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14795

Sigma-Aldrich

N,N,N′,N′-Tetramethyl-1,8-naphthalenediamine

purum, ≥99.0% (NT)

Synonym(s):

1,8-Bis(dimethylamino)naphthalene, DMAN, Proton-sponge®

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About This Item

Empirical Formula (Hill Notation):
C14H18N2
CAS Number:
20734-58-1
Molecular Weight:
214.31
Beilstein/REAXYS Number:
396782
EC Number:
244-001-6
MDL number:
MFCD00003920
UNSPSC Code:
12352100
PubChem Substance ID:
329750622
NACRES:
NA.22

grade

purum

Quality Level

200

assay

≥99.0% (NT)

form

solid

mp

45-49 °C

functional group

amine

SMILES string

CN(C)c1cccc2cccc(N(C)C)c12

InChI

1S/C14H18N2/c1-15(2)12-9-5-7-11-8-6-10-13(14(11)12)16(3)4/h5-10H,1-4H3

InChI key

GJFNRSDCSTVPCJ-UHFFFAOYSA-N

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Application

N,N,N′,N′-Tetramethyl-1,8-naphthalenediamine was used in protonation of multiple-charged oligonucleotide anions. It was used as reagent during reaction of benzaldehyde with acetic anhydride catalyzed by bismuth nitrate. It was used as extractant during separation of organic acids from fermentation broths by liquid-liquid extraction.

Other Notes

Strong amine base ("proton sponge") with unusual properties

Legal Information

Proton-sponge is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCD9416
BCCD9879
BCBR6285V
BCCB2342
BCCB1749

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Sigma-Aldrich

76830

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R.L. Benoit et al.
Canadian Journal of Chemistry, 65, 996-996 (1987)
Yu Xia et al.
Analytical chemistry, 77(11), 3683-3689 (2005-06-01)
A single sonic spray source has been used to generate both positive and negative ions for subsequent ion/ion reaction experiments. Ion/ion reactions took place after ions of each polarity were sequentially injected into a linear ion trap, where axial trapping
R.W. Alder et al.
Journal of the Chemical Society. Chemical Communications, 723-723 (1968)
Extractant screening for liquid-liquid extraction in environmentally benign production routes.
Krzyzaniak A, et al.
Chemical Engineering Transactions, 24, 709-714 (2011)
Bismuth compounds in organic synthesis. Bismuth nitrate catalyzed chemoselective synthesis of acylals from aromatic aldehydes.
Aggen DH, et al.
Tetrahedron, 60(16), 3675-3679 (2004)
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