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CAS No.: | 365564-11-0 |
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Name: | 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-pyrrole |
Article Data: | 26 |
Molecular Structure: | |
Formula: | C19H36BNO2Si |
Molecular Weight: | 349.397 |
Synonyms: | 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tris(1-methylethyl)silyl]-1H-pyrrole;tri(propan-2-yl)-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrol-1-yl]silane; |
Density: | 0.941g/cm3 |
Melting Point: | 59 °C |
Boiling Point: | 383.588oC at 760 mmHg |
Flash Point: | 185.788oC |
PSA: | 23.39000 |
LogP: | 4.81090 |
N-triisopropylsilylpyrrole
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole
Conditions | Yield |
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With 1-(2-borylphenyl)-2,2,6,6-tetramethylpiperidine dimer In chloroform at 80℃; for 16h; | 98% |
With Cp*Rh(η4-C6Me6) In cyclohexane at 150℃; for 41h; | 81% |
Stage #1: N-triisopropylsilylpyrrole With 2,6-dimethylpyridine; aluminum (III) chloride; boron trichloride In n-heptane; dichloromethane at 20℃; for 16h; Inert atmosphere; Stage #2: 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With triethylamine In n-heptane; dichloromethane for 0.25h; Inert atmosphere; | 52% |
With poly((2-(piperidin-1-ium-1-yl)-5-vinylphenyl)trifluoroborate) In chloroform-d1 at 90℃; for 16h; Reagent/catalyst; Inert atmosphere; Glovebox; Sealed tube; |
2,3-dimethyl-2,3-butane diol
N-triisopropylsilylpyrrole
3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole
Conditions | Yield |
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With Et3N In dichloromethane byproducts: Et3NH-AlCl4; to borenium cation made in situ (in Schlenk, to soln. Et2N (CH2Cl2) added Cl4CatBCl, AlCl3; stirred) at 20°C arene added (CH2Cl2); excessEt3N added; pinacol added; stirred for 32 h;; (11)B (1H) NMR; volatiless remowed under vac; extracted (hexane); filtered through silica; removal of solvent;; | 95% |
2,3-dimethyl-2,3-butane diol
3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole
Conditions | Yield |
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With triethylamine In dichloromethane for 3h; | 90% |
With triethylamine In toluene at 20℃; for 1h; Schlenk technique; | 45% |
With triethylamine In dichloromethane for 1h; Inert atmosphere; | 101 mg |
With triethylamine at 0 - 20℃; for 1h; Inert atmosphere; | |
With triethylamine In 1,2-dichloro-ethane at 20℃; Schlenk technique; Inert atmosphere; |
2,3-dimethyl-2,3-butane diol
C13H24BCl2NSi
3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole
Conditions | Yield |
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With triethylamine at 20℃; for 0.5h; | 90% |
2,3-dimethyl-2,3-butane diol
N-triisopropylsilylpyrrole
boron trichloride
3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole
Conditions | Yield |
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With AlCl3; 2,6-lutidine In dichloromethane 1:1 mixt. of BCl3 and AlCl, pinacol (2.3-3.0 equiv.) and lutidine (15 equiv.) for 14 h; | 90% |
2,3-dimethyl-2,3-butane diol
N-triisopropylsilylpyrrole
3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole
Conditions | Yield |
---|---|
Stage #1: N-triisopropylsilylpyrrole With 2,6-dimethylpyridine; aluminum (III) chloride; boron trichloride In n-heptane; dichloromethane at 20℃; for 14h; Inert atmosphere; Stage #2: 2,3-dimethyl-2,3-butane diol With triethylamine In n-heptane; dichloromethane at 20℃; for 0.5h; Inert atmosphere; | 90% |
2,3-dimethyl-2,3-butane diol
N-triisopropylsilylpyrrole
3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole
Conditions | Yield |
---|---|
With Et3N In dichloromethane byproducts: Et3NH-AlCl4; to borenium cation made in situ (in Schlenk, to soln. Et2N (CH2Cl2) added CatBCl, AlCl3; stirred) at 20°C arene added (CH2Cl2); excess Et3N added; pinacol added; stirred for 32 h;; (11)B (1H) NMR; volatiless remowed under vac; extracted (hexane); filtered through silica; removal of solvent;; | 89% |
3-bromo-1-triisopropylsilanyl-1H-pyrrole
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole
Conditions | Yield |
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With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; triethylamine; dichloro bis(acetonitrile) palladium(II) In toluene at 90℃; for 18h; | 85% |
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; triethylamine; dichloro bis(acetonitrile) palladium(II) In toluene at 90℃; for 18h; | 85% |
With dichloro bis(acetonitrile) palladium(II); triethylamine In toluene 1.2 equiv. pinacol borane react. catalyzed by 3% (PdCl2(CH3CN)2), 9% dialkylmonophosphino biaryl (toluene) at 90°C; | 79% |
3-iodo-1-(triisopropylsilyl)-1H-pyrrole
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole
Conditions | Yield |
---|---|
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; dichloro bis(acetonitrile) palladium(II); triethylamine In toluene at 20 - 90℃; Inert atmosphere; | 80% |
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; dichloro bis(acetonitrile) palladium(II); triethylamine In toluene |
N-triisopropylsilylpyrrole
bis(pinacol)diborane
3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole
Conditions | Yield |
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bis(1,5-cyclooctadiene)diiridium(I) dichloride; 4,4'-di-tert-butyl-2,2'-bipyridine In octane at 80℃; for 16h; | 79% |
With [IrCl(COD)]2 In octane at 80℃; for 48h; Inert atmosphere; | 77% |
With 4,4'-di-tert-butyl-2,2'-bipyridine; bis(1,5-cyclooctadiene)diiridium(I) dichloride In hexane at 100℃; for 0.833333h; microwave irradiation; | |
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4′-di-(tert-butyl)-2,2′-bipyridyl In tetrahydrofuran at 80℃; for 24h; High pressure; Inert atmosphere; regioselective reaction; |