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239075-02-6

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Basic Information
CAS No.: 239075-02-6
Name: 2,2'-Bithiophene-5,5'-diboronic acid bis(pinacol) ester
Article Data: 10
Molecular Structure:
Molecular Structure of 239075-02-6 (2,2'-Bithiophene-5,5'-diboronic acid bis(pinacol) ester)
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
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Synthetic route
492-97-7

2,2'-Bithiophene

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4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

239075-02-6

5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

Conditions
ConditionsYield
With iridium-bipyridine periodic mesoporous organosilica In cyclohexane at 80℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;99%
76-09-5

2,3-dimethyl-2,3-butane diol

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2,2'-Bithiophene

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boron trichloride

239075-02-6

5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

Conditions
ConditionsYield
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%
...Expand
76-09-5

2,3-dimethyl-2,3-butane diol

492-97-7

2,2'-Bithiophene

239075-02-6

5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

Conditions
ConditionsYield
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%
492-97-7

2,2'-Bithiophene

73183-34-3

bis(pinacol)diborane

239075-02-6

5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

Conditions
ConditionsYield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In hexane at 50℃; for 0.25h;82%
61676-62-8

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

492-97-7

2,2'-Bithiophene

239075-02-6

5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

Conditions
ConditionsYield
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%
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2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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4,4,5,5-tetramethyl-2-(5-(trimethylstannyl)thiophen-2-yl)-1,3,2-dioxaborolane

239075-02-6

5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) In toluene at 100℃; for 4h; Microwave irradiation;52%
76-09-5

2,3-dimethyl-2,3-butane diol

492-97-7

2,2'-Bithiophene

A

479719-88-5

2-([2,2'-bithiophen]-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

B

239075-02-6

5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

Conditions
ConditionsYield
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
...Expand
76-09-5

2,3-dimethyl-2,3-butane diol

1412912-74-3

5,5′-bis(dichloroboryl)-2,2′-bithiophene

239075-02-6

5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

Conditions
ConditionsYield
With triethylamine at 20℃; for 0.5h; Inert atmosphere;44 mg
With triethylamine at 0 - 20℃; for 1h; Inert atmosphere;
492-97-7

2,2'-Bithiophene

239075-02-6

5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

Conditions
ConditionsYield
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
103-64-0

bromostyrene

1408285-51-7

4,4,5,5-tetramethyl-2-(5-(trimethylstannyl)thiophen-2-yl)-1,3,2-dioxaborolane

A

(E)-4,4,5,5-tetramethyl-2-(5-styrylthiophen-2-yl)-1,3,2-dioxaborolane

B

239075-02-6

5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In N,N-dimethyl-formamide at 60℃; for 16h;
...Expand
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Specification

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