3-Bromopyridazine

Base Information

• Chemical Name: 3-Bromopyridazine
• CAS No.: 88491-61-6
• Molecular Formula: C4H3BrN2
• Molecular Weight: 158.985
• Hs Code.: 2933990090
• European Community (EC) Number: 811-583-3
• DSSTox Substance ID: DTXSID10520082
• Nikkaji Number: J1.002.398J
• Wikidata: Q72511817
• Mol file: 88491-61-6.mol

Synonyms:3-bromopyridazine;88491-61-6;3-Bromo-pyridazine;Pyridazine, 3-bromo-;MFCD10688587;Pyridazine, 3-bromo- (9CI);SCHEMBL180986;DTXSID10520082;ILYSUJOMLYXAOC-UHFFFAOYSA-N;BCP27608;AKOS009548430;CS-W004020;GS-4388;MB08580;AC-25814;AM804482;SY007900;EN300-42334;J-512136

Chemical Property of 3-Bromopyridazine

Chemical Property:

• Vapor Pressure: 0.012mmHg at 25°C
• Melting Point: 73-74 °C
• Refractive Index: 1.568
• Boiling Point: 269.972 °C at 760 mmHg
• PKA: 0.99±0.10(Predicted)
• Flash Point: 117.075 °C
• PSA: 25.78000
• Density: 1.727 g/cm³
• LogP: 1.23910
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 157.94796
• Heavy Atom Count: 7
• Complexity: 57.7

Purity/Quality:

96% 1H NMR ^*data from raw suppliers

3-Bromopyridazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=NN=C1)Br
• Description: 3-Bromopyridine can undergo lithiation with LDA at low temperatures in the 4-position: Heterocycles, involved in formation of the Grignard by Mg exchange with i-PrMgCl and in transmetallation of the lithiated derivative with zinc chloride followed by treatment with an electrophile as a route to 4-substituted 3-bromopyridines1-4. 3-Bromopyridine is also used as an intermediate in the synthesis of Active Pharmaceutical Ingredients especially Abiraterone acetate (an antiandrogen medication which is used in the treatment of prostate cancer) and Zimelidine (selective serotonin reuptake inhibitor (SSRI) antidepressants)5.

Technology Process of 3-Bromopyridazine

There total 2 articles about 3-Bromopyridazine 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: 69.0%

3-hydroxypyridazine (504-30-3) → 3-bromopyridazine (88491-61-6)

Guidance literature:

With phosphorus(V) oxybromide; at 80 - 120 ℃; for 3h;

Reference yield:

2H-Pyridazin-3-one (504-30-3) → 3-bromopyridazine (88491-61-6)

Guidance literature:

With phosphorus(V) oxybromide;

Reference yield: 73.9%

3-bromopyridazine (88491-61-6) + 5-((1,2,3,5,6,7-hexahydro-s-indacen-4-yl)amino)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazole-3-thiol → N-(1,2,3,5,6,7-hexahydro-s-indacen-4-yl)-3-(pyridazin-3-ylthio)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-5-amine

Guidance literature:

With N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In 1,4-dioxane; at 100 ℃; for 2h; Inert atmosphere;

upstream raw materials:

2H-Pyridazin-3-one

3-hydroxypyridazine

Downstream raw materials:

3-hydrazinyl pyridazine

pyridazine-3-carbonitrile

2-(3-pyridazinyl)-9-vinyloxycarbonyl-9-azabicyclo[4.2.1]non-2-ene

(S)-benzyl 1-[1-(ethoxymethyl)-2-(pyridazin-3-yl)-1H-imidazol-4-yl]ethylcarbamate

Refernces

• 1、 -. "3-OXO-TETRAHYDRO-FURO[3,2-B]PYRROL-4(5H)-YL) DERIVATIVES II". Page/Page column 19; 20. . Retrieved 2015/12/11.