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Dibenzofuran-4-boronic acid

CAS No.100124-06-9
Chemical Name:Dibenzofuran-4-boronic acid
CBNumber:CB1671054
Molecular Formula:C12H9BO3
Formula Weight:212.01
MOL File:100124-06-9.mol

Dibenzofuran-4-boronic acid Property

Melting point 286-291 °C (lit.)
Boiling point 438.5±37.0 °C(Predicted)
Density 1.34±0.1 g/cm3(Predicted)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
pka 8.04±0.30(Predicted)
form powder
color white to off-white
BRN 1645426
InChIKey ZXHUJRZYLRVVNP-UHFFFAOYSA-N
CAS DataBase Reference 100124-06-9(CAS DataBase Reference)
UNSPSC Code 12352103
NACRES NA.22

Safety

Hazard Codes :Xi
Risk Statements :36/37/38
Safety Statements :37/39-26-24/25
WGK Germany :3
TSCA :No
HazardClass :IRRITANT
HS Code :29321900

NFPA 704:

	0
2		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H315-H319-H335
Precautionary statements P261-P280a-P304+P340-P305+P351+P338-P405-P501a

Dibenzofuran-4-boronic acid Price More Price(3)

Brand: Sigma-Aldrich(India)
Product number: 499951
Product name : 4-(Dibenzofuranyl)boronic acid
Purity: ≥95.0%
Packaging: 5G
Price: ₹7469.25
Updated: 2022/06/14
Buy: Buy

Brand: TCI Chemicals (India)
Product number: D4567
Product name : Dibenzofuran-4-boronic Acid (contains varying amounts of Anhydride)
Purity:
Packaging: 1G
Price: ₹3400
Updated: 2022/05/26
Buy: Buy

Brand: TCI Chemicals (India)
Product number: D4567
Product name : Dibenzofuran-4-boronic Acid (contains varying amounts of Anhydride)
Purity:
Packaging: 5G
Price: ₹6000
Updated: 2022/05/26
Buy: Buy

Dibenzofuran-4-boronic acid Chemical Properties,Usage,Production

Description Dibenzofuran-4-boronic acid (DBFBA) is a boronic acid that has been used as a cross-coupling agent in the Suzuki coupling reaction. It has been shown to have low efficiency, but advances in this area have been made through the use of methanol extraction and photophysical properties. DBFBA is often coupled with imidazole derivatives to form anti-inflammatory compounds. The bond cleavage and hydrogen bonding properties of DBFBA make it a good target for drug synthesis.
Chemical Properties off-white to beige powder
Uses Dibenzofuran-4-boronic acid is a water-soluble boronic acid, and the boronic acid molecule is a very useful functional group for the preparation of glycosensors. Water-soluble boronic acids that change their fluorescence properties upon binding to sugars are particularly useful as reporter units for carbohydrate fluorescence sensors. Dibenzofuran-4-boronic acid displays distinctive fluorescence changes at three wavelengths when bound to sugars under near-physiological conditions^[1].
Synthesis In a 300 ml three-necked flask, 7.2 g of 4-bromodibenzofuran was dissolved in -78° C. anhydrous tetrahydrofuran (THF) under an argon atmosphere. Then, 20 ml of an n-butyl lithium-n-hexane solution (1.6 M, 1.1 eq) was added and stirred for 1 hour. 4.23 ml (1.3 eq) of trimethoxyborane (B(OMe)3) was added and stirred for 2 hours, and the temperature of the reaction system was increased to room temperature. 200 ml of 1 N hydrochloric acid was added into the reactant and stirred for 3 hours. An organic layer was separated, and solvents were distilled off. In the crude product thus obtained, hexane was added. Precipitated product was filtered to obtain 4.94 g of dibenzofuran-4-boronic acid as a white solid (yield 80%).
References [1] JUNFENG WANG Binghe W Shan Jin. A new boronic acid fluorescent reporter that changes emission intensities at three wavelengths upon sugar binding[J]. Tetrahedron Letters, 2005. DOI:10.1016/j.tetlet.2005.08.053.