Benzophenone imine

Source: Wikipedia, the free encyclopedia.
Benzophenone imine
Names
Preferred IUPAC name
Diphenylmethanimine
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.103.715 Edit this at Wikidata
EC Number
  • 600-205-0
  • 440-870-2
UNII
  • InChI=1S/C13H11N/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,14H
    Key: SXZIXHOMFPUIRK-UHFFFAOYSA-N
  • C1=CC=C(C=C1)C(=N)C2=CC=CC=C2
Properties
C13H11N
Molar mass 181.238 g·mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
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).

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]

catalysts. Benzophenone imine can be used as an ammonia-equivalent in such reactions.[1]

References

  1. ^
    ISSN 0040-4039
    .
  2. doi:10.15227/orgsyn.010.0028
    .
  3. ISSN 0022-3263
    .
  4. ISBN 9780470638859. {{cite book}}: |journal= ignored (help); Missing or empty |title= (help
    )
  5. doi:10.1080/00397918808081307
    .
  6. hdl:20.500.11820/c801073c-6b4b-4a85-be68-2c4313b6e53d
    .
  7. ISBN 978-0471936237. {{cite book}}: |journal= ignored (help); Missing or empty |title= (help
    )
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