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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:
14268-66-7
Molecular Weight:
137.14
Beilstein/REAXYS Number:
4919
EC Number:
238-161-6
MDL number:
MFCD00005832
UNSPSC Code:
12352100
PubChem Substance ID:
24849933
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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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