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403555

Sigma-Aldrich

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

98%

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About This Item

Empirical Formula (Hill Notation):
C14H10N4
CAS Number:
6830-78-0
Molecular Weight:
234.26
MDL number:
MFCD00023646
UNSPSC Code:
12352100
PubChem Substance ID:
24865201
NACRES:
NA.22

Assay

98%

mp

198 °C (dec.) (lit.)

solubility

chloroform: soluble 25 mg/mL, clear, very dark red

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

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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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Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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.
Basicity of 3, 6-diphenyl-1, 2, 4, 5-tetrazine.
Trifonov RE, et al.
Chemistry of Heterocyclic Compounds, 34(1), 111-114 (1998)
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)
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)
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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