36022-11-4

Basic information

• Product Name: 3-Phenyl-1,2,4,5-tetrazine
• Synonyms: 3-Phenyl-1,2,4,5-tetrazine
• CAS NO: 36022-11-4
• Molecular Formula: C₈H₆N₄
• Molecular Weight: 158.16004
• Mol File: 36022-11-4.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 339.1°C at 760 mmHg
• Flash Point: 163.4°C
• Appearance: /
• Density: 1.239g/cm³
• Vapor Pressure: 0.000184mmHg at 25°C
• Refractive Index: 1.592
• CAS DataBase Reference: 3-Phenyl-1,2,4,5-tetrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Phenyl-1,2,4,5-tetrazine(36022-11-4)
• EPA Substance Registry System: 3-Phenyl-1,2,4,5-tetrazine(36022-11-4)

Safety Data

• Hazardous Substances Data: 36022-11-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H6N4/c1-2-4-7(5-3-1)8-11-9-6-10-12-8/h1-6H

Upstream product

• 35011-53-1 3-bromo-6-phenyl-1,2,4,5-tetrazine 
• 98-80-6 phenylboronic acid 
• 3473-63-0 formamidine acetic acid 
• 825-60-5 benzimidic acid ethyl ester 
• 5333-86-8 ethyl benzimidate hydrochloride 
• 5873-90-5 methyl benzimidate hydrochloride 
• 832112-48-8 3-phenyl-1,4-dihydro-1,2,4,5-tetrazine 

Downstream Products

• 83182-69-8 4-Butyl-3-phenyl-5-(trimethylsilyl)pyridazin 
• 112513-77-6 1-Methyl-9-phenyl-2,3,4,5-tetrahydro-1H-pyridazino[4,5-b]azepine 
• 78113-93-6 6-n-octylamino-3-phenyl-1,2,4,5-tetrazine 
• 83182-77-8 3-Phenyl-5-(trimethylsilyl)-4-<(trimethylsilyl)ethinyl>pyridazin 
• 32139-58-5 (4aS,4bR)-4a,4b-Dimethyl-2-phenyl-2a,2b,4a,4b-tetrahydro-cyclopropa[cd]pentalene 
• 37385-32-3 3,4-diphenylpyridazine 
• 83182-73-4 4-Acetyl-5-(trimethylsilyl)-3-phenyl-pyridazin 
• 83182-74-5 4-Propionyl-3-phenyl-5-(trimethylsilyl)pyridazin 
• 83182-78-9 3-Phenyl-5-(trimethylsilyl)-4-<6-(trimethylsilyl)-5-hexinyl>pyridazin 
• 83182-75-6 4-(1-Butinyl)-3-phenyl-5-(trimethylsilyl)pyridazin 
• 83182-70-1 4-(1-Cyclohexen-1-yl)-3-phenyl-5-(trimethylsilyl)pyridazin 
• 83182-76-7 3-Phenyl-4-(phenylethinyl)-5-(trimethylsilyl)pyridazin 
• 83182-71-2 4-(1-Cyclopenten-1-yl)-3-phenyl-5-(trimethylsilyl)pyridazin 
• 83182-72-3 4-Benzoyl-3-phenyl-5-(trimethylsilyl)pyridazin 

Relevant articles and documents

Cross-Coupling Reactions of Monosubstituted Tetrazines

A Ag-mediated Pd-catalyzed cross-coupling method for 3-bromo-1,2,4,5-tetrazine with boronic acids is presented. Electronic modification of the 1,1′-bis(diphenylphosphine)ferrocene (dppf) ligand was found to be crucial for good turnover. Using this fast method, a variety of alkyl-, heteroatom-, and halide-substituted aryl- and heteroaryl-tetrazines were prepared (29 examples, up to 87% yield).

Boron Trifluoride-Mediated Cycloaddition of 3-Bromotetrazine and Silyl Enol Ethers: Synthesis of 3-Bromo-pyridazines

Pyridazines are important scaffolds for medicinal chemistry or crop protection agents, yet the selective preparation of 3-bromo-pyridazines with high regiocontrol remains difficult. We achieved the Lewis acid-mediated inverse electron demand Diels-Alder reaction between 3-monosubstituted s-tetrazine and silyl enol ethers and obtained functionalized pyridazines. In the case of 1-monosubstituted silyl enol ethers, exclusive regioselectivity was observed. Downstream functionalization of the resulting 3-bromo-pyridazines was demonstrated utilizing several cross-coupling protocols to synthesize 3,4-disubstituted pyridazines with excellent control over the substitution pattern.

Synthesis of 3-Phenyl-5-silylpyridazines by Regioselective -Cycloadditions

The cycloaddition of 3-phenyl-1,2,4,5-tetrazine (1) with the silylethyne 2a proceeds highly regioselectively to give 3-phenyl-5-(trimethylsilyl)pyridazine (3a).Similarly the reactions of 1 with the silylalkynes 2b - f, the silylalkynones 2g - i, and the s