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3-Chloropropyltriethoxysilane

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Name

3-Chloropropyltriethoxysilane

EINECS 225-805-6
CAS No. 5089-70-3 Density 0.989 g/cm3
PSA 27.69000 LogP 2.66370
Solubility 113-1000000mg/L at 20℃ Melting Point N/A
Formula C9H21ClO3Si Boiling Point 230.8 °C at 760 mmHg
Molecular Weight 240.802 Flash Point 78.8 °C
Transport Information UN 1993 3/PG 3 Appearance colorless transparent liquid
Safety 16-26-36 Risk Codes 10-36/37/38
Molecular Structure Molecular Structure of 5089-70-3 (3-Chloropropyltriethoxysilane) Hazard Symbols IrritantXi
Synonyms

(3-Chloropropyl)triethoxysilane;(g-Chloropropyl)triethoxysilane;3-(Triethoxysilyl)-1-chloropropane;3-(Triethoxysilyl)propyl chloride;KH 230;NSC 252156;Si 223;Si 230;Triethoxy(g-chloropropyl)silane;g-Chloropropylltriethoxysilane;3-chloropropyl-triethoxy-silane;

Article Data 28

3-Chloropropyltriethoxysilane Synthetic route

998-30-1

Triethoxysilane

107-05-1

3-chloroprop-1-ene

5089-70-3

(3-chloropropyl)triethoxysilane

Conditions
ConditionsYield
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.
64-17-5

ethanol

2550-06-3

3-chloropropyltrichlorosilane

5089-70-3

(3-chloropropyl)triethoxysilane

Conditions
ConditionsYield
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

chloro-(1,5cyclooctadiene) iridium(I) dimer

998-30-1

Triethoxysilane

107-05-1

3-chloroprop-1-ene

5089-70-3

(3-chloropropyl)triethoxysilane

Conditions
ConditionsYield
In para-xylene83%
954114-17-1

(3-chloropropyl)trivinylsilane

64-17-5

ethanol

5089-70-3

(3-chloropropyl)triethoxysilane

Conditions
ConditionsYield
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;
998-30-1

Triethoxysilane

107-05-1

3-chloroprop-1-ene

A

78-10-4

tetraethoxy orthosilicate

B

135795-91-4

(3-chloropropyl)-diethoxy-chlorosilane

C

4667-99-6

chlorotriethoxysilane

D

2550-02-9

propyltriethoxysilane

E

5089-70-3

(3-chloropropyl)triethoxysilane

Conditions
ConditionsYield
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;
40372-72-3

bis(3-triethoxysilylpropyl) tetrasulfide

111-64-8

n-octanoic acid chloride

A

220727-26-4

3-(octanoylsulfanyl)-1-propyltriethoxysilane

B

106-32-1

octanoic acid ethyl ester

C

5089-70-3

(3-chloropropyl)triethoxysilane

D

14814-09-6

3-Mercaptopropyltriethoxysilane

E

60764-86-5

bis-[γ-(triethoxysilyl)propyl]sulfide

F

56706-10-6

4,4,13,13-tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane

G

56706-11-7

4,4,14,14-tetraethoxy-3,15-dioxa-8,9,10-trithia-4,14-disilaheptadecane

Conditions
ConditionsYield
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;
14814-09-6

3-Mercaptopropyltriethoxysilane

111-64-8

n-octanoic acid chloride

A

220727-26-4

3-(octanoylsulfanyl)-1-propyltriethoxysilane

B

106-32-1

octanoic acid ethyl ester

C

5089-70-3

(3-chloropropyl)triethoxysilane

D

60764-86-5

bis-[γ-(triethoxysilyl)propyl]sulfide

Conditions
ConditionsYield
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;
56706-10-6

4,4,13,13-tetraethoxy-3,14-dioxa-8,9-dithia-4,13-disilahexadecane

111-64-8

n-octanoic acid chloride

A

220727-26-4

3-(octanoylsulfanyl)-1-propyltriethoxysilane

B

106-32-1

octanoic acid ethyl ester

C

5089-70-3

(3-chloropropyl)triethoxysilane

D

14814-09-6

3-Mercaptopropyltriethoxysilane

E

60764-86-5

bis-[γ-(triethoxysilyl)propyl]sulfide

F

56706-11-7

4,4,14,14-tetraethoxy-3,15-dioxa-8,9,10-trithia-4,14-disilaheptadecane

Conditions
ConditionsYield
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;
998-30-1

Triethoxysilane

107-05-1

3-chloroprop-1-ene

A

4667-99-6

chlorotriethoxysilane

B

2550-02-9

propyltriethoxysilane

C

5089-70-3

(3-chloropropyl)triethoxysilane

Conditions
ConditionsYield
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.
998-30-1

Triethoxysilane

107-05-1

3-chloroprop-1-ene

A

4667-99-6

chlorotriethoxysilane

B

5089-70-3

(3-chloropropyl)triethoxysilane

Conditions
ConditionsYield
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-Chloropropyltriethoxysilane Specification

The 3-Chloropropyltriethoxysilane, with the CAS registry number 5089-70-3, is also known as Triethoxy(gamma-chloropropyl)silane. It belongs to the product categories of 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. Its EINECS registry number is 225-805-6. Its IUPAC name is called 3-chloropropyl(triethoxy)silane. The product which is colorless transparent liquid should be sealed and stored in dark, cool and dry place. What's more, it can be used for making silicone and silane coupling agent. Meanwhile, its own can also be used as a coupling agent of epoxy composite materials.

Physical properties of 3-Chloropropyltriethoxysilane: (1)ACD/LogP: 2.72; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.72; (4)ACD/LogD (pH 7.4): 2.72; (5)ACD/BCF (pH 5.5): 68.43; (6)ACD/BCF (pH 7.4): 68.43; (7)ACD/KOC (pH 5.5): 716.63; (8)ACD/KOC (pH 7.4): 716.63; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 9; (12)Index of Refraction: 1.427; (13)Molar Refractivity: 62.54 cm3; (14)Molar Volume: 243.3 cm3; (15)Surface Tension: 25.5 dyne/cm; (16)Density: 0.989 g/cm3; (17)Flash Point: 78.8 °C; (18)Enthalpy of Vaporization: 44.85 kJ/mol; (19)Boiling Point: 230.8 °C at 760 mmHg; (20)Vapour Pressure: 0.0978 mmHg at 25°C.

Preparation: this chemical can be prepared by allyl chloride and dichloro-silane which will conduct the addition reaction, and they will conduct alcoholysis reaction with ethanol. At last, you can obtaine γ-chloropropyl triethoxysilane.

Uses of 3-Chloropropyltriethoxysilane: it can be used to produce Triethoxy-(3-iodopropyl)-silan by heating. This reaction is will need reagent NaI and solvent acetone with reaction time of 24 hours. The yield is about 58%.

When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is flammable. In addition, it is irritating to eyes, respiratory system and skin. You should keep away from sources of ignition - No smoking. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CCO[Si](CCCCl)(OCC)OCC
(2)InChI: InChI=1S/C9H21ClO3Si/c1-4-11-14(12-5-2,13-6-3)9-7-8-10/h4-9H2,1-3H3
(3)InChIKey: KSCAZPYHLGGNPZ-UHFFFAOYSA-N

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