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1161009-89-7

1161009-89-7

Identification

  • Product Name:4,4,5,5-tetramethyl-2-(9,9'-spirobi[9H-fluoren]-4-yl)-1,3,2-Dioxaborolane

  • CAS Number: 1161009-89-7

  • EINECS:

  • Molecular Weight:442.365

  • Molecular Formula: C31H27BO2

  • HS Code:

  • Mol File:1161009-89-7.mol

Synonyms:4,4,5,5-tetramethyl-2-(9,9'-spirobi[9H-fluoren]-4-yl)-1,3,2-Dioxaborolane;9,9'-Spirobi[9H-fluoren]-4-ylboronic acid pinacol ester

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  • Manufacture/Brand:TRC
  • Product Description:4-(9,9''-Spirobifluorenyl)pinacolboronate
  • Packaging:100mg
  • Price:$ 70
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2-(9,9'-Spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane >98.0%(HPLC)(T)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2-(9,9'-Spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane >98.0%(HPLC)(T)
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  • Manufacture/Brand:Crysdot
  • Product Description:2-(9,9'-Spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 97%
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  • Manufacture/Brand:Crysdot
  • Product Description:2-(9,9'-Spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 97%
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  • Manufacture/Brand:Ambeed
  • Product Description:2-(9,9'-Spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 97%
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  • Manufacture/Brand:Ambeed
  • Product Description:2-(9,9'-Spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 97%
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  • Manufacture/Brand:Ambeed
  • Product Description:2-(9,9'-Spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 97%
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  • Manufacture/Brand:Ambeed
  • Product Description:2-(9,9'-Spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 97%
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  • Manufacture/Brand:Alichem
  • Product Description:2-(9,9'-Spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
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Relevant articles and documentsAll total 11 Articles be found

C1-Linked Spirobifluorene Dimers: Pure Hydrocarbon Hosts for High-Performance Blue Phosphorescent OLEDs

Sicard, Lambert J.,Li, Hong-Cheng,Wang, Qiang,Liu, Xiang-Yang,Jeannin, Olivier,Rault-Berthelot, Jo?lle,Liao, Liang-Sheng,Jiang, Zuo-Quan,Poriel, Cyril

, p. 3848 - 3853 (2019)

Reported here are C1-linked spiro-bifluorene dimers. A comprehensive study is carried out to analyze the electronic properties of these highly twisted structures. This work shows that the C1-position enables the design of pure hydrocarbon materials, with a high triplet energy, for hosting blue phosphors in efficient phosphorescent OLEDs (PhOLEDs). To date, this work describes the highest performance of blue PhOLEDs ever reported for pure hydrocarbons (external quantum efficiency of ca. 23 %), thus highlighting the potential of the C1-spirobifluorene scaffold in organic electronics.

Organometallic complex and organic elcetroluminescent device including the same

-

Paragraph 0192-0194, (2021/08/10)

The present invention provides an organic metal complex contributing to the substantial light color and light efficiency improvement of an organic electroluminescent device. 1 Is a perspective view of an organic electroluminescent device according to the

NITROGEN-CONTAINING FUSED HETEROCYCLIC RING COMPOUND AND APPLICATION THEREOF

-

Paragraph 0344-0346, (2020/08/12)

The present invention relates to a nitrogen-containing fused heterocyclic ring compound and application thereof. The compound has the structural formula (I): using the described compound, it is possible to fabricate a device having higher stability and a longer service life.

COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF

-

Paragraph 0225; 0517; 0622-0625; 0701, (2020/06/02)

The present invention provides: a novel mixture capable of improving luminous efficiency, stability, and lifespan of an element; an organic electronic element using the same; and an electronic device thereof. By using the mixture according to the present

ORGANIC MIXTURE, COMPOSITION, AND ORGANIC ELECTRONIC COMPONENT

-

Paragraph 0183; 0184, (2020/01/03)

Disclosed in the present application is an organic mixture. The organic mixture comprises two organic compounds H1 and H2. The organic compound H1 has electron transmission performance, and the organic compound H1 satisfies: Δ((LUMO+1)?LUMO)≥0.1 eV, and min((LUMO(H1)?HOMO(H2), LUMO(H2)?HOMO(H1))≤min(ET(H1), ET(H2)). The organic compound H1 and the organic compound H2 are easy to form exciplexes and have balanced electron transmission properties, the organic compound Hi has high stability of electron transmission, and accordingly the efficiency and the service life of related electronic components can be effectively improved, and a feasible solution for improving overall performance of the electronic components is provided.

Process route upstream and downstream products

Process route

4-bromo-9,9’-spirobi[9H-fluorene]
1161009-88-6

4-bromo-9,9’-spirobi[9H-fluorene]

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

2-(9,9'-spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
1161009-89-7

2-(9,9'-spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
Conditions Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In toluene; for 16h; Reflux;
96%
With potassium acetate; bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; at 100 ℃; for 12h; Inert atmosphere;
82.1%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 120 ℃;
71%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; for 24h; Reflux;
62.5%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium diacetate; In toluene; for 16h; Reflux;
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
61676-62-8

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

4-bromo-9,9’-spirobi[9H-fluorene]
1161009-88-6

4-bromo-9,9’-spirobi[9H-fluorene]

2-(9,9'-spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
1161009-89-7

2-(9,9'-spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
Conditions Yield
4-bromo-9,9’-spirobi[9H-fluorene]; With n-butyllithium; In tetrahydrofuran; at -78 ℃; Inert atmosphere;
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; at -78 - 20 ℃; for 12h;
90%
4-bromo-9,9’-spirobi[9H-fluorene]; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 2h; Inert atmosphere;
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; at -78 - 20 ℃; for 12h;
80%
4-bromo-9,9’-spirobi[9H-fluorene]; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h;
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; at -78 - 20 ℃; for 12h;
73%
4-bromo-9,9’-spirobi[9H-fluorene]; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; hexane; at -78 - 20 ℃; Inert atmosphere;
72%
4-bromo-9,9’-spirobi[9H-fluorene]
1161009-88-6

4-bromo-9,9’-spirobi[9H-fluorene]

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

2-(9,9'-spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
1161009-89-7

2-(9,9'-spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
Conditions Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In toluene; for 16h; Reflux;
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
61676-62-8

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

4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

2-(9,9'-spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
1161009-89-7

2-(9,9'-spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
Conditions Yield
With n-butyllithium; In tetrahydrofuran; at -78 - 20 ℃; for 1h; Inert atmosphere;
77%
4-bromo-9H-fluorene-9-one
4269-17-4

4-bromo-9H-fluorene-9-one

2-(9,9'-spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
1161009-89-7

2-(9,9'-spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1.1: magnesium / diethyl ether / Inert atmosphere
1.2: 0.5 h
2.1: hydrogenchloride; acetic acid / water / 1.17 h / 120 °C
3.1: potassium acetate / bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 12 h / 100 °C / Inert atmosphere
With hydrogenchloride; potassium acetate; magnesium; acetic acid; bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; diethyl ether; water;
Multi-step reaction with 2 steps
1: tetrahydrofuran / Inert atmosphere
2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium diacetate / toluene / 16 h / Reflux
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium diacetate; In tetrahydrofuran; toluene;
Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
1.2: Inert atmosphere
2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / toluene / 16 h / Reflux
With n-butyllithium; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In tetrahydrofuran; hexane; toluene;
2-Bromobiphenyl
2052-07-5

2-Bromobiphenyl

2-(9,9'-spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
1161009-89-7

2-(9,9'-spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
Conditions Yield
Multi-step reaction with 3 steps
1.1: magnesium / diethyl ether / Inert atmosphere
1.2: 0.5 h
2.1: hydrogenchloride; acetic acid / water / 1.17 h / 120 °C
3.1: potassium acetate / bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 12 h / 100 °C / Inert atmosphere
With hydrogenchloride; potassium acetate; magnesium; acetic acid; bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; diethyl ether; water;
Multi-step reaction with 3 steps
1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
2: tetrahydrofuran / Inert atmosphere
3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium diacetate / toluene / 16 h / Reflux
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; n-butyllithium; palladium diacetate; In tetrahydrofuran; hexane; toluene;
C<sub>25</sub>H<sub>17</sub>BrO

C25H17BrO

2-(9,9'-spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
1161009-89-7

2-(9,9'-spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: hydrogenchloride; acetic acid / water / 1.17 h / 120 °C
2: potassium acetate / bis-triphenylphosphine-palladium(II) chloride / 1,4-dioxane / 12 h / 100 °C / Inert atmosphere
With hydrogenchloride; potassium acetate; acetic acid; bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; water;
methyl 2-iodo-3-bromobenzoic acid
121772-84-7

methyl 2-iodo-3-bromobenzoic acid

2-(9,9'-spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
1161009-89-7

2-(9,9'-spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h / Inert atmosphere
1.2: 0.33 h / Reflux
2.1: sodium hydroxide; ethanol / 6 h
3.1: methanesulfonic acid / 24 h / 30 °C
4.1: tetrahydrofuran / Inert atmosphere
5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium diacetate / toluene / 16 h / Reflux
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium(0); methanesulfonic acid; ethanol; palladium diacetate; sodium hydroxide; In tetrahydrofuran; toluene;
Multi-step reaction with 5 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h / Inert atmosphere
1.2: Reflux
2.1: sodium hydroxide / ethanol / 6 h / Reflux
3.1: methanesulfonic acid / 24 h / 30 °C
4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
4.2: Inert atmosphere
5.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / toluene / 16 h / Reflux
With tetrakis(triphenylphosphine) palladium(0); n-butyllithium; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; methanesulfonic acid; potassium acetate; sodium hydroxide; In tetrahydrofuran; ethanol; hexane; toluene;
phenylboronic acid
98-80-6

phenylboronic acid

2-(9,9'-spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
1161009-89-7

2-(9,9'-spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
Conditions Yield
Multi-step reaction with 5 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h / Inert atmosphere
1.2: 0.33 h / Reflux
2.1: sodium hydroxide; ethanol / 6 h
3.1: methanesulfonic acid / 24 h / 30 °C
4.1: tetrahydrofuran / Inert atmosphere
5.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium diacetate / toluene / 16 h / Reflux
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium(0); methanesulfonic acid; ethanol; palladium diacetate; sodium hydroxide; In tetrahydrofuran; toluene;
Multi-step reaction with 5 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h / Inert atmosphere
1.2: Reflux
2.1: sodium hydroxide / ethanol / 6 h / Reflux
3.1: methanesulfonic acid / 24 h / 30 °C
4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
4.2: Inert atmosphere
5.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / toluene / 16 h / Reflux
With tetrakis(triphenylphosphine) palladium(0); n-butyllithium; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; methanesulfonic acid; potassium acetate; sodium hydroxide; In tetrahydrofuran; ethanol; hexane; toluene;
C<sub>14</sub>H<sub>11</sub>BrO<sub>2</sub>

C14H11BrO2

2-(9,9'-spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
1161009-89-7

2-(9,9'-spirobi[fluoren]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: sodium hydroxide; ethanol / 6 h
2: methanesulfonic acid / 24 h / 30 °C
3: tetrahydrofuran / Inert atmosphere
4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium diacetate / toluene / 16 h / Reflux
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; methanesulfonic acid; ethanol; palladium diacetate; sodium hydroxide; In tetrahydrofuran; toluene;
Multi-step reaction with 4 steps
1.1: sodium hydroxide / ethanol / 6 h / Reflux
2.1: methanesulfonic acid / 24 h / 30 °C
3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C
3.2: Inert atmosphere
4.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / toluene / 16 h / Reflux
With n-butyllithium; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; methanesulfonic acid; potassium acetate; sodium hydroxide; In tetrahydrofuran; ethanol; hexane; toluene;

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