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161497

Sigma-Aldrich

3,4-(Methylenedioxy)aniline

97%

Synonym(s):

5-Amino-1,3-benzodioxole

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About This Item

Empirical Formula (Hill Notation):
C7H7NO2
CAS Number:
Molecular Weight:
137.14
Beilstein:
4919
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

97%

bp

144 °C/16 mmHg (lit.)

mp

39-41 °C (lit.)

SMILES string

Nc1ccc2OCOc2c1

InChI

1S/C7H7NO2/c8-5-1-2-6-7(3-5)10-4-9-6/h1-3H,4,8H2

InChI key

XGNXYCFREOZBOL-UHFFFAOYSA-N

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General description

3,4-(Methylenedioxy)aniline is an pharmaceutically important aniline derivative. It undergoes N-alkylation with cyclic secondary alkylamines in the presence of Shvo catalyst to yield N-arylpyrrolidines.

Application

3,4-(Methylenedioxy)aniline was used in the synthesis of γ-glutamylanilides.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A general ruthenium-catalyzed synthesis of aromatic amines.
Dirk Hollmann et al.
Angewandte Chemie (International ed. in English), 46(43), 8291-8294 (2007-09-25)
A Rsoswsky et al.
Journal of medicinal chemistry, 22(9), 1034-1037 (1979-09-01)
Nine heretofore unknown mono- and dihydroxyanilide analogues of the cytotoxic mushroom metabolites L-glutamic acid gamma-(4-hydroxyanilide) (1) and L-glutamic acid gamma-(3,4-dihydroxyanilide) (3, agaridoxin) were synthesized and tested as inhibitors of the growth of B16 mouse melanoma cells in culture. The naturally
K N Vennila et al.
Bioorganic chemistry, 81, 184-190 (2018-08-24)
The induced fit docking of anilino quinoline scaffold results in the required hydrogen bonding interactions with amino acid residues in the orthosteric site of 3 Phosphoinositide dependent kinase (PDK1). The rational design of 4-substituted amino quinolines is carried out and

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