2-Methyl-3-phenylpropanamide CAS 7499-19-6 is a chiral organic compound primarily recognized as a key synthetic intermediate in pharmaceutical manufacturing. Its structure, featuring a phenylpropionate backbone with a methyl side chain and an amide terminal, makes it a valuable building block, most notably for the synthesis of the Class III antiarrhythmic drug Ibutilide.
Name :
2-methyl-3-phenylpropanamideCAS No. :
7499-19-6MF :
C₁₀H₁₃NOMW :
163.22Purity :
97%Appearance :
a white to off-white crystalline powderStorage Condition :
Store in a tightly sealed container in a cool, dry, and well-ventilated place at room temperature.Chemical Properties
Chemical Name: 2-Methyl-3-phenylpropanamide
IUPAC Name: 2-Methyl-3-phenylpropanamide
Common Synonyms: α-Methyl-3-phenylpropionamide; (RS)-2-Methyl-3-phenylpropionamide
CAS Registry Number: 7499-19-6
Molecular Formula: C₁₀H₁₃NO
Molecular Weight: 163.22 g/mol
Chemical Structure: It consists of a three-carbon propanoic acid chain (propanamide) substituted with a phenyl group at the 3-position and a methyl group at the 2-position (the alpha carbon relative to the amide). The presence of a chiral center at the 2-carbon means it can exist as (R)- and (S)- enantiomers. The commercial material is often supplied as the racemate.
Appearance: Typically a white to off-white crystalline powder.
Solubility: Soluble in common organic solvents (e.g., methanol, ethanol, ethyl acetate, dichloromethane). Sparingly soluble or insoluble in water.
Melting Point: ~116-118 °C
Optical Rotation: For enantiopure forms, specific optical rotation values would be defined (e.g., for (S)-enantiomer).
Stability: Stable under normal storage conditions. As an amide, it is more stable to hydrolysis than esters but can be hydrolyzed under strongly acidic or basic conditions at elevated temperatures.
Biological Activities
2-Methyl-3-phenylpropanamide itself is not a therapeutically active drug substance. Its primary biological and pharmacological significance is exclusively as a precursor.
Role as a Critical Intermediate: It is an essential chiral intermediate in the multi-step synthesis of Ibutilide fumarate, a potent Class III antiarrhythmic agent used for the rapid conversion of atrial fibrillation and flutter.
Mechanism Relevance: The structure of 2-methyl-3-phenylpropanamide forms the core moiety of Ibutilide, which is responsible for the drug's activity as a potassium channel blocker, prolonging the cardiac action potential and refractory period.
Biosynthesis
This compound is not produced via biological fermentation or enzymatic pathways on an industrial scale. It is manufactured through chemical synthesis. Common synthetic routes involve:
1.From 3-Phenylpropionic Acid Derivatives: Starting from ethyl 3-phenylpropionate, alpha-alkylation to introduce the methyl group, followed by hydrolysis and amidation.
2.Via Grignard or Reformatsky-Type Reactions: Reaction of benzyl halides with alpha-methylated acrylate or nitrile derivatives, followed by functional group transformation to the amide.
3.Asymmetric Synthesis: For producing enantiomerically pure material, methods may employ chiral auxiliaries, asymmetric hydrogenation, or enzymatic resolution.
Applications
Key Advantages & Benefits
1. Dual-Functionality for Molecular Diversification
Benefit: Contains two key reactive sites: the primary amide group (which can be hydrolyzed, dehydrated, reduced, or used in condensation reactions) and the benzylic/alpha-branched carbon chain (susceptible to functionalization or serving as a lipophilic spacer). This allows for sequential modifications to build complexity.
Application Scenario: In medicinal chemistry, this compound can serve as the starting point for a library of kinase inhibitor candidates. The amide can be reduced to a primary amine for coupling to a heterocyclic carboxylic acid, while the phenyl and methyl groups provide optimal lipophilicity and stereochemical bulk to fit a hydrophobic pocket in the target enzyme's active site.
2. Chiral Pool Potential for Enantioselective Synthesis
Benefit: The presence of a stereocenter (in the enantiomerically pure form) makes it a potential chiral building block (chiral pool) for the asymmetric synthesis of bioactive molecules, avoiding the need for external chiral auxiliaries or catalysts in early steps.
Application Scenario: A manufacturer of a chiral herbicide uses (R)- or (S)-2-methyl-3-phenylpropanamide as a starting material. The pre-existing chirality is carried through the synthesis to produce the final active ingredient with the required enantiopurity, ensuring high biological activity and meeting regulatory standards for isomerically pure agrochemicals.
3. Structural Mimic and Bioisostere
Benefit: Its phenylpropionamide backbone is a common pharmacophore and bioisostere found in neurotransmitters (e.g., GABA analogs) and various active pharmaceutical ingredients (APIs). It serves as an ideal core for structure-activity relationship (SAR) studies.
Application Scenario: Researchers developing a new series of GABA-modulating analgesics use this amide as a core scaffold. It mimics the structure of endogenous neurotransmitters, allowing them to systematically modify the amide and alkyl regions to optimize binding affinity, metabolic stability, and blood-brain barrier penetration.
4. Favorable Physicochemical Properties
Benefit: As a solid, crystalline amide, it generally exhibits good stability, manageable solubility in organic solvents, and lower hygroscopicity compared to corresponding carboxylic acids or amine salts, facilitating handling and purification in process chemistry.
Application Scenario: In a scale-up process for an antidepressant intermediate, the use of 2-methyl-3-phenylpropanamide, rather than the free amine or acid, prevents issues like emulsification during workup and simplifies isolation by filtration. Its consistent quality ensures reproducible yields in the coupling step to form the final drug scaffold.
2-Methyl-3-phenylpropanamide (CAS 7499-19-6) is a highly functionalized and strategic intermediate in fine chemical synthesis. Its advantages stem from its well-defined molecular architecture that incorporates lipophilicity, chirality, and a reactive amide group in one scaffold. For researchers in pharmaceutical and agrochemical development, it provides a reliable and versatile starting point for constructing complex target molecules, especially those requiring a sterically defined phenylalkyl moiety. While simpler analogs like 3-phenylpropionamide are more economical for some applications, the presence of the α-methyl group in this compound is a critical differentiator, offering enhanced stereochemical control, metabolic stability, and the ability to fine-tune the steric profile of the final active ingredient. Its value is realized in the synthesis of enantiomerically pure, biologically active compounds.
FAQs
Q1: What is the main application of this compound?
A1: Its exclusive and main industrial application is as a high-value intermediate in the synthesis of the antiarrhythmic drug Ibutilide fumarate. Its quality and chiral purity directly impact the efficacy and safety of the final Active Pharmaceutical Ingredient (API).
Q2: Do you supply the racemic mixture or the single enantiomer?
A2: We can supply both based on your synthetic needs. The racemic mixture (CAS 7499-19-6) is commonly used. For asymmetric synthesis requiring high enantiomeric excess (e.e.), we provide the (R)- or (S)-2-Methyl-3-phenylpropanamide under separate specifications. Please inquire for specific chiral purity and pricing.
Q3: What documentation do you provide with the product?
A3: We provide a comprehensive Certificate of Analysis (CoA) detailing batch number, purity (by HPLC/NMR), chiral purity (if applicable), melting point, residual solvents, and heavy metals analysis. A Material Safety Data Sheet (MSDS/SDS) is always included.
Q4: Is this compound a controlled substance or have any special regulatory requirements?
A4: 2-Methyl-3-phenylpropanamide itself is not a controlled substance on major international lists (e.g., UN, INCB). However, as a direct precursor to a prescription drug (Ibutilide), transactions are subject to responsible vetting. We sell only to legitimate and verified companies for approved research or manufacturing purposes under strict compliance with applicable laws.
Q5: Can you provide custom synthesis or scale-up services for this intermediate?
A5: Yes. Custom synthesis is a core service. We can optimize routes, perform kilogram-scale synthesis under cGMP guidelines if required for pharmaceutical registration, and tailor specifications (purity, particle size, polymorphic form) to meet your exact process development and production needs.
Q6: How should it be stored, and what is the typical shelf life?
A6: Store in a tightly sealed container in a cool, dry, and well-ventilated place at room temperature or as specified. Protect from moisture and light. Under these conditions, the material is typically stable for at least 2-3 years. Long-term storage under inert atmosphere (e.g., nitrogen) is recommended for optimal stability.
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