(1,2-oxazol-4-yl)boronic acid

EN300-212574

Product class

Building Blocks

CAS number

1008139-25-0

MW

112.88

Purity

95%

Stock Availability

EU, US, UA, DE

Lead time

1-5 days delivery time

Reagent for DNA-compatible cyanomethylation of (hetero)aryl halides or triflates

Isoxazol-4-ylboronic acid is a reagent that offers an easy DNA-compatible cyanomethylation procedure with high yield[1]. It solid, bench-stable reagent well soluble in polar solvents. The reaction of cyanomethylation of the heteroaryl halides or triflates proceeds by a tandem process involving palladium-mediated Suzuki−Miyaura coupling and base-promoted isoxazole fragmentation. This process doesn’t damage DNA in a significant way. Heteroaryl halides and aryl triflates containing both electron-donating or electron-withdrawing substituent groups can be efficiently converted into the corresponding products under procedure in good to excellent yields. After the reaction, the product can be converted into the corresponding carboxylic acids.

Synonyms: B-4-Isoxazolylboronic acid (ACI); (1,2-Oxazol-4-yl)boronic acid; Isoxazol-4-ylboronic acid; Isoxazole-4-boronic acid

1. DNA-Compatible Cyanomethylation of (Hetero)Aryl Halides or Triflates under a Tandem Reaction for DNA-Encoded Library Synthesis. Zhang J.; Wang L.; Ji Q.; Liu F. Org Lett 2023, 25 (37), 6931–6936. DOI: 10.1021/acs.orglett.3c02850

Name:

(1,2-oxazol-4-yl)boronic acid

SMILES:

OB(O)C=1C=NOC1

CAS number:

1008139-25-0

Product class:

Building Blocks

ACD number:

MFCD06657892

CLogP:

-0.426

Class:

Lab Reagents, Boronic Acids and Derivatives

Formula:

C₃H₄BNO₃

Subclass:

Aromatic Boronates

MW:

112.88