Methyl 6-methylpyridazine-3-carboxylate

Base Information

• Chemical Name: Methyl 6-methylpyridazine-3-carboxylate
• CAS No.: 106584-51-4
• Molecular Formula: C₇H₈N₂O₂
• Molecular Weight: 152.153
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID70543732
• Nikkaji Number: J742.916I
• Wikidata: Q82420680
• Mol file: 106584-51-4.mol

Synonyms:METHYL 6-METHYLPYRIDAZINE-3-CARBOXYLATE;106584-51-4;MFCD13174778;3-Pyridazinecarboxylicacid,6-methyl-,methylester(9CI);3-Pyridazinecarboxylic acid, 6-methyl-, methyl ester;Methyl6-Methylpyridazine-3-carboxylate;SCHEMBL11886132;DTXSID70543732;XQLCQIIROGASBW-UHFFFAOYSA-N;AKOS015903648;SB13768;AS-31297;SY007132;CS-0152722;EN300-367412;3-pyridazinecarboxylic acid,6-methyl-,methyl ester;A895764;Z1255400513

Chemical Property of Methyl 6-methylpyridazine-3-carboxylate

Chemical Property:

• PSA: 52.08000
• LogP: 0.57160
• Storage Temp.: 2-8°C
• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 152.058577502
• Heavy Atom Count: 11
• Complexity: 149

Purity/Quality:

98%min ^*data from raw suppliers

Methyl6-Methylpyridazine-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NN=C(C=C1)C(=O)OC

Technology Process of Methyl 6-methylpyridazine-3-carboxylate

There total 4 articles about Methyl 6-methylpyridazine-3-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

3-chloro-6-methylpyridazine (1121-79-5) + methanol (67-56-1) + carbon monoxide (201230-82-2) → methyl 6-methylpyridazine-3-carboxylate (106584-51-4)

Guidance literature:

With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine; In acetonitrile; at 170 ℃; under 17251.7 Torr; Flow reactor;

DOI:10.1002/cctc.201801974

Reference yield: 62.0%

methanol (67-56-1) + carbon monoxide (201230-82-2) + Trifluoromethanesulfonic acid 6-methylpyridazine-3-yl ester (157200-06-1) → methyl 6-methylpyridazine-3-carboxylate (106584-51-4)

Guidance literature:

With triethylamine; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; In N,N-dimethyl-formamide; at 50 ℃; for 12h;

Reference yield:

6-Methylpyridazin-3(2H)-on (13327-27-0) → methyl 6-methylpyridazine-3-carboxylate (106584-51-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / pyridine / 6 h / 0 - 20 °C

2: 62 percent / Et₃N / Pd(OAc)2, 1,1'-bis(diphenylphosphino)ferrocene / dimethylformamide / 12 h / 50 °C

With triethylamine; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; In pyridine; N,N-dimethyl-formamide;

upstream raw materials:

diazomethane

2-Benzoyl-6-methyl-2,3-dihydro-pyridazine-3-carbonitrile

methanol

carbon monoxide

Refernces

• 1、 Rohr, Markus,Toussaint, Dominique,Chayer, Said,Mann, Andre,Suffert, Jean,Wermuth, Camille-Georges. "Convenient preparation of 3-methoxycarbonylpyridazines by palladium catalyzed alkoxycarbonylation of pyridazinetriflates". . p. 1459 - 1464. Retrieved 2007/10/03.