tert-butyldimethylsilane
3-Chloro-2-methylpropene
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
palladium diacetate | 99.8% |
tert-butyl(dimethyl)(phenylseleno)silane
A
diphenyl diselenide
B
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
With chlorine In tetrachloromethane | A 96% B 93% |
phosgene
chloro-trimethyl-silane
tert-butyldimethylsilanol
1,2-dichloro-ethane
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide | 96% |
phosgene
chloro-trimethyl-silane
tert-butyldimethylsilanol
1,2-dichloro-ethane
N-methyl-N-phenylformamide
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
92% |
tert-butyldimethylsilane
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
With hexachloroethane; palladium dichloride In tetrahydrofuran at 20℃; for 2h; | 89% |
With tetrabutylammonium perchlorate; copper(l) chloride In 1,2-dimethoxyethane electrochemical reaction; | 83% |
With copper(l) iodide; copper dichloride In tetrahydrofuran; diethyl ether at 20℃; for 60h; | 73% |
tri-t-butylsilane
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
With hydrogenchloride; palladium on activated charcoal In hexane at 25℃; for 2h; | 87% |
tertiary butyl chloride
dimethylsilicon dichloride
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
With magnesium In tetrahydrofuran; hexane | 78% |
With copper(l) cyanide; magnesium In tetrahydrofuran for 2h; Heating; | 74% |
di(methyl)tert-butyl(methoxy)silane
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
With hydrogenchloride In water at 20℃; for 10h; | 78% |
With hydrogenchloride In hexane at 0℃; for 2h; | 71% |
With hydrogenchloride In water at 20℃; for 5 - 10h; Product distribution / selectivity; | 60% |
tert.-butyl lithium
dimethylsilicon dichloride
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
In pentane for 2h; Heating; | 61% |
dimethylsilicon dichloride
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
With t-C4H9Li In not given | 58% |
With tert.-butyl lithium In not given | 58% |
bis(trifluoromethyl)germanium chloride
1,3-di-tert-butyl-1,1,3,3-tetramethyldisilatellurane
A
bistris(trifluoromethyl)germyl telluride
B
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
Ar atmosphere, heating (80°C, 2 d); protection against light; fractional sublimation; elem. anal.; | A 52% B n/a |
tert-butyldimethylsilanol
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
With thionyl chloride In chloroform for 0.5h; | 39% |
With hydrogenchloride In hexane at 0℃; for 2h; | 98 % Chromat. |
tert-butyldimethylfluorosilane
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; aluminium trichloride |
1-(tert-butyldimethylsilyloxy)-1-isopropoxycyclopropane
A
isopropyl chloride
B
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
With titanium tetrachloride In chloroform-d1 Product distribution; Mechanism; |
Conditions | Yield |
---|---|
at 319.84℃; Thermolysis; |
2-(trimethylsilyl)propene
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NH4F*HF, H2SO4 2: ClSiMe3, AlCl3 View Scheme |
1H-imidazole
7'-chloro-4'-methylfluorescein
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide |
tert-butylmagnesium chloride
dimethylsilicon dichloride
tert-butyldimethylsilyl chloride
1H-imidazole
(2R)-4-(3-pyridyl)-1,2-butanediol
p-toluenesulfonyl chloride
A
(2R)-2-(tert-butyldimethylsilyloxy)-4-(pyridin-3-yl)-1-(4-toluenesulfonyloxy)butane
B
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
In pyridine; dichloromethane |
tert-butyldimethylsilane
copper(I) iodide
copper(II) chloride
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
In tetrahydrofuran |
1,2-dimethoxybenzene
tert-butyldimethylsilane
dimethylsilicon dichloride
A
dimethylmonochlorosilane
B
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
AlCl3 | A n/a B 91% and 92% |
1H-imidazole
potassium hydrogensulfate
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
In N-methyl-acetamide |
2,2'-Anhydrouridine
tert-butyldimethylsilyl chloride
(2R,3R,3aS,9aR)-3-((tert-butyldimethylsilyl)oxy)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,3a-dihydro-2H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6(9aH)-one
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 2h; Inert atmosphere; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide for 3h; Ambient temperature; | 92% |
With pyridine; 1H-imidazole Ambient temperature; | 61% |
With 1H-imidazole | |
With 1H-imidazole In N,N-dimethyl-formamide for 1h; |
1-Octyn-3-ol
tert-butyldimethylsilyl chloride
3-(tert-butyldimethylsilyloxy)oct-1-yne
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide for 8h; Ambient temperature; | 100% |
With 1H-imidazole silylation; | 99% |
With 1H-imidazole; dmap In dichloromethane at 0 - 20℃; for 20h; | 99% |
glycolic Acid
tert-butyldimethylsilyl chloride
(tert-butyldimethylsiloxy) acetic acid tert-butyldimethylsilyl ester
Conditions | Yield |
---|---|
With pyridine for 2h; Ambient temperature; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide for 10h; Ambient temperature; | 97% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 16h; | 95% |
pent-1-yn-5-ol
tert-butyldimethylsilyl chloride
1-(tert-butyldimethylsilyloxy)-4-pentyne
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 25℃; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide at 25℃; for 4h; Inert atmosphere; | 100% |
With 1H-imidazole In dichloromethane at 0 - 20℃; for 0.5h; Inert atmosphere; | 100% |
cyclopent-3-enol
tert-butyldimethylsilyl chloride
4-tert-butyldimethylsilyloxycyclopentene
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; | 100% |
With 1H-imidazole In dichloromethane at 0 - 20℃; for 16.5h; | 100% |
With 1H-imidazole In tetrahydrofuran at 0℃; | 95% |
tert-butyldimethylsilyl chloride
benzyl alcohol
(benzyloxy)(tert-butyl)dimethylsilane
Conditions | Yield |
---|---|
With P(MeN(CH3)CH2CH2)3N; triethylamine In acetonitrile at 24℃; for 2.5h; | 100% |
With ferric hydrogen sulphate; triethylamine In acetonitrile at 20℃; for 60h; Inert atmosphere; chemoselective reaction; | 100% |
With 1H-imidazole; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 20℃; for 0.5h; | 99% |
tetrahydrofuran
tert-butyldimethylsilyl chloride
1-{[dimethyl(1,1-dimethylethyl)silyl]oxy}-4-iodobutane
Conditions | Yield |
---|---|
With sodium iodide In acetonitrile at 55℃; for 16h; Inert atmosphere; | 100% |
With sodium iodide In tetrahydrofuran; acetonitrile at 55℃; for 18h; Inert atmosphere; | 100% |
With sodium iodide In acetonitrile at 20℃; Inert atmosphere; Darkness; | 93% |
(2-furyl)methyl alcohol
tert-butyldimethylsilyl chloride
tert-butyl(furan-2-ylmethoxy)dimethylsilane
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at -78 - 20℃; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide | 99% |
With 1H-imidazole In N,N-dimethyl-formamide at 23℃; for 0.5h; | 97% |
furan-3-methanol
tert-butyldimethylsilyl chloride
tert-butyl (furan-3-ylmethoxy)dimethylsilane
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane at 20℃; for 2h; | 100% |
With 1H-imidazole In dichloromethane | 100% |
With N-ethyl-N,N-diisopropylamine In dichloromethane for 1h; Ambient temperature; | 98% |
indole
tert-butyldimethylsilyl chloride
N-tert-butyldimethylsilylindole
Conditions | Yield |
---|---|
Stage #1: indole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Stage #2: tert-butyldimethylsilyl chloride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; | 100% |
Stage #1: indole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Stage #2: tert-butyldimethylsilyl chloride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h; | 100% |
Stage #1: indole With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.75h; Inert atmosphere; Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran; mineral oil at 0 - 20℃; for 12h; Inert atmosphere; | 93% |
pyridine-4-methanol
tert-butyldimethylsilyl chloride
4-((tert-butyldimethylsilyloxy)methyl)pyridine
Conditions | Yield |
---|---|
With 1H-imidazole In DMF (N,N-dimethyl-formamide) for 3.25h; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; | 100% |
Stage #1: tert-butyldimethylsilyl chloride With 1H-imidazole In dichloromethane; N,N-dimethyl-formamide for 0.166667h; Inert atmosphere; Stage #2: pyridine-4-methanol In dichloromethane; N,N-dimethyl-formamide at 20℃; for 13h; Inert atmosphere; | 99% |
5-hydroxymethyl-2-furfuraldehyde
tert-butyldimethylsilyl chloride
5-(((tert-butyldimethylsilyl)oxy)methyl)furan-2-carbaldehyde
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane at 20℃; for 24h; Inert atmosphere; | 100% |
Stage #1: 5-hydroxymethyl-2-furfuraldehyde With 1H-imidazole In dichloromethane at 20℃; for 0.25h; Inert atmosphere; Stage #2: tert-butyldimethylsilyl chloride In dichloromethane at 20℃; Inert atmosphere; Darkness; | 99% |
With potassium carbonate In dichloromethane at 20℃; for 12h; | 99% |
1,3-dihydroxyacetone dimer
tert-butyldimethylsilyl chloride
1,3-bis-O-(tert-butyldimethylsilyl)-1,3-dihydroxy-2-propanone
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane for 18h; | 100% |
With triethylamine In dichloromethane at 20℃; for 12h; | 99% |
With 1H-imidazole In N,N-dimethyl-formamide for 3h; Ambient temperature; | 98% |
2-(3-indole)-ethanol
tert-butyldimethylsilyl chloride
3-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1H-indole
Conditions | Yield |
---|---|
With 1H-imidazole In tetrahydrofuran at 0 - 20℃; for 0.5h; Inert atmosphere; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide for 16h; Ambient temperature; | 99% |
7-hydroxychroman-2-one
tert-butyldimethylsilyl chloride
7-((tert-butyldimethylsilyl)oxy)chroman-2-one
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 25℃; for 10h; | 100% |
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; | 91% |
2'-deoxyuridine
tert-butyldimethylsilyl chloride
3',5'-O-di(tert-butyldimethylsilyl)-2'-deoxyuridine
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 50℃; for 3h; | 100% |
With pyridine; 1H-imidazole at 0 - 20℃; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide Etherification; | 97% |
5-bromo-2'-deoxyuridine
tert-butyldimethylsilyl chloride
3',5'-di-O-(tert-butyldimethylsilyl)-5-bromo-2'-deoxyuridine
Conditions | Yield |
---|---|
With pyridine at 40℃; for 20h; Inert atmosphere; | 100% |
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 20℃; for 12h; | 99% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 60h; | 96% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 1.5h; | 94% |
With TEA In tetrahydrofuran at 75℃; for 40h; | 65% |
lithium cyanide
cyclohexanone
tert-butyldimethylsilyl chloride
1-<(tert-butyldimethylsilyl)oxy>-1-cyanocyclohexane
Conditions | Yield |
---|---|
In tetrahydrofuran for 70h; Ambient temperature; | 100% |
2'-Deoxyguanosine
tert-butyldimethylsilyl chloride
3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide silylation; | 97% |
With 1H-imidazole In N,N-dimethyl-formamide; toluene for 3h; Inert atmosphere; Heating; Large scale; | 97% |
4-hydroxy-benzaldehyde
tert-butyldimethylsilyl chloride
p-[(tert-butyldimethylsilyl)oxy]benzaldehyde
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran | 100% |
With dmap; triethylamine In [D3]acetonitrile at 25℃; for 0.2h; | 99% |
With triethylamine In dichloromethane at 20℃; for 2h; | 98% |
salicylaldehyde
tert-butyldimethylsilyl chloride
2-((tert-butyldimethylsilyl)oxy)benzaldehyde
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 20℃; for 1h; | 100% |
With dmap; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; | 100% |
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 12h; Schlenk technique; Glovebox; | 100% |
vanillin
tert-butyldimethylsilyl chloride
O-tert-butyldimethylsilylvanillin
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane at 20℃; for 2h; | 100% |
With 1H-imidazole; dmap In dichloromethane at 20℃; Inert atmosphere; | 100% |
With 1H-imidazole; dmap In dichloromethane at 20℃; for 2h; | 100% |
ethylene glycol
tert-butyldimethylsilyl chloride
2-(tert-butyldimethylsilyloxy)ethanol
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 0.166667h; Cooling with ice; | 100% |
With dmap; triethylamine In dichloromethane at 0 - 20℃; | 99% |
With pyridine at 20℃; for 2h; Inert atmosphere; | 99% |
isovanillin
tert-butyldimethylsilyl chloride
p-methoxy-m-(tert-butyldimethylsilyloxy)-benzaldehyde
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; | 100% |
With 2-(Dimethylamino)pyridine; triethylamine In dichloromethane at 0 - 20℃; for 12h; | 100% |
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; N,N-dimethyl-formamide Inert atmosphere; | 100% |
ethyl 2-hydroxypropionate
tert-butyldimethylsilyl chloride
(S)-(-)-ethyl 2-(tert-butyldimethylsilyloxy)propanoate
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane a) RT, overnight, b) reflux, 10 h; | 100% |
With 1H-imidazole | |
With 1H-imidazole In dichloromethane Ambient temperature; | |
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 12h; |
5-Hexen-1-ol
tert-butyldimethylsilyl chloride
tert-butyl(5-hexenyloxy)dimethylsilane
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide | 100% |
With 1H-imidazole In tetrahydrofuran at 20℃; | 100% |
With 1H-imidazole In dichloromethane at 20℃; for 19h; | 100% |
6-Hydroxyhexanoic acid
tert-butyldimethylsilyl chloride
6-(tert-butyldimethylsilyloxy)hexanoic acid
Conditions | Yield |
---|---|
Stage #1: 6-Hydroxyhexanoic acid With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: tert-butyldimethylsilyl chloride In N,N-dimethyl-formamide at 20℃; for 0.5h; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide at 25℃; for 0.25h; | 87% |
With 1H-imidazole In N,N-dimethyl-formamide at 50℃; Inert atmosphere; | 86% |
With 1H-imidazole In N,N-dimethyl-formamide at 50℃; | 80% |
With 1H-imidazole In N,N-dimethyl-formamide at 50℃; Inert atmosphere; |
2,3-O-isopropylidene-L-threitol
tert-butyldimethylsilyl chloride
[(4S,5S)-5-[(tert-butyl(dimethyl)silyl)oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methanol
Conditions | Yield |
---|---|
Stage #1: 2,3-O-isopropylidene-L-threitol With sodium hydride In tetrahydrofuran at 0 - 20℃; Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran at 20℃; for 16h; | 100% |
With 1H-imidazole; dmap In dichloromethane at 20℃; for 3h; Inert atmosphere; | 100% |
Stage #1: 2,3-O-isopropylidene-L-threitol With sodium hydride In tetrahydrofuran at 20℃; for 0.75h; Inert atmosphere; Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran at 20℃; for 0.75h; Inert atmosphere; | 98% |
p-cresol
tert-butyldimethylsilyl chloride
tert-Butyl(dimethyl)-(4-methylphenoxy)silane
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide | 100% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 16h; | 99% |
With 1H-imidazole; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 20℃; for 2h; | 97% |
4-Fluorophenol
tert-butyldimethylsilyl chloride
4-<(dimethyl-tert-butylsilyl)oxy>fluorobenzene
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide at 25℃; for 12h; | 98% |
With 1H-imidazole In N,N-dimethyl-formamide at 0℃; for 1h; | 91% |
Reported in EPA TSCA Inventory.
The tert-Butyldimethylsilyl chloride, with the CAS registry number 18162-48-6,is also known as TBSCl; tert-Butylchlorodimethylsilane; t-Butyldimethylsilyl chloride; t-Butyldimethylchlorosilane. It belongs to the product categories of organosilicon compounds;Miscellaneous Reagents.Its EINECS number is 242-042-4. This chemical's molecular formula is C6H15ClSi and molecular weight is 150.72. What's more,Its systematic name is Ttert-Butylchlorodimethylsilane .It is a White solid which is Flammable, Corrosive and Moisture Sensitive.The tert-Butylchlorodimethylsilane (CAS NO.18162-48-6) is used for pharmaceutical intermediates, and is also used in organic synthesis as hydroxyl protectant.
Physical properties about tert-Butyldimethylsilyl chloride are:
(1)ACD/LogP: 2.833; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.83; (4)ACD/LogD (pH 7.4): 2.83; (5)ACD/BCF (pH 5.5): 83.82; (6)ACD/BCF (pH 7.4): 83.82; (7)ACD/KOC (pH 5.5): 828.61; (8)ACD/KOC (pH 7.4): 828.61; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.411; (13)Molar Refractivity: 43.378 cm3; (14)Molar Volume: 174.746 cm3; (15)Surface Tension: 18.7350006103516 dyne/cm; (16)Density: 0.863 g/cm3; (17)Flash Point: 22.778 °C; (18)Enthalpy of Vaporization: 34.789 kJ/mol; (19)Boiling Point: 124.999 °C at 760 mmHg; (20)Vapour Pressure: 15.0319995880127 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES:Cl[Si](C(C)(C)C)(C)C;
(2)Std. InChI:InChI=1S/C6H15ClSi/c1-6(2,3)8(4,5)7/h1-5H3;
(3)Std. InChIKey:BCNZYOJHNLTNEZ-UHFFFAOYSA-N.
The toxicity data of tert-Butyldimethylsilyl chloride are as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LDLo | intraperitoneal | 1gm/kg (1000mg/kg) | IMMUNOLOGICAL INCLUDING ALLERGIC: DECREASED IMMUNE RESPONSE | Personal Communication from G.D. Stoner, Dept. of Community Medicine, School of Medicine, Univ. of California, La Jolla, CA 92037, May 25, 1975Vol. 27MAY1975, |
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