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 :
in a cool, dry, and well-ventilated place at room temperatureChemical 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
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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