4-(N,N-Dimethylamino)butanal Dimethyl Acetal Chemical Properties

Boiling point:

164°C

Density 

0.892

refractive index 

1.4200-1.4240

Flash point:

25°C

storage temp. 

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

solubility 

Chloroform (Sparingly), Ethyl Acetate (Slightly)

form 

clear liquid

pka

9.71±0.28(Predicted)

color 

Colorless to Light yellow

Stability:

Moisture Sensitive

InChI

InChI=1S/C8H19NO2/c1-9(2)7-5-6-8(10-3)11-4/h8H,5-7H2,1-4H3

InChIKey

WDZKKBDOGYBYBG-UHFFFAOYSA-N

SMILES

C(N(C)C)CCC(OC)OC

CAS DataBase Reference

19718-92-4(CAS DataBase Reference)

Safety Information

HS Code 

2922.19.9690

4-(N,N-Dimethylamino)butanal Dimethyl Acetal Usage And Synthesis

Chemical Properties

Pale Brown Oil.

Uses

4-(N,N-Dimethylamino)butanal Dimethyl Acetal is a reactant used in the synthesis of hallucinogenic tryptamines.

General Description

4-(N,N-Dimethylamino)butanal Dimethyl Acetal is the acetal of 4-(N,N-dimethylamino)butanal. It is soluble in organic solvents and can be used as a building block for various organic syntheses, such as the synthesis of amides or sulfones. 4-(N,N-Dimethylamino)butanal Dimethyl Acetal has a high yield and can be prepared in one step by reacting methanesulfonic acid with dimethyl acetaldehyde. This reaction requires sulfuric acid and methane as catalysts.

Synthesis

synthesis of 4-(N,N-Dimethylamino)butanal dimethyl acetal: 4- Chlorobutanal dimethyl acetal (2) (100 g, 0.655 mol) was dissolved in aqueous dimethyl amine solution (200 mL) and the solution is stirred for 15 min at ambient temperature. The reaction mixture was then warmed to 50 oC and stirred for 3 h. After the reaction mixture was cooled to room temperature, the product was extracted with methylene chloride (2 × 250 mL). The combined organic layers were washed with 5 % NaHCO3 solution (2 × 100 mL) and brine solution (2 × 100 mL). The organic layer was evaporated and the residue was distilled to afford 88 g (84 %) of 4-(N,Ndimethylamino)butanal dimethyl acetal as a colourless liquid with 99.6 % purity by GC: b.p. 40 oC/1 mm Hg.

(a) (i) Sodium carbonate, dichloromethane, 5 oC, 0.5 h (ii) Methanol, conc. H2SO4, room temperature, 3 h, 87 %. (b) Aqueous dimethyl amine solution (30 %), 50 oC, 3 h, 76.0 %
1H NMR (CDCl3, 200 MHz): δ 1.47-1.63 (m, 4H), 2.21 (s, 6H), 2.24 (t, J = 7.0 Hz, 2H), 3.31 (s, 6H), 4.37 (t, J = 5.4 Hz, 2H). IR (cm-1): 2945 (-CH2-), 2816 (-CH-), 1464 (C-N), 1074 (-C-O-). Mass: m/z 162.5 (M+1).

4-(N,N-Dimethylamino)butanal Dimethyl Acetal(19718-92-4)Related Product Information

• ETHANE
• Dimethyl ether
• Dimethyl fumarate
• Bromoacetaldehyde dimethyl acetal
• Acetal
• Dimethyl carbonate
• POLY(VINYL BUTYRAL)
• Dimethyl sulfoxide
• N,N-Dimethylformamide
• Aminoacetaldehyde dimethyl acetal
• Dacthal
• 3-Dimethylaminopropylamine
• 2-Dimethylaminoethanol
• 4,4-Diethoxy-N,N-dimethyl-1-butanamine
• Acetylspiramycin
• Oxamisole
• SPINOSAD
• DOTARIZINE