9-Anthraceneboronic acid Chemical Properties

Melting point:

203-250 °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 Methanol

pka

8.53±0.30(Predicted)

form 

Crystalline Solid

color 

White to tan

BRN 

3301031

InChI

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

InChIKey

VHHDLIWHHXBLBK-UHFFFAOYSA-N

SMILES

C1=C2C(C=C3C(=C2)C=CC=C3)=CC=C1B(O)O

CAS DataBase Reference

100622-34-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

T

Risk Statements 

36/37/38-25

Safety Statements 

26-36-45

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

TSCA 

No

HazardClass 

IRRITANT

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

29319090

MSDS

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9-Anthraceneboronic acid Usage And Synthesis

Description

9-Anthraceneboronic acid is a boronic acid compound mainly used as an organic synthesis and reaction reagent. The addition of 9-Anthraceneboronic acid introduces a borate ester bond and an anthracene functional group into ordinary polyvinyl alcohol, which can be used to prepare the composite material poly(vinyl alcohol) anthraceneboronic acid (PVA-ABA), which is suitable for sustainable engineering applications due to its high mechanical strength and toughness, good water resistance, chemical durability, and ease of recycling. It can also be used to prepare stimuli-responsive polymeric materials and highly efficient luminescent materials.

Chemical Properties

Tan solid

Uses

suzuki reaction

Synthesis

9-bromoanthracence (10.0 g, 38.9 mmol) was dissolved in an 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 after 30 min. After the reaction, the solution was acidified with 2 N HCl solution at room temperature and extracted with ethyl acetate and water. The organic layer was dried with anhydrous MgSO4 and filtered. The solution was evaporated. The residue was dissolved in hexane and added to ethyl acetate. The precipitate was filtered and washed with hexane to obtain a beige compound 9-Anthraceneboronic acid (7.70 g, 89 percent).

Purification Methods

Crystallise the boronic acid from dilute HCl (m 180-184o). The disodium salt has m 209-213o. [Beilstein 16 IV 1679.]

Advantages

As a monomer containing boric acid and anthracene functional groups, 9-anthraceneboronic acid can not only embed anthracene into the PVA chain to endow PVA with hydrophobic properties but also induce the crosslinking of anthracene under ultraviolet light to make the film have good chemical stability, and the dynamic borate ester bonds can construct a covalent network to make the film recyclable[1].

References

[1] Qizhou Sang and Zixing Shi*. “Waterproof, Chemically Durable, and Closed-Loop Recyclable Poly(vinyl alcohol) Plastic Enabled by Dynamic Covalent Modification.” ACS Applied Polymer Materials 5 11 (2023): 9403–9412.
[2] Zhiyong Liu. “Integrating Boronic Esters and Anthracene into Covalent Adaptable Networks toward Stimuli-Responsive Elastomers.” Polymers (2022).

9-Anthraceneboronic acid(100622-34-2)Related Product Information

• 9-phenanthrenylboronic acid
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• Stearic acid
• Citric acid
• Ascoric Acid
• Anthracene
• [10-(1-Naphthalenyl)-9-anthracenyl]boronic acid
• 2-Anthraceneboronic Acid (contains varying amounts of Anhydride)
• THIANTHRENE-1-BORONIC ACID
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• 9-Anthraceneboronic acid