| Product | Structure | Comments |
|---|---|---|
| SIT8510.0 Trimethylchorosilane, TMCS [75-77-4] |  | Reacts in presence of HCl acceptor.6 Will silylate strong acids with expulsion of HCl.119 High purity grade available, SIT8510.1. Protects hindered alcohols w/ Mg/DMF.120 |
| SIT8430.0 Trimethylbromosilane, TMBS [2857-97-8] |  | More reactive than SIT8510.0. Less reactive, but more photolytically stable than SIT8564.0.121 |
| SIT8564.0 Trimethyliodosilane, TMIS [16029-98-4] |  | Extremely reactive silylating agent.121 Used with HMDS for hindered alcohols.122 Forms enol silyl ethers with ketones and SIT8620.0.123 |
| SIT8620.0 Trimethylsilyltrifluoromethanesulfonate, TMSOTf [27607-77-8] |  | Strong silylating agent for C- or O-silylations.123,124 Reacts w/ nitroalkanes to give N, N-bis (trimethylsiloxy)enamines.125,126 These are useful reagents.127 |
| SIT8585.0 Trimethysilyl cyanide, TMSCN [7677-24-9] |  | Releases toxic HCN upon reaction. Extremely reactive silylating agent for acids and alcohols. Amines and thiols react more slowly than acids and alcohols. Does not react with amides, ureas or carbonates.128 Silylates amino acids.129 *includes liquid dispensing cylinder |
| SIH6110.0 Hexamethyldisilazane, HMDS [999-97-3] |  | Releases ammonia upon reaction. Both trimethylsilyl groups used. Silylations catalyzed by SIT8510.0and other reagents.6 |
| SID3605.0 Dimethylaminotrimethylsilane, TMSDMA [2083-91-2] |  | Similar to SID6110.0. Liberates Me2NH upon reaction. Silylates ureaformaldehyde polycondensates.130 Silylates phosphorous acids.131 |
| SID3398.0 Diethylaminotrimethylsilane, TMSDMEA [996-50-9] |  | Releases diethylamine upon reaction. Moderately strong silylating agent. Selectively silylates equatorial over axial hydroxyls.132 |
| SIB1846.0 Bis(trimethylsilyl)acetamide, BSA [10416-59-8] |  | More reactive than SIH6110.0. Releases neutral acetamide upon reaction. Both silyl groups used. Used for silylation in analytical applications.133 Reactions catalyzed by acid. Forms enol silyl ethers in ionic liquids.134 |
| SIB1876.0 Bis(trimethylsilyl)trifluoroacetamide, BSTFA [25561-30-2] |  | More reactive than BSA (SIB1846.0). Commonly used for analytical purposes. Reacts very well in DMF or acetonitrile.14,133 |
| SIB1878.0 Bis(trimethylsilyl)urea, BSU [18297-63-7] |  | Byproduct is urea. Used for alcohols and acids.135 Used in synthesis of penicillins and cephalosporins.136 |
| SIM6576.0 N-methyl-N-trimethylsilyltrifluoroacetamide, MSTFA [24589-78-4] |  | Silylation reagent similar to SIB1846.0, but with liquid, volatile byproduct. |
| SIT8590.0 Trimethylsilylimidazole, TMSIM [7449-74-3] |  | Powerful silylating agent for alcohols. Does not react with aliphatic amines.6 |
| SIT8572.0 2-trimethylsiloxypent-2-en-4-one [13257-81-3] |  | Reacts with 1°, 2° and 3° alcohols.137 |
| SII6460.0 Isopropenoxytrimethylsilane, IPOTMS [1833-53-0] |  | Byproduct is acetone. Good for alcohols and acids.138 Provides acetonides with diols.115 |
| SIM6496.0 1-methoxy-1-trimethysiloxy-2-methyl-1-propene [31469-15-5] |  | Used for silylation of acids, alcohols, thiols, amides and ketones.139,140 |
| SIM6571.5 Methyl trimethylsilylacetate [2916-76-9] |  | Used for 3° alcohols and enolizable ketones.141,142 |
| SIE4901.6 Ethyl trimethylsilylacetate [4071-88-9] |  | Silylation of ketones, alcohols, acetylenes, thiols under the influence of fluoride ion.143-145d |
| SIA0555.0 Allytrimethylsilane [762-72-1] |  | Neutral propylene byproduct. Acid-catalyzed silylations. Used for acids146 and thiols.147 Employed in the synthesis of N-trimethylsilylpyridinium triflate an active trimethylsilylating agent.148 |
| SIT8588.5 2-(Trimethylsilyl)ethoxymethylchloride, SEM-Cl [76513-69-4] |  | Hydroxyl group protecting unit. Deprotected with fluoride ion.149 Used to protect carboxylic acids.150,151 Protects anomeric center of pyranosides.152 Used for the introduction of hydroxymethyl group.153 |
| SIT8580.0 Trimethylsilyl azide [4648-54-8] |  |
| Product | Structure | Comments |
|---|---|---|
| SIT8250.0 Triethylchlorosilane [994-30-9] |  | Stability of ethers intermediate between TMS and TBS ethers.154 Good for 1°, 2°, 3° alcohols. Can be cleaved in presence of TBS, TIPS, and TBDPS ethers.10 |
| SID3603.0 N,N-dimethylaminotriethylsilane [3550-35-4] |  | Very reactive triethylsilyl protecting group. Dimethylamine byproduct produced. |
| SIB1937.0 n-butyldimethyl(dimethylamino) silane [181231-67-4] |  | Reactive aminofunctional organosilane. |
| SIT8335.0 Triethylsilyl-trifluoromethanesulfonate [79271-56-0] |  | More reactive than SIT8250.0. Useful for more hindered alcohols.155 |
| SII6462.0 Isopropyldimethylchlorosilane [3634-56-8] |  | Ethers comparable in stability to those of TES-protected ethers.156 |
| SIB1935.0, SIB1935.2, SIB1935.4, SIB1935.5 tert-butyldimethylchlorosilane [18162-48-6] |  | Excellent for 1° and 2° alcohols. Silylation catalyzed by imidazole. Stable to many reagents.22 Can be selectively cleaved in presence of acetate, THP, and benzyl ethers157 among others.158 |
| SIB1938.0 tert-butyldimethylsilane [29681-57-0] |  | Sterically hindered organosilane capable of dehydrogenative coupling.76 |
| SIB1967.0 tert-butyldimethylsilyltrifluoromethanesulfonate [69739-34-0] |  | More reactive than SIB1935.0.159 Converts acetates to TBS ethers.160 |
| SIB1966.0 N-(tert-butyldimethylsilyl)-N-trifluoroacetamide [77377-52-7] |  | Employed in silylations for analytical purposes.161,162 |
| SIB1964.0 tert-butyldimethylsilylimidazole |  | Reactive sterically hindered orgaosilane. |
| SID4065.0 3,3-dimethylbutyldimethylchlorosilane [56310-20-4] |  | Sterically hindered neohexylchlorosilane protecting group. |
| SID3120.0 Di-tert-butylchlorosilane [56310-18-0] |  | Used in selective silylation of internal alcohols or diols.163 Employed in the o-vinylation of phenols via silylation/direction sequence.164 |
| SIT8384.0 Triisopropylchlorosilane [13154-24-0] |  | TIPS ethers more stable than TBS ethers.24 Protects carboxylic acids.165 Used in synthesis of free-4-hydroxylhexopyranoses.166 |
| SIT8387.0 Triisopropylsilyltrifluoromethanesulfonate [80522-42-5] |  | More reactive than SIT8384.0.167 Used to make Tsoc, (triisopropylsilyloxycarbonyl) protecting groups for amines.168 |
| SIT8384.5 Triisopropyl(dimethylamino)silane [181231-66-3] |  | Reactive sterically hindered organosilane. |
| SIT8385.0 Triisopropylsilane [6485-79-6] |  | Silylates strong acids with loss of hydrogen.167 Silylates 1° alcohols selectively.25 |
| SIA0535.0 Allyltriisopropylsilane [24400-84-8] |  | Reaction w/ triflic acid and then pyridine gives the active triisopropylsilylating agent, triisopropylsilylpyridinium triflate.148 |
| SIT7906.0 Thexyldimethylchlorosilane [67373-56-2] |  | Ethers show stability similar to or greater than the TBS ethers. Used for 1° and 2° amines.29,169 Selective for 1° alcohols.169 |
| SID3226.0 Di-tert-butylisobutylsilyltrifluoromethanesulfonate, BIBS [1314639-86-5] |  | Highly sterically-hindered blocking agent useful for protection of alcohols, amines, acids, enol silyl ethers.37 |
| SID3224.0 Di-tert-butylisobutylsilane, BIBS-H [1314639-86-4] |  | Highly sterically-hindered silane for potential dehydrogenative silylation.37,76 |
| SID3258.0 Di-tert-butylmethylsilane [56310-20-4] |  | Highly sterically-hindered silane for potential dehydrogenative silylation. |
| Product | Structure | Comments |
|---|---|---|
| SIB1968.0 tert-butyldiphenylchlorosilane [58479-61-1] |  | Forms more stable ethers than TBS ethers.31 Used to protect phenols,170 amines,171 carboxylic acids, and amides.172,173 |
| SIP6728.0 Phenyldimethylchlorosilane [768-33-2] |  | Used in analytical procedures.175 |
| SID4586.0 Diphenyltetramethyldisilazane [3449-26-1] |  | Similar to SIP6728.0. Emits ammonia upon reaction. Used for silylation of capillary columns.176 |
| SIP6729.0 Phenyldimethylsilane [766-77-8] |  | Reacts with alcohols in presence of Wilkinson’s catalyst.177 |
| SID4552.0 Diphenylmethylchlorosilane [144-79-6] |  | Stability versus other silyl ethers studied.60 |
| SIT8645.0 Triphenylchlorosilane [76-86-8] |  | Ethers hydrolyze comparably to TMS ethers in base and 4 times slower in acid.178 Can lead to solid products.179 |
| SIA0575.0 Allyltriphenylsilane [18752-21-1] |  | Reaction w/triflic acid and then pyridine gives triphenylsilylpyridinium triflate, an active triphenylsilylating agent.148 |
| SID4552.5 Diphenylmethyl(dimethylamino)-silane [68733-63-1] |  | More reactive than SID4552.0. Liberates dimethylamine upon reaction. |
| SIB1026.4 1,3-bis(4-biphenyl)-1,1,3,3-tetramethyldisilazane |  | Reactivity and stability similar to that of SID4586.0. |
| Product | Structure | Comments |
|---|---|---|
| SIP6716.1 Pentafluorophenyldimethylchlorosilane Flophemesyl chloride [20082-71-7] |  | Ethers detectable at femtogram level by ECD. Forms excellent derivatives for mass spectral analysis.117,118,180,181 |
| SIT8589.2 Trimethylsilylethanol [2916-68-9] |  | Used for protection of acids.182,183 |
| SIC2285.0 Chloromethyldimethylchlorosilane [1719-57-9] |  | Can form cyclic products with appropriate 1,2-difunctional substrates.184 Used in analytical applications for greater ECD detectability.185 |
| SIB1890.0 Bromomethyldimethylchlorosilane [16532-02-8] |  | Has been applied to the synthesis of diols and β-methyl alcohols.186,187 |
| SID3535.0 Diisopropylchlorosilane [2227-29-4] |  | Silylates and reduces β-hydroxy ketones selectively.188 Photochemically removable.189 |
| SIH5840.4 (Heptadecafluoro-1,1,2-2-tetrahydradecyl)-dimethylchlorosilane [74612-30-9] |  | Potential blocking agent for fluorous phase synthesis.190 |
| SIB1815.5 Bis(tridecafluoro-1,1,2,2-tetrahydrooctyldimethylsiloxy)-methylchlorosilane |  | Potential blocking agent for fluorous phase synthesis.190 |
| SIB1837.0 Bis(trimethylsiloxy)dichlorosilane [2750-44-9] |  | Sterically-hindered for the protection of diols. |
| SIC2266.8 7-[3-(Chlorodimethylsilyl)propoxy]-4-methylcoumarin [129119-77-3] |  | Flourescent tag silicon-based protecting group.116 |
| SIC2056.2 (-)-Camphanyldimethylchlorosilane [684284-12-6] |  | Chiral silicon-based protecting group. |
| SID4074.0 (Dimethylchlorosilyl)methyl-7,7-dimethylnorpinane [72269-53-5] |  | Chiral silicon-based blocking agent. |
| SIM6472.7 (-)-Menthyldimethylsilane |  | Chiral silicon-based protecting group via dehydrogenative silylation.76 |
| Product | Structure | Comments |
|---|---|---|
| SID4120.0, SID4120.1 Dimethyldichlorosilane [75-78-5] |  | Reacts with alcohols,191 diols,925 and hydroxy carboxylic acids.193 Employed as a protecting group/template in C-glycoside synthesis.194 |
| SIB1072.0 Bis(dimethylamino)dimethylsilane [3768-58-9] |  | More reactive than SIB4120.0. Reacted with diols,195 diamines,196 and treatment for glass.197 |
| SIB1068.0 Bis(diethylamino)dimethylsilane [4669-59-4] |  | Similar to SIB1072.0. |
| SIH6102.0 Hexamethylcyclotrisilazane [1009-93-4] |  | Silylates diols with loss of ammonia. Similar in reactivity to HMDS.198,199 |
| SID4510.1 Diphenyldichlorosilane [80-10-4] |  | Reacts with alcohols,200 diols,195 2-hydroxybenzoic acids.201 |
| SID3402.0 Diethyldichlorosilane [996-50-9] |  | Similar to, but more stable derivatives than dimethylsilylenes. |
| SID3537.0 Diisopropyldichlorosilane [7751-38-4] |  | Forms tethered silyl ethers from diols.42,202,203 Protects 3’,5’ hydroxyls of nucleosides, but less effectively than SIT7273.0.204 |
| SID3205.0 Di-tert-butyldichlorosilane [18395-90-9] |  | Used to protect 1,2-diols,43 and 1,3- diols.205 Forms 4,6-cyclic ditert- butylsilylenediyl ethers w/glycopyranosides.206 |
| SID3345.0 Di-tert-butylsilylbis(trifluoromethanesulfonate) [85272-31-7] |  | More reactive than SID3205.0.42 Converts 1,3-diols to cyclic protected 1,3-diols.207 Reacts w/1,3-diols in preference to 1,2-diols.208 |
| SID3534.0 Di-isopropylbis(trifluoromethanesulfonyl)silane [85272-30-6] |  | More reactive than SID3345.0. Protects diols.209 |
| SIB1042.0 Bis(dimethylchlorosilyl)ethane [13528-93-3] |  | Protection for 1° amines,210,211 including amino acid esters.212 |
| SIT7273.0 Tetraisopropyldichlorodisiloxane [69304-37-6] |  | Highly useful for protection of 3’,5’- dihydroxynucleosides.46 Protects 1,2-diequatorial diols.213 |
| SIB1084.0 1,2-bis(dimethylsilyl)benzene [17985-72-7] |  | Used to protect anilines,48 amines,188 and amino acids.214 |
| SIB1048.2 1,3-bis(chlorodimethylsilyl)-propane [2295-06-9] |  | Potentially useful silylating agent for diols and related systems. |
| SIT7087.0 1,1,3,3-tetracyclopentyldichlorodisiloxane |  | Used in the protection of 3’,5’-dihydroxynucleosides. |