13103-75-8

Basic information

• Product Name: 4-(2-PYRIDYLAZO)-N,N-DIMETHYLANILINE
• Synonyms: PYRIDYLAZO-4-DIMETHYLANILINE;PYRIDINE-2-AZO-P-DIMETHYLANILINE;PYRIDINE-2-AZO-P-DIMETHYL-ANILINE TRANS ISOMER;PADA, TRANS ISOMER;PADA;TRANS-PYRIDINE-2-AZO-P-DIMETHYLANILINE;n,n-dimethyl-4-(2-pyridinylazo)-benzenamin;4-(2-PYRIDYLAZO)-N,N-DIMETHYLANILINE
• CAS NO: 13103-75-8
• Molecular Formula: C₁₃H₁₄N₄
• Molecular Weight: 226.28
• EINECS: 236-026-6
• Product Categories: Pyridines, Pyrimidines, Purines and Pteredines
• Mol File: 13103-75-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 108-110°C
• Boiling Point: 392.8°Cat760mmHg
• Flash Point: 191.4°C
• Appearance: /
• Density: 1.08g/cm³
• Vapor Pressure: 2.22E-06mmHg at 25°C
• Refractive Index: 1.588
• PKA: 3.27±0.10(Predicted)
• Water Solubility: 21.27mg/L(temperature not stated)
• BRN: 185623
• CAS DataBase Reference: 4-(2-PYRIDYLAZO)-N,N-DIMETHYLANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-PYRIDYLAZO)-N,N-DIMETHYLANILINE(13103-75-8)
• EPA Substance Registry System: 4-(2-PYRIDYLAZO)-N,N-DIMETHYLANILINE(13103-75-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 13103-75-8(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 4606, 1951 DOI: 10.1021/ja01154a031

InChI:InChI=1/C13H14N4/c1-17(2)12-8-6-11(7-9-12)15-16-13-5-3-4-10-14-13/h3-10H,1-2H3/b16-15+

Upstream product

• 13103-75-8 N,N-dimethyl-4-([2]pyridyl-cis-azo)-aniline 
• 504-29-0 2-aminopyridine 
• 138-89-6 p-dimethylaminonitrosobenzene 
• 108-88-3 toluene 
• 100-23-2 N,N-Dimethyl-4-nitroaniline 
• 91-20-3 naphthalene 
• 77038-70-1 pyridine-azo-p-dimethyl aniline 

Downstream Products

• 109401-83-4 N,N-dimethyl-4-(1-oxy-[2]pyridylazo)-aniline-N-oxide 
• 77038-70-1 pyridine-azo-p-dimethyl aniline 
• 13103-75-8 N,N-dimethyl-4-([2]pyridyl-cis-azo)-aniline 
• 863638-71-5 Br^(1-)*C₁₉H₂₆BrN₄⁽¹⁺⁾ 
• 890710-13-1 Br^(1-)*C₁₆H₂₀BrN₄⁽¹⁺⁾ 

Relevant articles and documents

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Photoactive azoimine dyes: 4-(2-Pyridylazo)-N,N-diethylaniline and 4-(2-pyridylazo)-N,N-dimethylaniline: Computational and experimental investigation

4-(2-Pyridylazo)-N,N-dimethylaniline and 4-(2-pyridylazo)-N,N- diethylaniline, two photoactive azoimine dyes, were prepared from the reaction of 2-aminopyridine with N,N-dialkyl-1,4-nitrosoaniline at room temperature. Structural characterizations of these dyes using single crystal X-ray diffraction, 1H NMR, elemental analysis, mass spectroscopy and IR spectroscopy have been carried out. The X-ray structure indicates a trans configuration around the azo group. The photochemical behavior of these compounds differs from that of 2-phenylazopyridine, the non-dialkylamino substituent compound. The synthesized compounds show emission spectra at room temperature while 2-phenylazopyridine does not. The excitation spectra of these compounds differ from their absorption spectra which can be explained on the basis of the trans to cis photoisomerization which is supported by the TD-PBE0/6-31G(d,p) calculations. Both oxidation of the dialkylamino substituents (-NR2; R = -CH3 and -C2H5) and reduction of -NN-/-NN-- and -NN--/-NN-2- were observed in the cyclic voltammogram indicating a π-acidity of both dyes.