20734-56-9

Basic information

• Product Name: 1,8-Bis(methylamino)naphthalene
• Synonyms: 1,8-Bis(methylamino)naphthalene;N,N'-diMethyl-1,8-diaMino naphthalene;N~1~,N~8~-dimethyl-1,8-naphthalenediamine
• CAS NO: 20734-56-9
• Molecular Formula: C₁₂H₁₄N₂
• Molecular Weight: 186.253
• Mol File: 20734-56-9.mol
• Article Data: 13

Chemical Properties

• Melting Point: 102-103 °C
• Boiling Point: 359 °C at 760 mmHg
• Flash Point: 229.3 °C
• Appearance: /
• Density: 1.146 g/cm³
• PKA: 5.83±0.40(Predicted)
• CAS DataBase Reference: 1,8-Bis(methylamino)naphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,8-Bis(methylamino)naphthalene(20734-56-9)
• EPA Substance Registry System: 1,8-Bis(methylamino)naphthalene(20734-56-9)

Safety Data

• Hazardous Substances Data: 20734-56-9(Hazardous Substances Data)

Usage

General Description

1,8-Bis(methylamino)naphthalene, also known as Proton sponge, is a chemical compound with the molecular formula C14H16N2. It is a highly basic and sterically hindered amine that has been used in various chemical and pharmaceutical applications. Its unique structure and properties make it useful as a strong base, a reagent for the synthesis of organic compounds, and as a sensor for metal ions. Due to its strong basicity, it can be used to deprotonate weak acids and facilitate a variety of reactions in organic chemistry. Additionally, its ability to bind to metal ions makes it useful in the detection and quantification of metal contaminants in water and other environmental samples. Overall, 1,8-Bis(methylamino)naphthalene is a versatile compound with important applications in both industrial and research settings.

Upstream product

• 74-88-4 methyl iodide 
• 64482-94-6 2,3-dihydro-1,2,2,3-tetramethyl-1H-perimidine 
• 479-27-6 naphthalene-1,8-diamine 
• 34904-46-6 1,2-dimethyl-1H-perimidine 
• 5157-10-8 2-methyl-1H-perimidine 
• 187403-04-9 C₈BH₁₄NHC₁₀H₆NH₂ 
• 2306-08-3 1,3-dimethyl-1H-perimidin-2(3H)-one 
• 77-78-1 dimethyl sulfate 
• 80-48-8 methyl p-toluene sulfonate 
• 50295-67-5 1,2,3-trimethyl-1H-perimidin-3-ium iodide 

Downstream Products

• 80703-36-2 1,5-dimethylnaphtho-<1,8-bc>-1,5-diazacyclo-nonane 
• 80703-37-3 1,5-dimethylnaphtho-<1,8-bc>-1,5-diazacyclo-nonane 
• 135838-73-2 2-Dodecyl-1,3-dimethyl-2,3-dihydro-1H-perimidine 
• 80703-34-0 1,5-dimethylnaphtho<1,8-bc>-1,5-diazacycloheptane 
• 99643-50-2 1',3'-dimethylspirodihydro<1H>-perimidine> 
• 2306-08-3 1,3-dimethyl-1H-perimidin-2(3H)-one 
• 1179428-54-6 2-[2-(1,3-dimethyl-2-[2-(1,2,3-trimethyl-2,3-dihydro-1H-2-perimidinyl)ethyl]-2,3-dihydro-1H-2-perimidinyl)ethyl]-1,2,3-trimethyl-2,3-dihydro-1H-perimidine 
• 1179428-56-8 C₆₀H₆₆N₈ 
• 1179428-51-3 1,2,3-trimethyl-2-[2-(1,2,3-trimethyl-2,3-dihydro-1H-2-perimidinyl)ethyl]-2,3-dihydro-1H-perimidine 
• 1179428-59-1 C₉₀H₉₈N₁₂ 
• 1179428-49-9 2,2-diethyl-1,3-dimethyl-2,3-dihydro-1H-perimidine 
• 1247022-48-5 3-(4,5-bis(dimethylamino)naphthalen-1-yl)furan-2,5-dione 

Relevant articles and documents

Selective Syntheses of N-Monoalkyl and N,N'-Dialkyl Derivatives of 1,8-Diaminonaphthalene - 9-BBN as an Activating and Directing Group

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Poly(1,1-bis(dialkylamino)propan-1,3-diyl)s; Conformationally-controlled oligomers bearing electroactive groups

The design of polymers with repeating [C(NR2)2CH 2CH2] units which may simultaneously provide conformational control and contain repeating electroactive centres is discussed; (NR2)2 groups would be ideally provided by ortho-phenylenediamine derivatives, with 1,8-diaminonaphthalenes as alternatives. Oligomers containing 1,8-bis(methylamino)naphthalenes, up to the hexamer, were obtained by condensation of oligomers of CH3[COCH 2CH2]nCOCH3 with 1,8-bis(methylamino)naphthalene, but attempts to prepare related oligomers from 1,2-bis(alkylamino)benzenes were unsuccessful, as only terminal ketone groups could be converted to aminals. Evidence for a strong preference for all-anti conformations of the main chain in the naphthalenediamine oligomers is provided by ring current effects on 1H NMR shifts, and by X-ray structures, which also provide evidence of intercalation in the solid state. Electrochemical studies of these oligomers show irreversible oxidation of oligomers in solution, but oxidation of longer oligomers leads to the deposition of a reddish-pink insoluble material which shows two reversible oxidation waves. Possible interpretation of these results is discussed. The Royal Society of Chemistry 2009.

Synthesis, structure, and stereodynamics of an N,N-chiral 'proton sponge'

1,8-Bis(N-benzyl-N-methylamino)naphthalene (2) and its hydrogen iodide salt [2H]+[I]- were synthesised from 1,8-diaminonaphthalene. The thermodynamic diastereomer ratios of (2) and [2H]+ in [D7]DMF are 73.4:26.6 and 89.7:10.3 respectively at 293 K. The solid state structures of the major dl-(R(N)R(N)/S(N)S(N)) diastereomers were determined by single crystal X-ray diffraction. The minor diastereomers were shown to be the meso-(R(N)S(N)) forms by performing 1H-NMR NOE studies on isotopically desymmetrized 1-(N- benzyl-N-[13C]-methylamino)-8-(N'-benzyl-N'-methylamino)naphthalene [13C]-2 and the salt [13C]-[2H]+. In [D7]DMF at 298 K, the meso form of the free base 2 is 0.6 (± 0.07) kcal · mol-1 less stable than the d1 form (ΔH°= -0.64 (±0.03) kcal · mol-1; ΔS°= -0.18 (±0.13) cal · K- 1mol-1) and the activation barriers for interconversion are ca. 14,2 (±0.4) and 14,8 (±0.4) kcal · mol-1 respectively. The effect of solvent polarity on the entropy and enthalpy change on approach to the transition state was studied. An approximate correlation with the solvent dielectric constant was found for both ΔH((+)) and ΔS((+)) and this may be ascribed to the development of a net dipole in the transition state due to substantially different hybridisation and geometry at the two nitrogen centres.