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9-Anthraceneboronic acid

9-Anthraceneboronic acid structure

CAS No:
100622-34-2
Formula:
C14H11BO2
Chemical Name:
9-Anthraceneboronic acid
Synonyms:
9-ANTHRACENEBORONIC ACID;ANTHRACENE-9-BORONIC ACID;9-Anthracenylboronic acid;9-Anthrylboronicacid;9-Boronoanthracene;9-Anthracenylboronicacid,9-Anthrylboronicacid;Anthracen-9-ylboronic acid;9-Anthracenylboronic
Categories:
Chemical Reagents > Organic Reagents

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Description

Tan solid

9-Anthraceneboronic acid Basic Attributes

Molecular Weight：

222.05

Exact Mass：

222.085205

BRN：

3301031

EC Number：

-0

HScode：

29319090

Characteristics

PSA：

40.5

Appearance：

White to tan Crystalline Solid

Density：

1.26±0.1 g/cm3(Predicted)

Melting Point：

214-216°C

Boiling Point：

479.5±28.0 °C(Predicted)

Flash Point：

243.8±24.0 °C

Refractive Index：

1.710

Safety Information

Packing level：

Ⅲ

Hazard category：

6.1

Transport codes：

UN28116.1/PG3

wgk germany：

hazard class code：

36/37/38-25

safety instructions：

26-36-45

Marks：

Precautionary statement(s)：

P301 + P310

Hazard Statements：

H301

9-Anthraceneboronic acid Use and Manufacturing

Methods of Manufacturing

9-bromoanthracence (10.0 g, 38.9 mmol) was dissolvedin anhydrous THF solution (500 mL) and stirred at −78C. Then, 1.6 M n-BuLi (29.3 mL, 46.7 mmol) was added. Triethyl borate (9.3 mL, 54.5 mmol) was added to the reaction after30 min. After the reaction was finished, the solution was acidified with 2 N HCl solutionat room temperature and extracted with ethyl acetate and water. The organic layer wasdried with anhydrous MgSO4 and filtered. The solution was evaporated. The residue wasredissolved in hexane and added to ethyl acetate. The precipitate was filtered and washedwith hexane to obtain a beige compound (7.70 g, 89percent). 1H-NMR (300 MHz, CDCl3):δ(ppm) = 8.47 (s, 1H), 8.14 (d, J = 9.2 Hz, 2H), 8.04 (d, J = 9.8 Hz, 2H), 7.53–7.44 (m, 4H), 5.07 (s, 2H).9-Bromoanthracene 38.6 g was dissolved in dehydrated toluene 80 ml and dehydrated THF (tetrahydrofuran) 160 ml, and the solution was cooled to -40°C. (i) As shown in Reaction Scheme 3 9-Bromoanthracene (10 g, 38.9 mmol) was added to a solution of Placed in a 3-neck round bottom flask and 300 mL of anhydrous THF under nitrogen. 2M n-BuLi (24.0 mL, 46.7 mmol) was slowly added while maintaining the temperature at -78 dege C. In the middle of the reaction, TLC was taken under the condition of EA: hexane = 1: 10, and the progress of the reaction was examined. After the spot of the reaction disappeared, triethyl borate (9.50 mL, 54.5 mmol) was added to -78 deg. The progress of the reaction was examined by taking TLC under the conditions of EA: hexane = 1: 10. After the reaction was completed, HCl (7.20 mL, 85.6 mmol) was added at room temperature, EA and H2O. A small amount of H2O in the EA layer was removed with MgSO4. After the MgSO4 was filtered off, the product in the EA layer was evaporated. The product was dissolved in a small amount of THF and reprecipitated with hexane, followed by filtration to obtain 7.55 g (yield 87percent) of Compound 6 as an orange solid.Compound 42d.; Step a: Preparation of 9-anthracene boronic acid; A solution of 9-bromoanthracene (1 g, 3.9 mmol) and triisopropylborate (1.35 ml, 5.85 mmol) in absolute THF (30 ml) was cooled down to -78°C and stirred under argon. roe-BuLi (2.9 ml, 1.6 M in hexanes, 4.68 mmol) was then added dropwise over one hour and it was stirred at -78° C for one hour.

Uses

suzuki reaction

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