Good quality 2-Amino-5-chloro-3-methylbenzoic acid CAS 20776-67-4 CAS NO.20776-67-4

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Wuhan Fortuna Chemical Co.,Ltd established in 2006, is a big integrative chemical enterprise being engaged in Pharmaceutical & its intermediates, Food/Feed additives, Fine chemicals in distributing the products of our own company and affiliated enterprises, are the members of Hubei E-commerce Chamber.

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2-Amino-5-chloro-3-methylbenzoic acid is a substituted benzoic acid derivative with the molecular formula C?H?ClNO?. Below is a detailed breakdown of its structure, properties, synthesis, and applications:

Structure:

• Core: A benzene ring substituted with four functional groups:

  1. Carboxylic acid (-COOH) at position 1.

  2. Amino group (-NH?) at position 2.

  3. Methyl group (-CH?) at position 3.

  4. Chlorine atom (-Cl) at position 5.

• Numbering: Positions are assigned relative to the carboxylic acid group (position 1).

Key Features:

Amphoteric nature: Contains both acidic (-COOH) and basic (-NH?) groups, enabling zwitterionic behavior in aqueous solutions.

Electronic effects: The electron-withdrawing -Cl and -COOH groups and electron-donating -CH? and -NH? influence reactivity.

Physical Properties:

Appearance: Typically a white to off-white crystalline solid.

• Solubility:

  • Soluble in polar aprotic solvents (e.g., DMSO, DMF) and alcohols (e.g., methanol, ethanol).

  • Limited solubility in water due to the hydrophobic benzene ring.

• Melting Point: Expected to be moderately high (150–250°C range) due to hydrogen bonding and aromatic stacking.

Synthesis:

1. Starting Material: Often derived from 3-methylbenzoic acid.

2. Key Steps:

   • Nitration: Introduce a nitro (-NO?) group at position 2 (directed by -COOH and -CH?).

   • Chlorination: Electrophilic substitution at position 5 (meta to -NH? after reduction).

   • Reduction: Convert the nitro group (-NO?) to an amino group (-NH?) using catalysts (e.g., H?/Pd) or reducing agents (e.g., Sn/HCl).

3. Challenges:

   • Protecting the amino group during chlorination to avoid side reactions.

   • Managing regioselectivity due to competing directing effects of substituents.

Applications:

1. Pharmaceutical Intermediate:

   • Used to synthesize bioactive molecules, such as diuretics (e.g., analogs of furosemide) or antibiotics.

   • The -NH? and -COOH groups allow further derivatization (e.g., amide bond formation).

2. Agrochemicals:

   • Potential building block for herbicides or fungicides due to its halogen and aromatic structure.

3. Research:

   • Explored in organic synthesis for constructing heterocycles or metal-organic frameworks.

Safety:

Handling: May cause skin/eye irritation. Use gloves, goggles, and proper ventilation.

Storage: Keep in a cool, dry place away from strong oxidizers (due to -NH? sensitivity).

Significance:

This compound exemplifies the versatility of benzoic acid derivatives in drug discovery and materials science. Its functional groups enable diverse reactivity, making it valuable for designing molecules with tailored electronic and steric properties.