4-(Morpholinylmethyl)phenylboronic acid

Name: 4-(Morpholinylmethyl)phenylboronic acid
Brand: ChemScene
Availability: InStock
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CAS No. 279262-23-6
Cat. No. CS-W000908
Molecule weight221.06
Purity≥97%
MDL No.MFCD06801707

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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4-(Morpholinylmethyl)phenylboronic acid|CS-W000908

Structure of 279262-23-6

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General Information

CAS No. 279262-23-6
Cat. No. CS-W000908
Purity ≥97%
MDL No. MFCD06801707
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₆BNO₃
Molecular Weight 221.06
Synonym(s) Boronicacid, [4-(4-morpholinylmethyl)phenyl]-
SMILES OB(O)C1=CC=C(CN2CCOCC2)C=C1

Description

4-(Morpholinylmethyl)phenylboronic acid features a boronic acid group appended to a phenyl ring bearing a morpholinylmethyl substituent. This configuration enables efficient Suzuki-Miyaura coupling under mild conditions, with the morpholinyl moiety enhancing solubility and stability in aqueous-organic media. The compound serves as a key building block for biologically active arylated scaffolds in medicinal chemistry and materials synthesis.

Application

4-(Morpholinylmethyl)phenylboronic acid serves as a versatile building block in Suzuki-Miyaura cross-coupling reactions, enabling efficient construction of biaryl scaffolds. The morpholinylmethyl group imparts enhanced solubility and metabolic stability, while the boronic acid functionality ensures reliable coupling under mild conditions. Its bench-stable solid form and tolerance to common functional groups facilitate straightforward handling and purification in medicinal chemistry and process synthesis workflows.

Synthesis

Route1
- 1072960-75-8
- ~73%
- In-stock
  
  279262-23-6
References
- Gillis, Eric P.; Burke, Martin D. Journal of the American Chemical Society, 2008 , vol. 130, # 43 p. 14084 - 14085
Route2
- 110-91-8
- In-stock
  
  68162-47-0
- ~90%
- In-stock
  
  279262-23-6
References
- Gravel, Michael; Thompson, Kim A.; Zak, Mark; Berube, Christian; Hall, Dennis G. Journal of Organic Chemistry, 2002 , vol. 67, # 1 p. 3 - 15

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 52.93
LogP -0.8014
H_Acceptors 4
H_Donors 2
Rotatable_Bonds 3

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Morpholine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

Key Words

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4-(Morpholinylmethyl)phenylboronic acid

CAS No. 279262-23-6

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