4668-00-2

Basic information

• Product Name: TRIMETHOXYCHLOROSILANEDISC 05/06/04
• Synonyms: Trimethoxychlorosilane;TRIMETHOXYCHLOROSILANEDISC 05/06/04;chlorotrimethoxysilane;Silane,chlorotrimethoxy-;Trimethoxysilyl chloride
• CAS NO: 4668-00-2
• Molecular Formula: C₃H₉ClO₃Si
• Molecular Weight: 156.64026
• Mol File: 4668-00-2.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 75.7°C at 760 mmHg
• Flash Point: 2.2°C
• Appearance: /
• Density: 1.085g/cm³
• Vapor Pressure: 114mmHg at 25°C
• Refractive Index: 1.397
• CAS DataBase Reference: TRIMETHOXYCHLOROSILANEDISC 05/06/04(CAS DataBase Reference)
• NIST Chemistry Reference: TRIMETHOXYCHLOROSILANEDISC 05/06/04(4668-00-2)
• EPA Substance Registry System: TRIMETHOXYCHLOROSILANEDISC 05/06/04(4668-00-2)

Safety Data

• RIDADR: 2985
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 4668-00-2(Hazardous Substances Data)

Usage

General Description

TRIMETHOXYCHLOROSILANEDISC 05/06/04 is a chemical compound used in the manufacturing of silicones and silanes. It is a colorless, flammable liquid that is highly reactive with water. TRIMETHOXYCHLOROSILANEDISC 05/06/04 is commonly used as a coupling agent, adhesion promoter, and surface modifier, particularly in the production of adhesives, sealants, and coatings. It has the ability to bond to both organic and inorganic surfaces, making it useful in a variety of industrial applications. However, it is also highly corrosive and can cause severe skin and eye irritation, as well as respiratory issues if inhaled. Therefore, proper handling and safety precautions are necessary when working with TRIMETHOXYCHLOROSILANEDISC 05/06/04.

InChI:InChI=1/C3H9ClO3Si/c1-5-8(4,6-2)7-3/h1-3H3

Synthetic route

tetramethylorthosilicate (681-84-5) + acetyl chloride (75-36-5) → chlorotrimethoxysilane (4668-00-2) + acetic acid methyl ester (79-20-9)

Conditions	Yield
With aluminium trichloride for 2h; Heating;	A 90% B n/a

tetramethylorthosilicate (681-84-5) + Phenyltrichlorosilane (98-13-5) → chlorotrimethoxysilane (4668-00-2) + phenyl trimethylsiloxane (2996-92-1) + chloro(dimethoxy)phenylsilane (18246-06-5) + phenylmethoxydichlorosilane (50971-88-5)

Conditions	Yield
at 20 - 22℃; for 70h;	A 8.51 g B 0.2% C 89% D 10%
at 20 - 22℃; for 70h;	A 8.51 g B 0.01 g C 5.41 g D 0.62 g

tert-butyl methyl ether (1634-04-4) → chlorotrimethoxysilane (4668-00-2)

Conditions	Yield
With bismuth(III) chloride; tetrachlorosilane at 20℃; for 17h; Inert atmosphere;	73.1%

isothiocyanato-trimethoxy-silane (18250-91-4) + Dichlorophenylphosphine (644-97-3) → chlorotrimethoxysilane (4668-00-2)

Conditions	Yield
	73%

disulfur dichloride (10025-67-9) + isothiocyanato-trimethoxy-silane (18250-91-4) → chlorotrimethoxysilane (4668-00-2)

Conditions	Yield
	50%

methanol (67-56-1) → chlorotrimethoxysilane (4668-00-2)

Conditions	Yield
With tetrachlorosilane
With tetrachlorosilane
With pyridine; tetrachlorosilane In diethyl ether
With tetrachlorosilane for 0.5h; Inert atmosphere;

tetramethylorthosilicate (681-84-5) → chlorotrimethoxysilane (4668-00-2)

Conditions	Yield
With tetrachlorosilane at 150℃;
With hydrogenchloride at -85℃; for 0.3h; Catalytic behavior; Temperature; Time;
With aluminum (III) chloride; acetyl chloride for 3h; Inert atmosphere; Reflux;

trimethoxysilane (2487-90-3) + 3-chloroprop-1-ene (107-05-1) → bis(trimethoxysilyl)propane + 3-chloropropyltrichlorosilane (253586-30-0) + chlorotrimethoxysilane (4668-00-2) + tetramethylorthosilicate (681-84-5) + 1-Chloropropane (540-54-5) + n-propyltrimethoxysilane (1067-25-0) + 3-Chloropropyltrimethoxysilan (2530-87-2)

Conditions	Yield
With toluene; ruthenium trichloride In methanol at 20 - 83℃; for 2h; Product distribution / selectivity;
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In dichloromethane at 20 - 83℃; for 2h; Product distribution / selectivity;
ruthenium trichloride In methanol at 75 - 169℃; for 18h; Product distribution / selectivity; Continuous operation;

...Expand

trimethoxysilane (2487-90-3) + 3-Chloro-2-methylpropene (563-47-3) → 3-chloroisobutylchlorodimethoxysilane (754992-03-5) + bis(trimethoxysilyl)isobutane + chlorotrimethoxysilane (4668-00-2) + tetramethylorthosilicate (681-84-5) + isobutyltrimethoxysilane (18395-30-7) + 3-chloro-2-methylpropyltrimethoxysilane (17256-27-8) + isobutyryl chloride (513-36-0)

Conditions	Yield
ruthenium trichloride In methanol at 20 - 83℃; for 2h; Product distribution / selectivity;
With 1,1'-(1,2-ethanediyl)bisbenzene; ruthenium trichloride In methanol at 20 - 83℃; for 2h; Product distribution / selectivity;
Stage #1: trimethoxysilane With 1,1'-(1,2-ethanediyl)bisbenzene; ruthenium trichloride In methanol at 20 - 80℃; Heating / reflux; Stage #2: 3-Chloro-2-methylpropene at 78 - 83℃; for 2h;
Stage #1: trimethoxysilane; ruthenium trichloride In methanol at 20 - 80℃; Heating / reflux; Stage #2: 3-Chloro-2-methylpropene at 78 - 83℃; for 2h;

...Expand

trimethoxysilane (2487-90-3) + 3-chloroprop-1-ene (107-05-1) → 3-chloropropyltrichlorosilane (253586-30-0) + chlorotrimethoxysilane (4668-00-2) + tetramethylorthosilicate (681-84-5) + 1-Chloropropane (540-54-5) + n-propyltrimethoxysilane (1067-25-0) + 3-Chloropropyltrimethoxysilan (2530-87-2)

Conditions	Yield
With toluene; ruthenium trichloride In methanol at 20 - 83℃; for 2h; Product distribution / selectivity;
Stage #1: trimethoxysilane; ruthenium trichloride In methanol; toluene at 20 - 80℃; Heating / reflux; Stage #2: 3-chloroprop-1-ene at 78 - 83℃; for 2h;

methanol (67-56-1) → chlorotrimethoxysilane (4668-00-2) + tetramethylorthosilicate (681-84-5)

Conditions	Yield
With tetrachlorosilane for 0.333333h;
With tetrachlorosilane Inert atmosphere; Schlenk technique;

tetrachlorosilane (10026-04-7, 53609-55-5) → chlorotrimethoxysilane (4668-00-2)

Conditions	Yield
With CH3OH In diethyl ether

tetrachlorosilane (10026-04-7, 53609-55-5) + tetramethylorthosilicate (681-84-5) → chlorotrimethoxysilane (4668-00-2)

Conditions	Yield
at 150°C;;

methanol (67-56-1) → chlorotrimethoxysilane (4668-00-2) + tetramethylorthosilicate (681-84-5) + methoxytrichlorosilane (1825-97-4) + dichlorodimethoxysilane (18544-45-1)

Conditions	Yield
With tetrachlorosilane

tetramethylorthosilicate (681-84-5) → chlorotrimethoxysilane (4668-00-2) + methoxytrichlorosilane (1825-97-4) + dichlorodimethoxysilane (18544-45-1)

Conditions	Yield
With aluminum (III) chloride; tetrachlorosilane
With thionyl chloride; N,N-dimethyl-formamide at 20℃; for 0.5h; Catalytic behavior; Reagent/catalyst; Time;
With thionyl chloride; N-butylamine at 20℃; for 48h; Catalytic behavior; Reagent/catalyst; Time;
With thionyl chloride; N-butylamine at 20℃; under 760.051 Torr; for 48h; Reagent/catalyst; Time; Concentration; Temperature;

tert-butyl methyl ether (1634-04-4) → chlorotrimethoxysilane (4668-00-2) + tetramethylorthosilicate (681-84-5)

Conditions	Yield
With bismuth(III) chloride; tetrachlorosilane at 0 - 20℃; Neat (no solvent); Inert atmosphere;	A Ca. 80 %Spectr. B Ca. 20 %Spectr.

tetramethylorthosilicate (681-84-5) → chlorotrimethoxysilane (4668-00-2) + dichlorodimethoxysilane (18544-45-1)

Conditions	Yield
With thionyl chloride; triethylamine at 20℃; for 2h; Catalytic behavior; Reagent/catalyst; Time;
With thionyl chloride; benzene at 20℃; for 48h; Catalytic behavior; Reagent/catalyst; Time;
With thionyl chloride; triethylamine at 20℃; under 760.051 Torr; for 2h; Reagent/catalyst; Time; Temperature; Concentration;
With thionyl chloride; benzene at 20℃; under 760.051 Torr; for 48h; Reagent/catalyst; Time; Concentration; Temperature;

chlorotrimethoxysilane (4668-00-2) + (R)-6,6'-dibromo-2,2'-bis(methoxyethoxymethyloxy)-1,1'-binaphthyl → (R)-6,6'-bis(trimethoxysilyl)-2,2'-di(methoxyethoxymethyloxy)-1,1'-binaphthyl

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -80 - 20℃; for 2.5h;	99%

chlorotrimethoxysilane (4668-00-2) + C24H46N2O5(2+)*2Cl(1-) → C27H54N2O8Si(2+)*2Cl(1-)

Conditions	Yield
With hydrogenchloride In dichloromethane; water at 20℃; for 6h;	98.5%

chlorotrimethoxysilane (4668-00-2) → trimethoxysilylamine (21692-64-8)

Conditions	Yield
With sodium amide In tetrahydrofuran at 0℃; for 6h;	97%
With sodium amide In tetrahydrofuran at 0℃; for 6h;	97%
With ammonia; dimethylsilicon dichloride In benzene

chlorotrimethoxysilane (4668-00-2) + C24H47N3O4(2+)*2Cl(1-) → C27H56N4O6Si(2+)*2Cl(1-)

Conditions	Yield
With hydrogenchloride In chloroform; water at 20℃; for 6h;	95.1%

chlorotrimethoxysilane (4668-00-2) + C37H76N2O5(2+)*2Cl(1-) → C40H84N2O8Si(2+)*2Cl(1-)

Conditions	Yield
With hydrogenchloride In dichloromethane; water at 20℃; for 18h;	92.5%

chlorotrimethoxysilane (4668-00-2) + C31H66N4O3(2+)*2Cl(1-) → C34H74N4O6Si(2+)*2Cl(1-)

Conditions	Yield
With hydrogenchloride In chloroform; water at 20℃; for 18h;	91.2%

chlorotrimethoxysilane (4668-00-2) → trimethoxysilyl azide

Conditions	Yield
With sodium azide In acetonitrile at 0℃; for 6h;	91%
With sodium azide In acetonitrile at 0℃; for 6h;	91%
With lithium azide In tetrahydrofuran for 24h; Ambient temperature;

chlorotrimethoxysilane (4668-00-2) + C34H71N3O4(2+)*2Cl(1-) → C37H79N3O7Si(2+)*2Cl(1-)

Conditions	Yield
With hydrogenchloride In dichloromethane; water at 20℃; for 20h;	89.6%

chlorotrimethoxysilane (4668-00-2) → trimethoxysilyl hydrazine

Conditions	Yield
With pyridine; hydrazine In dichloromethane at 0℃; for 8h;	89%
With pyridine; hydrazine In dichloromethane at 0℃; for 8h;	89%

chlorotrimethoxysilane (4668-00-2) + C34H70N2O5(2+)*2Cl(1-) → C37H78N2O8Si(2+)*2Cl(1-)

Conditions	Yield
With hydrogenchloride In dichloromethane; water at 20℃; for 20h;	87.5%

chlorotrimethoxysilane (4668-00-2) + C27H53N3O4(2+)*2Cl(1-) → C30H61N3O7Si(2+)*2Cl(1-)

Conditions	Yield
With hydrogenchloride In dichloromethane; water at 20℃; for 16h;	87.5%

chlorotrimethoxysilane (4668-00-2) + C27H52N2O5(2+)*2Cl(1-) → C30H60N2O8Si(2+)*2Cl(1-)

Conditions	Yield
With hydrogenchloride In dichloromethane; water at 20℃; for 8h;	85.3%

chlorotrimethoxysilane (4668-00-2) + C27H54N4O3(2+)*2Cl(1-) → C30H62N4O6Si(2+)*2Cl(1-)

Conditions	Yield
With hydrogenchloride In dichloromethane; water at 20℃; for 8h;	84.6%

chlorotrimethoxysilane (4668-00-2) + trimethylsilyl acetate (2754-27-0) → chloro-trimethyl-silane (75-77-4) + (acetoxy)tri(methoxy)silane (13170-06-4)

Conditions	Yield
at 20℃; for 8h;	A n/a B 82%

chlorotrimethoxysilane (4668-00-2) + C34H72N4O3(2+)*2Cl(1-) → C37H80N4O6Si(2+)*2Cl(1-)

Conditions	Yield
With hydrogenchloride In chloroform; water at 20℃; for 20h;	81.7%

chlorotrimethoxysilane (4668-00-2) + C34H71N3O4(2+)*2Cl(1-) → C37H79N3O7Si(2+)*2Cl(1-)

Conditions	Yield
With hydrogenchloride In chloroform; water at 20℃; for 20h;	79.8%

chlorotrimethoxysilane (4668-00-2) + C37H77N3O4(2+)*2Cl(1-) → C40H85N3O7Si(2+)*2Cl(1-)

Conditions	Yield
With hydrogenchloride In dichloromethane; water at 20℃; for 6h;	78.6%

chlorotrimethoxysilane (4668-00-2) + 7-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)-1,1,3,3,5,5,7,7-octamethyltetrasiloxane-1-ol → 9-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)-3,3,5,5,7,7,9,9-octamethyl-1,1,1-trimethoxypentasiloxane

Conditions	Yield
With pyridine In diethyl ether at 25℃; for 2.16667h; Inert atmosphere;	78.2%

chlorotrimethoxysilane (4668-00-2) + C37H78N4O3(2+)*2Cl(1-) → C40H86N4O6Si(2+)*2Cl(1-)

Conditions	Yield
With hydrogenchloride In chloroform; water at 20℃; for 18h;	75.5%

chlorotrimethoxysilane (4668-00-2) + 5-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)-1,1,3,3,5,5-hexamethyltrisiloxane-1-ol → 7-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)-3,3,5,5,7,7-hexamethyl-1,1,1-trimethoxypentasiloxane

Conditions	Yield
With pyridine In diethyl ether at 25℃; for 2.08333h; Inert atmosphere;	75.2%

chlorotrimethoxysilane (4668-00-2) + trimethylsilyl butyrate (16844-99-8) → chloro-trimethyl-silane (75-77-4) + trimethoxy(butanoyloxy)silane (122278-75-5)

Conditions	Yield
at 20℃; for 8h;	A n/a B 74%

chlorotrimethoxysilane (4668-00-2) + 2,2-dimethyl-3-pentanone (564-04-5) → tert-Butyl ethyl ketone trimethoxysilyl enol ether (332041-61-9)

Conditions	Yield
Stage #1: 2,2-dimethyl-3-pentanone With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; Stage #2: chlorotrimethoxysilane In tetrahydrofuran; hexane for 0.5h;	74%
Stage #1: 2,2-dimethyl-3-pentanone With lithium diisopropyl amide In diethyl ether Stage #2: chlorotrimethoxysilane In diethyl ether

chlorotrimethoxysilane (4668-00-2) + [Me2P=N]5 (52193-19-8) → C40H110N5O30P5Si10

Conditions	Yield
With n-butyllithium In tetrahydrofuran; n-heptane -78 deg C to r.t.;	72%

chlorotrimethoxysilane (4668-00-2) + [Me2P=N]5 (52193-19-8) → C25H70N5O15P5Si5

Conditions	Yield
With n-butyllithium In tetrahydrofuran; n-heptane 1) -78 deg C to r.t., 2) r.t., 12 h;	72%

chlorotrimethoxysilane (4668-00-2) + 5-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)-1,1,3,3 5,5-hexamethyltrisiloxane-1-ol → 7-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)-3,3,5,5,7,7-hexamethyl-1,1,1-trimethoxypentasiloxane

Conditions	Yield
With pyridine In diethyl ether at 25℃; for 3.33333h; Inert atmosphere;	71.9%

Upstream product

• 67-56-1 methanol 
• 681-84-5 tetramethylorthosilicate 
• 98-13-5 Phenyltrichlorosilane 
• 10026-04-7 tetrachlorosilane 
• 18250-91-4 isothiocyanato-trimethoxy-silane 
• 644-97-3 Dichlorophenylphosphine 
• 75-36-5 acetyl chloride 
• 1634-04-4 tert-butyl methyl ether 
• 10025-67-9 disulfur dichloride 
• 2487-90-3 trimethoxysilane 
• 107-05-1 3-chloroprop-1-ene 
• 563-47-3 3-Chloro-2-methylpropene 

Downstream Products

• 17947-85-2 acetoxy-tri-tert-butoxy-silane 
• 13170-06-4 (acetoxy)tri(methoxy)silane 
• 74098-43-4 tris-(trimethylsiloxy)-acetoxysilane 
• 17872-99-0 benzyltriethoxysilane 
• 90162-40-6 para-bis(trimethoxysilyl)benzene 
• 4371-91-9 hexamethoxydisiloxane 
• 4421-95-8 octamethoxytrisiloxane 
• 17873-01-7 (4-methylphenyl)trimethoxysilane 
• 412907-09-6 1-trimethoxysilyloxy-1-phenylethylene 

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FLUORINE-CONTAINING SILOXANE COMPOUND, METHOD FOR PRODUCING THE SAME, COATING AGENT COMPRISING THE SAME, AND SURFACE TREATMENT METHOD FOR GLASS BASE MATERIAL

PROBLEM TO BE SOLVED: To provide a fluorine-containing siloxane compound that can impart water repellent and antifouling properties to the surface of a base material, and allows distillation purification and can be produced conveniently, and provide a coating agent comprising the same. SOLUTION: The present invention provides a fluorine-containing siloxane compound produced by making a dihydroxy siloxane compound react with a fluoroalkyl-substituted silane compound, then a silane compound having a reactive group, and a coating agent comprising the fluorine-containing siloxane compound and a liquid medium. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT