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273937

Sigma-Aldrich

6,7-Dimethoxy-1-tetralone

97%

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1 G
$100.00

About This Item

Empirical Formula (Hill Notation):
C12H14O3
CAS Number:
13575-75-2
Molecular Weight:
206.24
MDL number:
MFCD00134100
UNSPSC Code:
12352100
PubChem Substance ID:
24856554
NACRES:
NA.22

$100.00

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Quality Level

100

assay

97%

form

powder

mp

98-100 °C (lit.)

functional group

ketone

SMILES string

COc1cc2CCCC(=O)c2cc1OC

InChI

1S/C12H14O3/c1-14-11-6-8-4-3-5-10(13)9(8)7-12(11)15-2/h6-7H,3-5H2,1-2H3

InChI key

YNNJHKOXXBIJKK-UHFFFAOYSA-N

Related Categories

General description

6,7-Dimethoxy-1-tetralone reacts with 2-amino-4,5-dimethoxyacetophenone to form 5,6-dihydro-2,3,9,10-tetramethoxybenz[c]acridine[1].

Application

6,7-Dimethoxy-1-tetralone was used in the synthesis of 2-bromotetralones by undergoing bromination[2]. It was also used as a precursor to quinolines with dopaminergic activity[3], naphthols with anti-inflammatory activity[4] and benzophenanthridine alkaloids with antitumor activity[5].

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
STBF5953V
S33803
08625BF
06309CG
05324PS

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The Journal of Organic Chemistry, 57, 5907-5907 (1992)
Colin J Dunsmore et al.
Bioorganic & medicinal chemistry letters, 18(5), 1730-1734 (2008-02-12)
Several 2-aminotetralones were identified as novel inhibitors of the bacterial enzymes MurA and MurZ. A number of these inhibitors demonstrated antibacterial activity against Staphylococcus aureus and Escherichia coli with MICs in the range 8-128 microg/ml. Based on structure-activity relationships we
J C Craig et al.
Journal of medicinal chemistry, 32(5), 961-968 (1989-05-01)
A series of 2-substituted octahydrobenzo[f]quinolines has been synthesized and assayed for dopamine agonist activity. Only the compounds corresponding to the beta-rotameric conformation of dopamine showed biphasic activity in competition binding studies with the radioligand [3H]spiroperidol. These findings suggest that the
D G Batt et al.
Journal of medicinal chemistry, 33(1), 360-370 (1990-01-01)
The synthesis, biological evaluation, and structure-activity relationships of a series of 1-naphthols bearing carbon substituents at the 2-position are described. These compounds are potent inhibitors of the 5-lipoxygenase from RBL-1 cells and also inhibit bovine seminal vesicle cyclooxygenase. Structure-activity relationships
D Makhey et al.
Bioorganic & medicinal chemistry, 8(5), 1171-1182 (2000-07-06)
Coralyne and several other synthetic benzo[a,g]quinolizium derivatives related to protoberberine alkaloids have exhibited activity as topoisomerase poisons. These compounds are characterized by the presence of a positively charged iminium group, which has been postulated to be associated with their pharmacological

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