14795

Sigma-Aldrich

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

purum, ≥99.0% (NT)

Synonym(s):
DMAN, 1,8-Bis(dimethylamino)naphthalene, Proton-sponge®
Empirical Formula (Hill Notation):
C14H18N2
CAS Number:
Molecular Weight:
214.31
Beilstein/REAXYS Number:
396782
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

grade

purum

assay

≥99.0% (NT)

mp

45-49 °C

solubility

chloroform: soluble 50 mg/mL, clear, colorless to faintly brownish-yellow

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 Sigma-Aldrich Co. LLC

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

235.4 °F

Flash Point(C)

113 °C

Certificate of Analysis

Certificate of Origin

R.W. Alder et al.
Journal of the Chemical Society. Chemical Communications, 723-723 (1968)
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)
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...
Extractant screening for liquid-liquid extraction in environmentally benign production routes.
Krzyzaniak A, et al.
Chemical Engineering Transactions, 24, 709-714 (2011)

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