Benzophenone imine

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]

Benzophenone imine

Names
Preferred IUPAC name Diphenylmethanimine
Identifiers
CAS Number	1013-88-3
3D model (JSmol)	Interactive image
ChemSpider	120561
ECHA InfoCard	100.103.715
EC Number	600-205-0 440-870-2
PubChem CID	136809
UNII	EJJ21NA7VI
CompTox Dashboard (EPA)	DTXSID10870832
InChI 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
SMILES C1=CC=C(C=C1)C(=N)C2=CC=CC=C2
Properties
Chemical formula	C13H11N
Molar mass	181.238 g·mol−1
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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). Infobox references

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]