6-DIMETHYLAMINO-2-NAPHTHALDEHYDE

6-DIMETHYLAMINO-2-NAPHTHALDEHYDE Property

Boiling point:

370.4±17.0 °C(Predicted)

Density 

1.150±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

3.55±0.40(Predicted)

Appearance

Light yellow to yellow Solid

InChI

InChI=1S/C13H13NO/c1-14(2)13-6-5-11-7-10(9-15)3-4-12(11)8-13/h3-9H,1-2H3

InChIKey

IVFSOOIWIYPDLX-UHFFFAOYSA-N

SMILES

C1=C2C(C=C(N(C)C)C=C2)=CC=C1C=O

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

6-DIMETHYLAMINO-2-NAPHTHALDEHYDE Chemical Properties,Usage,Production

Synthesis

1. 11.4 g of 6-bromo-N,N-dimethylnaphthalen-2-amine (Intermediate 1) was dissolved in 50 mL of anhydrous tetrahydrofuran and cooled to -78 °C under nitrogen protection. 2. 27.5 mL of n-butyllithium (2.5 M n-hexane solution) was added dropwise slowly, and the reaction was stirred at a temperature of -78 °C for 30 min. 3. 5.5 mL of N,N- dimethylformamide (DMF) to the reaction system, the reaction mixture was gradually warmed to room temperature and stirring was continued for 15 min. 4. The reaction solution was adjusted to acidic (pH<7) with 1 M hydrochloric acid and stirred for 15 min at room temperature. 5. The reaction solution was adjusted to basic (pH>7) with ammonia, and the resulting solid was collected by filtration. 6. The solid was washed several times with deionized water, and dried to afford 8.6 g of the yellow solid product 6-( dimethylamino)-2-naphthalenal in 93.5% yield.

References

[1] Patent: CN104140381, 2018, B. Location in patent: Paragraph 0057-0058
[2] Organic Letters, 2012, vol. 14, # 10, p. 2598 - 2601
[3] Patent: CN108218743, 2018, A. Location in patent: Paragraph 0040; 0045-0047
[4] Journal of the American Chemical Society, 2017, vol. 139, # 38, p. 13393 - 13403
[5] Chemistry - A European Journal, 2016, vol. 22, # 40, p. 14166 - 14170