IL90972A - תהליך להכנת פנאוקסי-פנילאלקיל-דימתי לסיליל הליד - Google Patents
תהליך להכנת פנאוקסי-פנילאלקיל-דימתי לסיליל הלידInfo
- Publication number
- IL90972A IL90972A IL9097289A IL9097289A IL90972A IL 90972 A IL90972 A IL 90972A IL 9097289 A IL9097289 A IL 9097289A IL 9097289 A IL9097289 A IL 9097289A IL 90972 A IL90972 A IL 90972A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- denotes
- compound
- preparation
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- -1 phenoxy, phenylthio Chemical group 0.000 claims abstract description 13
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 9
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 150000002366 halogen compounds Chemical class 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 5
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical class ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- 230000002140 halogenating effect Effects 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical class ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical class ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 125000001743 benzylic group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229950005499 carbon tetrachloride Drugs 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- VXJILKJPONNCPI-UHFFFAOYSA-N (4-ethoxyphenyl)-dimethyl-[(3-phenoxyphenyl)methoxymethyl]silane Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)COCC1=CC=CC(OC=2C=CC=CC=2)=C1 VXJILKJPONNCPI-UHFFFAOYSA-N 0.000 description 1
- HKYUYERZLISBJG-UHFFFAOYSA-N (6-ethylsulfanylpyridin-3-yl)-dimethyl-[(3-phenoxyphenyl)methoxymethyl]silane Chemical compound C1=NC(SCC)=CC=C1[Si](C)(C)COCC1=CC=CC(OC=2C=CC=CC=2)=C1 HKYUYERZLISBJG-UHFFFAOYSA-N 0.000 description 1
- WQXZKMUZWPUZGL-UHFFFAOYSA-N 5-bromo-2-ethoxypyridine Chemical compound CCOC1=CC=C(Br)C=N1 WQXZKMUZWPUZGL-UHFFFAOYSA-N 0.000 description 1
- LOZFITIIRWTYPM-UHFFFAOYSA-N 5-bromo-2-ethylsulfanylpyridine Chemical compound CCSC1=CC=C(Br)C=N1 LOZFITIIRWTYPM-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- UDEFOWDBDBTKJH-UHFFFAOYSA-N [Li]C1=CC=C(OCC)N=C1 Chemical compound [Li]C1=CC=C(OCC)N=C1 UDEFOWDBDBTKJH-UHFFFAOYSA-N 0.000 description 1
- FIRWXDWWYCRAIX-UHFFFAOYSA-N [Li]C1=CC=C(SCC)N=C1 Chemical compound [Li]C1=CC=C(SCC)N=C1 FIRWXDWWYCRAIX-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- RDSLIQNPPGSPBF-UHFFFAOYSA-N bromo-dimethyl-[(3-phenoxyphenyl)methoxymethyl]silane Chemical compound C[Si](C)(Br)COCC1=CC=CC(OC=2C=CC=CC=2)=C1 RDSLIQNPPGSPBF-UHFFFAOYSA-N 0.000 description 1
- ZOCGAKGFQQCKNX-UHFFFAOYSA-N bromo-dimethyl-[(3-phenoxyphenyl)methylsulfanylmethyl]silane Chemical compound C[Si](C)(Br)CSCC1=CC=CC(OC=2C=CC=CC=2)=C1 ZOCGAKGFQQCKNX-UHFFFAOYSA-N 0.000 description 1
- VQPFDLRNOCQMSN-UHFFFAOYSA-N bromosilane Chemical compound Br[SiH3] VQPFDLRNOCQMSN-UHFFFAOYSA-N 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- IDIOJRGTRFRIJL-UHFFFAOYSA-N iodosilane Chemical class I[SiH3] IDIOJRGTRFRIJL-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000010626 work up procedure Methods 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
- C07F7/12—Organo silicon halides
- C07F7/121—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20
- C07F7/123—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20 by reactions involving the formation of Si-halogen linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3823979A DE3823979A1 (de) | 1988-07-15 | 1988-07-15 | Verfahren zur herstellung von halosilanen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL90972A0 IL90972A0 (en) | 1990-02-09 |
| IL90972A true IL90972A (he) | 1994-02-27 |
Family
ID=6358718
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9097289A IL90972A (he) | 1988-07-15 | 1989-07-14 | תהליך להכנת פנאוקסי-פנילאלקיל-דימתי לסיליל הליד |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5028706A (he) |
| EP (1) | EP0350804B1 (he) |
| JP (1) | JPH0269486A (he) |
| AT (1) | ATE104673T1 (he) |
| DE (2) | DE3823979A1 (he) |
| ES (1) | ES2052824T3 (he) |
| IL (1) | IL90972A (he) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5523439A (en) * | 1994-08-08 | 1996-06-04 | Shin-Etsu Chemical Co., Ltd. | Process for preparing silacyclohexane compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0224024B1 (de) * | 1985-10-26 | 1990-06-20 | Hoechst Aktiengesellschaft | Neue Silanderivate, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung als Schädlingsbekämpfungsmittel |
-
1988
- 1988-07-15 DE DE3823979A patent/DE3823979A1/de not_active Withdrawn
-
1989
- 1989-07-07 DE DE58907486T patent/DE58907486D1/de not_active Expired - Fee Related
- 1989-07-07 ES ES89112427T patent/ES2052824T3/es not_active Expired - Lifetime
- 1989-07-07 AT AT8989112427T patent/ATE104673T1/de not_active IP Right Cessation
- 1989-07-07 EP EP89112427A patent/EP0350804B1/de not_active Expired - Lifetime
- 1989-07-13 US US07/379,094 patent/US5028706A/en not_active Expired - Fee Related
- 1989-07-13 JP JP1179198A patent/JPH0269486A/ja active Pending
- 1989-07-14 IL IL9097289A patent/IL90972A/he not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ATE104673T1 (de) | 1994-05-15 |
| IL90972A0 (en) | 1990-02-09 |
| US5028706A (en) | 1991-07-02 |
| JPH0269486A (ja) | 1990-03-08 |
| DE3823979A1 (de) | 1990-01-18 |
| EP0350804B1 (de) | 1994-04-20 |
| DE58907486D1 (de) | 1994-05-26 |
| ES2052824T3 (es) | 1994-07-16 |
| EP0350804A3 (en) | 1990-12-19 |
| EP0350804A2 (de) | 1990-01-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RH | Patent void |