| Identification | Back Directory | [Name]
3,4,5-TRICHLOROPYRIDAZINE | [CAS]
14161-11-6 | [Synonyms]
Nsc 75074
3,4,5-TrichL
Einecs 238-006-2
3,4,5-Trichlorpyridazin
3,4,5-TRICHLOROPYRIDAZINE
3,4,5-Trichloro-1,2-diazine
Pyridazine,3,4,5-trichloro-
3,4,5-TRICHLOROPYRIDAZINE 98%
3,4,5-TRICHLOROPYRIDAZINE ISO 9001：2015 REACH | [EINECS(EC#)]
238-006-2 | [Molecular Formula]
C4HCl3N2 | [MDL Number]
MFCD00006464 | [MOL File]
14161-11-6.mol | [Molecular Weight]
183.42 |
| Chemical Properties | Back Directory | [Melting point ]
56-58 °C | [Boiling point ]
117-118 °C(Press: 14-15 Torr) | [density ]
1.641±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [form ]
Pale lemon chunks / flakes | [pka]
-2.14±0.10(Predicted) | [Appearance]
Light yellow to brown Solid | [InChI]
InChI=1S/C4HCl3N2/c5-2-1-8-9-4(7)3(2)6/h1H | [InChIKey]
GBAOOJAWDCNOGO-UHFFFAOYSA-N | [SMILES]
C1(Cl)=NN=CC(Cl)=C1Cl |
| Hazard Information | Back Directory | [Uses]
3,4,5-Trichloropyridazine is an important nitrogen-containing heterocyclic compound, primarily used in the fine chemicals industry as a key intermediate in the synthesis of pharmaceuticals and agrochemicals. Due to the presence of multiple chlorine atoms in its molecular structure that readily undergo nucleophilic substitution reactions, it is widely used as a starting material for constructing complex pyridazine derivatives. | [Synthesis]
General procedure for the synthesis of 3,4,5-trichloropyridazine from 4,5-dichloropyridazin-3(2H)-one: 4,5-dichloro-3-hydroxypyridazine (25 g, 151 mmol) was mixed with phosphorochloridic acid chloride (80 mL), and the reaction was stirred under refluxing conditions (120 °C) for 24 hours. Upon completion of the reaction, the excess phosphoryl chloride was removed by distillation under reduced pressure. The residue was cooled to -78 °C and held for 5-10 min before ice (300 mL) was slowly added. Subsequently, the reaction system was transferred from a -78 °C bath to a 0 °C bath and gradually warmed to room temperature. After the ice was completely melted, the precipitated white solid was pulverized and the mixture continued to be stirred overnight. The solid product was collected by filtration, washed with water and dried to give Intermediate I-09 (26.105 g, 94% yield) as a white solid.HPLC-MS (Method 4) analyzed the results: retention time (Rt) = 3.3 min, [M + H]+ m/z = 183. | [References]
[1] Patent: WO2013/4984, 2013, A1. Location in patent: Page/Page column 70
[2] Patent: US2014/171435, 2014, A1. Location in patent: Paragraph 0451; 0452; 0453
[3] Patent: WO2015/189744, 2015, A1. Location in patent: Page/Page column 66-67
[4] Patent: US6800758, 2004, B1. Location in patent: Page column 12
[5] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10311 - 10322 |
| Spectrum Detail | Back Directory | [Spectrum Detail]
3,4,5-TRICHLOROPYRIDAZINE(14161-11-6)MS
3,4,5-TRICHLOROPYRIDAZINE(14161-11-6)1HNMR
3,4,5-TRICHLOROPYRIDAZINE(14161-11-6)13CNMR
3,4,5-TRICHLOROPYRIDAZINE(14161-11-6)IR1
3,4,5-TRICHLOROPYRIDAZINE(14161-11-6)IR2
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