Benzidine

• Formula: C₁₂H₁₂N₂
• Molecular weight: 184.2371
• IUPAC Standard InChI: InChI=1S/C12H12N2/c13-11-5-1-9(2-6-11)10-3-7-12(14)8-4-10/h1-8H,13-14H2 Copy

  
• IUPAC Standard InChIKey: HFACYLZERDEVSX-UHFFFAOYSA-N Copy
• CAS Registry Number: 92-87-5
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  View 3d structure (requires JavaScript / HTML 5)
• Other names: [1,1'-Biphenyl]-4,4'-diamine; p-Diaminodiphenyl; p,p'-Bianiline; p,p'-Diaminobiphenyl; C.I. Azoic Diazo Component 112; Fast Corinth Base B; 4,4'-Bianiline; 4,4'-Biphenyldiamine; 4,4'-Diaminobiphenyl; 4,4'-Diaminodiphenyl; 4,4'-Diphenylenediamine; Biphenyl -4,4'-ylenediamine; Benzidin; Benzidina; Benzydyna; Biphenyl,4,4'-diamino-; 4,4'-Biphenylenediamine; p,p-Bianiline; C.I. 37225; 4,4'-Diamino-1,1'-biphenyl; p,p'-Dianiline; NCI-C03361; Rcra waste number U021; UN 1885; NSC 146476
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas Chromatography
• Options:
  • Switch to SI units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Reaction thermochemistry data

Go To: Top, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

=

By formula: C₁₂H₁₂N₂ = C₁₂H₁₂N₂

 +  =

By formula: C₈H₄O₃ + C₁₂H₁₂N₂ = C₂₀H₁₆N₂O₃

Gas phase ion energetics data

Go To: Top, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

IR Spectrum

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, References, Notes

Data compiled by: Coblentz Society, Inc.

• SOLID (KBr DISC); PERKIN-ELMER 521 (GRATING); DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY (ADJUSTED subtractcm-110-0-0); 2 cm^-1 resolution
• SOLID (KBr PELLET); Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm^-1 resolution
• SOLID (SPLIT MULL); BECKMAN IR-9 (GRATING); DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm^-1 resolution

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

• gas; HP-GC/MS/IRD

Mass spectrum (electron ionization)

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

For Zoom

1.) Enter the desired X axis range (e.g., 100, 200)

2.) Check here for automatic Y scaling

3.) Press here to zoom

Additional Data

UV/Visible spectrum

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

For Zoom

1.) Enter the desired X axis range (e.g., 100, 200)

2.) Check here for automatic Y scaling

3.) Press here to zoom

Additional Data

References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Pongratz, Bohmert-Sub, et al., 1944
Pongratz, A.; Bohmert-Sub, S.; Scholtis, K., Zur thermochemie der benzidin-umlagerung, Ber., 1944, 77, 651-735. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Karyakin, Rabinovich, et al., 1978
Karyakin, N.V.; Rabinovich, I.B.; Pal'tseva, N.G., Thermodynamics of the reactions of aromatic diamines with dianhydrides of tetracarboxylic acids, Polym. Sci. USSR, 1978, 20, 2274-2279. [all data]

Pykhtina, Cherednichenko, et al., 1974
Pykhtina, E.V.; Cherednichenko, L.V.; Kardash, I.E.; Evlasheva, T.I.; Sorokin, V.V.; Potapov, V.K.; Pravednikov, A.N., Ionization potentials of amines and energies of charge transfer bands in the absorption spectra of complexes of 7,7,8,8-tetracyanoquinodimethan, High Energy Chem., 1974, 8, 257, In original 307. [all data]

Carlin, Nelb, et al., 1951
Carlin, R.B.; Nelb, R.G.; Odioso, R.C., The benzidine rearrangement. III. Kinetics of the rearrangements of hydrazobenzene, J. Am. Chem. Soc., 1951, 73, 1002-1007. [all data]

Notes

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References

• Symbols used in this document:
  

  ΔrH°	Enthalpy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.