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M11103

Sigma-Aldrich

4-Methoxybenzylamine

98%

Synonym(s):

(4-Methoxyphenyl)methanamine, (p-Methoxyphenyl)methanamine, 1-Aminomethyl-4-methoxybenzene, 4-Methoxybenzenemethanamine, Anisylamine, p-Methoxybenzylamine

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About This Item

Linear Formula:
CH3OC6H4CH2NH2
CAS Number:
2393-23-9
Molecular Weight:
137.18
Beilstein:
508206
EC Number:
219-247-2
MDL number:
MFCD00008122
UNSPSC Code:
12352100
PubChem Substance ID:
24896615
NACRES:
NA.22

Assay

98%

form

liquid

refractive index

n20/D 1.546 (lit.)

bp

236-237 °C (lit.)

density

1.05 g/mL at 25 °C (lit.)

SMILES string

COc1ccc(CN)cc1

InChI

1S/C8H11NO/c1-10-8-4-2-7(6-9)3-5-8/h2-5H,6,9H2,1H3

InChI key

IDPURXSQCKYKIJ-UHFFFAOYSA-N

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Application

4-Methoxybenzylamine is a primary amine and can be used for:
  • Amination reaction of functionalized aryl bromides.
  • Synthesis of functionalized organopolyphosphazenes for in vivo applications.
  • Synthesis of analogs of myoseverin, 8-azapurine, for their antiproliferative activities.
  • Studying the deprotection procedures of amino protecting groups such as 2-nitro- and 2,4-dinitrobenzenesulfonamides.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Synthesis and biological activity of 8-azapurine and pyrazolo [4, 3-d] pyrimidine analogues of myoseverin.
Krystof V, et al.
European Journal of Medicinal Chemistry, 41(12), 1405-1411 (2006)
Anna Berlicka et al.
Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 9(10), 1359-1366 (2010-09-08)
A variety of primary and secondary benzylic amines were oxidized efficiently to N-benzylidenebenzylamines and imines, respectively, using 2,7,12,17-tetrapropylporphycene (H(2)TPrPc) photocatalyst and blue light emitting diodes (LEDs). The photooxidation of 4-methoxybenzylamine in the presence of H(2)TPrPc and its tin(IV) complex Sn(TPrPc)Cl(2)
2-Nitro-and 2, 4-dinitrobenzenesulfonamides as protecting groups for primary amines.
Nihei KI, et al.
Synlett, 2001(07), 1167-1169 (2001)
T Jonsson et al.
Biochemistry, 33(49), 14871-14878 (1994-12-13)
Competitive kH/kT and kD/kT kinetic isotope effects on p-methoxybenzylamine oxidation by the 8 alpha-S-cysteinyl flavin adenine dinucleotide (FAD)-dependent enzyme monoamine oxidase B (MAO-B) have been measured as a function of temperature. At pH 7.5, exponents relating observed kH/kT and kD/kT
Mild and efficient copper-catalyzed amination of aryl bromides with primary alkylamines.
Kwong FY and Buchwald SL
Organic Letters, 5(6), 793-796 (2003)
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