4-Ethoxycarbonylphenylboronic acid Chemical Properties

Melting point:

135 °C (dec.) (lit.)

Boiling point:

355.5±44.0 °C(Predicted)

Density 

1.21±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

pka

7.69±0.10(Predicted)

form 

Powder

color 

White to off-white

InChI

InChI=1S/C9H11BO4/c1-2-14-9(11)7-3-5-8(6-4-7)10(12)13/h3-6,12-13H,2H2,1H3

InChIKey

ZLNFACCFYUFTLD-UHFFFAOYSA-N

SMILES

C1C=C(B(O)O)C=CC=1C(=O)OCC

CAS DataBase Reference

4334-88-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

36/37/38-26-22

Safety Statements 

37/39-26-45-36/37-28

WGK Germany 

3

TSCA 

No

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

• Language:English Provider:ACROS

4-Ethoxycarbonylphenylboronic acid Usage And Synthesis

Chemical Properties

white to off-white powder

Uses

Reactant involved in:• ;Oxidative hydroxylation for the preparation of phenols1• ;Homolytic aromatic substitution2• ;Cross-coupling with α-bromocarbonyl compounds3• ;Suzuki-coupling reaction with quinoline carboxylates4• ;Trifluoromethylation5• ;Carbometalation of ynamides6

Uses

suzuki reaction

Uses

4-(Ethoxycarbonyl)benzeneboronic acid is used as a reactant involved in oxidative hydroxylation for the preparation of phenols, homolytic aromatic substitution, cross-coupling with α-bromocarbonyl compounds, Suzuki-coupling reaction with quinoline carboxylates, trifluoromethylation and carbometalation of ynamides.

Synthesis

4-Carbethoxyphenylboronic acid was prepared as follows: 4-carboxyphenylboronic acid (350 mg, 2.109 mmol) was placed in a 100 mL three-necked round-bottomed flask and dissolved in anhydrous ethanol (10 mL). The device configuration included a condenser tube, thermometer, stirrer, and rubber stopper. A mixed ethanol/HCl solution (10 mL, pH about 3.0) was added to the reaction system and the mixture was subsequently heated to 70°C and refluxed for 1 hour. Upon completion of the reaction, the mixture was cooled to room temperature and stirred continuously overnight. Subsequently, the reaction mixture was concentrated under reduced pressure. The concentrate was dissolved in ethyl acetate and washed with water. The organic layer was dried with potassium carbonate, filtered and concentrated under reduced pressure to give 520 mg of white solid. The crude product was initially purified by silica gel chromatography (Chromatotron, 6000 micron rotor, eluent 1:1 hexane:ethyl acetate) to give 470 mg of unreacted raw material mixed with the product. Further, a Vydac C-18 reversed-phase column was used with water (containing 0.1% trifluoroacetic acid) and acetonitrile as the mobile phases with gradient elution (5%-70% acetonitrile), and the final purification yielded 4-ethoxycarbonylphenylboronic acid (350 mg, 85.5% yield) as a white solid. The product was characterized by electrospray mass spectrometry (ES-MS) with m/z of 195.0 ([M+H]+).

References

[1] Patent: US2003/225266, 2003, A1. Location in patent: Page 25
[2] Patent: US2002/55631, 2002, A1
[3] Patent: US2002/86887, 2002, A1

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