| Identification | More | [Name]
4-Quinolinecarboxaldehyde | [CAS]
4363-93-3 | [Synonyms]
4-FORMYLQUINOLINE
4-QUINOLINECARBALDEHYDE
4-QUINOLINECARBOXALDEHYDE
AKOS BBS-00005334
ASINEX-REAG BAS 01118292
CINCHONINALDEHYDE
QUINOLINE-4-ALDEHYDE
QUINOLINE-4-CARBALDEHYDE
QUINOLINE-4-CARBOXALDEHYDE
RARECHEM AQ NN 0218
TIMTEC-BB SBB004008
4-Quinolinealdehyde
4-QUINOLINECARBOXALDEHYDE 95%
Quinoline-4-carboxaldehyde,99%
4-fomylquinoline
Quinoline-4-carboxaldehyde, 97+%
4-Quinolinecarboxaldehyde ,97% | [EINECS(EC#)]
224-453-0 | [Molecular Formula]
C10H7NO | [MDL Number]
MFCD00006781 | [Molecular Weight]
157.17 | [MOL File]
4363-93-3.mol |
| Chemical Properties | Back Directory | [Appearance]
yellow to yellow-brown crystalline powder | [Melting point ]
45-52 °C (lit.) | [Boiling point ]
131-133°C 5mm | [density ]
1.1599 (rough estimate) | [refractive index ]
1.5000 (estimate) | [Fp ]
>230 °F
| [storage temp. ]
2-8°C
| [form ]
Crystalline Powder, Chunks, or Solid | [pka]
2.95±0.13(Predicted) | [color ]
Off-white to yellow-brown | [Water Solubility ]
Slightly soluble in water. | [Sensitive ]
Air Sensitive | [Detection Methods]
GC,NMR | [BRN ]
113072 | [InChI]
InChI=1S/C10H7NO/c12-7-8-5-6-11-10-4-2-1-3-9(8)10/h1-7H | [InChIKey]
MGCGJBXTNWUHQE-UHFFFAOYSA-N | [SMILES]
N1C2C(=CC=CC=2)C(C=O)=CC=1 | [CAS DataBase Reference]
4363-93-3(CAS DataBase Reference) | [Storage Precautions]
Store under nitrogen |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R37/38:Irritating to respiratory system and skin .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [F ]
10 | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29334900 |
| Hazard Information | Back Directory | [Chemical Properties]
yellow to yellow-brown crystalline powder | [Occurrence]
The common presence of 4-quinolinecarboxaldehyde in honey from Galicia (northwest of Spain). As opposed to other quinoline carboxylic acid derivatives, the 4- quinolinecarboxaldehyde species has not been correlated with the anti-diabetic properties of honey; nevertheless, it appears to be active against intestinal bacteria. | [Uses]
4-Quinolinecarboxaldehyde was used in the synthesis of lepidylamines. It also shows antimicrobial activity toward human intestinal bacteria such as Clostridium perfringens. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 35, p. 841, 1970 DOI: 10.1021/jo00828a074 | [Synthesis]
The general procedure for the synthesis of 4-quinolinecarboxaldehyde from 4-methylquinoline was as follows: 5.0 g (35 mmol) of 4-methylquinoline and 5.0 g (45 mmol) of selenium dioxide were dissolved in toluene under argon protection and heated to reflux for 24 hours. After completion of the reaction, the reaction mixture was diluted with dichloromethane, washed sequentially with saturated saline and dried with anhydrous magnesium sulfate. After concentration under reduced pressure, the reaction was purified by silica gel column chromatography using a solvent mixture of hexane and ethyl acetate (4:1, v/v) as eluent to give 4.0 g (73% yield) of the target product 4-quinolinecarboxaldehyde as a solid. Nuclear magnetic resonance hydrogen spectroscopy (1H NMR) data: δ 10.54 (s, 1H), 9.22 (d, J = 4.3 Hz, 1H), 9.04 (d, J = 8.6 Hz, 1H), 8.24 (d, J = 8.2 Hz, 1H), 7.84 (t, J = 7.6 Hz, 1H), 7.81 (d, J = 4.3 Hz, 1H), 7.76 (t , J = 8.0 Hz, 1H). Nuclear magnetic resonance carbon (13C NMR) data: δ 193.1, 150.7, 149.5, 137.0, 130.4, 130.3, 129.6, 126.0, 124.7, 124.1. mass spectrometry (electrospray ionization) data: m/z 158.0 (100%) ([M + H]+), 130.2. | [References]
[1] Tamara Rodríguez-Cabo. “Time-of-flight accurate mass spectrometry identification of quinoline alkaloids in honey.” Analytical and Bioanalytical Chemistry 407 20 (2015): 6159–6170. |
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