5089-70-3

Basic information

• Product Name: 3-Chloropropyltriethoxysilane
• Synonyms: (3-chloropropyl)triethoxy-silan;Triethxoxy-(3-chloropropyl)-silane;triethxoxy(3-chloropropyl)silane;DOW CORNING(TM) PRODUCT 1-6376;GAMA-CHLOROPROPYL TRIETHOXY SILANE;GAMMA-CHLOROPROPYLTRIETHOXYSILANE;3-CHLOROPROPYLTRIETHOXYSILANE;3-(TRIETHOXYSILYL)PROPYL CHLORIDE
• CAS NO: 5089-70-3
• Molecular Formula: C₉H₂₁ClO₃Si
• Molecular Weight: 240.8
• EINECS: 225-805-6
• Product Categories: Industrial/Fine Chemicals;Chloro;Chloroalkylsilanes, etc. (Silane Coupling Agents);Functional Materials;Si (Classes of Silicon Compounds);Silane Coupling Agents;Si-O Compounds;Trialkoxysilanes;Alkoxy Silanes;Silane series;Organometallic Reagents;Organosilicon;Chemical Synthesis;Organometallic Reagents;silane
• Mol File: 5089-70-3.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 100 °C
• Flash Point: 99 °F
• Appearance: Clear slightly yellow/Liquid
• Density: 1.000 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0978mmHg at 25°C
• Refractive Index: n20/D 1.418(lit.)
• Storage Temp.: Flammables area
• PKA: 10[at 20 ℃]
• Water Solubility: 113-1000000mg/L at 20℃
• BRN: 1754992
• CAS DataBase Reference: 3-Chloropropyltriethoxysilane(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chloropropyltriethoxysilane(5089-70-3)
• EPA Substance Registry System: 3-Chloropropyltriethoxysilane(5089-70-3)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 16-26-36
• RIDADR: UN 1993 3/PG 3
• F: 21
• TSCA: Yes
• Hazardous Substances Data: 5089-70-3(Hazardous Substances Data)

Usage

Chemical Properties

Colorless transparent liquid

Flammability and Explosibility

Notclassified

InChI:InChI=1/C9H21ClO3Si/c1-4-11-14(12-5-2,13-6-3)9-7-8-10/h4-9H2,1-3H3

Synthetic route

Triethoxysilane (998-30-1) + 3-chloroprop-1-ene (107-05-1) → (3-chloropropyl)triethoxysilane (5089-70-3)

Conditions	Yield
With Ru-B/γ-Al2O3 at 115℃; for 1h; Temperature; Inert atmosphere;	99.44%
With dihydrogen hexachloroplatinate; Triethoxyvinylsilane; isopropyl alcohol at 50 - 80℃; for 4h; Product distribution; Mechanism; influence unsaturated Si-comp. on rate of hydrosilylation; effect of other additives;	22.7 % Chromat.
bis(1,5-cyclooctadiene)diiridium(I) dichloride at -78 - 40℃; for 2h; Product distribution / selectivity; Inert atmosphere; pressure tight tube;	21.8 %Chromat.
With di-tert-butyl peroxide In methanol at 80 - 91℃; for 4h;	65 %Chromat.

ethanol (64-17-5) + 3-chloropropyltrichlorosilane (2550-06-3) → (3-chloropropyl)triethoxysilane (5089-70-3)

Conditions	Yield
at 80 - 90℃; under 600 Torr; Large scale;	99%
With tin(IV) chloride; cyclohexene for 1h; Ambient temperature;	94.5%
In dichloromethane for 3h; Heating;	92%

chloro-(1,5cyclooctadiene) iridium(I) dimer + Triethoxysilane (998-30-1) + 3-chloroprop-1-ene (107-05-1) → (3-chloropropyl)triethoxysilane (5089-70-3)

Conditions	Yield
In para-xylene	83%

(3-chloropropyl)trivinylsilane (954114-17-1) + ethanol (64-17-5) → (3-chloropropyl)triethoxysilane (5089-70-3)

Conditions	Yield
With hydrogenchloride; chlorobis(cyclooctene)rhodium(I) dimer In 1,4-dioxane; chloroform at 20℃; for 2h;	100 % Chromat.
hydrogenchloride; chlorobis(cyclooctene)rhodium(I) dimer In 1,4-dioxane; chloroform for 2h; Product distribution / selectivity;

Triethoxysilane (998-30-1) + 3-chloroprop-1-ene (107-05-1) → tetraethoxy orthosilicate (78-10-4) + (3-chloropropyl)-diethoxy-chlorosilane (135795-91-4) + chlorotriethoxysilane (4667-99-6) + propyltriethoxysilane (2550-02-9) + (3-chloropropyl)triethoxysilane (5089-70-3)

Conditions	Yield
Stage #1: Triethoxysilane; ruthenium trichloride at 20 - 120℃; Under N2 atmosphere; Stage #2: 3-chloroprop-1-ene at 70 - 120℃; for 1h; Product distribution / selectivity; Under N2 atmosphere;
chloro(1,5-cyclooctadiene)iridium(I) dimer at 20 - 70℃; for 18h; Product distribution / selectivity; Under N2 atmosphere;
ruthenium trichloride at 25℃; for 18h; Product distribution / selectivity; Under N2 atmosphere;

bis(3-triethoxysilylpropyl) tetrasulfide (40372-72-3) + n-octanoic acid chloride (111-64-8) → 3-(octanoylsulfanyl)-1-propyltriethoxysilane (220727-26-4) + octanoic acid ethyl ester (106-32-1) + (3-chloropropyl)triethoxysilane (5089-70-3) + 3-Mercaptopropyltriethoxysilane (14814-09-6) + bis-[γ-(triethoxysilyl)propyl]sulfide (60764-86-5) + 4,4,13,13-tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane (56706-10-6) + 4,4,14,14-tetraethoxy-3,15-dioxa-8,9,10-trithia-4,14-disilaheptadecane (56706-11-7)

Conditions	Yield
Stage #1: bis(3-triethoxysilylpropyl) tetrasulfide With sodium In Solvent 140 at 110℃; for 0.75h; Stage #2: n-octanoic acid chloride In Solvent 140 at 45 - 104℃; for 1h; Stage #3: With water In toluene at 45℃; Product distribution / selectivity;

...Expand

3-Mercaptopropyltriethoxysilane (14814-09-6) + n-octanoic acid chloride (111-64-8) → 3-(octanoylsulfanyl)-1-propyltriethoxysilane (220727-26-4) + octanoic acid ethyl ester (106-32-1) + (3-chloropropyl)triethoxysilane (5089-70-3) + bis-[γ-(triethoxysilyl)propyl]sulfide (60764-86-5)

Conditions	Yield
Stage #1: 3-Mercaptopropyltriethoxysilane With sodium In toluene at 105℃; for 0.5 - 1.36667h; Stage #2: n-octanoic acid chloride In toluene at 20 - 62℃; for 1 - 1.58333h; Stage #3: With water In toluene at 32 - 50℃; Product distribution / selectivity;

4,4,13,13-tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane (56706-10-6) + n-octanoic acid chloride (111-64-8) → 3-(octanoylsulfanyl)-1-propyltriethoxysilane (220727-26-4) + octanoic acid ethyl ester (106-32-1) + (3-chloropropyl)triethoxysilane (5089-70-3) + 3-Mercaptopropyltriethoxysilane (14814-09-6) + bis-[γ-(triethoxysilyl)propyl]sulfide (60764-86-5) + 4,4,14,14-tetraethoxy-3,15-dioxa-8,9,10-trithia-4,14-disilaheptadecane (56706-11-7)

Conditions	Yield
Stage #1: 4,4,13,13-tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane With sodium In toluene at 110℃; for 0.75 - 1.15h; Stage #2: n-octanoic acid chloride In toluene at 45 - 60℃; for 1 - 2h; Stage #3: With water In toluene at 45℃; Product distribution / selectivity;

Triethoxysilane (998-30-1) + 3-chloroprop-1-ene (107-05-1) → chlorotriethoxysilane (4667-99-6) + propyltriethoxysilane (2550-02-9) + (3-chloropropyl)triethoxysilane (5089-70-3)

Conditions	Yield
bis(1,5-cyclooctadiene)diiridium(I) dichloride at -78 - 60℃; for 1h; Product distribution / selectivity; Inert atmosphere; pressure tight tube;	A 33.2 %Chromat. B 5.7 %Chromat. C 34.8 %Chromat.

Triethoxysilane (998-30-1) + 3-chloroprop-1-ene (107-05-1) → chlorotriethoxysilane (4667-99-6) + (3-chloropropyl)triethoxysilane (5089-70-3)

Conditions	Yield
bis(1,5-cyclooctadiene)diiridium(I) dichloride at -78 - 30℃; for 2h; Product distribution / selectivity; Inert atmosphere; pressure tight tube;	A 16.2 %Chromat. B 48.8 %Chromat.
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 40 - 60℃; for 16h; Overall yield = 32 %Spectr.;

3-chloropropyltrichlorosilane (2550-06-3) + EtOMgCl → (3-chloropropyl)triethoxysilane (5089-70-3)

Conditions	Yield
In tetrahydrofuran at 30 - 180℃;

Triethoxysilane (998-30-1) + 3-chloroprop-1-ene (107-05-1) → tetraethoxy orthosilicate (78-10-4) + (3-chloropropyl)triethoxysilane (5089-70-3)

Conditions	Yield
With dihydrogen hexachloroplatinate; Triethoxyvinylsilane at 55 - 65℃;

C14H32Cl2O5Si2 (158588-47-7) + ethanol (64-17-5) → (3-chloropropyl)triethoxysilane (5089-70-3)

Conditions	Yield
With potassium hydroxide at 240℃; for 3h; Autoclave; Molecular sieve;

(3-chloropropyl)triethoxysilane (5089-70-3) + potassium 9-anthracene carboxylate → 9-anthracenecarboxylic acid (triethoxysilyl) propyl ester

Conditions	Yield
In N,N-dimethyl acetamide at 100℃; for 2h;	100%

(3-chloropropyl)triethoxysilane (5089-70-3) + 1-H-3-methylimidazolium chloride → 1-methyl-3-(3-triethoxysilanepropyl)imidazolium chloride

Conditions	Yield
at 120℃; for 24h; Inert atmosphere;	100%

potassium cyanate (590-28-3) + (3-chloropropyl)triethoxysilane (5089-70-3) → 3-(triethoxypropyl) isocyanate (24801-88-5)

Conditions	Yield
at 100℃; for 12h; Temperature; Inert atmosphere; Ionic liquid;	99.5%

tert-butyl (3-(1H-imidazol-1-yl)propyl)carbamate (279238-29-8) + (3-chloropropyl)triethoxysilane (5089-70-3) → 1-[(N-tert-butoxycarbonyl)aminopropyl]-3-(3-triethoxysilylpropyl)imidazolinium chloride (1005216-91-0)

Conditions	Yield
at 90℃; for 60h;	99%

(3-chloropropyl)triethoxysilane (5089-70-3) → 3-chloropropylsiloxane

Conditions	Yield
With hydrogenchloride In ethanol; water for 5h; Heating / reflux;	99%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + (3-chloropropyl)triethoxysilane (5089-70-3) → DABCO-SIL (1403993-57-6)

Conditions	Yield
In ethanol; acetone for 24h; Reflux;	99%
In toluene for 48h; Reflux; Inert atmosphere;	96%
With sodium hydride In tetrahydrofuran at 60℃; for 16h; Sonication;

(3-chloropropyl)triethoxysilane (5089-70-3) + 2-chloroethanamine hydrochloride (870-24-6) → C11H26ClNO3Si

Conditions	Yield
Stage #1: 2-chloroethanamine hydrochloride With potassium hydroxide for 1h; Cooling with ice; Stage #2: (3-chloropropyl)triethoxysilane In N,N-dimethyl-formamide at 110℃; for 24h; Inert atmosphere;	99%

(3-chloropropyl)triethoxysilane (5089-70-3) + 3-chloropropylamine hydrochloride (6276-54-6) → C12H28ClNO3Si

Conditions	Yield
Stage #1: 3-chloropropylamine hydrochloride With potassium hydroxide for 1h; Cooling with ice; Stage #2: (3-chloropropyl)triethoxysilane In N,N-dimethyl-formamide at 110℃; for 24h; Inert atmosphere;	99%

tetradecylamine (2016-42-4) + (3-chloropropyl)triethoxysilane (5089-70-3) → C32H71NO6Si2*ClH

Conditions	Yield
With sodium iodide In dimethyl sulfoxide at 90℃; for 2h;	98.6%

(3-chloropropyl)triethoxysilane (5089-70-3) + 1,1,3-trimethylthiourea (2489-77-2) → N,N,N'-trimethyl-N'-(3-(triethoxysilyl)propyl)thiourea

Conditions	Yield
Stage #1: (3-chloropropyl)triethoxysilane With sodium hydride In tetrahydrofuran at 50℃; for 0.5h; Inert atmosphere; Stage #2: 1,1,3-trimethylthiourea In tetrahydrofuran at 66℃; for 4h; Inert atmosphere;	98.5%

triisopropanolamine (122-20-3) + (3-chloropropyl)triethoxysilane (5089-70-3) → 1-(3-chloropropyl)-3,7,10-trimethyl-2,8,9-trioxa-5-aza-1-silabicyclo[3.3.3]undecane

Conditions	Yield
With potassium hydroxide at 90℃; under 100 - 350 Torr; for 4h;	98.2%

1-methyl-1H-imidazole (616-47-7) + (3-chloropropyl)triethoxysilane (5089-70-3) → 1-methyl-3-(3-triethoxysilanepropyl)imidazolium chloride

Conditions	Yield
at 78℃; for 24h; Inert atmosphere;	98%
at 80℃; for 30h; Inert atmosphere;	96%
at 245℃; for 0.0111111h; microwave irradiation;	95%

7,7,9,9-tetramethyl-1,3,8-triazaspiro[4,5]decane-2,4-dione potassium salt + (3-chloropropyl)triethoxysilane (5089-70-3) → N-halaminesiloxane monomer; unhalogenated precursor

Conditions	Yield
In DMF (N,N-dimethyl-formamide) at 100℃; for 8h;	98%

(3-chloropropyl)triethoxysilane (5089-70-3) + 3-Mercaptopropyltriethoxysilane (14814-09-6) → bis-[γ-(triethoxysilyl)propyl]sulfide (60764-86-5)

Conditions	Yield
Stage #1: (3-chloropropyl)triethoxysilane; 3-Mercaptopropyltriethoxysilane at 60℃; for 2h; Stage #2: With sodium ethanolate In ethanol at 65℃; for 2h; Temperature;	98%

N-Ethylimidazole (7098-07-9) + (3-chloropropyl)triethoxysilane (5089-70-3) → 1-ethyl-3-[3-(triethoxysilyl)propyl]imidazolium chloride

Conditions	Yield
at 100℃; for 0.0833333h; Inert atmosphere;	98%

(3-chloropropyl)triethoxysilane (5089-70-3) + N,N',N''-triphenylguanidine (101-01-9) → 1,2,3-triphenyl-1,3-bis(3-(triethoxysilyl)propyl)guanidine

Conditions	Yield
Stage #1: (3-chloropropyl)triethoxysilane With sodium hydride In toluene at 50℃; for 0.5h; Inert atmosphere; Stage #2: N,N',N''-triphenylguanidine In tetrahydrofuran at 110℃; for 5h;	97.9%

(3-chloropropyl)triethoxysilane (5089-70-3) → bis(3-triethoxysilylpropyl) tetrasulfide (40372-72-3)

Conditions	Yield
With sodium polysulfide In ethanol at 78℃; Product distribution / selectivity;	97.8%
With sodium sulfide; sodium hydrogencarbonate; sulfur In ethanol; water
With sodium sulfide; sulfur In ethanol; toluene for 4h; Reflux; Green chemistry;
With sodium sulfide; sodium borate; dodecyltrimethylammonium bromide; sulfur; potassium iodide In water at 40 - 55℃; for 1h; Temperature; Reagent/catalyst;

(3-chloropropyl)triethoxysilane (5089-70-3) + N,N'-diethylthiourea (105-55-5) → N,N'-diethyl-N,N'-bis(3-(triethoxysilyl)propyl)thiourea

Conditions	Yield
Stage #1: (3-chloropropyl)triethoxysilane With sodium hydroxide In toluene at 50℃; for 0.5h; Inert atmosphere; Stage #2: N,N'-diethylthiourea In toluene at 110℃; for 5h; Inert atmosphere;	97.8%

(3-chloropropyl)triethoxysilane (5089-70-3) + 1,3-Di(2-tolyl)guanidine (97-39-2) → 1,3-bis(2-methylphenyl)-1,2,3-tris(3-(triethoxysilyl)propyl)guanidine

Conditions	Yield
Stage #1: (3-chloropropyl)triethoxysilane With sodium hydride In tetrahydrofuran at 50℃; for 0.5h; Inert atmosphere; Stage #2: 1,3-Di(2-tolyl)guanidine In tetrahydrofuran at 65℃; for 4h;	97.5%

(3-chloropropyl)triethoxysilane (5089-70-3) + 1-methyl-1H-benzimidazole-2-thiol (2360-22-7) → 1-methyl-2-((3-(triethoxysilyl)propyl)thio)-1H-benzimidazole

Conditions	Yield
Stage #1: (3-chloropropyl)triethoxysilane With sodium hydride In tetrahydrofuran at 50℃; for 0.5h; Inert atmosphere; Stage #2: 1-methyl-1H-benzimidazole-2-thiol In tetrahydrofuran at 65 - 67℃; for 5h;	97.1%

pyridine (110-86-1) + (3-chloropropyl)triethoxysilane (5089-70-3) → ((3-triethoxysilyl)propyl)pyridinium iodide

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; potassium iodide In acetonitrile at 90℃; for 24h; Inert atmosphere;	97%

(3-chloropropyl)triethoxysilane (5089-70-3) + 4,5-dihydro-1-[3-(triethoxysilyl)propyl]imidazole → 1,3-bis(3-(triethoxysilyl)propyl)-4,5-dihydro-1H-imidazol-3-ium chloride

Conditions	Yield
In neat (no solvent) at 120℃; for 120h; Inert atmosphere;	97%

2-methylsulfanylbenzimidazole (7152-24-1) + (3-chloropropyl)triethoxysilane (5089-70-3) → 2-(methylthio)-1-(5-(trimethoxysilyl)propyl)-1H-benzimidazole

Conditions	Yield
Stage #1: (3-chloropropyl)triethoxysilane With sodium hydroxide In tetrahydrofuran at 50℃; for 0.5h; Inert atmosphere; Stage #2: 2-methylsulfanylbenzimidazole In tetrahydrofuran at 65℃; for 5h;	96.8%

Cyclohexanethiol (1569-69-3) + (3-chloropropyl)triethoxysilane (5089-70-3) → (3-(cyclohexylthio)propyl)triethoxysilane

Conditions	Yield
With dmap; potassium iodide; sodium hydroxide In 1,4-dioxane; Petroleum ether at 60℃; for 2h; Reagent/catalyst; Solvent; Temperature;	96.7%

(3-chloropropyl)triethoxysilane (5089-70-3) + C43H88N2O2(2+)*2Cl(1-) → 2-triethoxysilane propoxy-1-N,N-dimethyl oleoyl-3-octadecyldimethylammonium propane dichloride

Conditions	Yield
at 50℃; for 12h;	96.5%

(3-chloropropyl)triethoxysilane (5089-70-3) + C43H88N2O2(2+)*2Cl(1-) → 2-triethoxysilylpropoxy-1-N,N-dimethyloleoyl-3-octadecyldimethylammoniumpropane dichloride

Conditions	Yield
at 50℃; for 12h;	96.5%

(3-chloropropyl)triethoxysilane (5089-70-3) → 3-azidopropyltriethoxysilane

Conditions	Yield
With sodium azide In butanone for 72h; Inert atmosphere; Reflux;	96%
With sodium azide In dimethyl sulfoxide at 60℃;	95%
With sodium azide; tetrabutylammomium bromide In acetonitrile for 20h; Reflux; Inert atmosphere;	95%

(3-chloropropyl)triethoxysilane (5089-70-3) + 2-sulfanylpyrimidine (131242-36-9) → 2-((3-(triethoxysilyl)propyl)thio)pyrimidine

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 115℃; for 48h;	96%

Upstream product

• 64-17-5 ethanol 
• 2550-06-3 3-chloropropyltrichlorosilane 
• 998-30-1 Triethoxysilane 
• 107-05-1 3-chloroprop-1-ene 
• 40372-72-3 bis(3-triethoxysilylpropyl) tetrasulfide 
• 111-64-8 n-octanoic acid chloride 
• 14814-09-6 3-Mercaptopropyltriethoxysilane 
• 56706-10-6 4,4,13,13-tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane 
• 158588-47-7 C₁₄H₃₂Cl₂O₅Si₂ 
• 954114-17-1 (3-chloropropyl)trivinylsilane 

Downstream Products

• 919-30-2 3-aminopropyltriethoxysilane 
• 6044-50-4 N-methyl-3-(triethoxysilyl)propan-1-amine 
• 161678-38-2 octakis(3-chloropropyl)octasilsesquioxane 
• 200393-06-2 N-[3-(triethoxysilyl)propyl]-(-)-(1R,2R)-diaminocyclohexane 
• 13497-18-2 bis-(3-triethoxysilylpropyl)amine 
• 220727-26-4 3-(octanoylsulfanyl)-1-propyltriethoxysilane 
• 40372-72-3 bis(3-triethoxysilylpropyl) tetrasulfide 
• 60764-86-5 bis-[γ-(triethoxysilyl)propyl]sulfide 
• 56706-10-6 4,4,13,13-tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane 
• 56706-11-7 4,4,14,14-tetraethoxy-3,15-dioxa-8,9,10-trithia-4,14-disilaheptadecane 
• 1067-47-6 3-cyanopropyl-triethoxysilane 
• 473780-80-2 3-triethoxysilylpropyl-5,5-dimethylhydantoin 
• 13508-63-9 chloropropyl(dimethyl)ethoxysilane 
• 1417415-63-4 N-(pyridin-2-ylmethylene)-4-(3-(triethoxysilyl)propoxy)benzenamine 

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