| Identification | More | [Name]
3-CHLORO-6-METHOXYPYRIDAZINE | [CAS]
1722-10-7 | [Synonyms]
3-CHLORO-6-METHOXYPYRIDAZINE
SPECS AC-907/25014054
TIMTEC-BB SBB004124
3-Methoxy-6-chloropyridazine
6-Chloro-3-methoxypyridazine
pyridazine, 3-chloro-6-methoxy- | [EINECS(EC#)]
217-019-7 | [Molecular Formula]
C5H5ClN2O | [MDL Number]
MFCD00006467 | [Molecular Weight]
144.56 | [MOL File]
1722-10-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
84-85 °C(lit.)
| [Boiling point ]
285℃ | [density ]
1.292 | [Fp ]
126℃ | [storage temp. ]
Inert atmosphere,Room Temperature | [form ]
powder to crystal | [pka]
0.74±0.10(Predicted) | [color ]
White to Almost white | [BRN ]
118854 | [InChI]
InChI=1S/C5H5ClN2O/c1-9-5-3-2-4(6)7-8-5/h2-3H,1H3 | [InChIKey]
XBJLKXOOHLLTPG-UHFFFAOYSA-N | [SMILES]
C1(Cl)=NN=C(OC)C=C1 | [CAS DataBase Reference]
1722-10-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P264-P271-P280-P302+P352-P305+P351+P338 | [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 . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
2933998090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Uses]
3-Chloro-6-methoxypyridazine was used in the preparation of number of α-aryl-α-(pyridazin-3-yl)-acetonitriles. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 60, p. 1466, 1995 DOI: 10.1021/jo00110a059 | [General Description]
3-Chloro-6-methoxypyridazine undergoes regioselective metallation using various lithium alkylamides, temperatures and solvents (THF and ether). It was lithiated using lithium 2,2,6,6-tetramethylpiperidide during the synthesis of minaprine. | [Synthesis]
A methanolic solution of 0.5 M sodium methanolate (NaOMe/MeOH, 7.4 mL, 3.69 mmol) was slowly added dropwise to a solution of anhydrous tetrahydrofuran (12 mL) containing 3,6-dichloropyridazine (500 mg, 3.36 mmol), and the reaction mixture was stirred for 1 h at room temperature. Subsequently, the reaction was quenched by the addition of water. The reaction mixture was extracted with ethyl acetate and the organic phases were combined. The organic phase was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography to afford 6-methoxy-3-chloropyridazine (436 mg, 90% yield) as a white solid.1H NMR (400 MHz, CDCl3) δ 4.12 (s, 3H), 6.98 (d, J = 9.2 Hz, 1H), 7.38 (d, J = 9.2 Hz, 1H); 13C NMR (100 MHz, CDCl3) δ 55.5 (d, J = 9.2 Hz, 1H). CDCl3) δ 55.2, 119.9, 130.6, 150.9, 164.2. | [References]
[1] Journal of Heterocyclic Chemistry, 2005, vol. 42, # 4, p. 509 - 513
[2] Patent: US2010/261727, 2010, A1. Location in patent: Page/Page column 31
[3] ACS Chemical Neuroscience, 2017, vol. 8, # 11, p. 2374 - 2380
[4] Journal of Heterocyclic Chemistry, 2013, vol. 50, # 5, p. 1165 - 1173
[5] Journal of the American Chemical Society, 1959, vol. 81, p. 6511,6512 |
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