35692-30-9

Usage

Uses

Used in Rubber and Plastic Industries:
(p-Chlorophenyl)Trimethoxysilane is used as a coupling agent to enhance the compatibility and interfacial adhesion between organic polymers and inorganic fillers, improving the overall performance and durability of rubber and plastic products.
Used in Adhesives, Sealants, and Coatings:
This chemical compound serves as a key component in the formulation of adhesives, sealants, and coatings, providing improved adhesion, durability, and resistance to environmental factors such as moisture and temperature fluctuations.
Used in Glass and Metal Treatments:
(p-Chlorophenyl)Trimethoxysilane is employed as a surface modifier in glass and metal treatments, offering enhanced adhesion, corrosion resistance, and improved mechanical properties.
Used in Pharmaceutical and Agrochemical Synthesis:
Due to its ability to introduce silicon into organic molecules, (p-Chlorophenyl)Trimethoxysilane is utilized in the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of innovative and effective products in these industries.
However, it is crucial to handle (p-Chlorophenyl)Trimethoxysilane with care, as it is flammable and can cause skin and eye irritation upon direct contact. Proper safety measures should be taken during its use to ensure the well-being of individuals and the environment.

Synthetic route

1-Chloro-4-iodobenzene (637-87-6) + trimethoxysilane (2487-90-3) → (4-chlorophenyl)trimethoxysilane (35692-30-9)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 20℃; silylation;

tetramethylorthosilicate (681-84-5) + 4-chlorophenylmagnesium halide → (4-chlorophenyl)trimethoxysilane (35692-30-9)

Conditions	Yield
In tetrahydrofuran at -30 - 20℃; for 13h; Inert atmosphere;
In tetrahydrofuran at -30 - 20℃; for 13h;

1-methylindole (603-76-9) + (4-chlorophenyl)trimethoxysilane (35692-30-9) → 2-(4-chlorophenyl)-1-methyl-2-phenyl-1H-indole (5905-11-3)

Conditions	Yield
With tetrabutyl ammonium fluoride; palladium diacetate; acetic acid; silver(l) oxide In tetrahydrofuran; ethanol at 20℃; Inert atmosphere; regioselective reaction;	93%

5-chloro-1-(4-methoxybenzyl)-3-(phenylsulfanyl)pyrazin-2(1H)-one + (4-chlorophenyl)trimethoxysilane (35692-30-9) → 5-chloro-3-(4-chlorophenyl)-1-(4-methoxybenzyl)-2(1H)-pyrazinone

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); tetrabutyl ammonium fluoride In tetrahydrofuran at 60℃; for 1.5h; Hiyama coupling; Inert atmosphere;	92%

C8H14BrF2NO + (4-chlorophenyl)trimethoxysilane (35692-30-9) → 4-chloro-N,N-diisopropylbenzamide (79606-45-4)

Conditions	Yield
With potassium fluoride; 5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix-4-arene; copper(ll) bromide; magnesium chloride for 8h; Inert atmosphere; Heating;	92%

(4-chlorophenyl)trimethoxysilane (35692-30-9) + benzenesulfonyl chloride (98-09-9) → 4'-biphenyl chloride (2051-62-9)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tetrabutyl ammonium fluoride In N,N-dimethyl-formamide; acetonitrile at 100℃; for 3h; Hiyama Coupling; Inert atmosphere; Green chemistry;	86%

S-methyl-S-(p-tolyl)sulfoximine (20414-85-1, 22132-97-4, 52720-03-3, 121123-21-5) + (4-chlorophenyl)trimethoxysilane (35692-30-9) → N-(4-chloro)phenyl-S-(4-methyl)phenyl-S-methylsulfoximine (56158-16-8)

Conditions	Yield
With copper(l) iodide; tetrabutyl ammonium fluoride; oxygen In dichloromethane at 20℃; for 12h; Schlenk technique; Green chemistry;	84%

N-(2-pyrimidyl)indole (221044-05-9) + (4-chlorophenyl)trimethoxysilane (35692-30-9) → 2-(4-chlorophenyl)-1-(pyrimidin-2-yl)-1H-indole (1310708-95-2)

Conditions	Yield
With copper (II)-fluoride; silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In water at 140℃; for 20h; Hiyama Coupling; Inert atmosphere; Green chemistry;	81%
With copper (II)-fluoride; oxygen; cobalt(III) acetylacetonate In toluene at 160℃; under 760.051 Torr; for 24h; Hiyama Coupling; Sealed tube;	63%

(3-chlorophenyl)(imino)(methyl)-λ6-sulfanone (22133-00-2) + (4-chlorophenyl)trimethoxysilane (35692-30-9) → N-(4-chloro)phenyl-S-(3-chloro)phenyl-S-methylsulfoximine

Conditions	Yield
With copper(l) iodide; tetrabutyl ammonium fluoride; oxygen In dichloromethane at 20℃; for 12h; Schlenk technique; Green chemistry;	80%

carbon monoxide (201230-82-2) + (4-chlorophenyl)trimethoxysilane (35692-30-9) + aniline (62-53-3) → 4-chlorobenzanilide (6833-15-4)

Conditions	Yield
With copper (II)-fluoride; bis(triphenylphosphine)palladium(II) dichloride In acetonitrile at 80℃; under 760.051 Torr; for 24h; Hiyama Coupling; Schlenk technique;	80%

polytetrafluoroethylene (116-14-3) + (4-chlorophenyl)trimethoxysilane (35692-30-9) → 1-chloro-4-(1,2,2-trifluoroethenyl)benzene (82907-01-5)

Conditions	Yield
With triethoxyfluorosilane; [Pd2(dba)3]*benzene; tricyclopentylphosphine In tetrahydrofuran at 80℃; under 2660.18 Torr; for 24h; Hiyama Coupling; Inert atmosphere; Autoclave;	78%

(4-chlorophenyl)trimethoxysilane (35692-30-9) + S-methyl-S-phenylsulfoximine (4381-25-3) → (±)-((4-chlorophenyl)imino)(methyl)(phenyl)-λ6-sulfanone (56158-15-7)

Conditions	Yield
With copper(l) iodide; tetrabutyl ammonium fluoride; oxygen In dichloromethane at 20℃; for 12h; Schlenk technique; Green chemistry;	78%

n-benzoylpyrrolidine (3389-54-6) + (4-chlorophenyl)trimethoxysilane (35692-30-9) → C17H16ClNO

Conditions	Yield
With copper (II)-fluoride; silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In tetrahydrofuran at 140℃; for 20h;	77%

N-(quinolin-8-yl)but‐3‐enamide + (4-chlorophenyl)trimethoxysilane (35692-30-9) → 4-(4-chlorophenyl)-N-(quinolin-8-yl)butanamide

Conditions	Yield
With copper (II)-fluoride; water; palladium diacetate In tetrahydrofuran at 100℃; for 24h; Sealed tube; regioselective reaction;	76%

(4-chlorophenyl)trimethoxysilane (35692-30-9) + S-(4-methoxyphenyl)-S-methylsulfoximine (77970-95-7) → ((4-chlorophenyl)imino)(4-methoxyphenyl)(methyl)-λ6-sulfanone

Conditions	Yield
With copper(l) iodide; tetrabutyl ammonium fluoride; oxygen In dichloromethane at 20℃; for 12h; Schlenk technique; Green chemistry;	75%

1-(1-fluoro-2,2-diiodovinyl)-4-methylbenzene (1420041-79-7) + (4-chlorophenyl)trimethoxysilane (35692-30-9) → (Z)-1-chloro-4-(2-fluoro-2-(p-tolyl)vinyl)benzene

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutyl ammonium fluoride; palladium diacetate In tetrahydrofuran; 1,4-dioxane at 80℃; for 20h; Hiyama Coupling; regioselective reaction;	74%

(4-chlorophenyl)trimethoxysilane (35692-30-9) + 1-chloro-4-(1-fluoro-2,2-diiodovinyl)benzene → (Z)-4,4'-(1-fluoroethene-1,2-diyl)bis(chlorobenzene)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutyl ammonium fluoride; palladium diacetate In tetrahydrofuran; 1,4-dioxane at 80℃; for 20h; Hiyama Coupling; regioselective reaction;	73%

benzoimidazole (51-17-2) + (4-chlorophenyl)trimethoxysilane (35692-30-9) → 1-(4-chlorophenyl)-1H-benzo[d]imidazole

Conditions	Yield
With copper diacetate; tetrabutyl ammonium fluoride; oxygen In N,N-dimethyl-formamide at 20℃; for 48h; Arylation;	72%

(4-chlorophenyl)trimethoxysilane (35692-30-9) + (1-fluoro-2,2-diiodovinyl)benzene → (Z)-1-chloro-4-(2-fluoro-2-phenylethenyl)benzene

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; tetrabutyl ammonium fluoride; palladium diacetate In tetrahydrofuran; 1,4-dioxane at 80℃; for 20h; Hiyama Coupling; regioselective reaction;	70%

(4-chlorophenyl)trimethoxysilane (35692-30-9) + methyl 2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}-amino)-acrylate (79807-13-9) → Boc-Phe-DL-Phe(4-Cl)-OMe (1071149-07-9)

Conditions	Yield
[Rh(COD)2][BF4] In 1,4-dioxane; water at 110℃; for 24h;	60%

(4-chlorophenyl)trimethoxysilane (35692-30-9) + tert-butyl 2-diazo-2-phenylacetate (72410-67-4) → tert-butyl 2-(4-chlorophenyl)-2-phenylacetate

Conditions	Yield
With [Rh(OH)(cod)]2; tetrabutyl ammonium fluoride; tricyclohexylphosphine tetrafluoroborate In tetrahydrofuran; water at 80℃; for 5h; Hiyama Coupling; Inert atmosphere;	60%

N-ethylbenzimidazolinone (10045-45-1) + (4-chlorophenyl)trimethoxysilane (35692-30-9) → 1-(4-chlorophenyl)-3-ethyl-1H-benzo[d]imidazol-2(3H)-one

Conditions	Yield
With copper diacetate; tetrabutyl ammonium fluoride; oxygen In N,N-dimethyl-formamide at 20℃; for 48h; Arylation;	55%

4-tert-Butylaniline (769-92-6) + (4-chlorophenyl)trimethoxysilane (35692-30-9) → 4-(tert-Butyl)-N-(4-chlorophenyl)aniline

Conditions	Yield
With copper diacetate; tetrabutyl ammonium fluoride; oxygen In N,N-dimethyl-formamide at 20℃; for 48h; Arylation;	54%

(4-chlorophenyl)trimethoxysilane (35692-30-9) + Boc-Val-ΔAla-OMe (158068-95-2) → Boc-Val-DL-Phe(4-Cl)-OMe

Conditions	Yield
[Rh(COD)2][BF4] In 1,4-dioxane; water at 110℃; for 24h;	53%

4-(2-pyridinyl)anisole (5957-90-4) + (4-chlorophenyl)trimethoxysilane (35692-30-9) → 2-(4'-chloro-5-methoxybiphenyl-2-yl)pyridine (1335209-94-3)

Conditions	Yield
With palladium diacetate; silver fluoride; p-benzoquinone In 1,4-dioxane at 110℃; for 24h; Inert atmosphere; seal tube;	48%

2-phenylpyridine (1008-89-5) + (4-chlorophenyl)trimethoxysilane (35692-30-9) → 2-(4'-chloro-[1,1'-biphenyl]-2-yl)pyridine (1174895-50-1)

Conditions	Yield
With palladium diacetate; silver fluoride; p-benzoquinone In 1,4-dioxane at 110℃; for 24h; Inert atmosphere; seal tube;	43%

4-phenylpiperidine (771-99-3) + (4-chlorophenyl)trimethoxysilane (35692-30-9) → 1-(4-chloro-phenyl)-4-phenyl-piperidine

Conditions	Yield
With copper diacetate; tetrabutyl ammonium fluoride; oxygen In N,N-dimethyl-formamide at 20℃; for 48h; Arylation;	27%

N,N-bis-(2-hydroxyethyl)glycine (150-25-4) + (4-chlorophenyl)trimethoxysilane (35692-30-9) → 1-(4-chloro-phenyl)-2,8,9-trioxa-5-aza-1-sila-bicyclo[3.3.3]undecan-3-one (53883-55-9)

Conditions	Yield
In N,N-dimethyl-formamide; benzene

(4-chlorophenyl)trimethoxysilane (35692-30-9) + 3-[bis-(2-hydroxy-propyl)-amino]-propan-1-ol (57262-86-9) → 1-(4-chloro-phenyl)-8,11-dimethyl-2,9,10-trioxa-6-aza-1-sila-bicyclo[4.3.3]dodecane (76666-26-7)

Conditions	Yield
With potassium hydroxide In xylene

2-phenylpyridine (1008-89-5) + (4-chlorophenyl)trimethoxysilane (35692-30-9) → 2-(4,4''-dichloro-[1,1':3',1''-terphenyl]-2'-yl)pyridine (1041085-58-8)

Conditions	Yield
With copper (II)-fluoride; silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In 1,2-dichloro-ethane at 140℃; for 20h; Inert atmosphere;	70 %Chromat.

Upstream product

• 637-87-6 1-Chloro-4-iodobenzene 
• 2487-90-3 trimethoxysilane 
• 681-84-5 tetramethylorthosilicate 

Downstream Products

• 76666-26-7 1-(4-chloro-phenyl)-8,11-dimethyl-2,9,10-trioxa-6-aza-1-sila-bicyclo[4.3.3]dodecane 
• 1071149-07-9 Boc-Phe-DL-Phe(4-Cl)-OMe 
• 5905-11-3 2-(4-chlorophenyl)-1-methyl-2-phenyl-1H-indole 
• 82907-01-5 1-chloro-4-(1,2,2-trifluoroethenyl)benzene 
• 56158-15-7 (±)-((4-chlorophenyl)imino)(methyl)(phenyl)-λ⁶-sulfanone 
• 56158-16-8 N-(4-chloro)phenyl-S-(4-methyl)phenyl-S-methylsulfoximine 
• 1310708-95-2 2-(4-chlorophenyl)-1-(pyrimidin-2-yl)-1H-indole 
• 6833-15-4 4-chlorobenzanilide 
• 1517-46-0 4-chloro-N-methyl-N-phenyl-benzamide 
• 79606-45-4 N,N-diisopropyl 4-chlorobenzamide 
• 2051-62-9 4'-biphenyl chloride 

Relevant academic research and scientific papers

Direct Hiyama Cross-Coupling of (Hetero)arylsilanes with C(sp2)-H Bonds Enabled by Cobalt Catalysis

We report a chelation-assisted C-H arylation of various indoles with sterically and electronically diverse (hetero)arylsilanes enabled by cost-effective Cp*-free cobalt catalysis. Key to the success of this strategy is the judicious choice of copper(II) fluoride as a bifunctional sliane activator and catalyst reoxidant. This methodology features a broad substrate scope and good functional group compatibility. The synthetic versatility of this protocol has been highlighted by the gram-scale synthesis and late-stage diversification of biologically active molecules.

Directed palladium(II)-catalyzed intermolecular anti-markovnikov hydroarylation of unactivated alkenes with (hetero)arylsilanes

We describe herein a regioselective palladium(II)catalyzed intermolecular hydroarylation of unactivated aliphatic alkenes with electronically and sterically diverse (hetero)arylsilanes under redox-neutral conditions. A removable bidentate 8-amino-quinoline auxiliary was readily employed to dictate the regioselectivity, prevent β-hydride elimination, and facilitate protodepalladation. This silicon-based protocol features a broad substrate scope with excellent functional group compatibility and enables an expeditious route to a variety of γ-aryl butyric acid derivatives in good yields with exclusive anti-Markovnikov selectivity.