1,8-Bis(dimethylamino)naphthalene

Base Information

• Chemical Name: 1,8-Bis(dimethylamino)naphthalene
• CAS No.: 20734-58-1
• Molecular Formula: C14H18N2
• Molecular Weight: 214.31
• Hs Code.: 29215900
• European Community (EC) Number: 244-001-6
• UNII: 6S79D2P9H8
• DSSTox Substance ID: DTXSID10174807
• Nikkaji Number: J83.008I
• Wikipedia: 1,8-Bis(dimethylamino)naphthalene
• Wikidata: Q161564
• ChEMBL ID: CHEMBL1574733
• Mol file: 20734-58-1.mol

Synonyms:1,8-bis(dimethylamino)naphthalene;DMAN cpd

Chemical Property of 1,8-Bis(dimethylamino)naphthalene

Chemical Property:

• Appearance/Colour: Pale brownish-pink crystalline powder
• Melting Point: 49-51 °C(lit.)
• Boiling Point: 304.4 °C at 760 mmHg
• PKA: 12.1(at 25℃)
• Flash Point: 128.3 °C
• PSA: 6.48000
• Density: 1.074 g/cm³
• LogP: 2.97180
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: Soluble in organic solvents.
• Water Solubility.: insoluble
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 214.146998583
• Heavy Atom Count: 16
• Complexity: 203

Purity/Quality:

99% ^*data from raw suppliers

1,8-Bis(dimethylamino)naphthalene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, C
• Hazard Codes: Xn,C
• Statements: 22-36/37/38-34
• Safety Statements: 26-45-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Polyaromatic
• Canonical SMILES: CN(C)C1=CC=CC2=C1C(=CC=C2)N(C)C
• Uses: 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. Very strong base in organic synthesis and catalysis. Very strong base with weak nucleophilic character due to steric effects.

Technology Process of 1,8-Bis(dimethylamino)naphthalene

There total 14 articles about 1,8-Bis(dimethylamino)naphthalene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

1,1,3-Trimethyl-2,3-dihydroperimidinium iodide (53133-89-4) → N,N,N',N'-tetramethyl-1,8-diaminonaphthalene (20734-58-1)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 5h; Heating;

Reference yield: 95.0%

naphthalene-1,8-diamine (479-27-6) + methyl iodide (74-88-4) → N,N,N',N'-tetramethyl-1,8-diaminonaphthalene (20734-58-1)

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide; 1.) room temp., 2 h; 2.) 100 deg C, 1 h.;

Reference yield: 95.0%

2,3-dihydro-1,2,2,3-tetramethyl-1H-perimidine (64482-94-6) + methyl iodide (74-88-4) → N,N,N',N'-tetramethyl-1,8-diaminonaphthalene (20734-58-1)

Guidance literature:

In N,N-dimethyl-formamide; at 70 ℃; for 4h;

DOI:10.1023/A:1011359109826

upstream raw materials:

dimethyl sulfate

naphthalene-1,8-diamine

1,8-bis(dimethylamino)naphthalene hydroiodide

protonated 1,8-bis(dimethylaamino)naphthalene

Downstream raw materials:

N¹,N¹,N⁸,N⁸-Tetramethyl-4-(5-nitro-7-aci-nitro-3-oxy-4,7-dihydro-benzo[1,2,5]oxadiazol-4-yl)-naphthalene-1,8-diamine

2,4,5,7-tetranitro-1,8-bis(4-toluenesulphonamido)naphthalene bis(1,8-dimethylamino)napthalene salt

4-abenzoyl-1,8-bis(dimethylamino)naphthalene

4,5-dibenzoyl-1,8-bis(dimethylamino)naphthalene

Refernces

Total synthesis of (±)-oudemansin

10.1016/S0040-4039(00)87009-4

The research focuses on the total synthesis of (+)-oudemansin, an antibiotic with potent antifungal properties, originally isolated from Oudemansiella mucida. The purpose of the study was to develop a synthetic route to (+)-oudemansin starting from N-cinnamaldehyde, utilizing a stereoselective Zn(BH4)2 reduction of β-keto ester as a key step. The synthesis involved a series of chemical reactions, including the Reformatsky reaction, oxidation with PDC, Zn(BH4)2 reduction, methylation using Me3Al and 1,8-bis(dimethylamino)naphthalene (Proton Sponge), hydrolysis with LiOH, and a Wolff rearrangement with silver benzoate. The synthesized (+)-oudemansin was confirmed by comparing its spectral data (IR and NMR) with that of the natural oudemansin, showing identical results. The study concluded that the synthetic route was successful in producing (+)-oudemansin, with the major isomer's C12-H being cis-oriented to the carbonyl group, as indicated by NMR spectra.