35207-75-1

Basic information

• Product Name: 2-Diazomalonic acid ditert-butyl ester
• Synonyms: 2-Diazomalonic acid di-tert-butyl ester;2-Diazomalonic acid ditert-butyl ester;2-Diazopropanedioic acid ditert-butyl ester;Diazomalonic acid di-tert-butyl ester
• CAS NO: 35207-75-1
• Molecular Formula: C₁₁H₁₈N₂O₄
• Molecular Weight: 243.279
• Mol File: 35207-75-1.mol
• Article Data: 19

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: 2-Diazomalonic acid ditert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Diazomalonic acid ditert-butyl ester(35207-75-1)
• EPA Substance Registry System: 2-Diazomalonic acid ditert-butyl ester(35207-75-1)

Safety Data

• Hazardous Substances Data: 35207-75-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H19N2O4/c1-10(2,3)16-8(14)7(13-12)9(15)17-11(4,5)6/h12H,1-6H3/q+1

Upstream product

• 541-16-2 t-butyl malonate 
• 2158-14-7 4-acetamidobenzenesulfonyl azide 
• 624-90-8 Methanesulfonyl azide 
• 941-55-9 4-toluenesulfonyl azide 
• 64-17-5 ethanol 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 102127-55-9 Di-t-butyl-bicyclobutan-2,2-dicarboxylat 
• 168135-78-2 methyl N^α-Fmoc-4-O-tyrosinate 
• 35207-83-1 7,7-Di-t-butoxycarbonylnorcaran 
• 650616-53-8 di-tert-butyl 2-phenylcyclopropane-1,1-dicarboxylate 

Relevant articles and documents

Synthesis of bicyclic tetrahydrofurans from linear precursors using manganese(III) acetate

We have recently developed methodology based on oxidative radical reactions for the synthesis of [3.3.0]-bicyclic lactones containing both cyclopentanes and γ-lactams along with application of this methodology to the synthesis of natural products and complex molecular architectures. Herein we report an extension of this methodology to the synthesis of oxygen heterocycles including bicyclic bis-lactones.

Rhodium-Catalyzed [4+2] Annulation of N-Aryl Pyrazolones with Diazo Compounds To Access Pyrazolone-Fused Cinnolines

An efficient synthesis of novel dinitrogen-fused heterocycles such as pyrazolo[1,2-a]cinnoline derivatives have been accomplished by the rhodium(III)-catalyzed reaction of N-arylpyrazol-5-ones with α-diazo compounds. This reaction proceeds through a cascade C?H activation/intramolecular cyclization with a broad substrate scope. Furthermore, this protocol is successfully extended to the unusual phosphorus-containing α-diazo compounds and cyclic diazo compounds as the cross-coupling partners to deliver the two new kinds of pyrazolo[1,2-a]cinnolinones. The control experiments were performed to reveal insight into the mechanism of this reaction, involving reversible C?H activation, migratory insertion of the diazo compound, and cascade cyclization as the key steps of the transformation. Moreover, gram-scale synthesis and further transformation of the target product demonstrate the synthetic utility of the present protocol.

Kinetic Resolution of Propargylic Ethers via [2,3]-Wittig Rearrangement to Synthesize Chiral α-Hydroxyallenes

An efficient kinetic resolution of propargyloxy dicarbonyl compounds via asymmetric [2,3]-Wittig rearrangement was achieved by using a chiral N,N′-dioxide/NiII complex catalyst. Various chiral α-allenyl alcohols were obtained in high enantioselectivities under mild conditions. The utility of this method was readily demonstrated in the asymmetric synthesis of the chiral 2,5-dihydrofuran derivative.