| Identification | More | [Name]
2-CHLOROLEPIDINE | [CAS]
634-47-9 | [Synonyms]
2-CHLORO-4-METHYLQUINOLINE
2-CHLOROLEPIDINE
AKOS BB-6898
AKOS BBS-00000215
OTAVA-BB BB0116110026
2-chloro-4-methyl-quinolin
Lepidine, 2-chloro-
Chlorolepidine
3-chlorolepidine
2-Chloro-4-methylquinoline, 2-Chlorolepidine | [EINECS(EC#)]
211-209-3 | [Molecular Formula]
C10H8ClN | [MDL Number]
MFCD00006742 | [Molecular Weight]
177.63 | [MOL File]
634-47-9.mol |
| Questions And Answer | Back Directory | [Description]
4-Methyl-2-chloro-quinoline is an organic intermediate. It has been reported that it can be used to prepare graphite electrodes based on CrO-FeO-PbO and quinoline modified and a modified vermiculite adsorbent for the adsorption and removal of benzene in chemical wastewater. | [Preparation]
The mixture of 2-hydroxy-4-methylquinoline and phosphorus oxychloride was heated to 80-85°C. After the solid was completely dissolved, the mixture was poured into ice water, the mixture was extracted with ether, and the ether extract was distilled out of ether. Afterwards, carry out vacuum distillation, collect 132-135 ℃ (0.4kPa) fraction, namely 2-chloro-4-methylquinoline. For further purification, petroleum ether (boiling point 40-50°C) can be used for recrystallization, and the yield is 86%-89%. |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powder | [Melting point ]
55-58 °C(lit.) | [Boiling point ]
296 °C(lit.) | [density ]
1.1810 (rough estimate) | [refractive index ]
1.6224 (estimate) | [Fp ]
296°C | [storage temp. ]
Inert atmosphere,Room Temperature | [form ]
powder to crystal | [pka]
0.98±0.50(Predicted) | [color ]
White to Almost white | [BRN ]
118333 | [InChI]
InChI=1S/C10H8ClN/c1-7-6-10(11)12-9-5-3-2-4-8(7)9/h2-6H,1H3 | [InChIKey]
PFEIMKNQOIFKSW-UHFFFAOYSA-N | [SMILES]
N1C2C(=CC=CC=2)C(C)=CC=1Cl | [CAS DataBase Reference]
634-47-9(CAS DataBase Reference) | [NIST Chemistry Reference]
Quinoline, 2-chloro-4-methyl-(634-47-9) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HS Code ]
29334900 |
| Hazard Information | Back Directory | [Chemical Properties]
white to light yellow crystal powder | [Uses]
2-Chloro-4-methyl-quinoline is a useful synthetic intermediate. It is an intermediate used to synthesize 4-Methyl-2-(1-piperidinyl)-quinoline (M320715) which is a potent inhibitor of TRPC4 channels, responsible for various stimulation, muscle response due to interaction with the environment. 2-Chloro-4-methyl-quinoline is also considered as a cyanine dye. | [Synthesis Reference(s)]
Journal of the American Chemical Society, 63, p. 2367, 1941 DOI: 10.1021/ja01854a016
Organic Syntheses, Coll. Vol. 3, p. 194, 1955 | [Synthesis]
General method: 4-Methylquinoline-N-oxide (1.0 eq.) was dissolved in anhydrous dichloromethane (0.1 M) at 0 °C. Phosphorous trichloride (1.2 eq.) was added slowly with stirring, followed by the addition of N,N-dimethylformamide (0.5 eq.) dropwise under argon protection. The reaction mixture was gradually warmed to 25 °C with continuous stirring until the reaction was complete (monitored by TLC). After completion of the reaction, saturated aqueous sodium carbonate solution was slowly added and the pH was adjusted to 7~8. The aqueous phase was extracted with dichloromethane, the organic phases were combined, washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the organic phase was concentrated under reduced pressure to obtain the crude product. The crude product was purified by fast column chromatography using petroleum ether/ethyl acetate (80:1) as eluent to obtain 2-chloro-4-methylquinoline. | [References]
[1] Tetrahedron Letters, 2014, vol. 55, # 51, p. 7130 - 7132 |
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