Benzophenone imine
Chemical compound
From Wikipedia, the free encyclopedia
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]
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| Names | |
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| Preferred IUPAC name
Diphenylmethanimine | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.103.715 |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C13H11N | |
| Molar mass | 181.238 g·mol−1 |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H315, H319, H335 | |
| P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, 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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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]