Chemistry:Benzophenone imine
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| Preferred IUPAC name
Diphenylmethanimine | |
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3D model (JSmol)
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| Properties | |
| C13H11N | |
| Molar mass | 181.238 g·mol−1 |
| Hazards | |
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| GHS Signal word | Warning |
| H315, H319, H335 | |
| P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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Benzophenone imine is an organic compound with the formula of (C6H5)2C=NH. A pale yellow liquid, benzophenone imine is used as a reagent in organic synthesis.[1]
Synthesis
Benzophenone imine can be prepared by the thermal decomposition of benzophenone oxime:[2]
- 2 (C6H5)2C=NOH → (C6H5)2C=NH + (C6H5)2C=O
Benzophenone imine can also be synthesized by addition of phenylmagnesium bromide to benzonitrile followed by careful hydrolysis (lest the imine be hydrolyzed):[3]
- C6H5CN + C6H5MgBr → (C6H5)2C=NMgBr
- (C6H5)2C=NMgBr + H2O → (C6H5)2C=NH + MgBr(OH)
This method is known as Moureu-Mignonac ketimine synthesis.[4] Yet another route to benzophenone imine involves reaction of benzophenone and ammonia.[5]
Reactions
Benzophenone imine undergoes deprotonation with alkyl lithium reagents.[6]
- (C6H5)2C=NH + CH3Li → (C6H5)2C=NLi + CH4
- (C6H5)2C=NLi + CH3I → (C6H5)2C=NCH3 + LiI
Primary amines can be protected as benzophenone imines, and the protected amines are stable in flash chromatography.[7]
Buchwald-Hartwig amination involves coupling aromatic halide and amine to form carbon-nitrogen bonds with the help of palladium-based catalysts. Benzophenone imine can be used as an ammonia-equivalent in such reactions.[1]
References
- ↑ 1.0 1.1 Wolfe, John P.; Åhman, Jens; Sadighi, Joseph P.; Singer, Robert A.; Buchwald, Stephen L. (1997-09-08). "An Ammonia Equivalent for the Palladium-Catalyzed Amination of Aryl Halides and Triflates" (in en). Tetrahedron Letters 38 (36): 6367–6370. doi:10.1016/S0040-4039(97)01465-2. ISSN 0040-4039.
- ↑ Arthur Lachman (1930). "Diphenylmethane Imine Hydrochloride". Organic Syntheses 10: 28. doi:10.15227/orgsyn.010.0028.
- ↑ Pickard, P. L.; Tolbert, T. L. (December 1961). "An Improved Method of Ketimine Synthesis" (in EN). The Journal of Organic Chemistry 26 (12): 4886–4888. doi:10.1021/jo01070a025. ISSN 0022-3263.
- ↑ "Moureau-Mignonac Ketimine Synthesis" (in en). Hoboken, NJ, USA: John Wiley & Sons, Inc.. 2010-09-15. 1988–1990. doi:10.1002/9780470638859.conrr446. ISBN 9780470638859.
- ↑ Verardo, G.; Giumanini, A. G.; Strazzolini, P.; Poiana, M. (1988). "Ketimines From Ketones and Ammonia". Synthetic Communications 18 (13): 1501–1511. doi:10.1080/00397918808081307.
- ↑ Nottingham, Chris; Lloyd-Jones, Guy C. (2018). "Trimethylsilyldiazo[13C]methane: A Versatile 13C-Labelling Reagent". Organic Syntheses 95: 374–402. doi:10.15227/orgsyn.095.0374.
- ↑ O'Donnell, Martin J. (2001-04-15). "Benzophenone Imine" (in en). Chichester, UK: John Wiley & Sons, Ltd. doi:10.1002/047084289x.rb031. ISBN 978-0471936237.
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