10519-96-7

Basic information

• Product Name: Potassium trimethylsilanolate
• Synonyms: Trimethylsiloxypotassium;potassium trimethylsilanolate,2M in tetrahydrofuran;(Potassiooxy)trimethylsilane;(Trimethylsilyloxy) potassium;Potassiooxytrimethylsilane;Trimethyl(potassiooxy)silane;Potassium trimethylsilanolate,Trimethylsilanol potassium salt;PotassiuM triMethyl silanolate LR grade
• CAS NO: 10519-96-7
• Molecular Formula: C₃H₉KOSi
• Molecular Weight: 128.29
• EINECS: 234-062-7
• Mol File: 10519-96-7.mol

Chemical Properties

• Melting Point: 135-138 °C(lit.)
• Boiling Point: 75 °C at 760 mmHg
• Flash Point: -14°C (7°F)
• Appearance: /
• Density: 0.81g/cm3
• Storage Temp.: Inert atmosphere,Room Temperature
• BRN: 3560282
• CAS DataBase Reference: Potassium trimethylsilanolate(CAS DataBase Reference)
• NIST Chemistry Reference: Potassium trimethylsilanolate(10519-96-7)
• EPA Substance Registry System: Potassium trimethylsilanolate(10519-96-7)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3263 8/PG 2
• WGK Germany: 3
• F: 3-10-21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 10519-96-7(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Potassium trimethylsilanolate is used as a reagent for the hydrolysis of nitriles to primary amides, conversion of esters to carboxylic acids, and dialkyl phosphonates to their monoalkyl phosphonates. It facilitates these transformations by acting as a strong nucleophile and base, promoting the desired reactions efficiently.
Used in Organic Chemistry:
In the synthesis of E-alkenes, potassium trimethylsilanolate is employed as a reagent to selectively form the desired geometric isomer. Its ability to stabilize the transition state and control the reaction pathway contributes to the formation of the desired product.
Used in Pharmaceutical Chemistry:
Potassium trimethylsilanolate is used in the synthesis of nitrocefin, a compound used as a substrate for the detection and study of β-lactamase enzymes. This enzyme is responsible for the resistance of certain bacteria to β-lactam antibiotics, making the study of nitrocefin and its synthesis relevant in the development of new antimicrobial agents.
Used in Cross-Coupling Reactions:
In the field of organic chemistry, potassium trimethylsilanolate serves as a coupling promoter in the cross-coupling reaction of aliphatic alkynylsilanols with aryl iodides. Its role in this process enhances the reactivity and selectivity of the reaction, leading to the formation of the desired coupled products with improved yields.
Overall, potassium trimethylsilanolate is a versatile reagent with applications in various chemical and pharmaceutical industries, contributing to the synthesis of important compounds and the development of novel drug delivery systems.

Purification Methods

Recrystallise it from H2O and dry it at 100o/1-2mm. [Hyde et al. J Am Chem Soc 75 5615 1953, IR: Tatlock & Rochow J Org Chem 17 1555 1952, Beilstein 4 IV 3992.]

InChI:InChI=1/C3H10OSi.K/c1-5(2,3)4;/h4H,1-3H3;/q;+1

Synthetic route

allyl-trimethyl-silane (762-72-1) → potassium trimethylsilonate (10519-96-7)

Conditions	Yield
With potassium hydroxide In tetrahydrofuran for 3h; Heating;	94%

1,1,1,2,2,2-hexamethyldisilane (1450-14-2) → potassium trimethylsilonate (10519-96-7)

Conditions	Yield
With potassium hydroxide In tetrahydrofuran for 2h; Heating;	89%

Hexamethyldisiloxane (107-46-0) → potassium trimethylsilonate (10519-96-7)

Conditions	Yield
With KNH2 In diethyl ether (CH3)3SiOSi(CH3)3 and KNH2 in etheric suspension at room temp.;;	80%
With potassium amide In diethyl ether (CH3)3SiOSi(CH3)3 and KNH2 in etheric suspension at room temp.;;	80%
With potassium hydroxide In 1,2-dimethoxyethane for 72h; Heating;

Trimethylsilanol (1066-40-6) + potassium (7440-09-7) → potassium trimethylsilonate (10519-96-7) + hydrogen (1333-74-0)

Conditions	Yield
With Na In benzine heating of (CH3)3SiOH and K in benzine;;	A n/a B >99
With Na In diethyl ether heating of (CH3)3SiOH and K in ether;;	A n/a B >99

(CH3)3SiO(1-)*K(1+)*H2O=(CH3)3SiOK*H2O → potassium trimethylsilonate (10519-96-7)

Conditions	Yield
In neat (no solvent) byproducts: H2O; heating at 100°C and 1-2 torr;;

methyl 3-(tert-butoxycarbonyl(isopropyl)amino)-2-(4-chlorophenyl)propanoate (1000985-04-5) + potassium trimethylsilonate (10519-96-7) → potassium 3-(tert-butoxycarbonyl(isopropyl)amino)-2-(4-chlorophenyl)propanoate (1001179-27-6)

Conditions	Yield
In tetrahydrofuran at 20℃;	100%
In tetrahydrofuran at 20℃;	100%

methyl 2-(4-chlorophenyl)-3-((2,2,2-trifluoroethyl)amino)propanoate (1001180-65-9) + potassium trimethylsilonate (10519-96-7) → potassium 2-(4-chlorophenyl)-3-((2,2,2-trifluoroethyl)amino)propanoate (1001180-67-1)

Conditions	Yield
In tetrahydrofuran at 20℃; for 18h;	100%
In tetrahydrofuran at 20℃; for 18h;	100%

methyl tetrahydro-4-[[4-[4-(trifluoromethoxy)phenoxy]-1-piperidinyl]-sulfonyl]-2H-pyran-4-carboxylate (287952-74-3) + potassium trimethylsilonate (10519-96-7) → tetrahydro-4-[[4-[4-(trifluoromethoxy)phenoxy]-1-piperidinyl]-sulfonyl]-2H-pyran-4-carboxylic acid (287952-75-4)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; diethyl ether; water	100%

(Z)-3,4-bis(pl-diethylboryl)-3-hexene (138517-70-1) + potassium trimethylsilonate (10519-96-7) → potassium B,B,B',B'-tetraethyl-μ-(trimethylsilyloxy)-{(Z)-1,2-diethyl-1,2-ethenediyl}diborate tetrahydrofuran

Conditions	Yield
With C4H8O In tetrahydrofuran dropping soln. of cis-1,2-diborylalkene (15.6 mmol) in THF to KOSi(CH3)3 (15.6 mmol) in THF, 30 min.; stirring 2 h at room temp.;; evapn. in vac. (12 Torr); drying (20°C/0.001 Torr); elem. anal.;;	100%

ethyl 6,6a,7,10-tetrahydro-10AH-dibenzo[b,d]pyran-10a-carboxylate + potassium trimethylsilonate (10519-96-7) → Ethyl 6,6a,7,10-tetrahydro-10aH-dibenzo[b,d]pyran-10a-carboxylic acid

Conditions	Yield
In tetrahydrofuran; water	99%

4-carbomethoxyperfluoro-2-methyl-3-oxapentanoyl fluoride (86548-62-1) + potassium trimethylsilonate (10519-96-7) → Dipotassium perfluoro-2,4-dimethyl-3-oxa-1,5-pentanedioate

Conditions	Yield
	98%

methyl 3-(tert-butylamino)-2-(4-chlorophenyl)propanoate (1001271-02-8) + potassium trimethylsilonate (10519-96-7) → potassium 3-(tert-butylamino)-2-(4-chlorophenyl)propanoate (1001271-04-0)

Conditions	Yield
In tetrahydrofuran at 20℃; for 18h;	97%

triethyl borane (97-94-9) + potassium trimethylsilonate (10519-96-7) → potassium triethyl(trimethylsiloxy)borate (143592-67-0)

Conditions	Yield
In toluene dropping soln. of B(C2H5)3 (16.9 mmol) in toluene to suspn. of KOSi(CH3)3 (13.9 mmol) in toluene, 10 min.; stirring 10 min at room temp.; evapn. in vac.;; elem. anal.;;	97%

hexafluorophosphazene (15599-91-4) + potassium trimethylsilonate (10519-96-7) → C3H9F5N3OP3Si

Conditions	Yield
In hexane at 40℃; for 10h; Solvent; Temperature;	96%

7-((1-allylcyclopropyl)sulfonyl)-4-fluoro-5-(4-bromo-2-chlorophenyl)-5H-imidazo[4',5':4,5]benzo[1,2-d][1, 2, 3]thiadiazol-6(7H)-one + potassium trimethylsilonate (10519-96-7) → 1-allyl-N-(4-fluoro-5-((4-bromo-2-chlorophenyl)amino)benzo[d][1,2,3]thiadiazol-6-yl)cyclopropane-1-sulfonamide

Conditions	Yield
In tetrahydrofuran	94.5%

ethyl 6,6a,7,10-tetrahydro-10AH-dibenzo[b,d]thiopyran-10a-carboxylate + potassium trimethylsilonate (10519-96-7) → 6,6a,7,10-Tetrahydro-10AH-dibenzo[b,d]thiopyran-10a-carboxylic acid

Conditions	Yield
In tetrahydrofuran; water; ethyl acetate	94%

ethyl Pentafluoropropionate (426-65-3) + potassium trimethylsilonate (10519-96-7) → Potassium pentafluoropropionate (378-76-7)

Conditions	Yield
	93%

potassium trimethylsilonate (10519-96-7) + 2-(4-bromophenyl)-2-methylpropanenitrile (101184-73-0) → 4-(1-aminocarbonyl-1-methylethyl)-1-bromobenzene (850144-81-9)

Conditions	Yield
Stage #1: potassium trimethylsilonate; 2-(4-bromophenyl)-2-methylpropanenitrile In toluene for 4.5h; Heating / reflux; Stage #2: With water In toluene at 20℃; for 0.416667h;	92%

triethyl phosphate (78-40-0) + potassium trimethylsilonate (10519-96-7) → diethyl phosphoric acid potassium salt (53971-30-5)

Conditions	Yield
In tetrahydrofuran	92%

7-((1-allylcyclopropyl)sulfonyl)-4-fluoro-5-(2-fluoro-4-iodophenyl)-5H-imidazo[4',5':4,5]benzo[1,2-d]thiazol-6(7H)-one + potassium trimethylsilonate (10519-96-7) → 1-allyl-N-(4-fluoro-5-((2-fluoro-4-iodophenyl)amino)benzo[d]thiazol-6-yl)cyclopropane-1-sulfonamide

Conditions	Yield
In tetrahydrofuran	91.3%

2-furoic acid methyl ester (611-13-2) + potassium trimethylsilonate (10519-96-7) → potassium furan-2-carboxylate (20842-02-8)

Conditions	Yield
In tetrahydrofuran	90%

methyl 3-pyridinecarboxylate (93-60-7) + potassium trimethylsilonate (10519-96-7) → potassium nicotinate (16518-17-5)

Conditions	Yield
In tetrahydrofuran	90%

n-butyl pyrophosphate (1474-75-5) + potassium trimethylsilonate (10519-96-7) → potassium dibutylphosphate (25238-98-6)

Conditions	Yield
In tetrahydrofuran	90%

3-(4-morpholino)propan-l-ol + potassium trimethylsilonate (10519-96-7) + N-(3-chloro-4-fluorophenyl)-7-fluoro-6-nitroquinazolin-4-amine (162012-67-1) → (3-chloro-4-fluorophenyl)-[7-(3-morpholino-4-yl-propoxy)-6-nitroquinazolin-4-yl]-amine (267243-64-1)

Conditions	Yield
In P2O5; ice-water; water; dimethyl sulfoxide	89%

choloro(hydrotris(3-tert-butylpyrazolyl)borate)zinc(II) + potassium trimethylsilonate (10519-96-7) → tris{η3-(3-tert-butylpyrazolyl)hydroborato}Zn(OSiMe3)

Conditions	Yield
In benzene Zn complex/C6H6 added dropwise to KOSiMe3 with stirring over 10 min; filtered (Celite), crystd.; elem. anal.;	88%
In benzene shaking (room temp., 15 min); filtering;

7-((1-allylcyclopropyl)sulfonyl)-4-fluoro-5-(4-bromo-2-chlorophenyl)-5H-imidazo[4',5':4,5]benzo[1,2-d]oxazol-6(7H)-one (1448441-90-4) + potassium trimethylsilonate (10519-96-7) → 1-allyl-N-(4-fluoro-5-((4-bromo-2-chlorophenyl)amino)benzo[d]oxazol-6-yl)cyclopropane-1-sulfonamide (1448441-91-5)

Conditions	Yield
In tetrahydrofuran	87.6%

7-((1-allylcyclopropyl)sulfonyl)-5-(4-bromo-2-chlorophenyl)-4-fluoro-5H-imidazo[4',5':4,5]benzo[1,2-d]thiazol-6(7H)-one + potassium trimethylsilonate (10519-96-7) → 1-allyl-N-(5-((4-bromo-2-chlorophenyl)amino)-4-fluorobenzo[d]thiazol-6-yl)cyclopropane-1-sulfonamide

Conditions	Yield
In tetrahydrofuran	87.5%

7-((1-allylcyclopropyl)sulfonyl)-4-fluoro-5-(2-fluoro-4-iodophenyl)-5H-imidazo[4',5':4,5]benzo[1,2-d][1,2,3]thiadiazol-6(7H)-one + potassium trimethylsilonate (10519-96-7) → 1-allyl-N-(4-fluoro-5-((2-fluoro-4-iodophenyl)amino)benzo[d][1, 2, 3]thiadiazol-6-yl)cyclopropane-1-sulfonamide

Conditions	Yield
In tetrahydrofuran	87.3%

phenyl diphenylphosphinate (1706-96-3) + potassium trimethylsilonate (10519-96-7) → diphenylphosphinic acid potassium salt (17223-05-1)

Conditions	Yield
In tetrahydrofuran	87%

potassium trimethylsilonate (10519-96-7) + carbonic acid dimethyl ester (616-38-6) → potassium monomethylcarbonate (14660-45-8)

Conditions	Yield
	87%

9-ethyl-9-borabicyclo[3.3.1]nonane (52102-17-7) + potassium trimethylsilonate (10519-96-7) → potassium (1,5-cyclooctanediyl)ethyl(trimethylsilyloxy)borate (143592-73-8)

Conditions	Yield
In toluene dropping soln. of (C2H5)B(C8H14) (19.5 mmol) in toluene to suspn. of KOSi(CH3)3 (17.7 mmol) in toluene, 5 min.; stirring 3 h at room temp.; filtration;; evapn. in vac. (12, then 0.001 Torr); elem. anal.;;	87%

7-((1-allylcyclopropyl)sulfonyl)-4-fluoro-5-(2-fluoro-4-iodophenyl)-5H-imidazo[4',5':4,5]benzo[1,2-d]oxazol-6(7H)-one (1448441-86-8) + potassium trimethylsilonate (10519-96-7) → 1-allyl-N-(4-fluoro-5-((2-fluoro-4-iodophenyl)amino)benzo[d]oxazol-6-yl)cyclopropane-1-sulfonamide (1448441-87-9)

Conditions	Yield
In tetrahydrofuran	87%

(Z)-3,4-bis(pl-diethylboryl)-3-hexene (138517-70-1) + potassium trimethylsilonate (10519-96-7) → potassium B,B,B',B'-tetraethyl-μ-(trimethylsilyloxy)-{(Z)-1,2-diethyl-1,2-ethenediyl}diborate (143617-55-4)

Conditions	Yield
In toluene dropping soln. of cis-1,2-diborylalkene (15 mmol) in toluene to KOSi(CH3)3 (14 mmol) in toluene, 25 min.; stirring 2 h at 60°C; filtration;; evapn. in vac. (0.1 Torr); dissolving residue in hexane; filtration; washing (hexane); drying in vac.; elem. anal.;;	86%

Upstream product

• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 762-72-1 allyl-trimethyl-silane 
• 107-46-0 Hexamethyldisiloxane 
• 1066-40-6 Trimethylsilanol 
• 7440-09-7 potassium 

Downstream Products

• 17201-87-5 3-(chloromethyl)heptamethyltrisiloxane 
• 36046-65-8 1-phenyl-1-chlorotetramethyldisiloxane 
• 400-53-3 trimethylsilyl trifluoroacetate 
• 685-69-8 ethyl 3-oxo-2,4,4,4-tetrafluoro-butyrate 
• 19917-00-1 Trimethyl-((R)-1-phenyl-allyloxy)-silane 
• 1001180-67-1 potassium 2-(4-chlorophenyl)-3-((2,2,2-trifluoroethyl)amino)propanoate 
• 850144-81-9 4-(1-aminocarbonyl-1-methylethyl)-1-bromobenzene 
• 32454-35-6 2-(4-bromophenyl)-2-methylpropionic acid 
• 267243-64-1 (3-chloro-4-fluorophenyl)-[7-(3-morpholino-4-yl-propoxy)-6-nitroquinazolin-4-yl]-amine 
• 287953-08-6 tetrahydro-4-[[4-[4-(trifluoromethyl)phenoxy]-1-piperidinyl]-sulfonyl]-2H-thiopyran-4-carboxylic acid 
• 287952-13-0 tetrahydro-4-[[4-[4-(trifluoromethyl)phenoxy]-1-piperidinyl]sulfonyl]-2H-pyran-4-carboxylic acid 
• 287952-40-3 tetrahydro-4-[[4-(phenylmethyl)-1-piperidinyl]sulfonyl]-2H-pyran-4-carboxylic acid 
• 287952-72-1 [[4-[4-(trifluoromethoxy)-phenoxy]-1-piperidinyl]sulfonyl]acetic acid 
• 287953-05-3 tetrahydro-4-[[4-[4-(trifluoromethoxy)phenoxy]-1-piperidinyl]-sulfonyl]-2H-thiopyran-4-carboxylic acid 

Relevant articles and documents

Preparation method and application of trimethyl silicon alkoxide

The invention discloses a preparation method and an application of trimethyl silicon alkoxide. The preparation method includes the preparation steps: placing hexamethyldisiloxane and potassium hydroxide into a 10L three-mouth flask; adding 10ml of alcohol preparations; performing heating reflux for 48 hours; dividing water by a water knockout trap; cooling, filtering and drying materials to obtain white solid potassium trimethylsilanolate. Inexpensive trimethyl silicon alkoxide (MM) in industrial production serves as a raw material, and the trimethyl silicon alkoxide and the potassium hydroxide are subjected to heating reflux reaction under various catalysts to prepare potassium trimethylsilanolate with high content. All the catalysts are beneficial to dissolution of the potassium hydroxide, and reaction is facilitated.

Method for Attachment of Silicon-Containing Compounds to a Surface and for Synthesis of Hypervalent Silicon-Compounds

A method for inducing a hypervalent state within silicon-containing compounds by which they can be chemically attached to a surface or substrate and/or organized onto a surface of a substrate. The compounds when attached to or organized on the surface may have different physical and/or chemical properties compared to the starting materials.

Scope and limitations of sodium and potassium trimethylsilanolate as reagents for conversion of esters to carboxylic acids

Sodium or potassium trimethylsilanolate act as versatile and very powerful reagents for conversion of a wide variety of esters to carboxylic acids. The reactions were performed in tetrahydrofuran under mild reaction conditions with high to quantitative yields.

Organosubstituted cis-1,2-Diborylalkenes as Electrophilic Chelates

Triethylborane (1), 9-ethyl-9-borabicyclononane (9-ethyl-9-BBN) (2), and the cis-1,2-diborylalkenes (Z)-R2BC(R')=C(Et)BEt2 react with alkali metal salts MX in toluene to give the borates MX-1, MX-2, and the cyclic cis-1,2-diborates , resp., with BHB- and B(OR)B-bridges (IR, Multi NMR).Reaction of 1, 2, and 3 - 6 with KCN leads to the monoborates KCN-1, KCN-2, and to the acyclic cis-1,2-diborates KCN-3 to KCN-7. - The cis-2-Boryl-1-silylalkenes (E)-Me3SiC(R')=C(Et)BEt2 and KX form the acyclic borates K.The cyclic salts KOtBu-4 and KOSiEt3-4 undergo a B-substituent exchange to the acyclic cis-1,2-diborates K (K-10: R = tBu; K-11: R = OSiEt3).Key Words: cis-1,2-Diborylalkenes, electron acceptors, anion sponge / Diborates, hexaorgano, μ-hydro, μ-alkoxy, alkali metal salts / Borates, hydrotriorgano- / Substituent exchange, diborates