692-32-0

Basic information

• Product Name: 3-(DIMETHYLAMINO)ACROLEIN
• Synonyms: (E)-3-(DIMETHYLAMINO)ACRYLALDEHYDE;3-DIMETHYLAMINOACRYLALDEHYDE
• CAS NO: 692-32-0
• Molecular Formula: C₅H₉NO
• Molecular Weight: 99.13
• EINECS: 213-157-7
• Mol File: 692-32-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 270-273 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.99 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.584(lit.)
• PKA: 5.82±0.70(Predicted)
• CAS DataBase Reference: 3-(DIMETHYLAMINO)ACROLEIN(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(DIMETHYLAMINO)ACROLEIN(692-32-0)
• EPA Substance Registry System: 3-(DIMETHYLAMINO)ACROLEIN(692-32-0)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3267 8/PG 2
• WGK Germany: 3
• F: 8-19
• Hazardous Substances Data: 692-32-0(Hazardous Substances Data)

Usage

Uses

(E)-3-(Dimethylamino)acrylaldehyde is used in the preparation of Pyrrolo[1,2-b]pyridazine derivatives as IRAK4 inhibitors.

Upstream product

• 109-53-5 isobutyl vinyl ether 
• 68-12-2 N,N-dimethyl-formamide 
• 109-92-2 ethyl vinyl ether 
• 92444-70-7 N-benzyl-N-acetylaminoethane 
• 1186-70-5 bis(dimethylamino)methoxymethane 
• 75-07-0 acetaldehyde 
• 52950-92-2 dimethyl<3-(dimethylamino)-2-propylidene>immonium tetrafluoroborate 
• 542-78-9 Malondialdehyde 
• 506-59-2 N,N-dimethylammonium chloride 

Downstream Products

• 256376-59-7 ethyl 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboxylate 
• 1388020-66-3 (E)-3-(5-((2,6-diphenyl-4H-pyran-4-ylidene)methyl)thiazol-2-yl)acrylaldehyde 
• 62-75-9 N-Nitrosodimethylamine 
• 636-41-9 2-methyl-1H-pyrrole 
• 616-43-3 3-methylpyrrole 
• 37496-06-3 2-benzoyl-1-methyl-1H-pyrrole 
• 23466-27-5 ethyl 1-methyl-1H-pyrrole-2-carboxylate 
• 274-55-5 5-Azaindolizin 
• 3179-63-3 3-Dimethylamino-1-propanol 
• 90134-11-5 4-(dibutylamino)cinnamaldehyde 
• 110-86-1 pyridine 
• 90584-76-2 N-(3-(Dimethylamino)-2-(phenylthio)-2-propenylidene)-N-methylmethanaminium Perchlorate 
• 581-47-5 4-(2-pyridyl)pyridine 
• 26387-91-7 2-Methoxycarbonyl-1-oxo-3-dimethylamino-4,4-diphenyl-cyclo-buten-2 

Relevant articles and documents

REACTION OF AMINALS OF CONJUGATED ω-DIMETHYLAMINO ALDEHYDES WITH INDANEDIONE

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Red-fluorescent argininamide-type NPY Y1 receptor antagonists as pharmacological tools

Fluorescently labelled NPY Y1 receptor (Y1R) ligands were synthesized by connecting pyrylium and cyanine dyes with the argininamide-type Y1R antagonist core structure by linkers, covering a wide variety in length and chemical nature, attached to the guanidine group. The most promising fluorescent probes had Y1R affinities (radioligand binding) and antagonistic activities (calcium assay) in the one- to two-digit nanomolar range. These compounds turned out to be stable under assay conditions and to be appropriate for the detection of Y1Rs by confocal microscopy in live cells. To improve the signal-to-noise ratio by shifting the emission into the near infrared, a new benzothiazolium-type fluorescent cyanine dye (UR-DE99) was synthesized and attached to the parent antagonist via a carbamoyl linker yielding UR-MK131, a highly potent fluorescent Y1R probe, which was also successfully applied in flow cytometry.

1-Acceptor Substituted Vinamidinium Salts: Stability and Reactivity

1-Chloro- and 1,3-dichloro-vinamidinium salts react with potassium cyanide to afford 1-cyano- and 1,3-dicyano-vinamidinium salts.The former add nucleophiles at the C-3 position.MNDO calculations, competitive hydrolysis experiments and cyclic voltammetry reveal the following sequence of stabilities of vinamidinium salts: 1,3-(NMe2)2 > 1-NMe2 > 2-Aza > H > 2-(p-MeOC6H4) > 2-OMe > 2-Cl > 2-CN > 1,3-(SMe)2 > 1-Cl > 1-CO2Et > 2-NO2 > 1-CN > 1,3-(CN)2.Interestingly enough, reduction potentials show that 1,3-dicyanovinamidinium salt is more stable than a 1,3-dichlorovinamidinium salt, whereas a 1-chlorovinamidinium salt is more stable than a 1-cyanovinamidinium salt. - Keywords: Vinamidinium Salts, Hydrolysis, Cyclovoltammetry, MNDO Calculations