3,3'-Dimethylbiphenyl

Formula: C₁₄H₁₄
Molecular weight: 182.2610
IUPAC Standard InChI: InChI=1S/C14H14/c1-11-5-3-7-13(9-11)14-8-4-6-12(2)10-14/h3-10H,1-2H3
IUPAC Standard InChIKey: GVEDOIATHPCYGS-UHFFFAOYSA-N
CAS Registry Number: 612-75-9
Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript.
Other names: 1,1'-Biphenyl, 3,3'-dimethyl-; m,m'-Bitolyl; 3,3'-Ditolyl; 3,3'-Dimethyldiphenyl; 3,3-Dimethyldiphenyl; 1-Methyl-3-(3'-methylphenyl)benzene; Biphenyl, 3,3'-dimethyl-; 3,3'-dimethyl-1,1'-biphenyl; Diphenyl, 3,3'-dimethyl
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NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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Phase change data

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Data compiled as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Quantity	Value	Units	Method	Reference	Comment
T_boil	559.	K	N/A	Blades, Blades, et al., 1954	Uncertainty assigned by TRC = 8. K; TRC
T_boil	556.	K	N/A	Brull, 1935	Uncertainty assigned by TRC = 3. K; TRC
T_boil	559.	K	N/A	Mayer and Freitak, 1921	Uncertainty assigned by TRC = 3. K; TRC
T_boil	561.	K	N/A	Perrier, 1892	Uncertainty assigned by TRC = 5. K; TRC
T_boil	562.	K	N/A	Stolle, 1888	Uncertainty assigned by TRC = 5. K; TRC
Quantity	Value	Units	Method	Reference	Comment
T_fus	278.	K	N/A	Castro, Andrews, et al., 1958	Uncertainty assigned by TRC = 3. K; TRC
T_fus	282.4	K	N/A	Johnson, 1957	Uncertainty assigned by TRC = 1.5 K; TRC
T_fus	279.	K	N/A	Schultz, Rohde, et al., 1907	Uncertainty assigned by TRC = 3. K; TRC
Quantity	Value	Units	Method	Reference	Comment
Δ_vapH°	71.9	kJ/mol	A	Stephenson and Malanowski, 1987	Based on data from 288. to 308. K. See also Pribilová and Pouchlý, 1974.; AC
Quantity	Value	Units	Method	Reference	Comment
Δ_subH°	71.9	kJ/mol	ME	Pribilová and Pouchlý, 1974	Based on data from 288. to 308. K.; AC

Reduced pressure boiling point

T_boil (K)	Pressure (bar)	Reference	Comment
559.2	0.951	Aldrich Chemical Company Inc., 1990	BS
423.2	0.024	Weast and Grasselli, 1989	BS

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:

Gas phase ion energetics data

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Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

IE (eV)	Method	Reference	Comment
8.70 ± 0.05	EI	Loudon and Mazengo, 1974	LLK
7.85 ± 0.02	PE	Maier and Turner, 1972	LLK

Appearance energy determinations

Ion	AE (eV)	Other Products	Method	Reference	Comment
C₁₃H₁₁⁺	13.4 ± 0.2	CH₃	EI	Loudon and Mazengo, 1974	LLK
C₁₄H₁₃⁺	13.0 ± 0.2	H	EI	Loudon and Mazengo, 1974	LLK

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

Not specified, most likely a prism, grating, or hybrid spectrometer.; (NO SPECTRUM, ONLY SCANNED IMAGE IS AVAILABLE)

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

Gas Chromatography

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

Kovats' RI, non-polar column, isothermal

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Column type	Active phase	Temperature (C)	I	Reference	Comment
Capillary	OV-1	160.	1591.	Zhang, Chen, et al., 1997	25. m/0.2 mm/0.33 μm, N2

Kovats' RI, polar column, isothermal

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Column type	Active phase	Temperature (C)	I	Reference	Comment
Capillary	SP-1000	185.	2254.	Kríz, Popl, et al., 1974	N2; Column length: 50. m; Column diameter: 0.25 mm
Capillary	SP-1000	200.	2212.	Kríz, Popl, et al., 1974	N2; Column length: 50. m; Column diameter: 0.25 mm

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	DB-5	1589.0	Song, Lai, et al., 2003	30. m/0.25 mm/0.25 μm, He, 4. K/min; T_start: 40. C; T_end: 310. C
Capillary	DB-5	1588.6	Song, Lai, et al., 2003	30. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 4. K/min; T_end: 310. C
Capillary	DB-5	1580.2	Song, Lai, et al., 2003	30. m/0.25 mm/0.25 μm, He, 2. K/min; T_start: 40. C; T_end: 310. C
Capillary	DB-5	1589.0	Song, Lai, et al., 2003	30. m/0.25 mm/0.25 μm, He, 4. K/min; T_start: 40. C; T_end: 310. C
Capillary	DB-5	1594.2	Song, Lai, et al., 2003	30. m/0.25 mm/0.25 μm, He, 6. K/min; T_start: 40. C; T_end: 310. C
Capillary	DB-5	1589.0	Lai and Song, 1995	30. m/0.25 mm/0.25 μm, He, 4. K/min; T_start: 40. C; T_end: 310. C
Capillary	DB-5	1588.6	Lai and Song, 1995	30. m/0.25 mm/0.25 μm, He, 40. C @ 5. min, 4. K/min; T_end: 310. C
Capillary	DB-5	1580.2	Lai and Song, 1995	30. m/0.25 mm/0.25 μm, He, 2. K/min; T_start: 40. C; T_end: 310. C
Capillary	DB-5	1589.	Lai and Song, 1995	30. m/0.25 mm/0.25 μm, He, 4. K/min; T_start: 40. C; T_end: 310. C
Capillary	DB-5	1594.2	Lai and Song, 1995	30. m/0.25 mm/0.25 μm, He, 6. K/min; T_start: 40. C; T_end: 310. C
Capillary	DB-5	1597.	Rostad and Pereira, 1986	30. m/0.26 mm/0.25 μm, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min
Capillary	SE-52	1574.	Beernaert, 1979	He, 50. C @ 5. min, 6. K/min; Column length: 33.3 m; Column diameter: 0.50 mm; T_end: 320. C

Van Den Dool and Kratz RI, polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	Supelcowax-10	2209.	Chung, Yung, et al., 2002	60. m/0.25 mm/0.25 μm, He, 35. C @ 5. min, 2. K/min, 195. C @ 90. min
Capillary	Supelcowax-10	2209.	Chung, Yung, et al., 2001	60. m/0.25 mm/0.25 μm, He, 35. C @ 5. min, 2. K/min, 195. C @ 90. min
Capillary	Supelcowax-10	2208.	Chung, 1999	60. m/0.25 mm/0.25 μm, He, 35. C @ 5. min, 2. K/min, 195. C @ 90. min

Normal alkane RI, non-polar column, isothermal

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Column type	Active phase	Temperature (C)	I	Reference	Comment
Packed	Polydimethyl siloxane	183.	1580.	Ferrand, 1962

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5 MS	1594.	Radulovic, Blagojevic, et al., 2010	30. m/0.25 mm/0.25 μm, Helium, 5. K/min, 290. C @ 10. min; T_start: 70. C
Capillary	Ultra-1	1570.	Elizalde-González, Hutfliess, et al., 1996	50. m/0.2 mm/0.33 μm, H2, 3. K/min, 300. C @ 35. min; T_start: 60. C

Lee's RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	DB-5	271.27	Rostad and Pereira, 1986	30. m/0.26 mm/0.25 μm, He, 50. C @ 4. min, 6. K/min, 300. C @ 20. min
Capillary	DB-5	270.79	Tong, Centen, et al., 1985	He, 4. K/min; Column length: 30. m; Column diameter: 0.25 mm; T_start: 90. C; T_end: 325. C
Capillary	SE-52	271.87	Lee, Vassilaros, et al., 1979	12. m/0.3 mm/0.34 μm, He, 2. K/min; T_start: 50. C; T_end: 250. C

Lee's RI, non-polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	DB-5	271.87	Tong, Centen, et al., 1985	He; Column length: 30. m; Column diameter: 0.25 mm; Program: not specified

References

Go To: Top, Phase change data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, Notes

Blades, Blades, et al., 1954
Blades, H.; Blades, A.; Steacie, E.W.R., The Kinetics of Pyrolysis of Toluene, Can. J. Chem., 1954, 32, 298-311. [all data]

Brull, 1935
Brull, L., Sui calori di combustione di alcuni derivati del bifenil, Gazz. Chim. Ital., 1935, 65, 19-28. [all data]

Mayer and Freitak, 1921
Mayer, F.; Freitak, K., Chem. Ber., 1921, 54, 347. [all data]

Perrier, 1892
Perrier, G., Bull. Soc. Chim. Fr., 1892, 7, 180. [all data]

Stolle, 1888
Stolle, E., Chem. Ber., 1888, 21, 1096. [all data]

Castro, Andrews, et al., 1958
Castro, C.E.; Andrews, L.J.; Keefer, R.M., Molecular Complexes of Hindered Biphenyl Derivatives, J. Am. Chem. Soc., 1958, 80, 2322-6. [all data]

Johnson, 1957
Johnson, E.A., J. Chem. Soc., 1957, 1957, 4155. [all data]

Schultz, Rohde, et al., 1907
Schultz, G.; Rohde, G.; Vicari, F., Justus Liebigs Ann. Chem., 1907, 352, 111. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Pribilová and Pouchlý, 1974
Pribilová, J.; Pouchlý, J., Vapour pressure of some low-volatile hydrocarbons determined by the effusion method, Collect. Czech. Chem. Commun., 1974, 39, 5, 1118-1124, https://doi.org/10.1135/cccc19741118 . [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Loudon and Mazengo, 1974
Loudon, A.G.; Mazengo, R.Z., Steric strain and electron-impact. The behaviour of some n, n'-dimethyl- 1,1-binaphthyls, some n, n'-dimethylbiphenyls and model compounds, Org. Mass Spectrom., 1974, 8, 179. [all data]

Maier and Turner, 1972
Maier, J.P.; Turner, D.W., Steric inhibition of resonance studied by molecular photoelectron spectroscopy. Part I. Biphenyls, Faraday Discuss. Chem. Soc., 1972, 54, 149. [all data]

Zhang, Chen, et al., 1997
Zhang, M.; Chen, B.; Shen, S.; Chen, S., Compositional studies of high-temperature coal tar by g.c.-FT-i.r. analysis of middle oil fractions, Fuel, 1997, 76, 5, 415-423, https://doi.org/10.1016/S0016-2361(97)85518-4 . [all data]

Kríz, Popl, et al., 1974
Kríz, J.; Popl, M.; Mostecký, J., Retention indices of biphenyls and diphenylalkanes, J. Chromatogr., 1974, 97, 1, 3-13, https://doi.org/10.1016/S0021-9673(01)97577-6 . [all data]

Song, Lai, et al., 2003
Song, C.; Lai, W.-C.; Madhusudan Reddy, K.; Wei, B., Chapter 7. Temperature-programmed retention indices for GC and GC-MS of hydrocarbon fuels and simulated distillation GC of heavy oils in Analytical advances for hydrocarbon research, Hsu,C.S., ed(s)., Kluwer Academic/Plenum Publishers, New York, 2003, 147-193. [all data]

Lai and Song, 1995
Lai, W.-C.; Song, C., Temperature-programmed retention indices for g.c. and g.c.-m.s. analysis of coal- and petroleum-derived liquid fuels, Fuel, 1995, 74, 10, 1436-1451, https://doi.org/10.1016/0016-2361(95)00108-H . [all data]

Rostad and Pereira, 1986
Rostad, C.E.; Pereira, W.E., Kovats and Lee retention indices determined by gas chromatography/mass spectrometry for organic compounds of environmental interest, J. Hi. Res. Chromatogr. Chromatogr. Comm., 1986, 9, 6, 328-334, https://doi.org/10.1002/jhrc.1240090603 . [all data]

Beernaert, 1979
Beernaert, H., Gas Chromatographic Analysis of Polyclylic Aromatic Hydrocarbons, J. Chromatogr., 1979, 173, 1, 109-118, https://doi.org/10.1016/S0021-9673(01)80450-7 . [all data]

Chung, Yung, et al., 2002
Chung, H.-Y.; Yung, I.K.S.; Ma, W.C.J.; Kim, J.-S., Analysis of volatile components in frozen and dried scallops (Patinopecten yessoensis) by gas chromatography/mass spectrometry, Food Res. Int., 2002, 35, 1, 43-53, https://doi.org/10.1016/S0963-9969(01)00107-7 . [all data]

Chung, Yung, et al., 2001
Chung, H.Y.; Yung, I.K.S.; Kim, J.-S., Comparison of volatile components in dried scallops (Chlamys farreri and Patinopecten yessoensis) prepared by boiling and steaming methods, J. Agric. Food Chem., 2001, 49, 1, 192-202, https://doi.org/10.1021/jf000692a . [all data]

Chung, 1999
Chung, H.Y., Volatile components in crabmeats of Charybdis feriatus, J. Agric. Food Chem., 1999, 47, 6, 2280-2287, https://doi.org/10.1021/jf981027t . [all data]

Ferrand, 1962
Ferrand, R., Gas phase chromatography using retention indices for the analysis of tars and their hydrogenation products, Journees internationales d'etude des methodes de separation immediate at de chromatographie; Org. sur l'initiative du IX., 1962, 132-140. [all data]

Radulovic, Blagojevic, et al., 2010
Radulovic, N.; Blagojevic, P.; Palic, R., Comparative study of the leaf volatiles of Arctostaphylos uva-ursi (L.) Spreng. and Vaccinium vitis-idaea L. (Ericaceae), Molecules, 2010, 15, 9, 6168-6185, https://doi.org/10.3390/molecules15096168 . [all data]

Elizalde-González, Hutfliess, et al., 1996
Elizalde-González, M.P.; Hutfliess, M.; Hedden, K., Retention index system, adsorption characteristics, and sructure correlations of polycyclic aromatic hydrocarbons in fuels, J. Hi. Res. Chromatogr., 1996, 19, 6, 345-352, https://doi.org/10.1002/jhrc.1240190608 . [all data]

Tong, Centen, et al., 1985
Tong, H.Y.; Centen, J.D.; Karasek, F.W.; Jellum, E.; Helland, P., Identification of Trace Organic Compounds in Dimethyl Sulphoxide Solution Using High-Performance Liquid Chromatography and Gas Chromatography-Mass Spectrometry, J. Chromatogr., 1985, 324, 373-383, https://doi.org/10.1016/S0021-9673(01)81336-4 . [all data]

Lee, Vassilaros, et al., 1979
Lee, M.L.; Vassilaros, D.L.; White, C.M.; Novotny, M., Retention Indices for Programmed-Temperature Capillary-Column Gas Chromatography of Polycyclic Aromatic Hydrocarbons, Anal. Chem., 1979, 51, 6, 768-773, https://doi.org/10.1021/ac50042a043 . [all data]

Notes

Go To: Top, Phase change data, Gas phase ion energetics data, IR Spectrum, Gas Chromatography, References

Symbols used in this document:

AE Appearance energy

T_boil Boiling point

T_fus Fusion (melting) point

Δ_subH° Enthalpy of sublimation at standard conditions

Δ_vapH° Enthalpy of vaporization at standard conditions
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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AE	Appearance energy
T_boil	Boiling point
T_fus	Fusion (melting) point
Δ_subH°	Enthalpy of sublimation at standard conditions
Δ_vapH°	Enthalpy of vaporization at standard conditions