1,3-Diphenyltriazene

1,3-Diphenyltriazene
Names
Preferred IUPAC name
(1E)-1,3-Diphenyl-1-triazene
Other names
Diazoaminobenzene
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.004.764 Edit this at Wikidata
EC Number
  • 205-240-1
UNII
  • InChI=1S/C12H11N3/c1-3-7-11(8-4-1)13-15-14-12-9-5-2-6-10-12/h1-10H,(H,13,14)
    Key: ALIFPGGMJDWMJH-UHFFFAOYSA-N
  • C1=CC=C(C=C1)NN=NC2=CC=CC=C2
Properties
C12H11N3
Molar mass 197.241 g·mol−1
Appearance Pale yellow solid
Density 1.29 g/cm3
Melting point 95–96[1] °C (203–205 °F; 368–369 K)
Boiling point 180 °C (356 °F; 453 K) decomposes[2]
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H302, H312, H315, H319, H332, H335
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1,3-Diphenyltriazene is the organic compound with the formula PhN=N-N(H)Ph (Ph = C6H5). It is a prototypical triazene, i.e. a compound with the functional group RN=N-NR2. It is a pale yellow solid, prepared by the reaction of phenyldiazonium salts with aniline.[3] In practise, phenyldiazonium salts are also prepared from alanine, thus 1,3-diphenyltriazene can be prepared from analine in one-pot reaction via partial diazotization.[4][5] It is a planar molecule. The N-N distances are 1.287 and 1.337 Å.[6]

References

  1. ^ William B. Smith, Oliver Chenpu Ho (April 1990). "Application of the isoamyl nitrite-diiodomethane route to aryl iodides". The Journal of Organic Chemistry. 55 (8): 2543–2545. doi:10.1021/jo00295a056. ISSN 0022-3263. Retrieved 2021-05-27.
  2. ^ Shimura, Eiji. Preparation of electrophotographic toners using a foaming agent and an insulating substance. 1988. JP 63050863 A.
  3. ^ Hartman, W. W.; Dickey, J. B. (1934). "Diazoaminobenzene". Organic Syntheses. 14: 24. doi:10.15227/orgsyn.014.0024.
  4. ^ Kazem-Rostami, M.; Khazaei, A.; Moosavi-Zare, A. R.; Bayat, M.; Saednia, S. (2012). "Novel One-Pot Synthesis of Thiophenols from Related Triazenes under Mild Conditions". Synlett. 23 (13): 1893–1896. doi:10.1055/s-0032-1316557. S2CID 196805424.
  5. ^ Hartman, W. W.; Dickey, J. B. (1934). "Diazoaminobenzene". Organic Syntheses. 14: 24. doi:10.15227/orgsyn.014.0024.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  6. ^ Lego, Christian; Neumüller, Bernhard (2011). "Reaktionen von 1,3-Diphenyltriazenid mit Cu+ und Tl+". Zeitschrift für anorganische und allgemeine Chemie. 637 (12): 1784–1789. doi:10.1002/zaac.201100227.