19718-92-4

Basic information

• Product Name: 1,1-Dimethoxy-N,N-dimethyl-1-butanamine
• Synonyms: 4-(DIMETHYL AMINO)BUTYRALDEHYDE DIMETHYL ACETAL;4-(DIMETHYLAMINO)BUTANAL DIMETHYL ACETAL;4-DIMETHYLAMINO BUTYALDEHYDE DIETHYLACETAL;4-DIMETHYLAMINO BUTYALDEHYDE DIMETHYLACETAL;(4,4-DIMETHOXY-BUTYL)-DIMETHYL-AMINE;N,N-Dimethyl-4-aminobutanal dimethyl acetal;1-Butanamine,4,4-dimethoxy-N,N-dimethyl-;N,N-Dimethyl-4,4-Dimethoxy-1-Butanamine
• CAS NO: 19718-92-4
• Molecular Formula: C₈H₁₉NO₂
• Molecular Weight: 161.24
• EINECS: 1806241-263-5
• Product Categories: Amines;(intermediate of triptans);Other Products
• Mol File: 19718-92-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 164°C
• Flash Point: 25°C
• Appearance: /
• Density: 0.892
• Vapor Pressure: 2.02mmHg at 25°C
• Refractive Index: 1.4200-1.4240
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 9.71±0.28(Predicted)
• CAS DataBase Reference: 1,1-Dimethoxy-N,N-dimethyl-1-butanamine(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-Dimethoxy-N,N-dimethyl-1-butanamine(19718-92-4)
• EPA Substance Registry System: 1,1-Dimethoxy-N,N-dimethyl-1-butanamine(19718-92-4)

Safety Data

• Hazardous Substances Data: 19718-92-4(Hazardous Substances Data)

Usage

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).

InChI:InChI=1/C8H19NO2/c1-6-7-8(10-4,11-5)9(2)3/h6-7H2,1-5H3

Upstream product

• 109-54-6 3-(Dimethylamino)propyl chloride 
• 149-73-5 trimethyl orthoformate 
• 29882-07-3 4-chlorobutanal dimethyl acetal 
• 124-40-3 dimethyl amine 
• 19060-15-2 4-aminobutyraldehyde dimethyl acetal 
• 74-88-4 methyl iodide 

Downstream Products

• 144034-80-0 rizatriptan 
• 139264-17-8 zolmitriptan 
• 103628-46-2 sumatripan 
• 110626-61-4 N,N-Dimethyl-2-<5-(cyanomethyl)-1H-indol-3-yl>ethylamine 
• 156281-04-8 N,N-Dimethyl-5-isopropyl-1H-indole-3-ethanamine 
• 22120-36-1 N,N-Dimethyl-5-fluoro-1H-indole-3-ethanamine 
• 22120-32-7 2-(5-chloro-1H-indol-3-yl)-N, N-dimethylethanamine 
• 61-50-7 N,N-dimethyltryptamine 
• 1019-45-0 N,N-dimethyl-5-methoxytryptamine 
• 17274-65-6 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole 
• 22120-39-4 2-(5-methyl-1H-indol-3-yl)-N,N-dimethylethylamine 

Relevant articles and documents

Use of novel haptens in the production of antibodies for the detection of tryptamines

Tryptamines are a group of hallucinogenic drugs whose detection in body fluids could be simplified by immunochemical assay kits. Antibodies for these assays are obtained by the immunization of laboratory animals with conjugates of a hapten similar to the target analyte and a suitable protein. Therefore we synthesized novel haptens derived from tryptamine-based drugs, with N,N-dimethyltryptamine (DMT), 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT) and N,N-diisopropyltryptamine (DiPT) selected as the target analytes. Their structures were modified with a short linker ended with a carboxylic group. The haptens were conjugated with bovine serum albumin (BSA) and rabbits were immunized with the conjugates. The obtained polyclonal antibodies showed good reactivity and the LOD of the constructed ELISAs was in the range 0.006-0.254 ng mL-1. Thus, they are suitable for the development of immunochemical assay kits.

A NOVEL PROCESS FOR PREPARATION OF INDOLE DERIVATIVES

A novel process of preparation of a compound of 3-(2-Dimethylamino)-N-methyl-lH-indole-5-methane sulfonamide, which comprises of a reaction 4-hydrazino-N-methyl benzene methane sulfonamide with 4-dimethyl amino butyraldehyde diethyl acetal in a chlorinated solvent in the presence of ethyl poly phosphate and conversion of the crude product to a product of 3-(2-Dimethylamino)-N-methyl-lH-indole-5-methane sulfonamide succinate of extra high purity and colour.

Improved Fischer indole reaction for the preparation of N,N-dimethyltryptamines: Synthesis of L-695-894, a potent 5-HT(1D) receptor agonist

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