1-N,1-N,8-N,8-N-tetramethylnaphthalene-1,8-diamine

• ChemBase ID: 79457
• Molecular Formular: C14H18N2
• Molecular Mass: 214.30612
• Monoisotopic Mass: 214.14699859
• SMILES: N(c1c2c(ccc1)cccc2N(C)C)(C)C
• Canonical SMILES: CN(c1cccc2c1c(ccc2)N(C)C)C
• InChI: 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
• InChIKey: GJFNRSDCSTVPCJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-N,1-N,8-N,8-N-tetramethylnaphthalene-1,8-diamine
• IUPAC Traditional name: 1-N,1-N,8-N,8-N-tetramethylnaphthalene-1,8-diamine
• Synonyms: Proton-sponge; N1,N1,N8,N8-Tetramethylnaphthalene-1,8-diamine; 1,8-Bis(dimethylamino)naphthalene; 1,8-Bis(dimethylamino)naphthalene; N,N,N′,N′-Tetramethyl-1,8-naphthalenediamine; Proton-sponge®; Proton Sponge; N,N,N’,N’-Tetramethyl-1,8-diaminonaphthalene; N,N,N’,N’-Tetramethyl-1,8-naphthalenediamine; N1,N1,N8,N8-Tetramethyl-1,8-naphthalenediamine; N1,N1,N8,N8-Tetramethylnaphthalene-1,8-diamine; N,N,N',N'-Tetramethyl-1,8-naphthalenediamine; 1,8-Bis(dimethylamino)naphthalene; DMAN; Proton-sponge®; N,N,N′,N′-Tetramethyl-1,8-naphthalenediamine; 1,8-bis[Dimethylamino]naphthalene; N,N,N',N'-TETRAMETHYL-1,8-NAPHTHALENEDIAMINE; 1,8-双二甲氨基萘; N,N,N′,N′-四甲基-1,8-萘二胺; 1,8-双(二甲基氨基)萘; N,N,N′,N′-四甲基-1,8-萘二胺

Database IDs

• CAS Number: 20734-58-1
• EC Number: 244-001-6
• MDL Number: MFCD00003920
• Beilstein Number: 396782
• PubChem SID: 162044220; 24848867; 24849762
• PubChem CID: 88675
• Chemspider ID: 80012
• Wikipedia Title: 1,8-Bis(dimethylamino)naphthalene

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.9614348
• LogD (pH = 7.4): 3.175277
• Log P: 3.1788104
• Molar Refractivity: 71.3654 cm^3
• Polarizability: 27.593422 Å^3
• Polar Surface Area: 6.48 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 45-49 °C; 47.8°C; 47-51°C; 49-51 °C(lit.); 49-51°C
• Boiling Point: 144-145°C/7mm; 144-145°C/7mm
• Flash Point: >110°C(230°F); 113 °C; 113°C; 235.4 °F
• pKa: 12.1 (in water); 18.62 (in acetonitrile); (acidity of the conjugate acid C₁₄H₁₈N₂H^+)

Safety Information

• Storage Condition: 2-8°C, Protect from light
• Storage Warning: Air & Light Sensitive; Harmful/Light Sensitive/Air Sensitive
• European Hazard Symbols: Corrosive (C); Harmful (Xn)
• UN Number: UN3263
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: III
• Risk Statements: 22-36/37/38; 34
• Safety Statements: 26; 26-36/37/39-45-60
• TSCA Listed: 否
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335; H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

• Purity: ≥99.0% (NT); 98%; 98+%; 99%
• Grade: purum
• Linear Formula: C10H6[N(CH3)2]2
• Empirical Formula (Hill Notation): C14H18N2

DETAILS

MP Biomedicals - 02195518

A strong base with weak nucleophilic character caused by steric effects.

Sigma Aldrich - 158496

Packaging
10, 50 g in glass bottle
Application
Very strong base with weak nucleophilic character due to steric effects.1
Legal Information
Proton-sponge is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 14795

Other Notes
Strong amine base ("proton sponge") with unusual properties1,2
Legal Information
Proton-sponge is a registered trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - B429760

1,8-Bis(dimethylamino)naphthalene, also referred to as protone sponge, is a lipophilic proton trapping agent. 1,8-Bis(dimethylamino)naphthalene is used in the matrix for mass spectroscopy analysis of lipids and fatty acids.

REFERENCES

• Daniell, H. et al.: Biochem. Biophys. Res. Comm., 107, 1191 (1982)
• Shroff, R. et al.: Anal. Chem., 81, 7954 (1982)
• The steric strain is relieved on protonation, hence it is one of the strongest organic bases known, but is only weakly nucleophilic: Chem. Commun., 723 (1968). In DMF vic-dibromides are debrominated in high yield: Synth. Commun., 5, 87 (1975).
• Has been used In combination with Diphenylphosphonic azide, A12124, for the conversion of carboxylic acids to isocyanates: Synth. Commun., 23, 335 (1993). Preferred base for the conversion of aliphatic amines to isocyanates with Trichloromethyl chloroformate, A17444.