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301353

Sigma-Aldrich

2,6-Naphthalenedicarboxylic acid

95%

Synonym(s):

2,6-Naphthalic acid

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About This Item

Linear Formula:
C10H6(CO2H)2
CAS Number:
1141-38-4
Molecular Weight:
216.19
EC Number:
214-527-0
MDL number:
MFCD00004105
UNSPSC Code:
12352100
PubChem Substance ID:
24858182
NACRES:
NA.22

Quality Level

100

assay

95%

form

solid

mp

>300 °C (lit.)

functional group

carboxylic acid

SMILES string

OC(=O)c1ccc2cc(ccc2c1)C(O)=O

InChI

1S/C12H8O4/c13-11(14)9-3-1-7-5-10(12(15)16)4-2-8(7)6-9/h1-6H,(H,13,14)(H,15,16)

InChI key

RXOHFPCZGPKIRD-UHFFFAOYSA-N

Gene Information

human ... PTPN1(5770)

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General description

Self-assembly of 2,6-naphthalenedicarboxylic acid into two-dimensionally ordered supramolecular structures was studied at the liquid-solid interface by scanning tunneling microscopy. Solvothermal reaction of Mn(II) and 2,6-naphthalenedicarboxylic acid in diethylformamide to form a 3D porous metal-organic framework generating 1D channels was studied.

Application

2,6-Naphthalenedicarboxylic acid was used in preparation of poly-2,6-naphthalenes via metal-catalyzed polymerization.

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
05212LR
03113HP

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Hoi Ri Moon et al.
Inorganic chemistry, 45(21), 8672-8676 (2006-10-13)
A 3D porous metal-organic framework generating 1D channels, [Mn(NDC)(DEF)]n (1), has been prepared from the solvothermal reaction of Mn(II) and 2,6-naphthalenedicarboxylic acid (H2NDC) in diethylformamide (DEF). When DEF molecules coordinating Mn(II), which occupy the channels, are removed from 1 by
Hong-Ying Gao et al.
Journal of the American Chemical Society, 136(27), 9658-9663 (2014-06-18)
Metal-catalyzed polymerization of 2,6-naphthalenedicarboxylic acid (NDCA) to form poly-2,6-naphthalenes at various surfaces is reported. Polymerizations occur via initial formal dehydrogenation of self-assembled diacids with subsequent decarboxylation to give polymeric bisnaphthyl-Cu species at elevated temperature as intermediate structures (<160 °C). Further
Vladimir Setnicka et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 58(13), 2983-2989 (2002-12-13)
The host/guest complexation between cyclodextrins (CDs) and aromatic compounds was studied by vibrational circular dichroism (VCD) spectroscopy in mid-IR region. Benzoic acid, 4-aminobenzoic acid, and 2,6-naphthalene-dicarboxylic acid acting as the guests with aromatic skeleton, cause the significant changes in VCD
Christoph Heininger et al.
Langmuir : the ACS journal of surfaces and colloids, 25(2), 968-972 (2008-12-19)
Self-assembly into two-dimensionally ordered supramolecular structures of three aromatic dicarboxylic acids-2,6-naphthalenedicarboxylic acid (NDA), 4,4'-biphenyldicarboxylic acid (BPDA), and 4,4'-stilbenedicarboxylic acid (SDA)-is studied at the liquid-solid interface by scanning tunneling microscopy. All compounds possess structural similarities, namely, two interconnected aromatic moieties and
Ewa Dabek-Zlotorzynska et al.
Methods in molecular biology (Clifton, N.J.), 384, 43-64 (2008-04-09)
Within the last few years, capillary electrophoresis (CE), especially with indirect ultraviolet detection, has successfully been utilized for the analysis of low-molecular-weight (LMW) organic acids in a wide variety of matrices (e.g., food, pharmaceutical, environmental, industrial, clinical). The speed, resolution
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