5541-74-2

Basic information

• Product Name: 8-hydroxy-5-methylquinoline-7-carbaldehyde
• CAS NO: 5541-74-2
• Molecular Formula: C₁₁H₉NO₂
• Molecular Weight: 187.1947
• Mol File: 5541-74-2.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 343.3°C at 760 mmHg
• Flash Point: 161.4°C
• Density: 1.307g/cm³
• Vapor Pressure: 3.57E-05mmHg at 25°C
• Refractive Index: 1.705
• CAS DataBase Reference: 8-hydroxy-5-methylquinoline-7-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 8-hydroxy-5-methylquinoline-7-carbaldehyde(5541-74-2)
• EPA Substance Registry System: 8-hydroxy-5-methylquinoline-7-carbaldehyde(5541-74-2)

Safety Data

• Hazardous Substances Data: 5541-74-2(Hazardous Substances Data)

Upstream product

• 5541-67-3 5-methyl-8-quinolinol 
• 100-97-0 hexamethylenetetramine 
• 67-66-3 chloroform 

Downstream Products

• 3879-67-2 1-ethyl-3,3,6'-trimethyl-1,3-dihydro-spiro[indole-2,2'-pyrano[3,2-h]quinoline] 
• 13784-95-7 3-Methyl-2-(2-<8-hydroxy-5-methyl-chinolyl-(7)>-vinyl)-benzothiazolium 
• 13848-03-8 3-Methyl-2-(2-<8-hydroxy-5-methyl-chinolyl-(7)>-vinyl)-benzoselenazolium 

Relevant articles and documents

Synthesis, electrochemical and spectroscopic characterization of selected quinolinecarbaldehydes and their Schiff base derivatives

A new approach to the synthesis of selected quinolinecarbaldehydes with carbonyl groups located at C5 and/or in C7 positions is presented in this paper in conjunction with spectroscopic characterization of the products. The classical Reimer-Tiemann, Vilsmeier-Haack and Duff aldehyde synthesis methods were compared due to their importance. Computational studies were carried out to explain the preferred selectivity of the presented formylation transformations. A carbene insertion reaction based on Reimer-Tiemann methodology is presented for making 7-bromo-8-hydroxyquinoline-5-carbaldehyde. Additionally, Duff and Vilsmeier-Haack reactions were used in the double formylation of quinoline derivatives and their analogues benzo[h]quinolin-10-ol, 8-hydroxy-2-methylquinoline-5,7-dicarbaldehyde, 8-(dimethylamino) quinoline-5,7-dicarbaldehyde and 10-hydroxybenzo[h]quinoline-7,9-dicarbaldehyde. Four Schiff base derivatives of 2,6-diisopropylbenzenamine were prepared from selected quinoline-5-carbaldehydes and quinoline-7-carbaldehyde by an efficient synthesis protocol. Their properties have been characterized by a combination of several techniques: MS, HRMS, GC-MS, FTIR, electronic absorption spectroscopy and multinuclear NMR. The electrochemical properties of 8-hydroxy-quinoline-5-carbaldehyde, 6-(dimethylamino)quinoline-5-carbaldehyde and its methylated derivative were investigated, and a strong correlation between the chemical structure and obtained reduction and oxidation potentials was found. The presence of a methyl group facilitates oxidation. In contrast, the reduction potential of methylated compounds was more negative comparing to non-methylated structure. Calculations of frontier molecular orbitals supported the finding. The structures of 8-hydroxy-2-methylquinoline-5,7-dicarbaldehyde and four Schiff bases were determined by single-crystal X-ray diffraction measurements.