Technical Library

Outline
ProductStructureComments
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 and SID3398.0. 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]
ProductStructureComments
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.
ProductStructureComments
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.
ProductStructureComments
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
ProductStructureComments
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.