403555
3,6-Diphenyl-1,2,4,5-tetrazine
98%
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About This Item
Empirical Formula (Hill Notation):
C14H10N4
CAS Number:
Molecular Weight:
234.26
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
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
SMILES string
c1ccc(cc1)-c2nnc(nn2)-c3ccccc3
InChI key
XAUWSIIGUUMHQQ-UHFFFAOYSA-N
assay
98%
mp
198 °C (dec.) (lit.)
solubility
chloroform: soluble 25 mg/mL, clear, very dark red
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.
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Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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Reaction of 3, 6-diphenyl-1, 2, 4, 5-tetrazine with cis, cis-1, 5-cyclooctadiene: An attempt at preparing some dihydropyridazine derivatives.
Satish S, et al.
Tetrahedron, 35(2), 277-285 (1979)
Basicity of 3, 6-diphenyl-1, 2, 4, 5-tetrazine.
Trifonov RE, et al.
Chemistry of Heterocyclic Compounds, 34(1), 111-114 (1998)
Weixuan Chen et al.
Chemical communications (Cambridge, England), 48(12), 1736-1738 (2011-12-14)
Substituted tetrazines have been found to undergo facile inverse electron demand Diels-Alder reactions with "tunable" reaction rates.
Design of nanoscale molecular wire based on 3, 6-Diphenyl-1, 2, 4, 5-Tetrazine and effect of external electric field on electron transfer in conjugated molecular wire.
Bayat Z and Mahdizadeh SJ.
Physica E: Low-Dimensional Systems and Nanostructures, 43(9), 1569-1575 (2011)
Miller et al.
Organic letters, 2(20), 3091-3094 (2000-09-29)
Thermal Diels-Alder reactions between C(60) and electron-deficient 3, 6-diaryl-1,2,4,5-tetrazines yield monoadducts possessing a diaryldihydropyridazine function nested atop the fullerene. The diaryldihydropyridazine functions direct a completely regioselective 1,4-hydrogenation, resulting in a racemic mixture of bifunctional bisadduct (+/-)-3.
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