41264-06-6

Basic information

• Product Name: Methyl isodehydroacetate
• Synonyms: 4,6-dimethyl-2-oxo-2h-pyran-5-carboxylicacimethylester;2H-PYRAN-5-CARBOXYLIC ACID, 4,6-DIMETHYL-2-OXO-, METHYL ESTER;METHYL 4,6-DIMETHYL-2-OXO-2H-PYRAN-5-CARBOXYLATE;METHYL ISODEHYDROACETATE;Methyl isodehydracetate;isodehydroacetic acid methyl ester;Methyl isodehydrocetat;4,6-dimethyl-2-oxo-2h-pyran-5-carboxylic acid methyl ester
• CAS NO: 41264-06-6
• Molecular Formula: C₉H₁₀O₄
• Molecular Weight: 182.17
• EINECS: 255-283-5
• Product Categories: Acetics acid and esters
• Mol File: 41264-06-6.mol

Chemical Properties

• Melting Point: 68-70 °C(lit.)
• Boiling Point: 167 °C14 mm Hg(lit.)
• Flash Point: 139.317 °C
• Appearance: White needle-like crystals or crystalline powder
• Density: 1.1634 (rough estimate)
• Vapor Pressure: 0.00113mmHg at 25°C
• Refractive Index: 1.4209 (estimate)
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Methyl isodehydroacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl isodehydroacetate(41264-06-6)
• EPA Substance Registry System: Methyl isodehydroacetate(41264-06-6)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 41264-06-6(Hazardous Substances Data)

Usage

Uses

Used in Insect Control Industry:
Methyl isodehydroacetate is used as an active ingredient for the preparation of insect growth regulators with juvenile hormone activity. It plays a crucial role in controlling insect populations by disrupting their growth and development, leading to more effective pest management strategies.

InChI:InChI=1/C9H10O4/c1-5-4-7(10)13-6(2)8(5)9(11)12-3/h4H,1-3H3

Upstream product

• 67-56-1 methanol 
• 53891-40-0 isodehydroacetic acid chloride 
• 105-45-3 acetoacetic acid methyl ester 
• 3385-34-0 ethyl isodehydroacetate 
• 480-65-9 isodehydracetic acid 
• 74-88-4 methyl iodide 
• 23326-27-4 Methyl 2-butynoate 
• 186581-53-3 diazomethane 
• 6372-01-6 methyl (E)-3-chloro-2-butenoate 
• 34284-28-1 sodium methyl acetoacetate 

Downstream Products

• 14920-81-1 methyl 2,6-dimethylbenzoate 
• 107941-45-7 methyl 1,5-dimethyl-8-ethoxy-3-oxo-2-oxabicyclo<2.2.2>-oct-5-ene-6-carboxylate 
• 18958-19-5 2,6-dimethyl-terephthalic acid-1-methyl ester 
• 480-65-9 isodehydracetic acid 
• 53023-60-2 (Z,E)-(+/-)-4-(7-methoxy-3,7-dimethyloctylidene)-3-methylpent-2-ene-1,5-dioic acid 
• 107941-50-4 6,6-dimethoxy-3-(methoxycarbonyl)-4-methyl-2-methylenecyclohexanecarboxylic acid 
• 107941-49-1 2,4-dimethyl-6-methoxy-3-(methoxycarbonyl)benzoic acid 
• 52313-87-8 3-methyl-2-pentene-1,5-diacid dimethyl 

Relevant articles and documents

ReBr(CO)5-catalyzed sequential addition-cyclization of 1,3-dicarbonyl compounds with electron-deficient internal alkynes affording trisubstituted 2H-pyran-2-ones

The reaction of 1,3-dicarbonyl compounds such as acetoacetate, acetylacetone, dibenzoylmethane, and benzoylacetate with electron-deficient internal alkynes in the presence of catalytic amount of ReBr(CO)5 in toluene under neutral conditions resulted in the formation of 4,5,6-trisubstituted 2H-pyran-2-ones in moderate to high yield. The reaction took place via a two-step sequence including the rhenium(I)-catalyzed addition of the activated methylenes to alkynes to give enolic 2-alkenyl derivatives, and subsequently dealcoholic cyclization to form 2H-pyran-2-one derivatives.

A convenient procedure for the synthesis of 4,6-disubstituted 2-oxo-2H-pyran-5-carboxylic esters

A simple procedure for the synthesis of 2H-pyran-2-ones 2a is described: The initial Michael addition product of β-ketoester anions with acetylenic esters readily cyclizes under the basic reaction conditions to give the α-pyrones 2a (Scheme 2).

Studies on Metabolites of Macrophoma commelinae. IV. Substrate Specificity in the Biotransformation of 2-Pyrones to Substituted Benzoic Acids

Substrate specificity in the novel biotransformation from 2-pyrone derivatives to substituted benzoic acids by Macrophoma commelinae (IFO 9570) was investigated by means of feeding experiments with various compounds.Among them, 2-pyrone derivatives substituted by an electron-donating group at C-4, by an electron-withdrawing group at C-5 and by an alkyl group at C-6 were converted to the corresponding benzoic acid derivatives in fairly good yields.The C3-unit precursors and intermediates were examined in stationary or shaking culture.Based on the experimental results obtained, a mechanism for this unique reaction is proposed. macrophoma commelinae IFO 9570; fungi; 2-pyrone; substituted benzoic acid; biotransformation; substrate specificity; aromatic ring formation; macrophomic acid

Synthetic Approach to Aklavinone Using 2-Oxo-2H-pyran-5-carboxylate (Coumalate) Intermediates

A novel approach for the preparation of aklavinone 5 is described in which the key step is the cycloaddition of a substituted coumalate with a ketene acetal to produce a masked A ring with the C and D rings attached.The 4-(arylmethyl)coumalate 53 was prepared from naphthalene-1,5-diol (6) by a seven step route involving as the key step the cyclocondensation of the methyl (arylmethyl)propiolate 52 with methyl 3-oxopentanoate 10.Cycloaddition of 53 with dimethyl ketene acetal 12 produced the potential A-ring precursor 67, which could not be cleanly reduced, thereby ending this scheme.The preparation of functionalized 4,6-dialkylpyrone-5-carboxylates and their use in the synthesis of bicyclic lactones and substituted benzoates via cycloaddition reactions are also described.