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tert-Butyldimethylsilyl chloride Manufacturer/High quality/Best price/In stock
Cas No: 18162-48-6
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tert-Butyldimethylsilyl chloride
Cas No: 18162-48-6
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Tert-butyl dimethyl chloro silane
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tert-Butylchlorodimethylsilane
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tert-Butyldimethylsilyl chloride
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tert-Butyldimethylsilyl chloride
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18162-48-6 Usage

Purification Methods

Fractionally distil it at atmospheric pressure. [Sommer & Tyler J Am Chem Soc 76 1030 1954, Corey & Venkateswarlu J Am Chem Soc 94 6190 1972, Beilstein 4 IV 4076.]

Uses

Used to protect alcohols during organic synthesis.

Introduction

Triethylchlorosilane is a clear, colourless to yellowish, pungent smelling, caustic and flammable liquid. It can be dissolved in non-protonating solvents without decomposition.
It may be used as silylating agent for dervatization of primary and secondary alcohols etc.. Also it may be used to protect allylic esters as silylketene acetal which is ore stable but less volatile derivates than trimethylchlorosilane.

Chemical Properties

White solid

Definition

ChEBI: A silyl chloride consisting of a central silicon atom covalently bound to one chloro, one tert-butyl and two methyl groups. tert-Butyldimethylsilyl chloride is a derivatisation agent used in gas chromatography/mass spectrometry ap lications.
InChI:InChI=1/C6H15ClSi/c1-6(2,5-7)8(3)4/h8H,5H2,1-4H3

18162-48-6 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Aldrich (473464)  tert-Butylchlorodimethylsilanesolution  50 wt. % in toluene 18162-48-6 473464-100G 1,365.39CNY Detail
Aldrich (473464)  tert-Butylchlorodimethylsilanesolution  50 wt. % in toluene 18162-48-6 473464-50G 854.10CNY Detail
Aldrich (372951)  tert-Butyldimethylsilylchloridesolution  1.0 M in THF 18162-48-6 372951-100ML 1,458.99CNY Detail
Aldrich (384429)  tert-Butyldimethylsilylchloridesolution  1.0 M in methylene chloride 18162-48-6 384429-100ML 1,458.99CNY Detail
Aldrich (190500)  tert-Butyldimethylsilylchloride  reagent grade, 97% 18162-48-6 190500-500G 9,775.35CNY Detail
Aldrich (190500)  tert-Butyldimethylsilylchloride  reagent grade, 97% 18162-48-6 190500-100G 1,955.07CNY Detail
Aldrich (190500)  tert-Butyldimethylsilylchloride  reagent grade, 97% 18162-48-6 190500-25G 691.47CNY Detail
Aldrich (190500)  tert-Butyldimethylsilylchloride  reagent grade, 97% 18162-48-6 190500-5G 345.15CNY Detail
Sigma-Aldrich (06735)  tert-Butyldimethylsilylchloride  for GC derivatization 18162-48-6 06735-10X1G 1,100.97CNY Detail
Sigma-Aldrich (06735)  tert-Butyldimethylsilylchloride  for GC derivatization 18162-48-6 06735-10G 926.64CNY Detail
Alfa Aesar (A13064)  tert-Butyldimethylchlorosilane, 97%    18162-48-6 100g 1257.0CNY Detail
Alfa Aesar (A13064)  tert-Butyldimethylchlorosilane, 97%    18162-48-6 25g 385.0CNY Detail

18162-48-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name tert-butyldimethylsilyl chloride

1.2 Other means of identification

Product number -
Other names tert-Butyldimethylsilyl chloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:18162-48-6 SDS

18162-48-6Synthetic route

tert-butyldimethylsilane
29681-57-0

tert-butyldimethylsilane

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

Conditions
ConditionsYield
palladium diacetate99.8%
tert-butyl(dimethyl)(phenylseleno)silane
72726-46-6

tert-butyl(dimethyl)(phenylseleno)silane

A

diphenyl diselenide
1666-13-3

diphenyl diselenide

B

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

Conditions
ConditionsYield
With chlorine In tetrachloromethaneA 96%
B 93%
phosgene
75-44-5

phosgene

chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

tert-butyldimethylsilanol
18173-64-3

tert-butyldimethylsilanol

1,2-dichloro-ethane
107-06-2

1,2-dichloro-ethane

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

Conditions
ConditionsYield
In N,N-dimethyl-formamide96%
phosgene
75-44-5

phosgene

chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

tert-butyldimethylsilanol
18173-64-3

tert-butyldimethylsilanol

1,2-dichloro-ethane
107-06-2

1,2-dichloro-ethane

N-methyl-N-phenylformamide
93-61-8

N-methyl-N-phenylformamide

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

Conditions
ConditionsYield
92%
tert-butyldimethylsilane
29681-57-0

tert-butyldimethylsilane

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

Conditions
ConditionsYield
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
18159-55-2

tri-t-butylsilane

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

Conditions
ConditionsYield
With hydrogenchloride; palladium on activated charcoal In hexane at 25℃; for 2h;87%
tertiary butyl chloride
507-20-0

tertiary butyl chloride

dimethylsilicon dichloride
75-78-5

dimethylsilicon dichloride

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

Conditions
ConditionsYield
With magnesium In tetrahydrofuran; hexane78%
With copper(l) cyanide; magnesium In tetrahydrofuran for 2h; Heating;74%
di(methyl)tert-butyl(methoxy)silane
66548-21-8

di(methyl)tert-butyl(methoxy)silane

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

Conditions
ConditionsYield
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
594-19-4

tert.-butyl lithium

dimethylsilicon dichloride
75-78-5

dimethylsilicon dichloride

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

Conditions
ConditionsYield
In pentane for 2h; Heating;61%
dimethylsilicon dichloride
75-78-5

dimethylsilicon dichloride

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

Conditions
ConditionsYield
With t-C4H9Li In not given58%
With tert.-butyl lithium In not given58%
bis(trifluoromethyl)germanium chloride
66348-17-2

bis(trifluoromethyl)germanium chloride

1,3-di-tert-butyl-1,1,3,3-tetramethyldisilatellurane
80594-86-1

1,3-di-tert-butyl-1,1,3,3-tetramethyldisilatellurane

A

bistris(trifluoromethyl)germyl telluride
112438-43-4

bistris(trifluoromethyl)germyl telluride

B

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

Conditions
ConditionsYield
Ar atmosphere, heating (80°C, 2 d); protection against light; fractional sublimation; elem. anal.;A 52%
B n/a
tert-butyldimethylsilanol
18173-64-3

tert-butyldimethylsilanol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

Conditions
ConditionsYield
With thionyl chloride In chloroform for 0.5h;39%
With hydrogenchloride In hexane at 0℃; for 2h;98 % Chromat.
tert-butyldimethylfluorosilane
2357-76-8

tert-butyldimethylfluorosilane

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

Conditions
ConditionsYield
With chloro-trimethyl-silane; aluminium trichloride
1-(tert-butyldimethylsilyloxy)-1-isopropoxycyclopropane
96760-01-9

1-(tert-butyldimethylsilyloxy)-1-isopropoxycyclopropane

A

isopropyl chloride
75-29-6

isopropyl chloride

B

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

C

isopropyl 3-(trichlorotitanio)propionate

isopropyl 3-(trichlorotitanio)propionate

D

C9H19Cl3O2SiTi

C9H19Cl3O2SiTi

Conditions
ConditionsYield
With titanium tetrachloride In chloroform-d1 Product distribution; Mechanism;
Aminodichlorphosphan
85909-11-1

Aminodichlorphosphan

A

C6H15ClNPSi

C6H15ClNPSi

B

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

Conditions
ConditionsYield
at 319.84℃; Thermolysis;
2-(trimethylsilyl)propene
18163-07-0

2-(trimethylsilyl)propene

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NH4F*HF, H2SO4
2: ClSiMe3, AlCl3
View Scheme
1H-imidazole
288-32-4

1H-imidazole

7'-chloro-4'-methylfluorescein
389625-48-3

7'-chloro-4'-methylfluorescein

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

Conditions
ConditionsYield
In N,N-dimethyl-formamide
tert-butylmagnesium chloride
677-22-5

tert-butylmagnesium chloride

dimethylsilicon dichloride
75-78-5

dimethylsilicon dichloride

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

1H-imidazole
288-32-4

1H-imidazole

(2R)-4-(3-pyridyl)-1,2-butanediol
192376-55-9

(2R)-4-(3-pyridyl)-1,2-butanediol

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

A

(2R)-2-(tert-butyldimethylsilyloxy)-4-(pyridin-3-yl)-1-(4-toluenesulfonyloxy)butane
192376-56-0

(2R)-2-(tert-butyldimethylsilyloxy)-4-(pyridin-3-yl)-1-(4-toluenesulfonyloxy)butane

B

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

Conditions
ConditionsYield
In pyridine; dichloromethane
tert-butyldimethylsilane
29681-57-0

tert-butyldimethylsilane

copper(I) iodide
7681-65-4

copper(I) iodide

copper(II) chloride
7447-39-4

copper(II) chloride

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

Conditions
ConditionsYield
In tetrahydrofuran
1,2-dimethoxybenzene
91-16-7

1,2-dimethoxybenzene

tert-butyldimethylsilane
29681-57-0

tert-butyldimethylsilane

dimethylsilicon dichloride
75-78-5

dimethylsilicon dichloride

A

dimethylmonochlorosilane
1066-35-9

dimethylmonochlorosilane

B

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

Conditions
ConditionsYield
AlCl3A n/a
B 91% and 92%
1H-imidazole
288-32-4

1H-imidazole

potassium hydrogensulfate
7646-93-7

potassium hydrogensulfate

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

Conditions
ConditionsYield
In N-methyl-acetamide
2,2'-Anhydrouridine
3736-77-4

2,2'-Anhydrouridine

tert-butyldimethylsilyl chloride
18162-48-6

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
55264-11-4

(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
ConditionsYield
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
818-72-4

1-Octyn-3-ol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

3-(tert-butyldimethylsilyloxy)oct-1-yne
60134-93-2

3-(tert-butyldimethylsilyloxy)oct-1-yne

Conditions
ConditionsYield
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
79-14-1

glycolic Acid

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

(tert-butyldimethylsiloxy) acetic acid tert-butyldimethylsilyl ester
67226-76-0

(tert-butyldimethylsiloxy) acetic acid tert-butyldimethylsilyl ester

Conditions
ConditionsYield
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
5390-04-5

pent-1-yn-5-ol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

1-(tert-butyldimethylsilyloxy)-4-pentyne
61362-77-4

1-(tert-butyldimethylsilyloxy)-4-pentyne

Conditions
ConditionsYield
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
14320-38-8

cyclopent-3-enol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

4-tert-butyldimethylsilyloxycyclopentene
68845-72-7

4-tert-butyldimethylsilyloxycyclopentene

Conditions
ConditionsYield
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
18162-48-6

tert-butyldimethylsilyl chloride

benzyl alcohol
100-51-6

benzyl alcohol

(benzyloxy)(tert-butyl)dimethylsilane
53172-91-1

(benzyloxy)(tert-butyl)dimethylsilane

Conditions
ConditionsYield
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
109-99-9

tetrahydrofuran

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

1-{[dimethyl(1,1-dimethylethyl)silyl]oxy}-4-iodobutane
92511-12-1

1-{[dimethyl(1,1-dimethylethyl)silyl]oxy}-4-iodobutane

Conditions
ConditionsYield
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
98-00-0

(2-furyl)methyl alcohol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

tert-butyl(furan-2-ylmethoxy)dimethylsilane
121389-55-7

tert-butyl(furan-2-ylmethoxy)dimethylsilane

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at -78 - 20℃;100%
With 1H-imidazole In N,N-dimethyl-formamide99%
With 1H-imidazole In N,N-dimethyl-formamide at 23℃; for 0.5h;97%
furan-3-methanol
4412-91-3

furan-3-methanol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

tert-butyl (furan-3-ylmethoxy)dimethylsilane
89861-06-3

tert-butyl (furan-3-ylmethoxy)dimethylsilane

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane at 20℃; for 2h;100%
With 1H-imidazole In dichloromethane100%
With N-ethyl-N,N-diisopropylamine In dichloromethane for 1h; Ambient temperature;98%
indole
120-72-9

indole

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

N-tert-butyldimethylsilylindole
40899-73-8

N-tert-butyldimethylsilylindole

Conditions
ConditionsYield
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
586-95-8

pyridine-4-methanol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

4-((tert-butyldimethylsilyloxy)methyl)pyridine
117423-41-3

4-((tert-butyldimethylsilyloxy)methyl)pyridine

Conditions
ConditionsYield
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
67-47-0

5-hydroxymethyl-2-furfuraldehyde

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

5-(((tert-butyldimethylsilyl)oxy)methyl)furan-2-carbaldehyde
155108-06-8

5-(((tert-butyldimethylsilyl)oxy)methyl)furan-2-carbaldehyde

Conditions
ConditionsYield
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
62147-49-3

1,3-dihydroxyacetone dimer

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

1,3-bis-O-(tert-butyldimethylsilyl)-1,3-dihydroxy-2-propanone
127382-65-4

1,3-bis-O-(tert-butyldimethylsilyl)-1,3-dihydroxy-2-propanone

Conditions
ConditionsYield
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
526-55-6

2-(3-indole)-ethanol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

3-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1H-indole
101079-48-5

3-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1H-indole

Conditions
ConditionsYield
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
5631-67-4

7-hydroxychroman-2-one

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

7-((tert-butyldimethylsilyl)oxy)chroman-2-one
82861-23-2

7-((tert-butyldimethylsilyl)oxy)chroman-2-one

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 25℃; for 10h;100%
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;91%
2'-deoxyuridine
951-78-0

2'-deoxyuridine

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

3',5'-O-di(tert-butyldimethylsilyl)-2'-deoxyuridine
64911-18-8

3',5'-O-di(tert-butyldimethylsilyl)-2'-deoxyuridine

Conditions
ConditionsYield
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
59-14-3

5-bromo-2'-deoxyuridine

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

3',5'-di-O-(tert-butyldimethylsilyl)-5-bromo-2'-deoxyuridine
154925-95-8

3',5'-di-O-(tert-butyldimethylsilyl)-5-bromo-2'-deoxyuridine

Conditions
ConditionsYield
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
2408-36-8

lithium cyanide

cyclohexanone
108-94-1

cyclohexanone

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

1-<(tert-butyldimethylsilyl)oxy>-1-cyanocyclohexane
114114-74-8

1-<(tert-butyldimethylsilyl)oxy>-1-cyanocyclohexane

Conditions
ConditionsYield
In tetrahydrofuran for 70h; Ambient temperature;100%
2'-Deoxyguanosine
961-07-9

2'-Deoxyguanosine

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine
51549-35-0

3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine

Conditions
ConditionsYield
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
123-08-0

4-hydroxy-benzaldehyde

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

p-[(tert-butyldimethylsilyl)oxy]benzaldehyde
120743-99-9

p-[(tert-butyldimethylsilyl)oxy]benzaldehyde

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran100%
With dmap; triethylamine In [D3]acetonitrile at 25℃; for 0.2h;99%
With triethylamine In dichloromethane at 20℃; for 2h;98%
salicylaldehyde
90-02-8

salicylaldehyde

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

2-((tert-butyldimethylsilyl)oxy)benzaldehyde
116585-12-7

2-((tert-butyldimethylsilyl)oxy)benzaldehyde

Conditions
ConditionsYield
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
121-33-5

vanillin

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

O-tert-butyldimethylsilylvanillin
69404-94-0

O-tert-butyldimethylsilylvanillin

Conditions
ConditionsYield
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
107-21-1

ethylene glycol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

2-(tert-butyldimethylsilyloxy)ethanol
102229-10-7

2-(tert-butyldimethylsilyloxy)ethanol

Conditions
ConditionsYield
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
621-59-0

isovanillin

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

p-methoxy-m-(tert-butyldimethylsilyloxy)-benzaldehyde
97315-18-9

p-methoxy-m-(tert-butyldimethylsilyloxy)-benzaldehyde

Conditions
ConditionsYield
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
97-64-3, 2676-33-7

ethyl 2-hydroxypropionate

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

(S)-(-)-ethyl 2-(tert-butyldimethylsilyloxy)propanoate
105198-38-7

(S)-(-)-ethyl 2-(tert-butyldimethylsilyloxy)propanoate

Conditions
ConditionsYield
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
821-41-0

5-Hexen-1-ol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

tert-butyl(5-hexenyloxy)dimethylsilane
85807-84-7

tert-butyl(5-hexenyloxy)dimethylsilane

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide100%
With 1H-imidazole In tetrahydrofuran at 20℃;100%
With 1H-imidazole In dichloromethane at 20℃; for 19h;100%
6-Hydroxyhexanoic acid
1191-25-9

6-Hydroxyhexanoic acid

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

6-(tert-butyldimethylsilyloxy)hexanoic acid
77744-44-6

6-(tert-butyldimethylsilyloxy)hexanoic acid

Conditions
ConditionsYield
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
50622-09-8

2,3-O-isopropylidene-L-threitol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

[(4S,5S)-5-[(tert-butyl(dimethyl)silyl)oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methanol
108817-96-5

[(4S,5S)-5-[(tert-butyl(dimethyl)silyl)oxymethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methanol

Conditions
ConditionsYield
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
106-44-5

p-cresol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

tert-Butyl(dimethyl)-(4-methylphenoxy)silane
62790-85-6

tert-Butyl(dimethyl)-(4-methylphenoxy)silane

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide100%
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
371-41-5

4-Fluorophenol

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

4-<(dimethyl-tert-butylsilyl)oxy>fluorobenzene
113984-68-2

4-<(dimethyl-tert-butylsilyl)oxy>fluorobenzene

Conditions
ConditionsYield
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%

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