4-DIMETHYLAMINO-1-NAPHTHALDEHYDE

Base Information

• Chemical Name: 4-DIMETHYLAMINO-1-NAPHTHALDEHYDE
• CAS No.: 1971-81-9
• Molecular Formula: C13H13NO
• Molecular Weight: 199.252
• Hs Code.: 2922399090
• Mol file: 1971-81-9.mol

Synonyms:4-(Dimethylamino)-1-naphthalenecarboxaldehyde;4-(Dimethylamino)-1-naphthaldehyde;1-Naphthaldehyde,4-(dimethylamino)- (6CI,7CI,8CI);

Chemical Property of 4-DIMETHYLAMINO-1-NAPHTHALDEHYDE

Chemical Property:

• Vapor Pressure: 5.69E-05mmHg at 25°C
• Melting Point: 43-45 °C(lit.)
• Refractive Index: 1.676
• Boiling Point: 346.6 °C at 760 mmHg
• PKA: 0?+-.0.40(Predicted)
• Flash Point: 136.7 °C
• PSA: 20.31000
• Density: 1.15 g/cm³
• LogP: 2.71830
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-Dimethylamino-1-naphthaldehyde 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-Dimethylamino-1-naphthaldehyde was used in the preparation of leuco base via reaction with 1-phenylpyrrolidine in dilute HCl.

Technology Process of 4-DIMETHYLAMINO-1-NAPHTHALDEHYDE

There total 8 articles about 4-DIMETHYLAMINO-1-NAPHTHALDEHYDE 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: 89.0%

N,N-dimethyl-1-naphthalenamine (86-56-6,112790-02-0,651316-60-8) + trimethyl orthoformate (149-73-5) → 4-dimethylamino-1-naphthaldehyde (1971-81-9)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at 0 - 25 ℃; for 5.5h;

DOI:10.1016/j.tetlet.2007.01.079

Reference yield: 82.0%

vinyl pivalate (3377-92-2,26715-88-8) + (E)-3-(N,N-dimethylamino)-1-phenyl-2-propen-1-one (1131-80-2,1201-93-0,31919-75-2) → 4-dimethylamino-1-naphthaldehyde (1971-81-9)

Guidance literature:

With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; potassium acetate; copper diacetate; lithium hydroxide; In 1,2-dichloro-ethane; at 125 ℃; for 72h; Reagent/catalyst; Catalytic behavior; Inert atmosphere; Molecular sieve; Sealed tube; Schlenk technique;

DOI:10.1021/acs.orglett.8b03284

Reference yield: 67.0%

N,N-dimethyl-1-naphthalenamine (86-56-6,112790-02-0,651316-60-8) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 4-dimethylamino-1-naphthaldehyde (1971-81-9)

Guidance literature:

With trichlorophosphate; In toluene; at 30 - 80 ℃; for 2h;

DOI:10.1134/S107042800603002X

upstream raw materials:

N,N-dimethyl-1-naphthalenamine

N-Formylpiperidine

4-bromo-1-(N,N-dimethylamino)naphthalene

N,N-dimethyl-formamide

Downstream raw materials:

N,N-dimethyl-4-(1-phenyl-1H-phenanthro[9,10-d]imidazol-2-yl)naphthalen-1-amine

4-((4-(dimethylamino)naphthalen-1-yl)methyleneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

methyl (2S,5E)-6-(4-dimethylaminonaphthalen-1-yl)-4-oxo-2-(tritylamino)hex-5-enoate

3-[9-(1-{[4-(dimethylamino)-1-naphthyl]methyl}piperidin-4-yl)-6-morpholin-4-yl-9H-purin-2-yl]phenol

Refernces

• 1、 Liang, Gaohui,Rong, Jiaxin,Sun, Wangbin,Chen, Gengjia,Jiang, Yaojia,Loh, Teck-Peng. "Synthesis of Polyaromatic Rings: Rh(III)-Catalyzed [5 + 1] Annulation of Enaminones with Vinyl Esters through C-H Bond Functionalization". supporting information. p. 7326 - 7331. Retrieved 2018/11/25.
• 2、 Vinogradova,Filatova,Vistorobskii,Pozharskii,Borovlev,Starikova. "Resonance-stabilized α-naphthylmethyl carbocations and spiro compounds based thereon: VII. Transformations of α-naphthylmethyl carbocations stabilized by one electron-donor group or peri-fused heteroring". . p. 338 - 348. Retrieved 2007/10/03.