ChemicalBook CAS DataBase List 4-Nitrophenylboronic acid

4-Nitrophenylboronic acid synthesis

11synthesis methods

Product Name:4-Nitrophenylboronic acid
CAS Number:24067-17-2
Molecular formula:C6H6BNO4
Molecular Weight:166.93

100-01-6

24067-17-2

GENERAL METHOD: To a solution of 4-nitroaniline (0.5 mmol, 1.0 eq.) in methanol (1.0 mL) was added hydrochloric acid (0.5 mL, 1.5 mmol, 3.0 eq.) followed by water (0.5 mL). The reaction mixture was stirred for 2 minutes and then sodium nitrite solution (0.25 mL) was added. Sodium nitrite solution was prepared by dissolving 35 mg of sodium nitrite in water (0.25 mL). The mixture was stirred at 0-5 °C for 30 min, followed by the addition of hydrochloric acid (135 mg, 1.5 mmol, 3.0 equiv) in methanol (1.0 mL). Stirring of the reaction mixture was continued for 60 min. Upon completion of the reaction, it was diluted with the addition of water (10 mL) and extracted with dichloromethane (50 mL, 3 times). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 4-nitrophenylboronic acid.

67-56-1 Synthesis

67-56-1
792 suppliers
$7.29/5ml-f

55124-35-1 Synthesis

55124-35-1
27 suppliers
$60.00/100mg

586-78-7
38 suppliers
$14.00/5g

24067-17-2
260 suppliers
$19.00/1g

Yield:24067-17-2 78%

Reaction Conditions:

Stage #1:diisopropylamine borane with magnesium;phenylmagnesium bromide in tetrahydrofuran at 20; for 0.166667 h;
Stage #2:para-nitrophenyl bromide in tetrahydrofuran at 70;
Stage #3:methanolFurther stages;

Steps:

PhMgBr dehydrogenation followed by the addition under Barbier conditions (procedure B)
General procedure: To a solution in THF (4 mL) of DIPAB (863 mg, 7.5 mmol) and Mg (182 mg, 7.5 mmol) were added a PhMgBr 1M THF solution (375 μL, 375μmol) at room temperature. After 10 min, 30 mL of anhydrous THF were added followed by the arylbromide (5 mmol). The reaction mixture was cooled down to 0 °C and quenched slowly with 7 mL of MeOH. After 1h, volatile were removed under reduced pressure and the resulting solid was dissolved in 1N HCl/MeOH (7/3). After 1h at room temperature, 100 mL of AcOEt were added, the organic phase was washed with 1N HCl (30 mL) and brine (3×30 mL). Organic phases were concentrated under reduced pressure yielding a solid which was recrystallized from H₂O.

References:

Marciasini, Ludovic D.;Richard, Jimmy;Cacciuttolo, Bastien;Sartori, Guillaume;Birepinte, Melodie;Chabaud, Laurent;Pinet, Sandra;Pucheault, Mathieu [Tetrahedron,2019,vol. 75,# 2,p. 164 - 171]

FullText

100-01-6
86 suppliers
$11.19/25G

24067-17-2
260 suppliers
$19.00/1g

References

13675-18-8 Synthesis