| Identification | More | [Name]
2,6-Dichlorobenzoxazole | [CAS]
3621-82-7 | [Synonyms]
2,6-DICHLOROBENZOXAZOLE
2,6-DICHLOROBENZOXAZOLE 99+%
Benzoxazole, 2,6-dichloro- | [EINECS(EC#)]
222-818-9 | [Molecular Formula]
C7H3Cl2NO | [MDL Number]
MFCD07368635 | [Molecular Weight]
188.01 | [MOL File]
3621-82-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
49-51°C | [Boiling point ]
110°C/13mmHg(lit.) | [density ]
1.522±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,2-8°C | [form ]
fused solid | [pka]
-0.96±0.30(Predicted) | [color ]
White | [InChI]
InChI=1S/C7H3Cl2NO/c8-4-1-2-5-6(3-4)11-7(9)10-5/h1-3H | [InChIKey]
LVVQTPZQNHQLOM-UHFFFAOYSA-N | [SMILES]
O1C2=CC(Cl)=CC=C2N=C1Cl | [CAS DataBase Reference]
3621-82-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
22 | [WGK Germany ]
WGK 3 | [HS Code ]
2934999090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [Chemical Properties]
This product is solid, insoluble in water, soluble in chlorobenzene. | [Uses]
2,6-Dichlorobenzoxazole is used in the synthesis of 2-(3-(2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy)propoxy)-5-(trifluoromethyl)benzo[d]oxazole, an insecticide against Spodoptera exigua. | [Synthesis]
General procedure for the synthesis of 2,6-dichlorobenzoxazole from 6-chlorobenzo[d]oxazole-2(3H)-thione: In a 500-mL four-neck reaction flask, 50 g (0.27 mol) of 6-chlorobenzo[d]oxazole-2(3H)-thione, 300 mL of toluene, and 40 g (0.135 mol) of tris(trichloromethyl)carbonate were added. The reaction mixture was slowly warmed to 50°C and the temperature was continued at a rate of 0.5°C/min, holding the temperature for 10 minutes after each 10°C increase. When the temperature reached 105°C, the reaction was maintained for 1 hour. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure (the initial vacuum was maintained at -0.07 MPa, and when the temperature was raised to 100°C-110°C, the vacuum was increased to -0.095 MPa to completely evaporate the solvent). After evaporation, the residue was removed while hot and cooled and crystallized to give 50.82 g of 2,6-dichlorobenzoxazole with a product purity of 98.1% and a molar yield of 98.4%. | [References]
[1] Patent: CN102432559, 2016, B. Location in patent: Paragraph 0020; 0037; 0038
[2] Patent: WO2018/37223, 2018, A1. Location in patent: Page/Page column 197; 198
[3] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 7, p. 1975 - 1980
[4] Journal of Organic Chemistry, 2009, vol. 74, # 8, p. 3229 - 3231
[5] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 9, p. 3044 - 3049 |
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