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3,4,5-Trimethoxybenzaldehyde (C₁₀H₁₂O₄) is a symmetric aromatic aldehyde with three methoxy (–OCH₃) groups at positions 3,4,5 on the benzene ring.
Key Facts:
Appearance: White to pale yellow crystals (mp: 74–76°C).
Solubility: Organic solvents (e.g., ethanol, chloroform); insoluble in water.
Reactivity:
Aldehyde (–CHO) undergoes oxidation/reduction.
Electron-rich ring allows electrophilic substitution (e.g., at position 2).
Applications:
Key precursor for pharmaceuticals (e.g., antibiotic trimethoprim).
Synthesizes agrochemicals, dyes, and natural products (e.g., mescaline).
Building block for ligands and polymers.
Why Important: Combines aldehyde reactivity with sterically symmetric methoxy groups, enabling precise synthesis of bioactive molecules.
3,4,5-Trimethoxybenzaldehyde (C₁₀H₁₂O₄) is a synthetic aromatic aldehyde widely used as a building block in organic chemistry and pharmaceutical synthesis. Here are its key chemical details:
Core: Benzaldehyde derivative with three methoxy (–OCH₃) groups at positions 3, 4, and 5 on the benzene ring.
Formula: C₁₀H₁₂O₄
Molar Mass: 196.20 g/mol
CAS Number: 86-81-7
OCH₃
│
OCH₃─1─2─3─CHO
│ │
H₃CO 4
*(Positions: 1,2,3 = methoxy groups; position 4 = aldehyde group)*
Appearance: White to pale yellow crystalline solid.
Melting Point: ~74–76 °C.
Solubility: Soluble in organic solvents (ethanol, acetone, chloroform); low solubility in water.
Odor: Characteristic almond-like (common to aldehydes).
Typically produced by:
Etherification of Gallic Acid: Methylation of 3,4,5-trihydroxybenzoic acid (gallic acid), followed by oxidation/decarboxylation.
Rimer-Tiemann Reaction: On 1,2,3-trimethoxybenzene.
Pharmaceuticals: Precursor to antibiotics (e.g., trimethoprim), antivirals, and anticancer agents.
Agrochemicals: Synthesis of herbicides and fungicides.
Alkaloid Synthesis: Used to prepare hallucinogens (e.g., mescaline) and other natural product analogs.
Organic Intermediates: For ligands, dyes, and polymers.
Aldehyde Group: Undergoes typical reactions (oxidation, reduction, nucleophilic addition).
Electron-Rich Ring: Electrophilic substitution favors the 2-position (ortho to one methoxy, para to another).
Symmetry: The 3,4,5-substitution pattern enhances regioselectivity in reactions.
Irritant: May cause skin/eye irritation.
Handling: Use gloves/goggles; avoid inhalation.
Summary: A versatile aldehyde with symmetric methoxy substitution, enabling precise functionalization in drug design and organic synthesis. Its stability and reactivity make it valuable for constructing complex molecules.
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