3425-89-6

Basic information

• Product Name: 1,2,3,6-Tetrahydro-4-methylphthalic anhydride
• Synonyms: 3-Isobenzofurandione,3a,4,7,7a-tetrahydro-5-methyl-1;4-METHYLTETRAHYDROPHTHALIC ANHYDRIDE (4-MTHPA);3a,4,7,7a-tetrahydro-5-methyl-1,3-Isobenzofurandione;1,2,3,6-Tetrahydro-4-methylphthalic anhydride;4-METHYL-2,3,6,7-TETRAHYDROPHTHALIC ANHYDRIDE;4-Methyltetrahydro ;cis-4-Methyltetrahydrophthalic anhydride;cis-5-Methyl-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione
• CAS NO: 3425-89-6
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.17
• EINECS: 222-323-8
• Product Categories: Diels-Alder Adducts
• Mol File: 3425-89-6.mol
• Article Data: 16

Chemical Properties

• Melting Point: 59-60°C
• Boiling Point: 295°C
• Flash Point: >100°C
• Appearance: Crystalline powder
• Density: 1.204 g/cm³
• Vapor Pressure: 0.000957mmHg at 25°C
• Refractive Index: 1.507
• Storage Temp.: 2-8°C
• Water Solubility: 13.2g/L at 20℃
• CAS DataBase Reference: 1,2,3,6-Tetrahydro-4-methylphthalic anhydride(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,6-Tetrahydro-4-methylphthalic anhydride(3425-89-6)
• EPA Substance Registry System: 1,2,3,6-Tetrahydro-4-methylphthalic anhydride(3425-89-6)

Safety Data

• Statements: 41-42/43
• Safety Statements: 22-24-26-37/39
• RIDADR: 3335
• Hazardous Substances Data: 3425-89-6(Hazardous Substances Data)

Usage

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C9H10O3/c1-5-2-3-6-7(4-5)9(11)12-8(6)10/h2-3,5-7H,4H2,1H3

Upstream product

• 78-79-5 isoprene 
• 108-31-6 maleic anhydride 
• 32187-82-9 (+/-)-4-methyl-cyclohex-4-ene-1r,2t-dicarbonitrile 

Downstream Products

• 1071525-05-7 4-Methyl-cyclohex-4-en-cis-1,2-dicarbonsaeure 
• 19309-12-7 (+/-)-4r,5c-bis-hydroxymethyl-1-methyl-cyclohexene 
• 86905-77-3 4-methyl-cyclohex-4-ene-1,2-dicarboxylic acid dimethyl ester 
• 78149-76-5 2-(2,4-Dimethoxy-benzoyl)-5-methyl-6-oxa-bicyclo[3.2.1]octan-7-one 
• 78149-78-7 (1S,6S,7R)-3-(2,4-Dimethoxy-phenyl)-1-methyl-2,4-dioxa-tricyclo[4.3.1.0^3,7]decan-5-one 
• 19438-61-0 4-methylphthalic anhydride 
• 19438-59-6 4-Methyl-Δ¹-tetrahydrophthalic anhydride 
• 19438-60-9 4-methyl-hexahydrophthalic anhydride 
• 19438-64-3 4-Methyl-Δ³-tetrahydrophthalic anhydride 
• 2028-11-7 4-methyl-1,2,3,4-tetrahydrophthalimide 
• 19309-12-7 Cis-4-methyl-4-cyclohexene-1,2-dimethanol 
• 100-21-0 terephthalic acid 
• 4316-23-8 4-methylphthalic acid 
• 99-94-5 p-Toluic acid 

Relevant articles and documents

Sensitive and accurate 13c kinetic isotope effect measurements enabled by Polarization transfer

Polarization transfer is demonstrated as a sensitive technique for the measurement of isotopic fractionation of protonated carbons at natural abundance. This method allows kinetic isotope effects (KIEs) to be determined with substantially less material or shorter acquisition time compared with traditional experiments. Computations quantitatively reproduce the KIEs in a Diels-Alder reaction and a catalytic glycosylation. The glycosylation is shown to occur by an effectively concerted mechanism.

Synthesis and identification of epoxy derivatives of 5-methylhexahydroisoindole-1,3-dione and biological evaluation

Cyclic imides belong to a well-known class of organic compounds with various biological activities, promoting a great interest in compounds with this functional group. Due to the structural complexity of some molecules and their spectra, it is necessary to use several spectrometric methods associated with auxiliary tools, such as the theoretical calculation for the structural elucidation of complex structures. In this work, the synthesis of epoxy derivatives of 5-methylhexahydroisoindole-1,3-diones was carried out in five steps. Diels–Alder reaction of isoprene and maleic anhydride followed by reaction with m-anisidine afforded the amide (2). Esterification of amide (2) with methanol in the presence of sulfuric acid provided the ester (3) that cyclized in situ to give imides 4 and 4-ent. Epoxidation of 4 and 4-ent with meta-chloroperbenzoic acid (MCPBA) afforded 5a and 5b. The diastereomers were separated by silica gel flash column chromatography, and their structures were determined by analyses of the spectrometric methods. Their structures were confirmed by matching the calculated1 H and13 C NMR chemical shifts of (5a and 5b) with the experimental data of the diastereomers using MAE, CP3, and DP4 statistical analyses. Biological assays were carried out to evaluate the potential herbicide activity of the imides. Compounds 5a and 5b inhibited root growth of the weed Bidens pilosa by more than 70% at all the concentrations evaluated.

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A dehydrogenative diels-alder reaction of prenyl derivatives with 2,3-dichloro-5,6-dicyanobenzoquinone

An efficient dehydrogenative Diels-Alder (DHDA) reaction of prenyl derivatives with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) has been developed under mild conditions, leading to a series of cyclohexene derivatives with good to excellent yields and excellent diastereoselectivity.