Tetrahydromethyl-1,3-isobenzofurandione
[CAS# 11070-44-3]

Identification

• Classification: Chemical reagent >> Organic reagent >> Carboxylic anhydride
• Name: Tetrahydromethyl-1,3-isobenzofurandione
• Synonyms: 4-Methyl tetrahydro phthalic anhydride
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.18
• CAS Registry Number: 11070-44-3
• EC Number: 234-290-7
• SMILES: CC12CCCC=C1C(=O)OC2=O

Properties

• Solubility: 433 mg/L (25 ºC water)
• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.528, Calc.^*
• Melting point: 28.76 ºC
• Boiling Point: 306.7±21.0 ºC (760 mmHg), Calc.^*, 247.98 ºC
• Flash Point: 145.3±19.2 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS08 Danger
• Hazard Statements: H302-H317-H318-H334
• Precautionary Statements: P233-P260-P261-P264-P264+P265-P270-P271-P272-P280-P284-P301+P317-P302+P352-P304+P340-P305+P354+P338-P317-P321-P330-P333+P317-P342+P316-P362+P364-P403-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Respiratory sensitization	Resp. Sens.	1	H334
Serious eye damage	Eye Dam.	1	H318
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Acute toxicity	Acute Tox.	4	H312

Discovory and Applicatios

Tetrahydromethyl-1,3-isobenzofurandione, also known as THIF, is a unique chemical compound with significant implications in organic chemistry and material science. Its structure includes a tetrahydro-1,3-isobenzofurandione core, which contributes to its distinctive chemical properties and applications.

The synthesis of tetrahydromethyl-1,3-isobenzofurandione involves the hydrogenation of 1,3-isobenzofurandione, a compound that provides the core structure for THIF. This hydrogenation process introduces additional hydrogen atoms into the benzofurandione ring system, resulting in the formation of the tetrahydro derivative. The development of THIF was part of broader research efforts to explore the reactivity and functionalization of benzofurandione derivatives, which have applications in various chemical transformations and material formulations.

One of the primary applications of THIF is in the synthesis of polymers and copolymers. Its structure allows it to act as a valuable monomer or cross-linking agent in polymerization reactions. When incorporated into polymer chains, THIF contributes to the formation of polymers with enhanced mechanical properties and thermal stability. This makes it particularly useful in the production of high-performance materials used in coatings, adhesives, and composite materials.

In addition to its role in polymer chemistry, tetrahydromethyl-1,3-isobenzofurandione is employed in the development of specialty chemicals and pharmaceuticals. Its reactivity enables it to participate in various chemical transformations, including condensation reactions and functional group modifications. This versatility makes THIF a useful building block in the synthesis of complex organic molecules and bioactive compounds.

THIF is also explored for its potential applications in the field of organic electronics. Its unique chemical structure and reactivity allow it to be used in the development of electronic materials, such as semiconductors and organic light-emitting diodes (OLEDs). The incorporation of THIF into these materials can enhance their electronic properties and contribute to the development of advanced electronic devices.

Handling tetrahydromethyl-1,3-isobenzofurandione requires attention to safety, as it may pose health risks if not managed properly. Proper protective measures and safety protocols should be observed to ensure safe handling and minimize exposure to the compound.

Overall, the discovery and application of tetrahydromethyl-1,3-isobenzofurandione highlight its significance in various fields of chemistry and materials science. Its role as a monomer, cross-linking agent, and building block for specialty chemicals underscores its value in the development of advanced materials and organic molecules.

References

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2022. Magnetic field-induced orientation of Fe3O4-GO and toughening effect on epoxy resin. Applied Physics A.
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