Methyl 2-amino-4-iodobenzoate

Name: Methyl 2-amino-4-iodobenzoate
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CAS No. 144550-76-5
Cat. No. CS-0041211
Molecule weight277.06
Purity≥98%
MDL No.MFCD13182440

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Methyl 2-amino-4-iodobenzoate|CS-0041211

Structure of 144550-76-5

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General Information

CAS No. 144550-76-5
Cat. No. CS-0041211
Purity ≥98%
MDL No. MFCD13182440
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₈INO₂
Molecular Weight 277.06
Synonym(s) Methyl2-Amino-4-Iodobenzoate
SMILES COC(=O)C1=C(N)C=C(I)C=C1

Description

Methyl 2-amino-4-iodobenzoate features a para-iodinated benzene core with an ortho-amino group and ester functionality, enabling direct coupling in cross-coupling reactions. This bench-stable, moisture-tolerant reagent integrates seamlessly into synthetic workflows requiring iodinated aryl building blocks.

Application

Methyl 2-amino-4-iodobenzoate serves as a versatile building block in medicinal chemistry and cross-coupling synthesis. The iodine moiety enables reliable Suzuki, Stille, and Negishi couplings, while the amino and ester groups provide orthogonal functionality for further derivatization. Bench-stable and readily purified by recrystallization, it facilitates efficient access to substituted benzimidazoles, biaryl scaffolds, and advanced API intermediates under standard reaction conditions.

Synthesis

Route1
- 67-56-1
- 117324-10-4
- ~90%
- In-stock
  
  144550-76-5
References
- MILLENNIUM PHARMACEUTICALS, INC. Patent: WO2006/41773 A2, 2006 ; Location in patent: Page/Page column 303-304 ; WO 2006/041773 A2
Route2
- 117324-10-4
- ~%
- In-stock
  
  144550-76-5
References
- Hoechst Aktiengesellschaft Patent: US5463081 A1, 1995 ;
Route3
- 186581-53-3
- In-stock
  
  20776-54-9
- ~99%
- In-stock
  
  144550-76-5
References
- Levesque, Patrick; Fournier, Pierre-Andre Journal of Organic Chemistry, 2010 , vol. 75, # 20 p. 7033 - 7036

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

Quality Control

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Computational Chemistry Data

TPSA 52.32
LogP 1.66
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Iodide

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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Methyl 2-amino-4-iodobenzoate

CAS No. 144550-76-5

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