1,2,4-Trimethoxybenzene CAS 135-77-3 is a uniquely versatile, electron-rich aromatic building block. Its core value lies in its unsymmetrical yet highly predictable substitution pattern, which provides exceptional regiocontrol in synthetic chemistry. This makes it a privileged scaffold for constructing complex molecules in pharmaceuticals, agrochemicals, and advanced materials.
Nome :
1,2,4-TrimethoxybenzeneNº CAS. :
135-77-3MF :
C₉H₁₂O₃MW :
168.19Pureza :
98%Aparência :
White to off-white crystalline solid.Condição de armazenamento :
Store in a tightly sealed container under inert gas (N₂/Ar) at 2–8 °C, protected from light and moisture.Chemical Properties
IUPAC Name: 1,2,4-Trimethoxybenzene
Common Synonyms: Unsymmetrical trimethoxybenzene; TMB
Molecular Formula: C₉H₁₂O₃
Molecular Weight: 168.19 g/mol
CAS Registry Number: 135-77-3
Chemical Structure: A benzene ring with three methoxy (-OCH₃) groups at the 1, 2, and 4 positions. This unsymmetrical substitution pattern creates an electron-rich aromatic system with distinct reactivity.
Appearance: White to off-white crystalline solid.
Melting Point: ~44–46 °C.
Boiling Point: ~247–249 °C.
Density: ~1.11 g/cm³.
Solubility:
Soluble in organic solvents (ethanol, ether, acetone, chloroform).
Insoluble in water.
Key Reactivity:
Electron-rich aromatic ring: Highly activated toward electrophilic aromatic substitution (e.g., Friedel–Crafts acylation/alkylation, nitration, halogenation), with regioselectivity controlled by the methoxy groups.
Methoxy groups: Can be selectively demethylated under harsh conditions (e.g., BBr₃, HI) to reveal polyphenolic compounds.
Oxidation susceptibility: The electron-rich ring is prone to oxidation, requiring careful handling under inert atmospheres.
Biological Activities
Primarily used as a synthetic intermediate rather than a bioactive compound.
Precursor to bioactive molecules: Key intermediate in synthesizing natural products (e.g., lignans, flavonoids) and pharmaceuticals with reported antioxidant, anticancer, or antimicrobial properties.
Fragrance applications: Contributes to sweet, anisic, or herbal odor profiles in perfumery.
Biosynthesis
Not produced via commercial biosynthesis.
Chemical synthesis routes:
1.Partial methylation of polyhydroxybenzenes: Selective methylation of 1,2,4-trihydroxybenzene (hydroxyhydroquinone) using dimethyl sulfate or methyl iodide in the presence of a base.
2.Demethylation of higher methoxybenzenes: Controlled demethylation of pentamethoxybenzene.
3.Electrophilic substitution: Methoxylation of 1,4-dimethoxybenzene under controlled conditions.
Applications
Key Advantages & Benefits
1. Unsymmetrical, Regioselective Reactivity for Targeted Synthesis
Benefit: Unlike its symmetrical isomer (1,3,5-trimethoxybenzene), the unsymmetrical 1,2,4-pattern creates distinct sites of varying electron density. This allows for highly predictable and regioselective electrophilic aromatic substitutions. The position parato two methoxy groups (C-5) is exceptionally nucleophilic, enabling clean mono-functionalization.
Application Scenario: In the synthesis of a complex natural product like a lignan or an alkaloid, a chemist needs to introduce a single formyl group. Using 1,2,4-Trimethoxybenzene in a Vilsmeier-Haack formylation yields 2,4,5-trimethoxybenzaldehyde with high regioselectivity, providing a key intermediate in fewer steps and with easier purification than from isomer mixtures.
2. Electron-Rich, Stabilized Cation Intermediate ("Trityl-like" Stability)
Benefit: The three electron-donating methoxy groups generate a highly stable cation (benzenium ion) upon protonation or alkylation. This facilitates Friedel-Crafts and other electrophilic reactions under milder conditions and minimizes polymerization or side reactions common with less-activated arenes.
Application Scenario: For a materials scientist synthesizing a triarylmethane dye, Friedel-Crafts alkylation of 1,2,4-Trimethoxybenzene with a benzaldehyde derivative proceeds efficiently. The stabilized intermediate leads to high yields of the chromophore core, which is critical for the dye's intense color and stability.
3. Orthogonal Functionality: A Protected Polyol Synthon
Benefit: The three methoxy groups act as robust protecting groups for a trihydroxybenzene (hydroxyhydroquinone) core. They stabilize the molecule for a wide range of transformations, yet can be selectively deprotected under controlled acidic conditions (e.g., with BBr₃) to reveal the polyphenol, a valuable motif in antioxidants and metal chelators.
Application Scenario: In developing a novel antioxidant compound, a researcher can use 1,2,4-Trimethoxybenzene as a stable starting material, perform various elaborations on the aromatic ring, and in the final step, demethylate to unveil the active catechol/resorcinol-type polyphenolic structure, maximizing synthetic efficiency.
1,2,4-Trimethoxybenzene is the synthesis strategist's isomer. Its superiority lies in its unsymmetrical, electron-rich architecture, which provides unparalleled regiochemical control for efficient, stepwise molecular construction. For chemists tasked with synthesizing complex, polyfunctional aromatic targets—from natural product analogs and modern pharmaceuticals to tailored organic materials—this compound offers a unique combination of high reactivity, predictable selectivity, and versatile protecting group strategy that symmetrical or less-functionalized analogs cannot match. It transforms complex retrosynthetic analyses into straightforward, high-yielding synthetic routes.
FAQs
Q1: What makes 1,2,4-Trimethoxybenzene preferable to other isomers in synthesis?
A1: Its unsymmetrical substitution allows for regioselective functionalization. The 5-position (between two methoxy groups) is highly activated, enabling targeted electrophilic attacks—critical for synthesizing complex, unsymmetrical molecules like natural products.
Q2: How should this compound be stored to prevent degradation?
A2: Store in a tightly sealed container under inert gas (N₂/Ar) at 2–8 °C, protected from light and moisture. Its electron-rich ring is prone to oxidation, which can cause discoloration (yellowing) and impurity formation over time.
Q3: Can the methoxy groups be selectively removed?
A3: Yes, demethylation is achievable under controlled conditions. Reagents like boron tribromide (BBr₃) or hydroiodic acid (HI) can selectively remove methoxy groups, often starting with the least sterically hindered one, yielding polyhydroxybenzene intermediates for further synthesis.
Q4: What safety precautions are necessary during handling?
A4: Use standard PPE (gloves, goggles) and handle in a fume hood. Avoid inhalation or skin contact. While not highly toxic, its dust or vapors may cause irritation. Dispose of via approved hazardous waste protocols.
Q5: Is this product available in high purity for sensitive reactions?
A5: Yes, suppliers typically offer ≥98% purity (GC/HPLC). For critical applications (e.g., pharmaceutical synthesis), request a Certificate of Analysis (CoA) with detailed impurity profiles (e.g., isomers, oxidation byproducts).
Q6: What are its main industrial uses?
A6: Primarily as a key intermediate in pharmaceuticals and fragrances. It is also employed in academic and industrial research to develop organic electronic materials or as a model substrate in methodology studies (e.g., catalytic demethylation).
Q7: Can it be used in metal-catalyzed cross-coupling reactions?
A7: Indirectly, yes. While not directly participating in couplings (lacking halogens/boronic acids), it can be functionalized via electrophilic substitution (e.g., bromination) to introduce handles for Suzuki or other cross-coupling reactions, enabling further diversification.
Cloridrato de Procaína CAS 51-05-8 é o sal cloridrato de procaína solúvel em água. É a formulação específica usada na medicina clínica, comercializada sob a famosa marca Procaína.NovocaínaEmbora seu uso na prática clínica tenha diminuído, continua sendo um medicamento historicamente fundamental e ainda é empregado em contextos médicos e terapêuticos específicos.
Detalhes
4-Bromo-3-hydroxybenzoic acid CAS 14348-38-0 is a premium, multifunctional aromatic building block engineered for complexity-driven synthesis. Its core value lies in the strategic placement of three distinct, orthogonally reactive functional groups on a benzene ring, making it an indispensable tool for convergent molecular construction in advanced research and development.
Detalhes
Ethyl β-Oxo-1,3-benzodioxole-5-butanoate CAS 31127-23-8 is a β-ketoester derivative featuring a 1,3-benzodioxole (methylenedioxyphenyl) aromatic system. Structurally, it consists of a benzodioxole ring attached through a three-carbon chain to an ethyl β-ketoester functional group (-CO-CH₂-COOEt). This makes it a versatile bifunctional building block for organic synthesis, combining the electronic properties of the benzodioxole group with the high reactivity of a β-ketoester.
Detalhes![4-Nitrophenyl 3-(Benzo[d][1,3]dioxol-5-yl)-2-methylpropanoate](https://pt.qixiolivetol.com/storage/uploads/images/202604/17/1776427287_qZy87IjHSQ.jpg)
4-Nitrophenyl 3-(Benzo[d][1,3]dioxol-5-yl)-2-methylpropanoate is a chirally defined, pre-activated acylating agent that combines a metabolically stable benzo[1,3]dioxole (piperonyl) pharmacophore with the exceptional reactivity of a 4-nitrophenyl ester. It enables the efficient, racemization-free introduction of a complex, chiral acid moiety under mild conditions, making it invaluable for advanced synthetic and bioconjugation chemistry. 4-Nitrophenyl 3-(Benzo[d][1,3]dioxol-5-yl)-2-methylpropanoate is a specialty ester designed as a reactive biochemical or synthetic intermediate. Its structure strategically combines three key units: (1)A 3-(benzo[1,3]dioxol-5-yl)-2-methylpropanoic acid (piperonyl-substituted, chiral acid) moiety. (2)A 4-nitrophenyl ester leaving group. This design makes it an activated ester, where the 4-nitrophenol is an excellent leaving group, facilitating efficient acyl transfer reactions under mild conditions.
Detalhes
2'-Ethoxyacetophenone CAS 2142-67-8 is a specialized aromatic ketone characterized by an ethoxy substituent at the orthoposition relative to the acetyl group. This structural feature imparts distinct chemical and physical properties, making it a privileged building block for synthesizing complex molecules, particularly in the flavor/fragrance and pharmaceutical sectors.
Detalhes
2-Amino-5-bromobenzoic acid CAS 5794-88-7 is a highly versatile aromatic building block that integrates three distinct functional groups—an amine, a carboxylic acid, and an aryl bromide—into a single, synthetically valuable scaffold. This multifunctionality makes it a crucial intermediate in pharmaceutical and advanced materials chemistry.
Detalhes
4-Butylbenzonitrile CAS 20651-73-4 is a strategically designed hydrophobic building block that combines a rigid aromatic core with a flexible linear alkyl chain and a highly versatile nitrile functional group. This triad of features makes it an exceptionally valuable intermediate for modulating physicochemical properties and enabling diverse synthetic pathways in advanced material and pharmaceutical and agrochemical research.
Detalhes
1,2,4-Trimethoxybenzene CAS 135-77-3 is a uniquely versatile, electron-rich aromatic building block. Its core value lies in its unsymmetrical yet highly predictable substitution pattern, which provides exceptional regiocontrol in synthetic chemistry. This makes it a privileged scaffold for constructing complex molecules in pharmaceuticals, agrochemicals, and advanced materials.
Detalhes
CONTATE-NOS
1st Floor, No. 477, Huancheng West Road, Nanqiao Town, Fengxian District, Shanghai,China
sales@qxscientific.com
+86 -13701740203
IPv6 SUPORTADO POR REDE
|
Mapa do site
|
XML |
Blogue |
política de Privacidade
Deixe um recado
Scan to Wechat/Whatsapp :
Português
English
Español
Português
