2,4-Dimethoxy-3-methylbenzaldehyde - ≥99% , CAS No.7149-92-0

CAS: 7149-92-0 Cat. No.: D474388 Formula: C₁₀H₁₂O₃ Molecular Weight: 180.2 EC Number: 628-374-6

GRADE & PURITY ≥99%

Synonyms

2,4-dimethoxy 3-methyl benzaldehyde | FT-0636371 | 2,4-Dimethoxy-3-methylbenzaldehyde, 99% | 2-methoxy-3-methylanisaldehyde | DTXSID50291007 | 2-chloro-9-isopropyl-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-purin-6-amine | MFCD00011489 |

Storage

Argon charged,Room temperature

Shipped In

Normal

Overview

Description

2,4-Dimethoxy-3-methylbenzaldehyde has been used:as starting reagent in stereocontrolled total synthesis of (−)-kendomycinin total syntheses of renierol, renierol acetate and renierol propionate

Specifications

Synonyms

2,4-dimethoxy 3-methyl benzaldehyde | FT-0636371 | 2,4-Dimethoxy-3-methylbenzaldehyde, 99% | 2-methoxy-3-methylanisaldehyde | DTXSID50291007 | 2-chloro-9-isopropyl-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-purin-6-amine | MFCD00011489 |

Specifications & Purity

≥99%

Storage

Argon charged,Room temperature

Shipped In

Normal

Purity

≥99%

Names and Identifiers

Pubchem Sid

488189026

Canonical Smiles

CC1=C(C=CC(=C1OC)C=O)OC

IUPAC Name

2,4-dimethoxy-3-methylbenzaldehyde

InChIKey

UOKAZUWUHOBBMD-UHFFFAOYSA-N

INCHI

1S/C10H12O3/c1-7-9(12-2)5-4-8(6-11)10(7)13-3/h4-6H,1-3H3

Isomeric SMILES

CC1=C(C=CC(=C1OC)C=O)OC

Molecular Weight

180.2

Reaxy-Rn

1948407

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1948407&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Methoxybenzenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Methoxybenzenes
• Intermediate Tree Nodes: Not available
• Direct Parent: Dimethoxybenzenes
• Alternative Parents: Phenoxy compounds Benzoyl derivatives Benzaldehydes Anisoles Toluenes Alkyl aryl ethers Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Dimethoxybenzene - M-dimethoxybenzene - Anisole - Benzaldehyde - Benzoyl - Phenol ether - Phenoxy compound - Toluene - Aryl-aldehyde - Alkyl aryl ether - Ether - Organooxygen compound - Aldehyde - Organic oxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: souble in Methanol
• Sensitivity: air sensitive
• x_boil_point_char: 109 °C/4 mmHg
• x_melt_point_char: 54 °C
• Molecular Weight: 180.200 g/mol
• XLogP3: 1.700
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 180.079 Da
• Monoisotopic Mass: 180.079 Da
• Topological Polar Surface Area: 35.500 Ų
• Heavy Atom Count: 13
• Formal Charge: 0
• Complexity: 170.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

No assay or bioanalytical application protocols are specified for this chemical. Its use is in chemical synthesis and method development.

• Practical laboratory usage (general guidance):
  • For carbonyl condensations: combine aldehyde with nucleophilic partner under chosen catalyst/base and solvent; remove water (if applicable) to drive equilibrium; monitor by TLC/LC.
  • For olefinations: generate ylide or phosphonate anion under inert atmosphere in anhydrous solvent; add aldehyde at controlled temperature; quench and purify by column chromatography or crystallization as appropriate.
  • For reductions: choose reducing agent based on chemoselectivity needs; control temperature and add slowly to manage exotherm; confirm completion by disappearance of the aldehydic 1H NMR signal.

Because procedures are reaction-specific, consult peer-reviewed literature or internal SOPs for exact stoichiometries and workup conditions. Always review the SDS before scale-up.

Biological Roles

This product is supplied for research use only. No biological or clinical roles are claimed for this item.

• General context (literature):

  • Aromatic methoxybenzaldehydes occur as structural motifs in lignin-derived aromatics and natural product fragments, but 2,4-dimethoxy-3-methylbenzaldehyde itself is a synthetic derivative without a known endogenous biological role.
  • Functional chemistry: as an aldehyde, it can form reversible adducts with nucleophiles (e.g., imines with amines) under laboratory conditions; such reactivity underlies many derivatization strategies but does not imply biological activity.

• Laboratory bioscience utility (general):

  • Can serve as a probe substrate for enzyme-mimetic catalysis studies (e.g., organocatalytic iminium/enamine chemistry) or as a chromophore-bearing handle in synthesis of small-molecule libraries for SAR exploration.

Any biological testing must be conducted under appropriate approvals and controls. For definitive hazard/tox profile and exposure limits, consult the SDS; this catalog listing does not provide toxicological endpoints.

Buffer Applications

Not typically applicable. 2,4-Dimethoxy-3-methylbenzaldehyde is a hydrophobic organic aldehyde and is not used as an aqueous buffer component.

• Practical note: If aqueous-phase reactions (e.g., biphasic condensations) are attempted, buffering would pertain to the reaction medium (e.g., acetate or phosphate buffers) rather than to this compound itself.
• For preparative work, focus on the Solvent Selection and Reaction & Applications sections for guidance.

Green Alternatives

Greener practice primarily involves solvent and reagent choices, as the substrate is fixed.

• Prefer greener solvents where feasible (general guidance):

  • Replace DCM/chloroform with 2-methyltetrahydrofuran (2-MeTHF), dimethyl carbonate (DMC), cyclopentyl methyl ether (CPME), or ethyl acetate when reaction compatibility allows.
  • Use toluene or 2-MeTHF instead of diethyl ether for large-scale Grignard additions (improved safety and lower VOC impact compared to ether/THF in some settings).

• Example comparisons (general):

  • DCM vs 2-MeTHF: similar solvating ability for many carbonyl reactions; 2-MeTHF is bio-derived and has a better EHS profile. Trade-off: different polarity and azeotrope behavior; may affect rates/selectivity.
  • THF vs CPME: CPME offers broader liquid range and lower peroxide formation rate than many ethers; can simplify workups with water-immiscible behavior. Trade-off: higher cost, different solvation of ionic reagents.
  • Toluene vs Ethyl acetate: EtOAc is more biodegradable and has lower toxicity; toluene often superior at high temps and for Dean–Stark water removal.

• Reagent choices:

  • Choose catalytic methods (e.g., transfer hydrogenation, organocatalytic aldol/Knoevenagel) over stoichiometric reagents where compatible.
  • For oxidations to acids, consider catalytic TEMPO/O2 or electrochemical methods instead of chromium(VI) reagents.

Adopt minimal solvent volumes, efficient heat/mass transfer, and continuous processing where possible to reduce waste and energy consumption.

Pharmaceutical Uses

No excipient or pharmacopeial status is provided for this item. This product is for research use only.

• General context (literature):

  • Aromatic aldehydes like anisaldehyde derivatives are common synthetic intermediates en route to fragrance ingredients, agrochemical scaffolds, and small-molecule leads. In pharmaceutical process chemistry, such aldehydes may be elaborated to substituted styrenes, benzyl alcohols, or benzoic acids.
  • Role in formulation: Aldehydes are generally not used as excipients due to reactivity with amines and proteins; they are handled as reactive intermediates in API synthesis.

• Compliance note:

  • If intended for GMP or regulatory filings, procure appropriate grade and documentation. This catalog entry does not specify GMP/Ph. Eur./USP compliance. Verify impurity profile, residual solvents, and elemental impurities per ICH Q3A/Q3C/Q3D as applicable to your program.

Physical Properties

Only limited item-specific physical data are provided for this catalog entry.

• Item-specific data (from Product Data):

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general properties for 2,4-dimethoxy-3-methylbenzaldehyde (non-spec, for orientation only):

  • Phase at ambient conditions: typically an organic liquid or low-melting solid for many dimethoxybenzaldehydes; exact MP/phase for this isomer not confirmed here.
  • Expected solubility profile: low solubility in water; good solubility in common organic solvents (e.g., dichloromethane, THF, ethyl acetate, toluene, alcohols).
  • Acid/base behavior: non-basic; aldehyde may form hydrates/acetal/imine derivatives under appropriate conditions; no appreciable aqueous pKa in the physiological range.
  • Polarity/logP: aromatic aldehydes with two methoxy groups are moderately lipophilic and polarizable; exact logP for this isomer not confirmed.

• Numerical values (this item):

  • Melting point: Not specified for this item; refer to CoA/Spec Sheet.
  • Boiling point: Not specified for this item; refer to CoA/Spec Sheet.
  • Density: Not specified for this item; refer to CoA/Spec Sheet.
  • Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
  • UV/Vis: Not specified for this item; refer to CoA/Spec Sheet.

Always consult the item’s CoA/SDS for definitive, lot-specific properties before process design.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

• Interpreting grades (general guidance):

  • Research-grade aldehydes are typically supplied with assay (e.g., GC/HPLC area %) and impurity profiles (e.g., related aldehydes/acids). If HPLC or GC assay is stated on the CoA, it reflects the analytical method used for purity determination.
  • Stabilization: Many aldehydes are shipped under inert gas to limit air oxidation to acids. The Product Data specify “Argon charged,” indicating the headspace contains inert gas to maintain quality.
  • Low-water or low-peroxide specifications, UV cutoffs, and metal limits are sometimes relevant for chromatography or photochemical work. When required, consult the CoA/Spec Sheet for exact values.

• Practical quality notes for this structure (general):

  • Typical impurities may include the corresponding benzoic acid derivative (air oxidation), unreacted anisole-type precursors, and trace solvents.
  • For air- or base-sensitive transformations (e.g., enamine/Knoevenagel, Wittig), it is prudent to verify aldehyde content by NMR (distinctive formyl singlet ~9.5–10.5 ppm) prior to use.
  • If performing UV-detected chromatography, check baseline behavior; electron-rich anisaldehydes often have strong UV absorbance around 254 nm, aiding detection.

Reaction and Applications

As an electron-rich aryl aldehyde, 2,4-dimethoxy-3-methylbenzaldehyde is a versatile building block in synthesis. The methoxy substituents elevate ring electron density, while the aldehyde remains a robust electrophile.

• Representative transformations (literature/general):

  • Carbonyl condensations: Knoevenagel, aldol (via enolizable partners), Claisen–Schmidt with ketones, and formation of oximes/hydrazones (useful handles for further reductions or cyclizations).
  • Olefination: Wittig, Horner–Wadsworth–Emmons, and Julia–Kocienski to access styrenes and substituted alkenes bearing anisole motifs.
  • Nucleophilic additions: Grignard or organolithium add to give benzylic alcohols; control temperature and equivalents to avoid competitive deprotonation or overreaction.
  • Reductions/oxidations: Selective reduction to the benzyl alcohol (NaBH4, catalytic hydrogenation) or to the corresponding methyl (Wolff–Kishner/Clemmensen sequences); oxidation to the benzoic acid or to acids/esters under oxone, TEMPO/bleach, or nitric acid conditions.
  • Protecting-group chemistry: Acetalization/ketalization in alcohols with acid catalysts; deprotection under aqueous acid regenerates the aldehyde.

• Substituent effects (general):

  • Ortho/para methoxy groups strongly activate the ring, enabling further electrophilic aromatic substitution (e.g., halogenation, nitration under mild conditions). The formyl group is meta-directing but its influence is attenuated by the two methoxy substituents.
  • The 3-methyl substituent contributes sterics near the ortho methoxy/aldehyde region, which can influence regioselectivity and hinder ortho lithiation.

• Practical tips:

  • Work under inert atmosphere to limit air oxidation to the acid.
  • Monitor reactions by TLC/UPLC; the aldehyde shows characteristic UV at 254 nm and a distinctive aldehydic proton in 1H NMR (~9.5–10.5 ppm).

Reaction Conditions

General literature guidelines for typical transformations of electron-rich aryl aldehydes (not item-specific specs; optimize for your substrate and scale):

• Wittig olefination:

  • Solvent: THF or toluene (anhydrous).
  • Base/ylide: Ph3P=CHR generated with n-BuLi or from stabilized ylides.
  • Temperature: –78 to 25 °C depending on ylide type; 1–16 h.
  • Notes: Methoxy substituents generally favor E-selectivity with HWE; control by base and temperature.

• Knoevenagel condensation:

  • Solvent: toluene, EtOH, MeCN, or solvent-free; catalytic piperidine, ammonium acetate, or amine bases.
  • Temperature: RT to reflux; water removal (Dean–Stark) accelerates equilibrium.
  • Notes: Electron-rich ring typically accelerates condensation with active methylenes (malononitrile, ethyl cyanoacetate).

• Reduction to benzyl alcohol:

  • NaBH4 in MeOH/EtOH at 0–25 °C; or catalytic hydrogenation (Pd/C) in EtOH/EtOAc at 1–5 bar H2.
  • Chemoselectivity: Aldehyde reduces faster than aryl C–O groups; avoid over-reduction by controlling time and equivalents.

• Grignard addition:

  • Solvent: dry THF or Et2O under N2/Ar.
  • Temperature: –78 to 0 °C initially, then warm to RT; quench with NH4Cl.
  • Notes: Steric congestion near C2/C3 can slightly moderate rates; ensure thorough exclusion of moisture.

• Acetal formation:

  • Acid catalyst (p-TsOH) in ROH or with orthoformates; reflux with azeotropic removal of water.

These conditions are starting points; verify by small-scale trials and analytical monitoring (TLC, GC/LC, NMR).

Safety and Handling

• Item-specific hazard data (GHS, pictograms, H-statements): Not specified for this item; refer to SDS for authoritative information.

• General safety considerations for aromatic aldehydes (literature/generic guidance):

  • Hazards: May be irritant to skin/eyes/respiratory tract; aldehydes can be sensitizers in some cases. Avoid inhalation of vapors and contact with skin/eyes.
  • Reactivity: Aldehydes are susceptible to air oxidation (to the corresponding acid) and to polymerization/condensation under basic conditions. Electron-rich aryl aldehydes can also undergo electrophilic substitution on the ring.
  • Storage incompatibilities: Avoid strong oxidizers, strong bases, and strong acids (which can promote acetalization/condensation). Keep away from heat and sunlight.

• Handling practices:

  • Use in a well-ventilated fume hood. Wear appropriate PPE: lab coat, safety glasses or face shield, and chemical-resistant gloves (e.g., nitrile). For larger scale, consider splash protection and local exhaust.
  • Prevent moisture ingress when moisture-sensitive transformations (e.g., acetalization equilibria, organometallic additions) are planned; use dry glassware and anhydrous solvents.
  • Given the Product Data storage note “Argon charged,” minimize headspace oxygen exposure; recap promptly and purge the container headspace with inert gas after use.

• First aid (overview; consult SDS for details):

  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: rinse with plenty of water for at least 15 minutes; remove contaminated clothing; obtain medical evaluation.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.

Solvent Selection

This compound is an electron-rich aromatic aldehyde with low aqueous solubility and broad solubility in common organic media.

• Polarity and miscibility (general, literature-based):

  • Poorly soluble in water.
  • Readily soluble in chlorinated solvents (DCM, chloroform), ethers (THF, MTBE), esters (EtOAc), aromatics (toluene), and alcohols (MeOH, EtOH).

• Choosing a reaction solvent (practical guidance):

  • Nucleophilic additions (e.g., Grignard/organolithium): use rigorously anhydrous ethereal solvents (THF, diethyl ether); low temperatures often improve chemoselectivity at the aldehyde carbonyl.
  • Condensations (Knoevenagel/aldol/oxime): alcohols, acetonitrile, toluene, or mixed solvent/water systems depending on catalyst/base; Dean–Stark in toluene/xylene aids water removal.
  • Wittig/Horner–Wadsworth–Emmons: THF, toluene, or DCM depending on ylide/reagent base; maintain anhydrous conditions.
  • Reductions (NaBH4, borane, catalytic hydrogenation): protic alcohols (MeOH/EtOH) for NaBH4; ethereal/chlorinated solvents for chemoselective catalytic protocols.

• Comparison (general considerations):

  • DCM vs 2-MeTHF: DCM offers excellent solubility and fast workups; 2-MeTHF is a greener alternative with similar solvation for many transformations.
  • Toluene vs acetonitrile: toluene suits high-temperature condensations with azeotropic water removal; MeCN offers higher polarity for base-promoted reactions at lower temperatures.

Select solvents based on reaction mechanism, moisture sensitivity, and desired temperature window; consult CoA if low-UV or trace-metal specifications are required for analytical applications.

Storage and Reconstitution

• Storage (item-specific from Product Data):

  • Storage conditions: Room temperature, Argon charged.
  • Shipped in: Normal.

• General storage guidance for aromatic aldehydes:

  • Keep tightly closed in the original container; maintain the inert gas headspace (argon or nitrogen) to minimize air oxidation to the corresponding acid.
  • Store in a dry place away from direct light and sources of heat. Avoid prolonged exposure to air and moisture.
  • If frequent access is expected, consider aliquoting under inert atmosphere to reduce repeated oxygen exposure.

• Reconstitution/Preparation for use (general):

  • This aldehyde dissolves readily in common anhydrous organic solvents (e.g., dichloromethane, THF, toluene, methanol, ethanol). Select solvent based on intended reaction (see Solvent Selection).
  • For moisture-sensitive operations, dry solvents over molecular sieves and use oven-dried glassware. Purge containers with inert gas after dispensing.
  • Prior to use in sensitive transformations, verify identity and aldehyde content by NMR/GC or HPLC.

• Stability notes:

  • Aldehydes can slowly oxidize; if acidic impurities are detected after storage, pass through a short basic alumina plug or wash with aqueous sodium bicarbonate as appropriate to remove benzoic acid derivatives.

Always consult the product’s CoA and SDS for lot-specific handling instructions.

Structure and Identity

A substituted aromatic aldehyde bearing two methoxy groups and one methyl on a benzaldehyde core; useful as an electron-rich aryl aldehyde building block.

• Item-specific identifiers (Product Data):

  • CAS: 7149-92-0
  • CID (PubChem): 251693
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed identity (general reference data, not item-specific specs):

  • Preferred name: 2,4-Dimethoxy-3-methylbenzaldehyde
  • Molecular formula (literature): C10H12O3
  • Molecular weight (calculated from C10H12O3): ~180.20 g/mol

• Structural features (general):

  • Core: benzaldehyde ring (formyl group directly attached to an aromatic ring).
  • Substitution pattern relative to the aldehyde (position 1): methoxy at 2- (ortho) and 4- (para) positions; methyl at 3- (meta) position.
  • Functional groups: aromatic aldehyde (–CHO), two anisole-type methoxy substituents (–OCH3), one aryl methyl (–CH3).
  • Electronics: two methoxy groups are strong π-donors/orthpara directors; the formyl group is a meta-directing, strongly electron-withdrawing substituent. The combination renders the ring overall electron-rich at positions ortho/para to methoxy, while the formyl carbon remains a strong electrophilic site.
  • 2D description: a six-membered aromatic ring bearing, in order, –CHO at C1, –OCH3 at C2, –CH3 at C3, and –OCH3 at C4; remaining ring positions are unsubstituted hydrogens.

Synthetic Utility

Key features enabling broad utility:

• Electrophilic carbonyl center: The aldehyde carbonyl engages readily in nucleophilic additions (organometallics, cyanide equivalents), condensations (Knoevenagel, aldol, imine/oxime formation), and olefinations (Wittig/HWE). The anisole motif often enhances conjugation and stabilizes benzylic intermediates.

• Electron-rich arene: Two methoxy substituents activate the ring toward electrophilic aromatic substitution. Strategic halogenation, formylation, or Friedel–Crafts acylation at remaining positions can be leveraged, though the existing formyl group’s meta-directing influence can compete; careful condition selection (Lewis vs Brønsted acid, temperature) guides regioselectivity.

• Orthogonal derivatizations:

  • O-Demethylation (e.g., with BBr3 or AlCl3/thiols) to uncover phenolic OH groups for downstream coupling or etherification.
  • Oxidation ladder at benzylic/aldehydic positions (alcohol ↔ aldehyde ↔ acid) allowing access to esters/amides via standard coupling chemistry.
  • Conversion to vinyl/allyl systems via Wittig/HWE enables further cross-couplings (Suzuki, Heck, Negishi) after halogenation or borylation of the aromatic ring.

• Retrosynthetic value:

  • The aldehyde serves as a convergence point for late-stage diversification: install –CHO late to avoid overreaction, or use as a handle to introduce C=C linkages that position the anisole core within more complex scaffolds.

Overall, this substrate provides a balance of carbonyl reactivity and arene activation advantageous in route scouting and library synthesis.

Target Specificity

Not applicable. This product is a small-molecule chemical reagent, not a biological targeting agent (no antigen/epitope, clone, or isotype). For usage contexts, refer to Reaction & Applications and Synthetic Utility.

Frequently Asked Questions

What is the purity of this product?

This product is supplied at ≥99% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature under argon. It is supplied under an argon blanket; reseal under inert gas after each use.

How is this product shipped?

This product ships under standard ambient conditions. No temperature-controlled packaging is required.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 7149-92-0, the molecular formula is C10H12O3, and the molecular weight is 180.2 g/mol. InChIKey UOKAZUWUHOBBMD-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.