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
• Article Data: 4

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

Potassium trimethylsilanolate can be used as a reagent in the:Hydrolysis of nitriles to primary amides.Conversion of esters to carboxylic acids, and dialkyl phosphonates to their monoalkyl phosphonates.Synthesis of E-alkenes, and nitrocefin.It can also be used as a coupling promoter in cross-coupling reaction of aliphatic alkynylsilanols with aryl iodides.

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

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

Downstream Products

• 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 
• 14920-92-4 pentamethyl(phenyl)disiloxane 
• 17201-83-1 1-chloromethylpentamethyldisiloxane 
• 1438-82-0 1,1,1,3,3-pentamethyl-1,3-disiloxane 
• 1825-62-3 ethyl trimethylsilyl ether 
• 378-76-7 Potassium pentafluoropropionate 
• 1448441-91-5 1-allyl-N-(4-fluoro-5-((4-bromo-2-chlorophenyl)amino)benzo[d]oxazol-6-yl)cyclopropane-1-sulfonamide 
• 1448441-59-5 N-(4-fluoro-5-((4-bromo-2-chlorophenyl)amino)benzo[d]oxazol-6-yl)cyclopropanesulfonamide 

Relevant articles and documents

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.

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