| Identification | More | [Name]
4-CHLORO-2-PHENYLQUINAZOLINE | [CAS]
6484-25-9 | [Synonyms]
4-CHLORO-2-PHENYLQUINAZOLINE
AKOS 93518
AM-EX-OL(R)
QUINAZOLINE, 4-CHLORO-2-PHENYL-
4-CHLORO-2-PHENYLQUINAZOLINE
OR
AM-ex-OL
AM-EX-OL, 97% (4-CHLORO-2-PHENYL-QUINAZO LINE)
am-ex-ol tm
4-CHLORO-2-PHENYLQUINAZOLINE 97%
4-CHLORO-2-PHENYLQUINAZOLINE HPLC 99+%
2-Phenyl-4-chloroquinazoline | [EINECS(EC#)]
229-346-2 | [Molecular Formula]
C14H9ClN2 | [MDL Number]
MFCD00006713 | [Molecular Weight]
240.69 | [MOL File]
6484-25-9.mol |
| Chemical Properties | Back Directory | [Appearance]
slightly yellow to yellow crystalline powder | [Melting point ]
124-126 °C(lit.) | [Boiling point ]
383.11°C (rough estimate) | [density ]
1.285 | [refractive index ]
1.5749 (estimate) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2–8 °C | [form ]
Crystalline Powder | [pka]
0.67±0.30(Predicted) | [color ]
Slightly yellow to yellow | [InChI]
1S/C14H9ClN2/c15-13-11-8-4-5-9-12(11)16-14(17-13)10-6-2-1-3-7-10/h1-9H | [InChIKey]
OBHKONRNYCDRKM-UHFFFAOYSA-N | [SMILES]
Clc1nc(nc2ccccc12)-c3ccccc3 | [CAS DataBase Reference]
6484-25-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [HS Code ]
29339980 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [Chemical Properties]
slightly yellow to yellow crystalline powder | [Uses]
Reactant involved in the synthesis of biologically active molecules including:
- Nitrotriazole amines or nitroimidazole amines for use as antitrypanosomal activity and mammalian cytotoxicity
- Quinazoline-containing piperazinylpyrimidine derivatives with antitumor activity
- Quinazoline substituted cyclopentane as HCV NS3/4A protease inhibitors
- Quinazolines with antibacterial and antitumor activity
- Aurora inhibitor MK-0457
Reactant involved in Suzuki-Miyaura cross-coupling and catalyst-free / base-free water promoted nucleophilic aromatic substitution | [Uses]
4-Chloro-2-phenylquinazoline can be involved in the synthesis of biologically active molecules including: Nitrotriazole amines or nitroimidazole amines for use as antitrypanosomal activity and mammalian cytotoxicity.
| [Synthesis Reference(s)]
Journal of the American Chemical Society, 68, p. 1299, 1946 DOI: 10.1021/ja01211a055 | [Synthesis]
General procedure for the synthesis of 4-chloro-2-phenylquinazoline from 4-hydroxy-2-phenylquinazoline: 4-hydroxy-2-phenylquinazoline (10 mmol) was mixed with phosphorochloridic acid (10 mL) and the reaction was stirred under reflux conditions for 9 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure. Ice water was added to the residue and neutralized with ammonium hydroxide until a precipitate was formed, followed by filtration to collect the precipitate. The product 4-chloro-2-phenylquinazoline (7) was purified by recrystallization from ethanol to give a brown solid in 68% yield. The structure of the product was determined by 1H NMR (500 MHz, DMSO-d6) δ 8.19-8.12 (m, 3H), 7.90-7.85 (m, 2H), 7.67-7.62 (m, 1H), 7.61-7.55 (m, 3H) and 13C NMR (126 MHz, DMSO-d6) δ 161.80, 153.93, 146.17, 135.15, 132.29, 131.09, 128.78, 128.50, 127.31, 126.21, 125.70, 120.75 for confirmation. | [References]
[1] Medicinal Chemistry Research, 2012, vol. 21, # 7, p. 1199 - 1206
[2] Acta Chimica Hungarica, 1983, vol. 113, # 3, p. 247 - 256
[3] Organic Letters, 2016, vol. 18, # 9, p. 2150 - 2153
[4] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 6, p. 1987 - 1998
[5] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 24, p. 7858 - 7873 |
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