276888-00-7

Basic information

• Product Name: 2,2-DiMethyl 1,3-dihydroindene-2,2-dicarboxylate
• Synonyms: 2,2-DiMethyl 1,3-dihydroindene-2,2-dicarboxylate
• CAS NO: 276888-00-7
• Molecular Formula: C13H15O4
• Molecular Weight: 235.2558
• Mol File: 276888-00-7.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,2-DiMethyl 1,3-dihydroindene-2,2-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-DiMethyl 1,3-dihydroindene-2,2-dicarboxylate(276888-00-7)
• EPA Substance Registry System: 2,2-DiMethyl 1,3-dihydroindene-2,2-dicarboxylate(276888-00-7)

Safety Data

• Hazardous Substances Data: 276888-00-7(Hazardous Substances Data)

Usage

General Description

2,2-DiMethyl 1,3-dihydroindene-2,2-dicarboxylate, also known as DMDIDC, is a chemical compound with the molecular formula C14H16O4. It is an ester that is commonly used as a flavoring ingredient in food products and as a fragrance in perfumes and cosmetics. DMDIDC is also used in the synthesis of other organic compounds and as a reagent in chemical reactions. It is a colorless to pale yellow liquid with a fruity odor, and it is stable under normal temperature and pressure conditions. While DMDIDC itself is not considered to be highly toxic, it should be handled and stored with care to avoid potential irritation and adverse effects.

Upstream product

• 63104-44-9 dimethyl 2,2-di(prop-2-ynyl)malonate 
• 74-86-2 acetylene 
• 91-13-4 α,α'-dibromo-o-xylene 
• 108-59-8 malonic acid dimethyl ester 
• 81395-28-0 1-((benzyloxy)methyl)-2-bromobenzene 
• 119367-65-6 2-<(Benzyloxy)methyl>benzaldehyde 
• 80171-34-2 1-bromo-2-(ethoxymethyl)benzene 
• 873402-73-4 2-ethoxymethyl-benzaldehyde 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 

Downstream Products

• 68499-29-6 bistosylate of 2,2-bis(hydroxymethyl)-indan 

Relevant articles and documents

Ruthenium(II)-catalyzed selective intramolecular [2 + 2 + 2] alkyne cyclotrimerizations

In the presence of a catalytic amount of Cp*RuCl(cod), 1,6-diynes chemoselectively reacted with monoalkynes at ambient temperature to afford the desired bicyclic benzene derivatives in good yields. A wide variety of diynes and monoynes containing functional groups such as ester, ketone, nitrile, amine, alcohol, sulfide, etc. can be used for the present ruthenium catalysis. The most significant advantage of this protocol is that the cycloaddition of unsymmetrical 1,6-diynes with one internal alkyne moiety regioselectively gave rise to meta-substituted products with excellent regioselectivity. Completely intramolecular alkyne cyclotrimerization was also accomplished using triyne substrates to obtain tricyclic aromatic compounds fused with 5-7-membered rings. A ruthenabicycle complex relevant to these cyclotrimerizations was synthesized from Cp*RuCl(cod) and a 1,6-diyne possessing phenyl terminal groups, and its structure was unambiguously determined by X-ray analysis. The intermediary of such a ruthenacycle intermediate was further confirmed by its reaction with acetylene, giving rise to the expected cycloadduct. The density functional study on the cyclotrimerization mechanism elucidated that the cyclotrimerization proceeds via oxidative cyclization, producing a ruthenacycle intermediate and subsequent alkyne insertion initiated by the formal [2 + 2] cycloaddition of the resultant ruthenacycle with an alkyne.

Divergent Access to Seven/Five-Membered Rings Based on [1,6]-Hydride Shift/Cyclization Process

We have achieved a divergent access to seven/five-membered rings based on a [1,6]-hydride shift/cyclization process from benzylidenemalonate with an o-alkoxymethyl group. Whereas Yb(OTf)3 afforded benzoxepines (with a seven-membered ring) selectively, indanes (with a five-membered ring) were the main products when Sc(OTf)3 was employed.