IL98888A - Process for the preparation of arylalkylmethylsilanes - Google Patents

Process for the preparation of arylalkylmethylsilanes

Info

Publication number: IL98888A
Authority: IL; Israel
Prior art keywords: formula; halogen; preparation; iii; hal
Prior art date: 1990-07-21

Application number

IL9888891A

Other languages

English (en)

Hebrew (he)

Other versions

IL98888A0 (en

Original Assignee

Hoechst Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1990-07-21

Filing date

1991-07-18

Publication date

1994-12-29

1991-07-18 Application filed by Hoechst Ag filed Critical Hoechst Ag

1992-07-15 Publication of IL98888A0 publication Critical patent/IL98888A0/xx

1994-12-29 Publication of IL98888A publication Critical patent/IL98888A/en

Links

238000000034 method Methods 0.000 title claims abstract description 13
238000002360 preparation method Methods 0.000 title claims abstract description 7
150000002367 halogens Chemical class 0.000 claims abstract description 9
229910052736 halogen Inorganic materials 0.000 claims abstract description 8
UWGIJJRGSGDBFJ-UHFFFAOYSA-N dichloromethylsilane Chemical compound [SiH3]C(Cl)Cl UWGIJJRGSGDBFJ-UHFFFAOYSA-N 0.000 claims abstract description 7
125000000217 alkyl group Chemical group 0.000 claims abstract description 5
125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 3
125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 3
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 3
125000004995 haloalkylthio group Chemical group 0.000 claims abstract 2
239000002904 solvent Substances 0.000 abstract description 8
150000004791 alkyl magnesium halides Chemical class 0.000 abstract description 2
150000004792 aryl magnesium halides Chemical class 0.000 abstract description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
150000004795 grignard reagents Chemical class 0.000 description 14
239000000047 product Substances 0.000 description 12
239000007818 Grignard reagent Substances 0.000 description 11
150000001875 compounds Chemical class 0.000 description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
239000000243 solution Substances 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
239000000203 mixture Substances 0.000 description 7
239000012043 crude product Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
WVUYYXUATWMVIT-UHFFFAOYSA-N 1-bromo-4-ethoxybenzene Chemical compound CCOC1=CC=C(Br)C=C1 WVUYYXUATWMVIT-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
KTQYJQFGNYHXMB-UHFFFAOYSA-N dichloro(methyl)silicon Chemical compound C[Si](Cl)Cl KTQYJQFGNYHXMB-UHFFFAOYSA-N 0.000 description 3
-1 for example Substances 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
229910052749 magnesium Inorganic materials 0.000 description 3
CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 3
239000005048 methyldichlorosilane Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 2
238000003747 Grignard reaction Methods 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000012071 phase Substances 0.000 description 2
239000012266 salt solution Substances 0.000 description 2
DECGNXVVNBDTQK-UHFFFAOYSA-N (4-ethoxyphenyl)-dimethylsilane Chemical compound CCOC1=CC=C([SiH](C)C)C=C1 DECGNXVVNBDTQK-UHFFFAOYSA-N 0.000 description 1
BQHMIPMIXCLXEE-UHFFFAOYSA-N (6-ethylsulfanylpyridin-3-yl)-dimethylsilane Chemical compound CCSC1=CC=C([SiH](C)C)C=N1 BQHMIPMIXCLXEE-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
230000000895 acaricidal effect Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
230000003466 anti-cipated effect Effects 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
YGHUUVGIRWMJGE-UHFFFAOYSA-N chlorodimethylsilane Chemical compound C[SiH](C)Cl YGHUUVGIRWMJGE-UHFFFAOYSA-N 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
UBHZUDXTHNMNLD-UHFFFAOYSA-N dimethylsilane Chemical compound C[SiH2]C UBHZUDXTHNMNLD-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
230000002147 killing effect Effects 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
239000002243 precursor Substances 0.000 description 1
FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 1
YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/12—Organo silicon halides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0896—Compounds with a Si-H linkage

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)

IL9888891A 1990-07-21 1991-07-18 Process for the preparation of arylalkylmethylsilanes IL98888A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE4023288A DE4023288A1 (de)	1990-07-21	1990-07-21	Verfahren zur herstellung von aryl-alkylmethylsilanen

Publications (2)

Publication Number	Publication Date
IL98888A0 IL98888A0 (en)	1992-07-15
IL98888A true IL98888A (en)	1994-12-29

Family

ID=6410791

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9888891A IL98888A (en)	1990-07-21	1991-07-18	Process for the preparation of arylalkylmethylsilanes

Country Status (9)

Country	Link
US (1)	US5124470A (fr)
EP (1)	EP0468373B1 (fr)
JP (1)	JPH04234397A (fr)
KR (1)	KR920002618A (fr)
DE (2)	DE4023288A1 (fr)
IE (1)	IE912549A1 (fr)
IL (1)	IL98888A (fr)
PT (1)	PT98402A (fr)
ZA (1)	ZA915681B (fr)

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE467015A (fr) *	1940-12-26
US2561178A (en) *	1949-07-28	1951-07-17	Gen Electric	Organopolysiloxanes
US2813886A (en) *	1953-11-20	1957-11-19	Metal & Thermit Corp	Preparation of arylhalosilanes
US2813887A (en) *	1953-11-20	1957-11-19	Metal & Thermit Corp	Preparation of arylhalosilanes
BE758312A (fr) *	1969-11-03	1971-04-30	Dow Corning	Procede a haute temperature pour la preparation de composes contenant des liaisons silicium-hydrogene
JPS60222492A (ja) *	1984-04-17	1985-11-07	Shin Etsu Chem Co Ltd	第３級炭化水素シリル化合物の製造方法
FR2575465B1 (fr) *	1984-12-27	1987-02-20	Centre Nat Rech Scient	Complexes de silicium pentacoordines, leur procede de preparation et leur application a la preparation d'organosilanes
ES2016793B3 (es) *	1985-10-26	1990-12-01	Hoechst Ag	Nuevos derivados de silanos, procedimientos para su obtencion, productos que los contienen y su empleo como plaguicidas.

1990
- 1990-07-21 DE DE4023288A patent/DE4023288A1/de not_active Withdrawn
1991
- 1991-07-18 EP EP91112047A patent/EP0468373B1/fr not_active Expired - Lifetime
- 1991-07-18 IL IL9888891A patent/IL98888A/en not_active IP Right Cessation
- 1991-07-18 DE DE59107677T patent/DE59107677D1/de not_active Expired - Fee Related
- 1991-07-19 PT PT98402A patent/PT98402A/pt not_active Application Discontinuation
- 1991-07-19 JP JP3179615A patent/JPH04234397A/ja not_active Withdrawn
- 1991-07-19 ZA ZA915681A patent/ZA915681B/xx unknown
- 1991-07-19 IE IE254991A patent/IE912549A1/en unknown
- 1991-07-19 US US07/732,792 patent/US5124470A/en not_active Expired - Fee Related
- 1991-07-20 KR KR1019910012449A patent/KR920002618A/ko not_active Abandoned

Also Published As

Publication number	Publication date
KR920002618A (ko)	1992-02-28
DE4023288A1 (de)	1992-01-23
IL98888A0 (en)	1992-07-15
PT98402A (pt)	1992-05-29
US5124470A (en)	1992-06-23
EP0468373A1 (fr)	1992-01-29
ZA915681B (en)	1992-04-29
JPH04234397A (ja)	1992-08-24
EP0468373B1 (fr)	1996-04-17
DE59107677D1 (de)	1996-05-23
IE912549A1 (en)	1992-01-29

Legal Events

Date	Code	Title	Description
1998-07-15	RH	Patent void

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