4,4',4''-(1,1,1-Ethanetriyl)tris[2,6-bis(methoxymethyl)phenol]
[CAS 672926-26-0]

Identification

• Classification: Natural product >> Natural phenols
• Name: 4,4',4''-(1,1,1-Ethanetriyl)tris[2,6-bis(methoxymethyl)phenol]
• Molecular Formula: C₃₂H₄₂O₉
• Molecular Weight: 570.67
• CAS Registry Number: 672926-26-0
• SMILES: CC(C1=CC(=C(C(=C1)COC)O)COC)(C2=CC(=C(C(=C2)COC)O)COC)C3=CC(=C(C(=C3)COC)O)COC

Properties

• Density: 1.2$+/-$0.1 g/cm³, Calc.^*
• Index of Refraction: 1.571, Calc.^*
• Boiling Point: 613.5$+/-$50.0 $degree$C (760 mmHg), Calc.^*
• Flash Point: 324.8$+/-$30.1 $degree$C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319
• Safety Statements: P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Discovery and Applications

4,4',4''-(1,1,1-Ethanetriyl)tris[2,6-bis(methoxymethyl)phenol] is a highly substituted triphenolic organic compound featuring a central ethanetriyl (tert-butyl-like carbon center) core bonded to three phenolic aromatic rings. Each aromatic ring is further substituted with methoxymethyl (–CH₂OCH₃) groups at the 2- and 6-positions, resulting in a sterically hindered, multifunctional phenolic structure. The molecule belongs to the broader class of triphenylmethane- or triarylmethane-type frameworks with extensive alkyl ether functionalization.

The core structure consists of a central carbon atom (1,1,1-ethanetriyl unit) connected to three phenyl rings, forming a trigonal, three-fold symmetric architecture. This central carbon acts as a branching point that rigidly organizes the three aromatic units in space. Such triaryl systems are commonly encountered in advanced organic materials chemistry, where molecular geometry and steric protection play important roles in determining stability and reactivity.

Each phenolic ring in this compound contains hydroxyl functionality (–OH) and two methoxymethyl substituents at the ortho positions (2 and 6). The methoxymethyl groups are ether-protected hydroxymethyl derivatives, which reduce the direct reactivity of phenolic positions while maintaining strong electron-donating effects through oxygen atoms. These substituents increase steric bulk around the aromatic ring and can significantly influence hydrogen bonding, solubility, and conformational behavior.

The phenolic hydroxyl groups provide sites for hydrogen bonding and potential chemical reactivity, such as etherification, esterification, or oxidative coupling reactions. However, the presence of bulky methoxymethyl substituents at the ortho positions reduces the accessibility of these hydroxyl groups, making the molecule relatively sterically protected compared with simpler phenols.

Compounds of this structural class are often encountered in advanced synthetic organic chemistry, particularly in the design of protected polyphenols, resin precursors, and functional monomers. The methoxymethyl group is commonly used as a protecting group for phenolic hydroxyls in multistep synthesis because it can be introduced under mild conditions and later removed under acidic conditions when deprotection is required.

The synthesis of such a molecule typically involves stepwise functionalization of a tri-substituted phenolic precursor followed by introduction of methoxymethyl groups through reactions with chloromethyl methyl ether or related reagents under controlled conditions. The central ethanetriyl-triaryl framework is generally constructed through electrophilic aromatic substitution or condensation chemistry, depending on the synthetic route.

From a structural perspective, the molecule is highly rigid and sterically crowded. The three aromatic rings are arranged around the central carbon in a propeller-like geometry due to steric repulsion between ortho substituents. This spatial arrangement limits free rotation and can influence crystallization behavior and molecular packing in the solid state.

The electron-rich phenolic system, combined with ether substituents, gives the molecule strong donor characteristics. Such highly substituted phenols are sometimes explored in materials chemistry for their potential use in organic frameworks, resins, or as intermediates in more complex molecular architectures. However, specific applications depend strongly on further functionalization of the hydroxyl groups or deprotected intermediates.

Physicochemically, the compound is expected to exhibit low polarity relative to simple phenols due to extensive alkyl ether substitution, despite the presence of multiple hydroxyl groups. The methoxymethyl groups also reduce intermolecular hydrogen bonding, which can affect solubility and melting behavior.

Overall, 4,4',4''-(1,1,1-ethanetriyl)tris[2,6-bis(methoxymethyl)phenol] is a highly substituted triaryl phenolic compound with a rigid central carbon framework and extensive methoxymethyl protection. Its structure reflects design principles common in advanced organic synthesis, where steric control and functional group protection are used to tune reactivity, stability, and molecular architecture.

References

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