87848-38-2

Basic information

• Product Name: 2-Diazomethyl-N,N-diisopropyl-benzamide
• Synonyms: 2-Diazomethyl-N,N-diisopropyl-benzamide
• CAS NO: 87848-38-2
• Molecular Weight: 245.324
• Mol File: 87848-38-2.mol

Chemical Properties

• CAS DataBase Reference: 2-Diazomethyl-N,N-diisopropyl-benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Diazomethyl-N,N-diisopropyl-benzamide(87848-38-2)
• EPA Substance Registry System: 2-Diazomethyl-N,N-diisopropyl-benzamide(87848-38-2)

Safety Data

• Hazardous Substances Data: 87848-38-2(Hazardous Substances Data)

Upstream product

• 20383-28-2 N,N-diisopropyl benzamide 
• 68-12-2 N,N-dimethyl-formamide 

Relevant articles and documents

1-(Dialkylamino)isobenzofurans: Generation and Use for Annelation of Aromatic Rings

Three methods are reported for the generation of the heretofore unreported 1-(dialkylamino)isobenzofurans.These are (1) metal-catalyzed decomposition of an o-(diazomethyl)benzamide (9 to 3), (2) fluoride-induced α elimination of an o-benzamide (48 to 3), and (3) deprotonation of a cyclic imidate salt (51 to 3).The first two reactions are consistent with the intermediacy of a carbene.The precursors for all three approaches can be synthesized from tertiary benzamides by ortho-lithiation strategies.Reaction of the transient 1-(dialkylamino)isobenzofurans with dieneophiles in a ?4s + ?2s cycloaddition is the key step in a one-pot sequence that provides annelation of an aromatic ring by a 2,3-substituted 1-(dialkylamino)-4-hydroxycyclohex-1-ene ring.The sequence of formation of the 1-(dialkylamino)isobenzofuran, regio- and stereospecific cycloaddition, ring opening, and proton transfer, is illustrated by the preparations of 15-23, 32, and 33 from N,N-diisopropylbenzamides.The ring annelation is extended to naphthalene and pyridine rings to provide 40, 41, and 44, respectively.Transformations of annelated products to higher and lower oxidation states are reported.

2-AZAISOBENZOFURANS AS INTERMEDIATES IN A CONVENIENT ANNELATION OF AROMATIC TERTIARY AMIDES

The conversion of N,N-diisopropylbenzamide and dienophiles to N,N-diisopropylamino-2-carboxy-4-hydroxyl-3,4-dihydronaphthalenes via ortho lithiation, formylation, diazotization, ring closure, cycloaddition, and ring opening is reported and postulated to involve the intermediacy of a novel 2-azaisobenzofuran.