2,2'-Bithiophene-5,5'-diboronic acid bis(pinacol) ester supplier

Name
2,2'-Bithiophene-5,5'-diboronic acid bis(pinacol) ester
EINECS
CAS No. 239075-02-6
Article Data10
CAS DataBase
Density 1.17g/cm³
Solubility
Melting Point 208-212 °C
Formula C₂₀H₂₈B₂O₄S₂
Boiling Point 530.458 °C at 760 mmHg
Molecular Weight 418.194
Flash Point 274.612 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
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%;
PSA 93.40000
LogP 4.07500

Synthetic route

: 492-97-7
2,2'-Bithiophene

: 25015-63-8
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

Conditions	Yield
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

: 492-97-7
2,2'-Bithiophene

: 10294-34-5
boron trichloride

: 239075-02-6
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

Conditions

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%

...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

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%

: 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

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%

: 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

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%

: 61676-62-8
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

: 1408285-51-7
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

Conditions	Yield
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

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

...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

Conditions	Yield
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

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

: 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

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

...Expand

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

C: 239075-02-6
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In toluene at 60℃; for 17h;

...Expand

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

C: 886-65-7, 82598-07-0
1,4-diphenyl-1,3-butadiene

D: 239075-02-6
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; toluene at 65℃; for 26h; Reagent/catalyst; Solvent; Temperature;

...Expand

: 61676-62-8
2-Isopropoxy-4,4,5,5-tetramethyl-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

Conditions	Yield
Multi-step reaction with 2 steps 1.1: methyllithium / diethyl ether; tetrahydrofuran / 2 h / -100 °C 1.2: 13 h / -100 - 20 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 16 h / 60 °C View Scheme
Multi-step reaction with 2 steps 1.1: methyllithium / diethyl ether; tetrahydrofuran / 2 h / -100 °C 1.2: 13 h / -100 - 20 °C 2.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 4 h / 100 °C / Microwave irradiation View Scheme

: 61676-62-8
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

A: (Z)-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

Conditions	Yield
Multi-step reaction with 2 steps 1.1: methyllithium / diethyl ether; tetrahydrofuran / 2 h / -100 °C 1.2: 13 h / -100 - 20 °C 2.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 17 h / 60 °C View Scheme
Multi-step reaction with 2 steps 1.1: methyllithium / diethyl ether; tetrahydrofuran / 2 h / -100 °C 1.2: 13 h / -100 - 20 °C 2.1: tetrakis(triphenylphosphine) palladium(0) / toluene; 1,4-dioxane / 26 h / 65 °C View Scheme

: 5419-55-6
Triisopropyl borate

: 239075-02-6
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 2,3-dimethyl-2,3-butane diol / hexane / 90 °C 2: tetrakis(triphenylphosphine) palladium(0) / toluene / 4 h / 100 °C / Microwave irradiation View Scheme
Multi-step reaction with 3 steps 1.1: 2,3-dimethyl-2,3-butane diol / hexane / 90 °C 2.1: methyllithium / diethyl ether; tetrahydrofuran / 2 h / -100 °C 2.2: 13 h / -100 - 20 °C 3.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 16 h / 60 °C View Scheme
Multi-step reaction with 3 steps 1.1: 2,3-dimethyl-2,3-butane diol / hexane / 90 °C 2.1: methyllithium / diethyl ether; tetrahydrofuran / 2 h / -100 °C 2.2: 13 h / -100 - 20 °C 3.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 4 h / 100 °C / Microwave irradiation View Scheme

: 5419-55-6
Triisopropyl borate

A: (Z)-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

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 2,3-dimethyl-2,3-butane diol / hexane / 90 °C 2.1: methyllithium / diethyl ether; tetrahydrofuran / 2 h / -100 °C 2.2: 13 h / -100 - 20 °C 3.1: tetrakis(triphenylphosphine) palladium(0) / toluene / 17 h / 60 °C View Scheme
Multi-step reaction with 3 steps 1.1: 2,3-dimethyl-2,3-butane diol / hexane / 90 °C 2.1: methyllithium / diethyl ether; tetrahydrofuran / 2 h / -100 °C 2.2: 13 h / -100 - 20 °C 3.1: tetrakis(triphenylphosphine) palladium(0) / toluene; 1,4-dioxane / 26 h / 65 °C View Scheme

: 299963-46-5
5-bromo-2-hexylisoindoline-1,3-dione

: 239075-02-6
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

: 1572256-13-3
5,5'-(2,2'-bithiophene-5,5'-diyl)bis(2-hexylphthalimide)

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 0.5h; Reagent/catalyst; Suzuki Coupling; Microwave irradiation; Inert atmosphere;	100%

: 2-bromo-3-(6-(4-methoxyphenoxy)hexyl)thiophene

: 239075-02-6
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

: 3,3′′′-bis(6-(4-methoxyphenoxy)hexyl)-2,2′:5′,2″:5″,2′′′-quaterthiophene

Conditions

Conditions	Yield
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; potassium carbonate In methanol; toluene at 90℃; for 24h; Inert atmosphere; Schlenk technique;	97%

: 669763-44-4
(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-iodobenzene

: 239075-02-6
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

: 1262996-39-3
5,5'-bis-(4-[2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy]phenyl)-[2,2']-bithiophene

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; silver(l) oxide In 1,4-dioxane at 70℃; Suzuki-Miyaura coupling; Inert atmosphere;	91%

: 1046451-11-9
(S)-4-iodo-1-(6-(2-tert-butoxycarbonylamino-3-phenylpropanoyloxy)hexyloxy)benzene

: 239075-02-6
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

: 1262996-44-0
(S,S)-5,5'-bis-(4-(6-(2-tert-butoxycarbonylamino-3-phenylpropanoyloxy)hexyloxy)phenyl)-[2,2']-bithiophene

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; silver(l) oxide In 1,4-dioxane at 70℃; Suzuki-Miyaura coupling; Inert atmosphere;	91%

: 477727-73-4
2-(thiophen-2-yl)vinyl bromide

: 239075-02-6
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

: C20H14S4

Conditions

Conditions	Yield
With sodium hydroxide; bis(dibenzylideneacetone)-palladium(0); tri tert-butylphosphoniumtetrafluoroborate In tetrahydrofuran; water at 30℃; for 20h;	89%

: 683251-61-8
methyl 2-(2-bromothiophene-3-yl)acetate

: 239075-02-6
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

: 1352412-54-4
C22H18O4S4

Conditions

Conditions	Yield
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride; potassium carbonate In methanol; toluene at 70℃; for 0.25h; Suzuki coupling;	85%

: 4-bromo-9-butoxy-2,7-bis(2-ethylhexyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone

: 239075-02-6
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

: 9,9'-([2,2'-bithiophene]-5,5'-diyl)bis(4-butoxy-2,7-bis(2-ethylhexyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone)

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene for 24h; Reflux;	85%

: 4-bromo-9-(butylamino)-2,7-bis(2-ethylhexyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone

: 239075-02-6
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

: 9,9'-([2,2'-bithiophene]-5,5'-diyl)bis(4-(butylamino)-2,7-bis(2-ethylhexyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone)

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene for 24h; Reflux;	80%

: 1428236-28-5
C25H22BBr

: 239075-02-6
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

: 1499190-99-6
C58H48B2S2

Conditions

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium phosphate; XPhos In tetrahydrofuran; water at 20℃; for 3.5h; Suzuki-Miyaura Coupling; Reflux; Inert atmosphere;	77%

: C25H21BrO3S

: C53H41BrN4O3S

: 239075-02-6
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

: C86H66N4O6S4

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; tetramethylammonium bromide; sodium carbonate at 80℃; for 24h; Suzuki Coupling; Inert atmosphere;	76%

...Expand

: 2-bromo-4-methyl-3-(3-(pyren-1-yl)tetraethoxy)thiophene

: C57H49BrN4O5S

: 239075-02-6
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

: C94H82N4O10S4

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; tetramethylammonium bromide; sodium carbonate at 80℃; for 24h; Suzuki Coupling; Inert atmosphere;	76%

...Expand

: 1219042-09-7
2-[2-(2-(2-(4-iodophenoxy)ethoxy)ethoxy)ethoxy]ethanol

: 239075-02-6
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

: 1448006-24-3
C36H46O10S2

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In N,N-dimethyl-formamide at 50℃; for 16h; Inert atmosphere;	75%

: 1126528-86-6
C35H43BrN2S

: 239075-02-6
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

: 1505470-95-0
5,5'-bis(7-(9,9-dioctyl-9H-fluoren-2-yl)-2,1,3-benzothiadiazol-4-yl)-2,2'-bithiophene

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); Aliquat 336; potassium carbonate In water; toluene for 24h; Suzuki Coupling; Inert atmosphere; Reflux;	75%

: 4-bromo-9-(butylthio)-2,7-bis(2-ethylhexyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone

: 239075-02-6
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

: 9,9'-([2,2'-bithiophene]-5,5'-diyl)bis(4-(butylthio)-2,7-bis(2-ethylhexyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone)

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene for 12h; Reflux;	75%

: 14243-64-2
(triphenylphosphine)gold(I) chloride

: 239075-02-6
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

: 1333204-13-9
5,5'-bis[(triphenylphosphine)gold(I)]-2,2'-bithiophene

Conditions

Conditions	Yield
With cesium carbonate In isopropyl alcohol addn. of PPh3AuCl, 2,2'-bithiophene-5,5'-diboronic acid bis(pinacol ester) and Cs2CO3 under Ar, suspending in 2-propanol, stirring under Ar at 40°C for 24 h; removal of 2-propanol by rotary evapn., extn. into dry CH2Cl2, filtration, removal of CH2Cl2 by rotary evapn., trituration with pentane, filtration; elem. anal.;	69%

: 2712-78-9
bis-[(trifluoroacetoxy)iodo]benzene

: 239075-02-6
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

: 1417418-27-9
phenyl(5'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[2,2'-bithiophen]-5-yl)iodonium trifluoroacetate

Conditions

Conditions	Yield
With acetic acid In dichloromethane at 20℃; for 6h; regioselective reaction;	68%

: methyl 4-(5-iodothiophen-2-yl)butanoate

: 239075-02-6
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

: C26H26O4S4

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In ethanol; water; toluene for 18h; Inert atmosphere; Reflux;	60%

: 1240575-39-6
2-bromodithieno[3,2-b:2',3'-d]phosphole oxide

: 239075-02-6
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

: 1240575-50-1
C36H20O2P2S6

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); cesium fluoride In tetrahydrofuran at 70℃; for 72h; Suzuki-Miyaura crosscoupling; Inert atmosphere;	58%

: 1210390-72-9
N,N’-bis(rac-2-ethylhexyl)-6-bromoisoindigo

: 239075-02-6
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

: 1210390-76-3
C72H86N4O4S2

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); tetraethylammonium hydroxide; tris-(o-tolyl)phosphine In toluene at 85℃; Suzuki coupling; Inert atmosphere;	57%

: 239075-02-6
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

: 111881-86-8
methyl 2-(2-bromothiophen-3-yl)ethan-1-ol

: 1427213-81-7
C20H18O2S4

Conditions

Conditions	Yield
With potassium fluoride; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride In methanol; toluene at 55℃; for 0.75h; Suzuki Coupling; Inert atmosphere;	56%
With potassium fluoride; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride In methanol; toluene at 55℃; for 0.75h; Suzuki Coupling; Inert atmosphere;	56%

: 239075-02-6
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

: 634916-49-7
6-bromo-2,3-dihydrothieno[3,2-b][1,4]oxathiine

: C20H14O2S6

Conditions

Conditions	Yield
With cesium fluoride; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane for 48h; Suzuki coupling; Heating;	47%

: 70654-71-6
4-bromo-2,6-dimethoxyphenol

: 239075-02-6
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

A: 4,4'-([2,2'-bithiophene]-5,5'-diyl)-bis(2,6-dimethoxyphenol)

B: 4-([2,2'-bithiophen]-5-yl)-2,6-dimethoxyphenol

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 130℃; for 0.7h; Suzuki Coupling; Microwave irradiation;	A 7% B 46%

...Expand

: 891182-24-4
3,7-dibromo-5,5-di-n-octyl-dibenzo[b,d]silole

: 239075-02-6
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

Polymer, Mw = 127000; Monomer(s): 2,7-dibromo-9,9-dioctyldibenzosilole; 2,5-bis(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-2,2-bithiophene: Polymer, Mw = 127000; Monomer(s): 2,7-dibromo-9,9-dioctyldibenzosilole; 2,5-bis(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-2,2-bithiophene

Conditions

Conditions	Yield
With Aliquat 336; sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; toluene for 48h; Suzuki coupling; Heating;	45%

: 891182-24-4
3,7-dibromo-5,5-di-n-octyl-dibenzo[b,d]silole

: 239075-02-6
5,5'-di(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-2,2'-bithiophene

poly(9,9-di-n-octyldibenzosilole-alt-bithiophene), Mw (GPC) = 127 KD, PDI = 3.7; prepared by Suzuki coupling reaction; monomer(s): 2,7-dibromo-9,9'-di-n-octyldibenzosilole; 2,5'-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)bithiophene: poly(9,9-di-n-octyldibenzosilole-alt-bithiophene), Mw (GPC) = 127 KD, PDI = 3.7; prepared by Suzuki coupling reaction; monomer(s): 2,7-dibromo-9,9'-di-n-octyldibenzosilole; 2,5'-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)bithiophene

Conditions

Conditions	Yield
With Aliquat 336; sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In toluene for 48h; Suzuki coupling reaction; Heating;	45%

2,2'-Bithiophene-5,5'-diboronic acid bis(pinacol) ester 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

Product Name

2,2'-Bithiophene-5,5'-diboronic acid bis(pinacol) ester

Synthetic route

2,2'-Bithiophene-5,5'-diboronic acid bis(pinacol) ester Specification

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