2146-97-6

Basic information

• Product Name: 1,3-Disilacyclobutane, 1,1,3,3-tetrachloro-
• CAS NO: 2146-97-6
• Molecular Formula: C2H4Cl4Si2
• Molecular Weight: 226.037
• Mol File: 2146-97-6.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 1,3-Disilacyclobutane, 1,1,3,3-tetrachloro-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Disilacyclobutane, 1,1,3,3-tetrachloro-(2146-97-6)
• EPA Substance Registry System: 1,3-Disilacyclobutane, 1,1,3,3-tetrachloro-(2146-97-6)

Safety Data

• Hazardous Substances Data: 2146-97-6(Hazardous Substances Data)

Usage

General Description

1,3-Disilacyclobutane, 1,1,3,3-tetrachloro- is a chemical compound with the molecular formula C4H8Cl4Si2. It is a substituted cyclobutane with two silicon atoms and four chlorine atoms attached to the carbon ring. 1,3-Disilacyclobutane, 1,1,3,3-tetrachloro- is mainly used as a precursor in chemical synthesis and in the production of silicon-containing materials. It is also used in the research and development of organosilicon compounds and materials. 1,3-Disilacyclobutane, 1,1,3,3-tetrachloro- has potential applications in the field of materials science, particularly in the development of advanced materials with unique properties. However, it is important to handle this compound with care due to its potential hazards and toxicity.

Synthetic route

1,1,3,3-tetrakis(dimethylamino)-1,3-disilacyclobutane (74045-37-7) → 1,1,3,3-tetrachloro-1,3-disilacyclobutane (2146-97-6)

Conditions	Yield
With Dichlorophenylphosphine In pentane	100%

5,6-Bis(trifluormethyl)-2,2-dichlor-2-silabicyclo<2.2.2>octa-5,7-dien (78818-99-2) → 1,2-bis(trifluoromethyl)benzene (433-95-4) + 1,1,3,3-tetrachloro-1,3-disilacyclobutane (2146-97-6)

Conditions	Yield
at 650℃; under 0.2 Torr; Product distribution;	A 79% B 36%

1,1-dichlorosilacyclobutane (2351-33-9) → 1,1,3,3-tetrachloro-1,3-disilacyclobutane (2146-97-6)

Conditions	Yield
at 715℃;	43%
at 750℃;	11%
at 700℃;
at 850℃; high vacuum;

1,1-dimethylsilacyclobutane (2295-12-7) + 1,1-dichlorosilacyclobutane (2351-33-9) → 1,1,3,3-tetramethyl-1,3-disiletane (1627-98-1) + 1,1,3,3-tetrachloro-1,3-disilacyclobutane (2146-97-6) + 1,1-Dichloro-3,3-dimethyl-[1,3]disiletane

Conditions	Yield
at 690℃;	A n/a B n/a C 40%

(1R,4S)-2,2-Dichloro-5,6-bis-trifluoromethyl-2-sila-bicyclo[2.2.2]octa-5,7-diene (78818-99-2) → 1,2-bis(trifluoromethyl)benzene (433-95-4) + 1,1,3,3-tetrachloro-1,3-disilacyclobutane (2146-97-6)

Conditions	Yield
at 650℃; under 0.2 Torr;

1,1-dichlorosilacyclobutane (2351-33-9) → Methyltrichlorosilane (75-79-6) + ethene (74-85-1) + n-propyltrichlorosilane (141-57-1) + 1,1,3,3-tetrachloro-1,3-disilacyclobutane (2146-97-6)

Conditions	Yield
at 570℃; for 0.00333333h; Further byproducts given. Title compound not separated from byproducts;

1,1-dichlorosilacyclobutane (2351-33-9) → Methyltrichlorosilane (75-79-6) + ethene (74-85-1) + n-propyltrichlorosilane (141-57-1) + 1,1,3,3-tetrachloro-1,3-disilacyclobutane (2146-97-6) + 1,1,3,3-tetrachloro-1,3-disilacyclohexane + 1,1,2,2,4,4-hexachloro-1,2,4-trisilacyclopentane + 1,1,3,3,5,5-hexachloro-1,3,5-trisilacyclohexane, trichlorosilane

Conditions	Yield
at 570℃; for 0.00333333h; Product distribution; pulsed pyrolytic chromatography; thermal decomposition of 1,1-dichloro-1-silacyclobutane in inert atmosphere and in the presence of butadiene, role of intemediates;

1,1-dichlorosilacyclobutane (2351-33-9) → Methyltrichlorosilane (75-79-6) + methane (34557-54-5) + ethene (74-85-1) + 1,1,3,3-tetrachloro-1,3-disilacyclobutane (2146-97-6) + poly(dichlorocarbosilane)

Conditions	Yield
With sulphur hexafluoride In gas at 700 - 800℃; for 0.166667h; Mechanism; Irradiation;

1,1,3,3-tetrachloro-1,3-disilacyclobutane (2146-97-6) → 1,1,3,3-Tetrafluoro-[1,3]disiletane

Conditions	Yield
With silver(II) fluoride	90%

dimethyl amine (124-40-3) + 1,1,3,3-tetrachloro-1,3-disilacyclobutane (2146-97-6) → 1,3-bis(dimethylamino)-1,3-dichloro-1,3-disilacyclobutane (192461-46-4)

Conditions	Yield
Ambient temperature;	76%

phenylmagnesium bromide + 1,1,3,3-tetrachloro-1,3-disilacyclobutane (2146-97-6) → 1,3-Dichloro-1,3-diphenyl-[1,3]disiletane (160053-07-6)

Conditions	Yield
at 37℃; for 12h;	69%

1,1,3,3-tetrachloro-1,3-disilacyclobutane (2146-97-6) → 1,3-disilacyclobutane (287-55-8)

Conditions	Yield
With lithium aluminium tetrahydride In dibutyl ether at 0℃; for 12h;	68%
With lithium aluminium tetrahydride; dibutyl ether

vinylmagnesium chloride (3536-96-7) + 1,1,3,3-tetrachloro-1,3-disilacyclobutane (2146-97-6) → 1,1,3,3-tetravinyl-1,3-disilacyclobutane

Conditions	Yield
In tetrahydrofuran; hexane at 60℃; for 4h;	65.4%
at 67℃; for 24h;	59%

1,1,3,3-tetrachloro-1,3-disilacyclobutane (2146-97-6) → 1,1,3,3-Tetradeuterio-1,3-disilacyclobutan (63238-92-6)

Conditions	Yield
With lithium aluminium deuteride In dibutyl ether at 0℃; for 12h;	65%

methyl magnesium iodide (917-64-6) + 1,1,3,3-tetrachloro-1,3-disilacyclobutane (2146-97-6) → 1,1,3,3-tetramethyl-1,3-disiletane (1627-98-1)

Conditions	Yield
at 37℃; for 24h;	63%

phenylmagnesium bromide + 1,1,3,3-tetrachloro-1,3-disilacyclobutane (2146-97-6) → 1,1,3,3-tetraphenyl-1,3-disilacyclobutan (2319-40-6)

Conditions	Yield
at 110℃; for 2h;	56%

dimethyl amine (124-40-3) + 1,1,3,3-tetrachloro-1,3-disilacyclobutane (2146-97-6) → 1,1,3,3-tetrakis(dimethylamino)-1,3-disilacyclobutane (74045-37-7)

Conditions	Yield
at 36℃; for 5h;	54%

trimethylsilyl cyanide (7677-24-9) + 1,1,3,3-tetrachloro-1,3-disilacyclobutane (2146-97-6) → poly(dicyanosilylenemethylene); Monomer(s): trimethylsilylcyanide, 1,1,3,3-tetrachloro-1,3-disilacyclobutane

Conditions	Yield
Stage #1: 1,1,3,3-tetrachloro-1,3-disilacyclobutane; dihydrogen hexachloroplatinate In toluene at 80℃; for 12h; Stage #2: trimethylsilyl cyanide In toluene Heating;

Upstream product

• 2351-33-9 1,1-dichlorosilacyclobutane 
• 2295-12-7 1,1-dimethylsilacyclobutane 
• 74045-37-7 1,1,3,3-tetrakis(dimethylamino)-1,3-disilacyclobutane 
• 78818-99-2 5,6-Bis(trifluormethyl)-2,2-dichlor-2-silabicyclo<2.2.2>octa-5,7-dien 
• 78818-99-2 (1R,4S)-2,2-Dichloro-5,6-bis-trifluoromethyl-2-sila-bicyclo[2.2.2]octa-5,7-diene 

Downstream Products

• 160053-07-6 1,3-Dichloro-1,3-diphenyl-[1,3]disiletane 
• 2319-40-6 1,1,3,3-tetraphenyl-1,3-disilacyclobutan 

Relevant articles and documents

Laser-induced decomposition of 1,1-dichloro-1-silacyclobutane for gas-phase deposition of reactive solid polycarbosilane

Continuous-wave CO2 laser photosensitized (SF6) decomposition of 1,1-dichloro-1-silacyclobutane (DCSCB) leads to volatile ethene, methyltrichlorosilane, 1,1.3,3-tetrachloro-1,3-disilacyclobutane (TCDSCB) and a solid material.The reaction is assumed to be initiated by competitive (2+2) cycloreversion and dehydrochlorination.The amounts of depleted DCSCB and those of the ethene and CH3SiCl3 that are formed, as well as detection of methyltrichlorosilane-d1 and methyltrichlorosilane-d2 in the decomposition of DCSCB carried out in an excess of DCI provide indirect evidence for the intermediacy of dichlorosilene Cl2Si=CH2 and chlorosilyne CISiCH.The solid deposit is judged to be mostly poly(dichlorocarbosilane): it reacts with gaseous methanol, trifluoroethanol, trifluoroacetic acid and water. Key words: Silane; Laser-induced deposition; Polycarbosilane; Chlorosilyne

Hetero-?-Systems, 8. Silaethene

By means of a combination of vacuum flash pyrolysis and matrix isolation silaethene (1a) and its simply substituted derivatives 1b-f can be prepared starting with precursors 9a-f of the silabicyclooctadiene type.Silaolefins 1a-f are stable in argon at 10 K and can be identified by their characteristic IR and UV spectra.

Silaethen

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