Trimethylsilyl iodide (iodotrimethylsilane or TMSI) is an organosilicon compound with the chemical formula (CH3)3SiI. It is a colorless, volatile liquid at room temperature.
Trimethylsilyl iodide is used to introduce the trimethylsilyl group onto alcohols (ROH):
R-OH + TMSI → R-OTMS + HI
This type of reaction may be useful for gas chromatography analysis; the resultant silyl ether is more volatile than the underivatized original materials.[4] However, for the preparation of bulk trimethylsilylated material, trimethylsilyl chloride may be preferred due to its lower cost.
TMSI reacts with alkyl ethers (ROR′), forming silyl ethers (ROSiMe3) and iodoalkanes (RI) that can be hydrolyzed to alcohols (ROH).[5]
Trimethylsilyl iodide is also used for the removing of the Boc protecting group,[2][6][7] especially where other deprotection methods are too harsh for the substrate.[8]
Referencesedit
^ abcdMichael E. Jung, Michael J. Martinelli, George A. Olah, G. K. Surya Prakash, Jinbo Hu (October 15, 2005). "Iodotrimethylsilane". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.ri043.pub2. ISBN978-0471936237. {{cite book}}: |journal= ignored (help)CS1 maint: multiple names: authors list (link)
^ abcOlah, G; Narang, S. C. (1982). "Iodotrimethylsilane—a versatile synthetic reagent". Tetrahedron. 38 (15): 2225. doi:10.1016/0040-4020(82)87002-6.
^Michael E. Jung; Mark A. Lyster (1988). "Cleavage of Methyl Ethers with Iodotrimethylsilane: Cyclohexanol from Cyclohexyl Methyl Ether". Organic Syntheses; Collected Volumes, vol. 6, p. 353.
^"GC/MS Analysis for Morphine and Other Opiates in Urine" (PDF).
^Michael E. Jung; Mark A. Lyster (1977). "Quantitative dealkylation of alkyl ethers via treatment with trimethylsilyl iodide. A new method for ether hydrolysis". J. Org. Chem.42 (23): 3761–3764. doi:10.1021/jo00443a033.
^Michael E. Jung; Mark A. Lyster (1978). "Conversion of alkyl carbamates into amines via treatment with trimethylsilyl iodide". J. Chem. Soc., Chem. Commun. (7): 315–316. doi:10.1039/C39780000315.
^Richard S. Lott; Virander S. Chauhan; Charles H. Stammer (1979). "Trimethylsilyl iodide as a peptide deblocking agent". J. Chem. Soc., Chem. Commun. (11): 495–496. doi:10.1039/C39790000495.
^Zhijian Liu; Nobuyoshi Yasuda; Michael Simeone; Robert A. Reamer (2014). "N-Boc Deprotection and Isolation Method for Water-Soluble Zwitterionic Compounds". J. Org. Chem.79 (23): 11792–11796. doi:10.1021/jo502319z. PMID 25376704.
April 15, 2024
trimethylsilyl, iodide, iodotrimethylsilane, tmsi, organosilicon, compound, with, chemical, formula, 3sii, colorless, volatile, liquid, room, temperature, namespreferred, iupac, name, iodotri, methyl, silaneother, names, iodotrimethylsilane, tmsi, jung, reagen. Trimethylsilyl iodide iodotrimethylsilane or TMSI is an organosilicon compound with the chemical formula CH3 3SiI It is a colorless volatile liquid at room temperature Trimethylsilyl iodide NamesPreferred IUPAC name Iodotri methyl silaneOther names Iodotrimethylsilane TMSI TMS I Jung reagentIdentifiersCAS Number 16029 98 43D model JSmol Interactive imageChemSpider 76879ECHA InfoCard 100 036 503PubChem CID 85247UNII 7A65KRZ6NV YCompTox Dashboard EPA DTXSID4065997InChI InChI 1S C3H9ISi c1 5 2 3 4 h1 3H3Key CSRZQMIRAZTJOY UHFFFAOYSA NInChI 1 C3H9ISi c1 5 2 3 4 h1 3H3Key CSRZQMIRAZTJOY UHFFFAOYABSMILES I Si C C CPropertiesChemical formula C 3H 9I SiMolar mass 200 094 g mol 1Appearance Clear colorless liquid 1 Density 1 406 g mL 1 Boiling point 106 109 C 223 228 F 379 382 K 1 HazardsFlash point 31 C 24 F 242 K 1 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox referencesPreparation editTrimethylsilyl iodide may be prepared by the oxidative cleavage of hexamethyldisilane by iodine 2 or by the cleavage of hexamethyldisiloxane with aluminium triiodide 2 3 TMS TMS I2 2 TMSI TMS CH3 3Si 3 TMS O TMS 2 AlI3 6 TMSI Al2O3Applications editTrimethylsilyl iodide is used to introduce the trimethylsilyl group onto alcohols ROH R OH TMSI R OTMS HIThis type of reaction may be useful for gas chromatography analysis the resultant silyl ether is more volatile than the underivatized original materials 4 However for the preparation of bulk trimethylsilylated material trimethylsilyl chloride may be preferred due to its lower cost TMSI reacts with alkyl ethers ROR forming silyl ethers ROSiMe3 and iodoalkanes RI that can be hydrolyzed to alcohols ROH 5 Trimethylsilyl iodide is also used for the removing of the Boc protecting group 2 6 7 especially where other deprotection methods are too harsh for the substrate 8 References edit a b c d Michael E Jung Michael J Martinelli George A Olah G K Surya Prakash Jinbo Hu October 15 2005 Iodotrimethylsilane Encyclopedia of Reagents for Organic Synthesis doi 10 1002 047084289X ri043 pub2 ISBN 978 0471936237 a href Template Cite book html title Template Cite book cite book a journal ignored help CS1 maint multiple names authors list link a b c Olah G Narang S C 1982 Iodotrimethylsilane a versatile synthetic reagent Tetrahedron 38 15 2225 doi 10 1016 0040 4020 82 87002 6 Michael E Jung Mark A Lyster 1988 Cleavage of Methyl Ethers with Iodotrimethylsilane Cyclohexanol from Cyclohexyl Methyl Ether Organic Syntheses Collected Volumes vol 6 p 353 GC MS Analysis for Morphine and Other Opiates in Urine PDF Michael E Jung Mark A Lyster 1977 Quantitative dealkylation of alkyl ethers via treatment with trimethylsilyl iodide A new method for ether hydrolysis J Org Chem 42 23 3761 3764 doi 10 1021 jo00443a033 Michael E Jung Mark A Lyster 1978 Conversion of alkyl carbamates into amines via treatment with trimethylsilyl iodide J Chem Soc Chem Commun 7 315 316 doi 10 1039 C39780000315 Richard S Lott Virander S Chauhan Charles H Stammer 1979 Trimethylsilyl iodide as a peptide deblocking agent J Chem Soc Chem Commun 11 495 496 doi 10 1039 C39790000495 Zhijian Liu Nobuyoshi Yasuda Michael Simeone Robert A Reamer 2014 N Boc Deprotection and Isolation Method for Water Soluble Zwitterionic Compounds J Org Chem 79 23 11792 11796 doi 10 1021 jo502319z PMID 25376704 Retrieved from https en wikipedia org w index php title Trimethylsilyl iodide amp oldid 1134856762, wikipedia, wiki, book, books, library,
