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171408-76-7

171408-76-7

171408-76-7

Identification

Synonyms:2-Bromo-9,9'-spirobi[9H-fluorene];2-Bromo-9-spirobifluorene;

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Chemical Properties

  • Appearance/Colour:off-white crystal

  • Melting Point: 184 °C

  • Boiling Point: 517.213 °C at 760 mmHg

  • Flash Point:259.774 °C

  • Density: 1.522 g/cm3

  • Storage Temp.:Sealed in dry,Room Temperature

  • Vapor Pressure: 0-0.001Pa at 20-50℃

  • PSA: 0.00000

  • LogP: 6.79260

Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price view more

  • Manufacture/Brand
  • Product Description
  • Packaging
  • Price
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  • Purchase
  • Manufacture/Brand:TRC
  • Product Description:2-Bromo-9,9''-spirobi[fluorene]
  • Packaging:50mg
  • Price:$ 45
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2-Bromo-9,9'-spirobi[9H-fluorene] >98.0%(GC)
  • Packaging:1g
  • Price:$ 15
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:2-Bromo-9,9'-spirobi[9H-fluorene] >98.0%(GC)
  • Packaging:5g
  • Price:$ 40
  • Delivery:In stock
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:2-Bromo-9,9'-spirobi[fluorene]
  • Packaging:25 g
  • Price:$ 212
  • Delivery:In stock
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:2-Bromo-9,9'-spirobi[fluorene]
  • Packaging:10 g
  • Price:$ 106
  • Delivery:In stock
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:2-Bromo-9,9'-spirobi[fluorene] 95+%
  • Packaging:1g
  • Price:$ 115
  • Delivery:In stock
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:2-Bromo-9,9'-spirobi[fluorene] 95+%
  • Packaging:5g
  • Price:$ 365
  • Delivery:In stock
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  • Manufacture/Brand:Crysdot
  • Product Description:2-Bromo-9,9'-spirobi[fluorene] 97%
  • Packaging:100g
  • Price:$ 376
  • Delivery:In stock
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  • Manufacture/Brand:Chemenu
  • Product Description:2-Bromo-9,9''-spirobi[fluorene] 95+%
  • Packaging:100g
  • Price:$ 355
  • Delivery:In stock
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  • Manufacture/Brand:Chemenu
  • Product Description:2-Bromo-9,9''-spirobi[fluorene] 95+%
  • Packaging:25g
  • Price:$ 143
  • Delivery:In stock
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Relevant articles and documentsAll total 30 Articles be found

Side chain modification on PDI-spirobifluorene-based molecular acceptors and its impact on organic solar cell performances

Bolognesi, Margherita,Gedefaw, Desta,Cavazzini, Marco,Catellani, Marinella,Andersson, Mats R.,Muccini, Michele,Kozma, Erika,Seri, Mirko

, p. 18633 - 18640 (2018)

N-Substitution in perylene diimide (PDI) n-type semiconductors is critical for their performance in organic bulk heterojunction solar cells. In this work we synthesized and compared three perylene diimide-spirobifluorene derivatives, N-substituted with different alkyl side groups. These molecular systems were obtained by cost-effective methods, using straightforward synthetic procedures and easy purification. These PDI derivatives were used as electron acceptor materials, blended with a benchmark quinoxaline-benzodithiophene based donor polymer, in bulk heterojunction solar cells. All devices were processed by blade coating in air, and also using non-chlorinated solvents. The three molecules presented identical HOMO/LUMO energy levels and very similar optical properties but different photovoltaic responses. These different performances were discussed through optical, electrical and morphological characterizations. The highest power conversion efficiency was achieved for the active layer based on the derivative with branched and longer alkyl groups in N-positions, which favored a morphology with reduced donor:acceptor phase segregation.

Poly(vinylspirobifluorene): Synthesis and properties of a novel styrenic polymer

Ishiwari, Fumitaka,Shinichi Kawasaki,Koyama, Asuhito,Takata, Toshikazu

, p. 854 - 855 (2008)

Synthesis and properties of a new class of styrenic polymer are reported. The radical polymerization of 2-vinyl-9,9′-spirobifluorene yielded high molecular weight poly(vinylspirobifluorene) with high thermal stability and high solubility, which gave a self-standing transparent film with high refractive index. Copyright

Organic electroluminescent compound and organic electroluminescent device containing same

-

Paragraph 0149; 0150; 0151-0153, (2021/06/26)

The invention discloses an organic electroluminescent compound, which is formed by connecting a structural formula (1) and a structural formula (2), wherein * is a connecting site, the structural formula (1) and the structural formula (2) are defined in the specification, Y is O or S, X1-X8 are independently C-R5 or N, Z1-Z4 are independently C-R6 or N, the structural formula (1) can be connected with any non-N connecting site in Z1-Z4 on the A ring of the structural formula (2), and Ar is a substituted or unsubstituted C6-C60 aromatic hydrocarbon group or a substituted or unsubstituted C5-C60 heteroaromatic hydrocarbon group. When the organic electroluminescent compound is applied to the organic electroluminescent device, under the same current density, the luminous efficiency is greatly improved, the color purity is high, the starting voltage of the device is reduced, the power consumption of the device is relatively reduced, and the service life of the device is correspondingly prolonged.

Method for synthesizing 9,9'-spirobifluorene derivative

-

, (2019/01/05)

The invention relates to a method for synthesizing a 9,9'-spirobifluorene derivative, and belongs to the field of organic chemical synthesis. The method comprises the following steps: activating a C-Fbond in tetrahydrofuran under inert gas protection through reduction and lithiation reaction of raw materials of 2-fluorobiphenyl and a metal lithium sheet, thus establishing 2-biphenyl lithium; thenenabling the 2-biphenyl lithium to react with a fluorenone derivative, hydrolyzing, drying a solvent by distillation, and carrying out ring closing on solid in acetic acid, thus synthesizing the 9,9'-spirobifluorene derivative. According to the method disclosed by the invention, the 2-fluorobiphenyl in low cost is adopted as a raw material to replace 2-bromobiphenyl commonly adopted by a traditional method, the production cost is low, and reaction conditions are gentle; an applicable substrate range of the method is wide, and a new thought is provided for synthesis of the 9,9'-spirobifluorenederivative.

Process route upstream and downstream products

Process route

2-bromofluoren-9-one
3096-56-8

2-bromofluoren-9-one

2-bromo-9,9'-spirobifluorene
171408-76-7

2-bromo-9,9'-spirobifluorene

Conditions
Conditions Yield
2-bromofluoren-9-one; With n-butyllithium; 2-Bromobiphenyl; In tetrahydrofuran; at -78 - 20 ℃; Inert atmosphere; Schlenk technique;
With hydrogenchloride; acetic acid; In water; at 70 ℃; for 2h;
67%
With biphenyl-2-yl-lithium; Multistep reaction;
Multi-step reaction with 2 steps
1: diethyl ether / 3 h / Heating
2: conc. H2SO4 / 3 h
With sulfuric acid; In diethyl ether; 1: Grignard reaction / 2: Friedel-Crafts reaction;
Multi-step reaction with 2 steps
1.1: Mg / diethyl ether / Heating
1.2: diethyl ether / Heating
2.1: 10.4 g / conc. HCl / acetic acid / Heating
With hydrogenchloride; magnesium; In diethyl ether; acetic acid; 1.2: Grignard reaction;
Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran / -78 °C
1.2: 3 h / 20 °C
2.1: acetic acid / sulfuric acid / 1 h / Heating
With n-butyllithium; acetic acid; sulfuric acid; In tetrahydrofuran;
Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C
1.2: -78 - 20 °C
2.1: hydrogenchloride; acetic acid / water / 1 h / Reflux
With hydrogenchloride; n-butyllithium; acetic acid; In tetrahydrofuran; water;
Multi-step reaction with 2 steps
1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C
2: acetic acid; hydrogenchloride / water / 1 h / Reflux
With hydrogenchloride; n-butyllithium; acetic acid; In tetrahydrofuran; water;
9-(biphenyl-2-yl)-2-bromo-9-fluorenol
236389-20-1

9-(biphenyl-2-yl)-2-bromo-9-fluorenol

2-bromo-9,9'-spirobifluorene
171408-76-7

2-bromo-9,9'-spirobifluorene

Conditions
Conditions Yield
With acetic acid; sulfuric acid; for 1h; Heating;
97%
With acetic acid; at 100 ℃; for 12h; Inert atmosphere;
91%
With hydrogenchloride; acetic acid; In water; for 1h; Reflux;
85%
With hydrogenchloride; acetic acid; In water; for 1h; Reflux;
81%
With hydrogenchloride; acetic acid; for 0.5h; Heating / reflux;
79%
With hydrogenchloride; In water; acetic acid; for 2h; Heating / reflux;
57%
With hydrogenchloride; acetic acid; In water; for 2h; Heating / reflux;
57%
With hydrogenchloride; acetic acid; for 2h; Heating / reflux;
57%
With hydrogenchloride; acetic acid; at 120 ℃; for 2h;
57%
With hydrogenchloride; acetic acid; for 2h; Heating / reflux;
57%
With acetic acid; for 2h; Reflux; Acidic conditions;
57%
With sulfuric acid; for 3h;
With hydrogenchloride; In acetic acid; Heating;
10.4 g
With acetic acid; hydrogenchloride; at 100 ℃; for 1.5h;
With hydrogenchloride; In acetic acid;
With hydrogenchloride; acetic acid; In water; for 12h; Reflux;
11.3 g
1-Bromo-2-iodobenzene
583-55-1

1-Bromo-2-iodobenzene

2-bromofluoren-9-one
3096-56-8

2-bromofluoren-9-one

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

2-bromo-9,9'-spirobifluorene
171408-76-7

2-bromo-9,9'-spirobifluorene

Conditions
Conditions Yield
1-Bromo-2-iodobenzene; phenylmagnesium bromide; In 2-methyltetrahydrofuran; at 50 ℃; for 8h; Inert atmosphere;
2-bromofluoren-9-one; In 2-methyltetrahydrofuran; diethyl ether; for 2h; Reflux;
With hydrogenchloride; acetic acid; In 2-methyltetrahydrofuran; diethyl ether; at 75 ℃; for 4h;
78.2%
2-bromo-1-chlorobenzene
694-80-4

2-bromo-1-chlorobenzene

2-bromofluoren-9-one
3096-56-8

2-bromofluoren-9-one

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

2-bromo-9,9'-spirobifluorene
171408-76-7

2-bromo-9,9'-spirobifluorene

Conditions
Conditions Yield
2-bromo-1-chlorobenzene; phenylmagnesium bromide; In 2-methyltetrahydrofuran; at 100 ℃; for 20h; Inert atmosphere;
2-bromofluoren-9-one; In 2-methyltetrahydrofuran; diethyl ether; for 2h; Reflux;
With hydrogenchloride; acetic acid; In 2-methyltetrahydrofuran; diethyl ether; at 75 ℃; for 4h;
76%
2-bromofluoren-9-one
3096-56-8

2-bromofluoren-9-one

2-biphenylmagnesium bromide
82214-69-5

2-biphenylmagnesium bromide

2-bromo-9,9'-spirobifluorene
171408-76-7

2-bromo-9,9'-spirobifluorene

Conditions
Conditions Yield
With diisobutylaluminium hydride; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; toluene; at 65 ℃;
With hydrogenchloride; ammonium chloride; In acetic acid;
9,9'-spirobifluorene
159-66-0

9,9'-spirobifluorene

2-bromo-9,9'-spirobifluorene
171408-76-7

2-bromo-9,9'-spirobifluorene

Conditions
Conditions Yield
With bromine; iron(III) chloride; In dichloromethane; for 8h;
60%
With N-Bromosuccinimide; In dichloromethane; for 24.5h; Darkness;
2-Bromobiphenyl
2052-07-5

2-Bromobiphenyl

2-bromo-9,9'-spirobifluorene
171408-76-7

2-bromo-9,9'-spirobifluorene

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1.1: Mg / diethyl ether / Heating
1.2: diethyl ether / Heating
2.1: 10.4 g / conc. HCl / acetic acid / Heating
With hydrogenchloride; magnesium; In diethyl ether; acetic acid; 1.2: Grignard reaction;
Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran / -78 °C
1.2: 3 h / 20 °C
2.1: acetic acid / sulfuric acid / 1 h / Heating
With n-butyllithium; acetic acid; sulfuric acid; In tetrahydrofuran;
Multi-step reaction with 2 steps
1.1: n-butyllithium / hexane; tetrahydrofuran / 2.5 h / -78 °C / Inert atmosphere
1.2: -78 - 20 °C / Inert atmosphere
2.1: acetic acid; hydrogenchloride / water / 12 h / Reflux
With hydrogenchloride; n-butyllithium; acetic acid; In tetrahydrofuran; hexane; water;
Multi-step reaction with 2 steps
1.1: magnesium / diethyl ether; ethylene dibromide / 3 h / Inert atmosphere; Reflux
1.2: 14 h / Inert atmosphere; Reflux
2.1: acetic acid / 2 h / Reflux; Acidic conditions
With magnesium; acetic acid; In diethyl ether; ethylene dibromide;
2-biphenylmagnesium bromide
82214-69-5

2-biphenylmagnesium bromide

2-bromo-9,9'-spirobifluorene
171408-76-7

2-bromo-9,9'-spirobifluorene

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: diethyl ether / 3 h / Heating
2: conc. H2SO4 / 3 h
With sulfuric acid; In diethyl ether; 1: Grignard reaction / 2: Friedel-Crafts reaction;
2-bromofluoren-9-one
3096-56-8

2-bromofluoren-9-one

2-iodobiphenyl
2113-51-1

2-iodobiphenyl

2-bromo-9,9'-spirobifluorene
171408-76-7

2-bromo-9,9'-spirobifluorene

Conditions
Conditions Yield
With magnesium; In diethyl ether; for 65h; Heating;
78%
2-Bromobiphenyl
2052-07-5

2-Bromobiphenyl

2-bromofluoren-9-one
3096-56-8

2-bromofluoren-9-one

2-bromo-9,9'-spirobifluorene
171408-76-7

2-bromo-9,9'-spirobifluorene

Conditions
Conditions Yield
2-Bromobiphenyl; With magnesium; In tetrahydrofuran; for 3h; Heating;
2-bromofluoren-9-one; In tetrahydrofuran; Heating;
With hydrogenchloride; acetic acid; Further stages.; Heating;
68%
2-Bromobiphenyl; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 2h;
2-bromofluoren-9-one; In tetrahydrofuran; at -78 - 20 ℃; for 18h;
With hydrogenchloride; acetic acid; In water; for 12h; Reflux;

171408-76-7 Upstream products

171408-76-7 Downstream products

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