Methyl 4-amino-2,6-dimethylbenzoate

Name: Methyl 4-amino-2,6-dimethylbenzoate
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CAS No. 79909-92-5
Cat. No. CS-0098757
Purity≥97%
MDL No.MFCD20691178

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
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Methyl 4-amino-2,6-dimethylbenzoate|CS-0098757

Structure of 79909-92-5

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General Information

CAS No. 79909-92-5
Cat. No. CS-0098757
Purity ≥97%
MDL No. MFCD20691178
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₁₃NO₂
Molecular Weight 179.22
Synonym(s) Benzoic acid, 4-amino-2,6-dimethyl-, methyl ester
SMILES O=C(C1=C(C=C(C=C1C)N)C)OC

Description

Methyl 4-amino-2,6-dimethylbenzoate features a strategically positioned amino group flanked by two methyl substituents, enhancing electron density at the aromatic ring. This configuration supports efficient coupling reactions and improves solubility in common organic solvents. The compound serves as a robust scaffold for synthesizing pharmaceutical intermediates and functionalized dyes under standard conditions.

Application

Methyl 4-amino-2,6-dimethylbenzoate serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling efficient access to substituted benzimidazoles and other heterocyclic scaffolds. The ortho-methyl groups provide steric protection and enhance bench stability, while the amino and ester functionalities offer complementary reactivity for sequential transformations. Its compatibility with standard coupling, cyclization, and functional group interconversion protocols makes it a practical choice for multi-step syntheses.

Synthesis

Route1
- 114820-16-5
- ~99%
- In-stock
  
  79909-92-5
References
- Dell'Erba, Carlo; Sancassan, Fernando; Novi, Marino; Petrillo, Giovanni; Mugnoli, Angelo; et al. Journal of Organic Chemistry, 1988 , vol. 53, # 15 p. 3564 - 3568
Route2
- 186581-53-3
- In-stock
  
  16752-16-2
- ~%
- In-stock
  
  79909-92-5
References
- Goering et al. Journal of the American Chemical Society, 1954 , vol. 76, p. 787,788

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 52.32
LogP 1.67224
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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Methyl 4-amino-2,6-dimethylbenzoate

CAS No. 79909-92-5

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