska,Dominik Wójcik,Jacek W Morzycki. (2009-05-26) On reactions of steroidal 23-oxo and 23,24-epoxysapogenins with Lewis acids.. Steroids, 74 ((8)): (675-683). [PMID:19463690]
15. Feng Liu,Chaozhong Li. (2009-06-10) Intramolecular formal [4 + 2] cycloaddition of nitriles with amides triggered by TMSOTf/Et3N: highly efficient construction of pyrrolo[1,2-a]pyrimidin-4(6H)-ones.. The Journal of organic chemistry, 74 ((15)): (5699-5702). [PMID:19505104]
16. Dragana Milic,Tatjana Kop,Janos Csanadi,Zorica Juranic,Zeljko Zizak,Miroslav J Gasic,Bogdan Solaja. (2009-06-23) Estrone derived steroidal diepoxide: biologically active compound and precursor of a stable steroidal A,B-spiro system.. Steroids, 74 ((12)): (890-895). [PMID:19538979]
17. Stevenson Flemer,José S Madalengoitia. (2011-10-29) On-resin synthesis of novel arginine-isostere peptides bearing substituted amidine headgroups.. Journal of peptide science : an official publication of the European Peptide Society, 18 ((1)): (30-36). [PMID:22034042]
18. Sajal Kumar Maity,Nabamita Basu,Rina Ghosh. (2012-05-01) Efficient activation of thioglycosides with N-(p-methylphenylthio)-ε-caprolactam-TMSOTf.. Carbohydrate research, 354 (40-48). [PMID:22542575]
19. Pipas Saha,Priya Ghosh,Sabera Sultana,Anil K Saikia. (2012-10-06) Diastereoselective synthesis of substituted dihydropyrans via an oxonium-ene cyclization reaction.. Organic & biomolecular chemistry, 10 ((43)): (8730-8738). [PMID:23037969]
20. Recep Gök,Pia Bechtloff,Michael Ziegler,Hans-Georg Schmarr,Ulrich Fischer,Peter Winterhalter. (2019-05-16) Synthesis of Deuterium-Labeled 1,1,6-Trimethyl-1,2-dihydronaphthalene (TDN) and Quantitative Determination of TDN and Isomeric Vitispiranes in Riesling Wines by a Stable-Isotope-Dilution Assay.. Journal of agricultural and food chemistry, 67 ((22)): (6414-6422). [PMID:31088051]
21. U Henriksen. (2000-09-22) Facile synthesis of N-(1-alkenyl) derivatives of 2,4-pyrimidinediones.. Nucleosides, nucleotides & nucleic acids, 19 ((7)): (1093-1100). [PMID:10999249]
22. Eddie L Myers,Craig P Butts,Varinder K Aggarwal. (2006-10-24) BF3.OEt2 and TMSOTf: A synergistic combination of Lewis acids.. Chemical communications (Cambridge, England), ((42)): (4434-4436). [PMID:17057868]
23. Thomas R Hoye,Vadims Dvornikovs,Elena Sizova. (2006-11-03) Silylative Dieckmann-like cyclizations of ester-imides (and diesters).. Organic letters, 8 ((23)): (5191-5194). [PMID:17078675]
24. Jianjun Zhang,Cheng-Wei Tom Chang. (2009-01-10) Divergent synthesis of three classes of aryl N-glycosides by solvent control.. The Journal of organic chemistry, 74 ((2)): (685-695). [PMID:19132944]
25. Hannah W Mbatia,Daniel P Kennedy,Shawn C Burdette. (2012-03-13) Understanding the relationship between photolysis efficiency and metal binding using ArgenCast photocages.. Photochemistry and photobiology, 88 ((4)): (844-850). [PMID:22404178]
26. Miyi Yang,Xiaoling Wu,Xuefei Xi,Panjie Zhang,Xiaoling Yang,Runhua Lu,Wenfeng Zhou,Sanbing Zhang,Haixiang Gao,Jianyong Li. (2015-12-18) Using β-cyclodextrin/attapulgite-immobilized ionic liquid as sorbent in dispersive solid-phase microextraction to detect the benzoylurea insecticide contents of honey and tea beverages.. Food chemistry, 197 Pt B (1064-1072). [PMID:26675842]
27. Xiaoyan Zhang, Yufei Ren, Juyan Zhang, Xiangkun Wu, Chunhai Yi, Lan Zhang, Suitao Qi. (2022) Synergistic Effect of TMSPi and FEC in Regulating the Electrode/Electrolyte Interfaces in Nickel-Rich Lithium Metal Batteries. ACS Applied Materials & Interfaces, 14 (9): (11517–11527). [PMID:35195414]
28. Jing-Fang Shi, Ping Wu, Xiao-Li Cheng, Xiao-Yi Wei, Zi-Hua Jiang. (2020) Synthesis and Cytotoxic Property of Annonaceous Acetogenin Glycoconjugates. Drug Design Development and Therapy, [PMID:33235438]

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Trimethylsilyl trifluoromethanesulfonate - 98%, high purity , CAS No.27607-77-8

Basic Description

Names and Identifiers

Certificates

Certificate of Analysis(COA)

Show more⌵

Chemical and Physical Properties

Safety and Hazards(GHS)

Related Documents

Alternative Products

FAQs and Articles

Citations of This Product

References

Solution Calculators

Molarity Calculator

Dilution Calculator

Reconstitution Calculator

SKU	Size	Availability	Price
T106616-5g	5g	Available within 4-8 weeks(?) Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience!	$9.90
T106616-10g	10g	Available within 4-8 weeks(?) Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience!	$13.90
T106616-25g	25g	Available within 4-8 weeks(?) Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience!	$20.90
T106616-50g	50g	Available within 4-8 weeks(?) Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience!	$39.90
T106616-100g	100g	Available within 4-8 weeks(?) Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience!	$75.90
T106616-250g	250g	Available within 4-8 weeks(?) Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience!	$180.90
T106616-500g	500g	Available within 4-8 weeks(?) Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience!	$325.90