73764-13-3

Basic information

• Product Name: methyl (4-methylphenyl)diazoacetate
• Synonyms: methyl (4-methylphenyl)diazoacetate
• CAS NO: 73764-13-3
• Molecular Weight: 190.202
• Mol File: 73764-13-3.mol

Chemical Properties

• CAS DataBase Reference: methyl (4-methylphenyl)diazoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (4-methylphenyl)diazoacetate(73764-13-3)
• EPA Substance Registry System: methyl (4-methylphenyl)diazoacetate(73764-13-3)

Safety Data

• Hazardous Substances Data: 73764-13-3(Hazardous Substances Data)

Upstream product

• 622-47-9 4-tolylacetic acid 
• 108-88-3 toluene 
• 34966-53-5 methyl 4-methylphenylglyoxylate 
• 23786-13-2 methyl p-tolylacetate 

Downstream Products

• 1011458-51-7 ethyl 2-[(5-methyl-2-methoxycarbonylmethyl)phenyl]-2-(phenylthio)acetate 
• 1133798-33-0 methyl 2-(3,4-dichlorophenyl)-2-p-tolylacetate 
• 1133798-37-4 methyl 2-(3-formylphenyl)-2-p-tolylacetate 
• 1133798-38-5 methyl 2-(4-methoxyphenyl)-2-(p-tolyl)acetate 
• 5359-40-0 methyl 2,2-di(p-tolyl)acetate 
• 1133798-31-8 methyl 2-m-tolyl-2-p-tolylacetate 
• 1133798-32-9 methyl 2-(3-chlorophenyl)-2-p-tolylacetate 
• 1133798-40-9 methyl 2-(naphthalen-1-yl)-2-p-tolylacetate 
• 1133798-35-2 methyl 2-(3-nitrophenyl)-2-p-tolylacetate 
• 1186207-70-4 methyl 2-(1,2-dihydro-2,3-diphenylisoquinolin-1-yl)-2-hydroxy-2-p-tolylacetate 
• 1235982-67-8 methyl 2-cyclohexanoxy-2-(4-methylphenyl)acetate 
• 137420-77-0 methyl 2-phenoxy-2-(4-methylphenyl)acetate 

Relevant articles and documents

All-Carbon Tetrasubstituted Olefins Synthesis from Diazo Compounds and Iodonium Ylides under Blue LED Irradiation

A route for the construction of all-carbon tetra-substituted olefins through visible-light promoted coupling of diazo compounds with iodonium ylides was developed. A wide range of all-carbon tetra-substituted olefins was obtained in moderate to good yields. The synthetic values of the current method were further approved by the synthesis of natural isolates modified alkenes and the successful transformation of final olefins into important heterocycles. (Figure presented.).

B(C6F5)3-catalyzed O-H insertion reactions of diazoalkanes with phosphinic acids

A highly efficient base-, metal-, and oxidant-free catalytic O-H insertion reaction of diazoalkanes and phosphinic acids in the presence of B(C6F5)3has been developed. This powerful methodology provides a green approach towards the synthesis of a broad spectrum of α-phosphoryloxy carbonyl compounds with good to excellent yields (up to 99% yield). The protocol features the advantages of operational simplicity, high atom economy, practicality, easy scalability and environmental friendliness.

B(C6F5)3-Catalyzed site-selective N1-alkylation of benzotriazoles with diazoalkanes

Alkylation of benzotriazoles is synthetically challenging, often leading to mixtures of N1 and N2 alkylation. Herein, metal-free catalytic site-selective N1-alkylation of benzotriazoles with diazoalkanes is described in the presence of 10 mol% of B(C6F5)3. These reactions provide N1-alkylated benzotriazoles in good to excellent yields and this protocol is successfully adapted to gram-scale syntheses as well as a derivative with antimicrobial activity.

Insertion of Diazo Esters into C-F Bonds toward Diastereoselective One-Carbon Elongation of Benzylic Fluorides: Unprecedented BF3Catalysis with C-F Bond Cleavage and Re-formation

Selective transformation of C-F bonds remains a significant goal in organic chemistry, but C-F insertion of a one-carbon-atom unit has never been established. Herein we report the BF3-catalyzed formal insertion of diazo esters as one-carbon-atom sources into C-F bonds to accomplish one-carbon elongation of benzylic fluorides. A DFT calculation study revealed that the BF3 catalyst could contribute to both C-F bond cleavage and re-formation. This elongation provided α-fluoro-α,β-diaryl esters with a high level of diastereoselectivity. Various benzylic fluorides and diazo esters were applicable. The synthetic utility of this method was demonstrated by the synthesis of a fluoro analogue of a compound that is used as a transient receptor and potential canonical channel inhibitor.

Azide Radical Initiated Ring Opening of Cyclopropenes Leading to Alkenyl Nitriles and Polycyclic Aromatic Compounds

We report herein a radical-mediated amination of cyclopropenes. The transformation proceeds through a cleavage of the three-membered ring after the addition of an azide radical on the strained double bond and leads to tetrasubstituted alkenyl nitrile derivatives upon loss of N2. With 1,2-diaryl substituted cyclopropenes, this methodology could be extended to a one-pot synthesis of highly functionalized polycyclic aromatic compounds (PACs). This transformation allows the synthesis of nitrile-substituted alkenes and aromatic compounds from rapidly accessed cyclopropenes using only commercially available reagents.

Borane catalysed cyclopropenation of arylacetylenes

Triarylboranes have gained substantial attention as catalysts for C-C bond forming reactions due to their remarkable catalytic activities. Herein, we report B(C6F5)3catalysed cyclopropenation of a wide variety of arylacetylenes using donor-acceptor diazoesters. A mild reaction protocol has been developed for the synthesis of functionalised cyclopropenes (33 examples) in good to excellent yields.

Borane Catalyzed Selective Diazo Cross-Coupling Towards Pyrazoles

Decomposition of donor-acceptor diazo compounds leads to the formation of reactive carbene intermediates. These can undergo a wide variety of carbene transfer reactions to yield synthetically useful products. Herein, we report a selective borane catalyzed cyclization reaction from the combination of two different diazo compounds to afford N-substituted pyrazoles. The selective decomposition of the more reactive α-aryl α-diazoester and subsequent reaction with a vinyl diazoacetate produces N-alkylated pyrazoles in a regioselective manner. Catalytic amounts of tris(pentafluorophenyl)borane (10 mol%) were employed to afford the pyrazole products (36 examples) in yields from 59 to 80%. Extensive DFT studies have been undertaken to interpret the mechanism for this reaction which was found to go through two tandem catalytic cycles, both catalyzed by B(C6F5)3.

Visible-Light-Promoted Polysubstituted Olefins Synthesis Involving Sulfur Ylides as Carbene Trapping Reagents

A blue-light-emitting diode (LED) promoted coupling of aryl diazoacetates with sulfur ylides is described. This protocol features mild conditions, good functional group tolerance, and broad substrate scope for both aryl diazoacetates with sulfur ylides. Under optimal reaction conditions, a wide range of trisubstituted olefins is obtained in moderate to good yield, which can be further transferred to other biologically important heterocycles after a two-step simple operation.

Visible-light-promoted selective: O -alkylation of 2-pyridones with α-aryldiazoacetates

A visible-light-promoted O-H insertion reaction between 2-pyridones and α-aryldiazoacetates has been developed. Upon visible light irradiation, the reaction proceeds smoothly under mild and catalyst-free conditions. A wide scope of 2-pyridones and α-aryldiazoacetates are well tolerated, and various O-alkylated 2-pyridones are obtained with perfect selectivity and good functional group tolerance. A photoinduced radical process is probably responsible for the excellent selectivity. This journal is

Divergent Synthesis of Aziridine and Imidazolidine Frameworks under Blue LED Irradiation

We develop a visible light-promoted divergent cycloaddition of α-diazo esters with hexahydro-1,3,5-triazines, leading to a series of aziridine and imidazolidine frameworks in average good yield, by simply changing the reaction media used. It is noteworthy that the reaction occurs under sole visible light irradiation without the need for exogenous photoredox catalysts. More significantly, a reasonable reaction mechanism was proposed on the basis of the control experiments and density functional theory calculation results.