1,3-Diphenyltriazene

1,3-Diphenyltriazene
Names
	Preferred IUPAC name (1E)-1,3-Diphenyl-1-triazene
	Other names Diazoaminobenzene
Identifiers
CAS Number	136-35-6;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL573540;
ChemSpider	8365;
ECHA InfoCard	100.004.764
EC Number	205-240-1;
PubChem CID	8689;
UNII	5T4EEW75HJ;
CompTox Dashboard (EPA)	DTXSID9024934 ;
	InChI 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;
	SMILES C1=CC=C(C=C1)NN=NC2=CC=CC=C2;
Properties
Chemical formula	C12H11N3
Molar mass	197.241 g·mol−1
Appearance	Pale yellow solid
Density	1.29 g/cm3
Melting point	95–96 °C (203–205 °F; 368–369 K)
Boiling point	180 °C (356 °F; 453 K) decomposes
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H312, H315, H319, H332, H335
Precautionary statements	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). Infobox references

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

^ 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.
^ Shimura, Eiji. Preparation of electrophotographic toners using a foaming agent and an insulating substance. 1988. JP 63050863 A.
^ Hartman, W. W.; Dickey, J. B. (1934). "Diazoaminobenzene". Organic Syntheses. 14: 24. doi:10.15227/orgsyn.014.0024.
^ 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.
^ 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)
^ 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.

[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.

[:1-4] 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.

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