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ChemicalBook--->CAS DataBase List--->68572-87-2

68572-87-2

68572-87-2 Structure

68572-87-2 Structure
IdentificationMore
[Name]

9-Phenanthracenylboronic acid
[CAS]

68572-87-2
[Synonyms]

9-PHENANTHRENEBORONIC ACID
BORONIC ACID, 9-PHENANTHRENYL-
PHENANTHREN-9-YLBORONIC ACID
PHENANTHRENE-9-BORONIC ACID
RARECHEM AH PB 0056
9-Phenanthreneboronic acid (contains varying amounts of anhydride)
Phenanthreneboronicacid
Phenanthrene-9-boronic acid 98%
9-Phenanthracenylboronic acid
Phenanthracene-9-boronic acid
[EINECS(EC#)]

627-783-7
[Molecular Formula]

C14H11BO2
[MDL Number]

MFCD00143524
[Molecular Weight]

222.05
[MOL File]

68572-87-2.mol
Chemical PropertiesBack Directory
[Melting point ]

165-170 °C
[Boiling point ]

479.5±28.0 °C(Predicted)
[density ]

1.26±0.1 g/cm3(Predicted)
[storage temp. ]

Keep in dark place,Sealed in dry,Room Temperature
[solubility ]

Soluble in DMSO.
[form ]

Solid
[pka]

8.53±0.30(Predicted)
[color ]

Pale Yellow
[InChI]

InChI=1S/C14H11BO2/c16-15(17)14-9-10-5-1-2-6-11(10)12-7-3-4-8-13(12)14/h1-9,16-17H
[InChIKey]

JCDAUYWOHOLVMH-UHFFFAOYSA-N
[SMILES]

B(C1=CC2C(C3C1=CC=CC=3)=CC=CC=2)(O)O
[CAS DataBase Reference]

68572-87-2(CAS DataBase Reference)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
[WGK Germany ]

3
[Hazard Note ]

Irritant
[HazardClass ]

IRRITANT
[HS Code ]

29319090
Hazard InformationBack Directory
[Chemical Properties]

White solid
[Uses]

9-Phenanthracenylboronic acid is used as an fluorescent analytical reagent in sensing systems for glucose-specific detection and in suzuki reaction.
[Uses]

suzuki reaction
[Synthesis]

Triisopropyl borate

5419-55-6

9-Bromophenanthrene

573-17-1

9-phenanthrenylboronic acid

68572-87-2

The general procedure for the synthesis of 9-phenanthrenylboronic acid from triisopropyl borate and 9-bromophenanthrene is as follows: Step a: Preparation of 9-phenanthracenylboronic acid Under argon protection, 9-bromophenanthrene (1 g, 3.9 mmol) and triisopropyl borate (1.35 ml, 1.1 g, 5.85 mmol) were dissolved in anhydrous THF (30 ml) and the solution was cooled to -78 °C. Subsequently, n-BuLi (1.6 M hexane solution, 2.9 ml, 4.68 mmol) was added slowly dropwise over 1 h. The reaction temperature was maintained at -78 °C and stirring was continued for 1 h. The reaction mixture was then cooled to -78 °C. The reaction temperature was then adjusted to -78 °C. After that, the reaction mixture was slowly warmed up to -20°C, 2M HCl (20 ml) was added, and the temperature was continued to 18°C and stirring was continued for 1 hour. After completion of the reaction, ether (300 ml) was added for extraction, the organic phase was dried with MgSO4, filtered and concentrated under reduced pressure to afford the crude product 9-phenanthrenylboronic acid (770 mg, 89% yield) as a white solid, which can be used in subsequent reactions without further purification.

[References]

[1] Patent: WO2006/135973, 2006, A1. Location in patent: Page/Page column 31
[2] Patent: CN107652224, 2018, A. Location in patent: Paragraph 0086; 0089-0091
[3] Patent: CN107382748, 2017, A. Location in patent: Paragraph 0037; 0038; 0039; 0040
Spectrum DetailBack Directory
[Spectrum Detail]

9-phenanthrenylboronic acid(68572-87-2)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

68572-87-2(sigmaaldrich)
[TCI AMERICA]

9-Phenanthreneboronic Acid  (contains varying amounts of Anhydride)(68572-87-2)
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