1089687-03-5

Basic information

• Product Name: Di(2-ethylhexyl)dichlorosilane
• Synonyms: Di(2-ethylhexyl)dichlorosilane;1H-Pyrrole-2-carbonitrile,1-aMino;BIS(2-ETHYLHEXYL)DICHLOROSILANE;Dichlorodi(2-ethylhexyl)silane
• CAS NO: 1089687-03-5
• Molecular Formula: C₁₆H₃₄Cl₂Si
• Molecular Weight: 325.43266
• EINECS: -0
• Mol File: 1089687-03-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 132-138°C / 1.5
• Appearance: /
• Density: 0.924±0.06 g/cm3(Predicted)
• Refractive Index: 1.4590 to 1.4630
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: Di(2-ethylhexyl)dichlorosilane(CAS DataBase Reference)
• NIST Chemistry Reference: Di(2-ethylhexyl)dichlorosilane(1089687-03-5)
• EPA Substance Registry System: Di(2-ethylhexyl)dichlorosilane(1089687-03-5)

Safety Data

• Statements: 10-23/24/35-36/37/38
• Safety Statements: 36/37/39-62-43-26
• RIDADR: 1993
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 1089687-03-5(Hazardous Substances Data)

Usage

General Description

Di(2-ethylhexyl)dichlorosilane (C20H42Cl2Si) is a chemical compound characterized by its use for organic synthesis as well as a precursor for silicon-based materials. This organic silane has the unique capacity to undergo hydrolysis to form silanols and siloxanes, contributing to silicon's high reactivity. It is a colorless liquid that must be stored and handled with adequate safety measures, as it may be harmful if inhaled, cause eye irritation, or have toxic effects on aquatic life. This chemical is primarily used in the pharmaceutical industry and materials science research.

Synthetic route

trichloro(2-ethylhexyl)silane (222058-04-0) + 2-ethylhexylmagnesium bromide → dichloro-bis(2-ethylhexyl)silane (1089687-03-5)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃;	71%
In tetrahydrofuran at -10 - 20℃; for 6h;	20%

4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione (32281-36-0) → 3,6-dithiophen-2-yl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione + dichloro-bis(2-ethylhexyl)silane (1089687-03-5)

Conditions	Yield
In tetrahydrofuran	A 71% B n/a

2-ethylhexylmagnesium bromide → dichloro-bis(2-ethylhexyl)silane (1089687-03-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: magnesium; tetrachlorosilane / water; tetrahydrofuran / 12 h / 20 °C 2: tetrahydrofuran / 6 h / -10 - 20 °C View Scheme

dichloro-bis(2-ethylhexyl)silane (1089687-03-5) + 3,3'-dibromo-5,5'-bis(trimethylsilyl)-2,2'-bithiophene (207742-50-5) → 4,4'-bis(2-ethylhexyl)-5,5'-bis(trimethylsilyl)dithieno[3,2-b:2',3'-d]silole (1089687-04-6)

Conditions	Yield
Stage #1: 3,3'-dibromo-5,5'-bis(trimethylsilyl)-2,2'-bithiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Stage #2: dichloro-bis(2-ethylhexyl)silane In tetrahydrofuran; hexane at -78 - 20℃;	72%
Stage #1: 3,3'-dibromo-5,5'-bis(trimethylsilyl)-2,2'-bithiophene With n-butyllithium In tetrahydrofuran at 20℃; for 0.333333h; Stage #2: dichloro-bis(2-ethylhexyl)silane In tetrahydrofuran at 75℃; for 2h;	67%
Stage #1: 3,3'-dibromo-5,5'-bis(trimethylsilyl)-2,2'-bithiophene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.583333h; Inert atmosphere; Stage #2: dichloro-bis(2-ethylhexyl)silane In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;	58%
With n-butyllithium
Stage #1: 3,3'-dibromo-5,5'-bis(trimethylsilyl)-2,2'-bithiophene With n-butyllithium In tetrahydrofuran; hexane at -80℃; for 0.583333h; Stage #2: dichloro-bis(2-ethylhexyl)silane In tetrahydrofuran; hexane at -80 - 20℃; for 2h;

3,3'dibromo-2,2'-bithiophene (51751-44-1) + dichloro-bis(2-ethylhexyl)silane (1089687-03-5) → 4,4'-bis-(2-ethylhexyl)-dithieno[3,2-b:2',3'-d]silole (1207627-85-7)

Conditions	Yield
Stage #1: 3,3'dibromo-2,2'-bithiophene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: dichloro-bis(2-ethylhexyl)silane In tetrahydrofuran; hexane at -78 - 20℃;	67%
Stage #1: 3,3'dibromo-2,2'-bithiophene With n-butyllithium In tetrahydrofuran; diethyl ether; hexane at -78℃; for 3h; Inert atmosphere; Stage #2: dichloro-bis(2-ethylhexyl)silane In tetrahydrofuran; diethyl ether; hexane at -78 - 20℃; Inert atmosphere;	30%

dichloro-bis(2-ethylhexyl)silane (1089687-03-5) + 3,3'-dibromo-5,5'-bis(trimethylsilyl)-2,2'-bithiophene (207742-50-5) → 4,4'-bis-(2-ethylhexyl)-dithieno[3,2-b:2',3'-d]silole (1207627-85-7)

Conditions	Yield
Stage #1: 3,3'-dibromo-5,5'-bis(trimethylsilyl)-2,2'-bithiophene With n-butyllithium In tetrahydrofuran Stage #2: dichloro-bis(2-ethylhexyl)silane In tetrahydrofuran

dichloro-bis(2-ethylhexyl)silane (1089687-03-5) → 4,4’-bis(2-ethylhexyl)-5,5’-dibromo-dithieno[3,2-b:2',3'-d]silole (1089687-05-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 0.33 h / 20 °C 1.2: 2 h / 75 °C 2.1: N-Bromosuccinimide / water; tetrahydrofuran / 10 °C View Scheme

dichloro-bis(2-ethylhexyl)silane (1089687-03-5) → 2,2′-bistrimethylstannyl-4,4′-bis-(2-ethylhexyl)dithieno[3,2-b:2′,3′-d]silole (1089687-06-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran / 0.33 h / 20 °C 1.2: 2 h / 75 °C 2.1: N-Bromosuccinimide / water; tetrahydrofuran / 10 °C 3.1: n-butyllithium / tetrahydrofuran / 0.67 h / 20 °C 3.2: 2 h / 20 °C View Scheme

dichloro-bis(2-ethylhexyl)silane (1089687-03-5) → C74H94F2N6S6Si

Conditions	Yield
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran / 0.33 h / 20 °C 1.2: 2 h / 75 °C 2.1: N-Bromosuccinimide / water; tetrahydrofuran / 10 °C 3.1: n-butyllithium / tetrahydrofuran / 0.67 h / 20 °C 3.2: 2 h / 20 °C 4.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 2 h / 170 °C / Inert atmosphere View Scheme

Upstream product

• 32281-36-0 4,8-dihydrobenzo[1,2-b:4,5-b']dithiophene-4,8-dione 
• 222058-04-0 trichloro(2-ethylhexyl)silane 

Downstream Products

• 1089687-05-7 2,6-dibromo-4,4-bis(2-ethylhexyl)-4H-silolo[3,2-b:4,5-b']dithiophene 
• 1089687-06-8 2,2′-bistrimethylstannyl-4,4′-bis-(2-ethylhexyl)dithieno[3,2-b:2′,3′-d]silole 
• 1207627-85-7 4,4'-bis-(2-ethylhexyl)-dithieno[3,2-b:2',3'-d]silole 

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