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699446

Sigma-Aldrich

3-(4-Morpholinomethyl)phenylboronic acid pinacol ester

95%

Synonym(s):

3-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaboran-2-yl)benzyl]morpholine

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About This Item

Empirical Formula (Hill Notation):
C17H26BNO3
CAS Number:
364794-80-9
Molecular Weight:
303.20
MDL number:
MFCD06797489
UNSPSC Code:
12352103
PubChem Substance ID:
329762133
NACRES:
NA.22

assay

95%

form

powder

mp

52-56 °C

functional group

ether

SMILES string

CC1(C)OB(OC1(C)C)c2cccc(CN3CCOCC3)c2

InChI

1S/C17H26BNO3/c1-16(2)17(3,4)22-18(21-16)15-7-5-6-14(12-15)13-19-8-10-20-11-9-19/h5-7,12H,8-11,13H2,1-4H3

InChI key

RCGRLLZELIIKDH-UHFFFAOYSA-N

Application

3-(4-Morpholinomethyl)phenylboronic acid pinacol ester can be used as a reactant:
  • In the palladium-catalyzed Suzuki-Miyaura coupling reaction to synthesize biaryl derivatives.[1]
  • To prepare a morpholinylphenyl anilinoquinazoline lapatinib analog.[2]
  • To synthesize diaryl or heteroaryl triazole quinuclidine derivatives as potent α7 nicotinic acetylcholine receptor ligands.[3]

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

>230.0 °F

flash_point_c

> 110 °C

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKBR6484V
57096LJV
57096LJ

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Microwave-mediated synthesis of an arylboronate library
Spencer J, et al.
ACS Combinatorial Science, 13(1), 24-31 (2011)
Bis (het) aryl-1, 2, 3-triazole quinuclidines as α-7 nicotinic acetylcholine receptor ligands: Synthesis, structure affinity relationships, agonism activity,[18F]-radiolabeling and PET study in rats
Ouach A, et al.
European Journal of Medicinal Chemistry, 179(10), 449-469 (2019)
Gautam Patel et al.
Journal of medicinal chemistry, 56(10), 3820-3832 (2013-04-20)
Human African trypanosomiasis (HAT) is a neglected tropical disease caused by the protozoan parasite Trypanosoma brucei . Because drugs in use against HAT are toxic and require intravenous dosing, new drugs are needed. Initiating lead discovery campaigns by using chemical

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