4-Nitrophenylboronic acid pinacol ester Chemical Properties

Melting point:

112-116 °C (lit.)

Boiling point:

357.5±25.0 °C(Predicted)

Density 

1.14±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder or crystals

color 

White to Orange to Green

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C12H16BNO4/c1-11(2)12(3,4)18-13(17-11)9-5-7-10(8-6-9)14(15)16/h5-8H,1-4H3

InChIKey

LUWACRUAJXZANC-UHFFFAOYSA-N

SMILES

O1C(C)(C)C(C)(C)OB1C1=CC=C([N+]([O-])=O)C=C1

CAS DataBase Reference

171364-83-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

2

Hazard Note 

Harmful/Store Cold

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich

4-Nitrophenylboronic acid pinacol ester Usage And Synthesis

Chemical Properties

White solid

Uses

Reactant involved in: • ;Synthesis of aryl azides 1• ;Arylation of allylic chlorides2• ;Syntehsis of RNA conjugates3• ;Alkoxycarbonylation4• ;Synthesis of mTOR and PI3K inhibitors as antitumor agents5• ;Electrooxidative synthesis of biaryls6

Uses

suzuki reaction

Uses

4-Nitrobenzeneboronic acid pinacol ester is a reactant involved in synthesis of aryl azides, arylation of allylic chlorides, synthesis of RNA conjugates, alkoxycarbonylation, synthesis of mTOR and PI3K inhibitors as antitumor agents, electro oxidative synthesis of biaryls.

Synthesis Reference(s)

The Journal of Organic Chemistry, 60, p. 7508, 1995 DOI: 10.1021/jo00128a024

Synthesis

GENERAL PROCEDURE: 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 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 reaction mixture was stirred at 0-5 °C for 30 min, followed by the addition of a methanol (1.0 mL) solution of pinacol ester of bisboronic acid (2,381 mg, 1.5 mmol, 3.0 equiv). Stirring was continued for 60 minutes. Upon completion of the reaction, water (10 mL) was added to the mixture, which was then extracted with dichloromethane (50 mL, 3 times). The organic layers were combined and washed with saturated sodium bicarbonate solution followed by drying with anhydrous sodium sulfate. After drying, the solvent was evaporated and the crude product was purified by fast chromatography.

References

[1] Synlett, 2014, vol. 25, # 11, p. 1577 - 1584
[2] Angewandte Chemie - International Edition, 2010, vol. 49, # 10, p. 1846 - 1849
[3] Angewandte Chemie - International Edition, 2010, vol. 49, # 10, p. 1846 - 1849
[4] Tetrahedron Letters, 2016, vol. 57, # 14, p. 1551 - 1554
[5] Synlett, 2012, vol. 23, # 9, p. 1394 - 1396

4-Nitrophenylboronic acid pinacol ester(171364-83-3)Related Product Information

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• 3-NITROPHENYLBORONIC ACID, PINACOL ESTER
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