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403555 Sigma-Aldrich

3,6-Diphenyl-1,2,4,5-tetrazine

98%

  • CAS Number 6830-78-0

  • Empirical Formula (Hill Notation) C14H10N4

  • Molecular Weight 234.26

  •  MDL number MFCD00023646

  •  PubChem Substance ID 24865201

  •  NACRES NA.22

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Properties

Related Categories Building Blocks, Chemical Synthesis, Heterocyclic Building Blocks, N-Containing, Other Heterocyclic Building Blocks More...
assay   98%
mp   198 °C (dec.) (lit.)
solubility   chloroform: soluble 25 mg/mL, clear, very dark red
storage temp.   room temp
SMILES string   c1ccc(cc1)-c2nnc(nn2)-c3ccccc3
InChI   1S/C14H10N4/c1-3-7-11(8-4-1)13-15-17-14(18-16-13)12-9-5-2-6-10-12/h1-10H
InChI key   XAUWSIIGUUMHQQ-UHFFFAOYSA-N

Description

General description

3,6-Diphenyl-1,2,4,5-tetrazine is an an electron-deficient heteroaromatic azadiene. It participates in inverse electron demand cycloaddition reactions with various dienophiles. It is reported to participate in facile inverse electron demand Diels-Alder reactions with “tunable” reaction rates. The electron transport characteristics of 3,6-diphenyl-1,2,4,5-tetrazine (DPT) single molecular conductor have been studied by density functional theory (DFT) method. Basicity of 3,6-diphenyl-1,2,4,5-tetrazine in aqueous solutions of sulfuric acid (pKBH+) is -4.8. It undergoes thermal Diels-Alder reaction with C60 to afford monoadducts, possessing a diaryldihydropyridazine function nested atop the fullerene.

Application

3,6-Diphenyl-1,2,4,5-tetrazine may be used in the preparation of dihydropyridazine derivatives, via reaction with cis,cis-cycloocta-1,5-diene.

Packaging

1 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
XF6863300
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles
Peer-Reviewed Papers
15

References

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919950 3-(([1,1′-Biphenyl]-4-ylmethyl)thio)-6-methyl-1,2,4,5-tetrazine, >98%

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