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CAS No.: | 239075-02-6 |
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Name: | 2,2'-Bithiophene-5,5'-diboronic acid bis(pinacol) ester |
Article Data: | 10 |
Molecular Structure: | |
Formula: | C20H28B2O4S2 |
Molecular Weight: | 418.194 |
Synonyms: | 5,5'-Di(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,2'-bithiophene;2,2'-BITHIOPHENE-5,5'-DIBORONIC ACID BIS(PINACOL) ESTER, 97%; |
Density: | 1.17g/cm3 |
Melting Point: | 208-212 °C |
Boiling Point: | 530.458 °C at 760 mmHg |
Flash Point: | 274.612 °C |
PSA: | 93.40000 |
LogP: | 4.07500 |
2,2'-Bithiophene
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
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With iridium-bipyridine periodic mesoporous organosilica In cyclohexane at 80℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction; | 99% |
2,3-dimethyl-2,3-butane diol
2,2'-Bithiophene
boron trichloride
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
With AlCl3; Me2NTol In dichloromethane 1:1 mixt. of BCl3 and AlCl, pinacol (2.3-3.0 equiv.) and lutidine (15 equiv.) for 18 h; | 83% |
2,3-dimethyl-2,3-butane diol
2,2'-Bithiophene
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
Stage #1: 2,2'-Bithiophene With aluminum (III) chloride; boron trichloride; Dimethyl-p-toluidine In dichloromethane for 24h; Stage #2: 2,3-dimethyl-2,3-butane diol With triethylamine In dichloromethane at 20℃; for 0.5h; | 83% |
2,2'-Bithiophene
bis(pinacol)diborane
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In hexane at 50℃; for 0.25h; | 82% |
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
2,2'-Bithiophene
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
Stage #1: 2,2'-Bithiophene With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; | 72% |
Stage #1: 2,2'-Bithiophene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane for 1.41667h; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In hexane at -78 - 20℃; for 16h; | 57% |
Stage #1: 2,2'-Bithiophene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran; hexane for 0.5h; Heating; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; hexane at -78 - -20℃; for 19h; | 53% |
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
4,4,5,5-tetramethyl-2-(5-(trimethylstannyl)thiophen-2-yl)-1,3,2-dioxaborolane
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In toluene at 100℃; for 4h; Microwave irradiation; | 52% |
2,3-dimethyl-2,3-butane diol
2,2'-Bithiophene
A
2-([2,2'-bithiophen]-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
B
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
Stage #1: 2,2'-Bithiophene With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 4h; Stage #2: With Trimethyl borate In tetrahydrofuran for 2h; Stage #3: 2,3-dimethyl-2,3-butane diol In tetrahydrofuran for 12h; Further stages.; | A 44% B 0.35 g |
2,3-dimethyl-2,3-butane diol
5,5′-bis(dichloroboryl)-2,2′-bithiophene
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
With triethylamine at 20℃; for 0.5h; Inert atmosphere; | 44 mg |
With triethylamine at 0 - 20℃; for 1h; Inert atmosphere; |
2,2'-Bithiophene
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aluminum (III) chloride; boron trichloride; Dimethyl-p-toluidine / dichloromethane / 24 h / Inert atmosphere 2: triethylamine / 0.5 h / 20 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: aluminum (III) chloride; BCl3*C9H13N / dichloromethane / 24 h / 20 °C / Schlenk technique; Inert atmosphere 2: triethylamine / 1 h / 0 - 20 °C / Inert atmosphere View Scheme |
bromostyrene
4,4,5,5-tetramethyl-2-(5-(trimethylstannyl)thiophen-2-yl)-1,3,2-dioxaborolane
B
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene
Conditions | Yield |
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With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In N,N-dimethyl-formamide at 60℃; for 16h; |
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The 2,2'-Bithiophene-5,5'-diboronic acid bis(pinacol) ester with cas registry number of 239075-02-6, belongs to the following product categories: (1)Organoborons; (2)Thiophene; (3)Boronate Esters; (4)Boronic Acids and Derivatives; (5)Heteroaryl. Its systematic name is 2,2'-(2,2'-bithiene-5,5'-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane).
Physical properties about this chemical are: (1)#H bond acceptors: 4; (2)#H bond donors: 0; (3)#Freely Rotating Bonds: 3; (4)Polar Surface Area: 93.4 Å2; (5)Index of Refraction: 1.546; (6)Molar Refractivity: 113.15 cm3; (7)Molar Volume: 357.565 cm3; (8)Polarizability: 44.856×10-24cm3; (9)Surface Tension: 40.164 dyne/cm; (10)Enthalpy of Vaporization: 77.546 kJ/mol; (11)Vapour Pressure: 0 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES:O1B(OC(C1(C)C)(C)C)c2sc(cc2)c4sc(B3OC(C)(C)C(O3)(C)C)cc4;
(2)InChI:InChI=1/C20H28B2O4S2/c1-17(2)18(3,4)24-21(23-17)15-11-9-13(27-15)14-10-12-16(28-14)22-25-19(5,6)20(7,8)26-22/h9-12H,1-8H3;
(3)InChIKey:XWWXVHGWYCXJCJ-UHFFFAOYAU;
(4)Std. InChI:InChI=1S/C20H28B2O4S2/c1-17(2)18(3,4)24-21(23-17)15-11-9-13(27-15)14-10-12-16(28-14)22-25-19(5,6)20(7,8)26-22/h9-12H,1-8H3;
(5)Std. InChIKey:XWWXVHGWYCXJCJ-UHFFFAOYSA-N