Methyl 2-amino-5-iodobenzoate

Name: Methyl 2-amino-5-iodobenzoate
Brand: ChemScene
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CAS No. 77317-55-6
Cat. No. CS-0150866
Purity≥98%
MDL No.MFCD00798574

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Methyl 2-amino-5-iodobenzoate|CS-0150866

Structure of 77317-55-6

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General Information

CAS No. 77317-55-6
Cat. No. CS-0150866
Purity ≥98%
MDL No. MFCD00798574
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₈INO₂
Molecular Weight 277.06
Synonym(s) Methyl 5-Iodoanthranilate
SMILES COC(=O)C1=C(C=CC(=C1)I)N

Description

Methyl 2-amino-5-iodobenzoate features a para-iodo-substituted aromatic ring paired with an ortho-amino group, enabling selective cross-coupling reactions. This bench-stable derivative integrates readily into Suzuki-Miyaura and Buchwald-Hartwig protocols, delivering functionalized intermediates with high regiocontrol under standard conditions.

Application

Methyl 2-amino-5-iodobenzoate serves as a versatile building block in cross-coupling chemistry and heterocycle synthesis. The ortho-amino and iodide functionalities enable sequential transformations, including Suzuki-Miyaura and Buchwald-Hartwig couplings, with excellent functional group tolerance. Its bench-stable nature and straightforward purification make it well-suited for iterative synthetic sequences in medicinal chemistry and process development.

Synthesis

Route1
- 134-20-3
- ~90%
- In-stock
  
  77317-55-6
References
- PHARMACOSTECH CO., LTD.; KIM, Jae Won; CHA, Young Gwan; RYU, Hyung Chul; KIM, Sun Joo; KIM, Sang Hyun; JEON, Tae Hong Patent: WO2010/67912 A1, 2010 ; Location in patent: Page/Page column 10-11 ;
Route2
- In-stock
  
  116027-10-2
- ~99%
- In-stock
  
  77317-55-6
References
- Venuti, Michael C.; Stephenson, Robert A.; Alvarez, Robert; Bruno, John J.; Strosberg, Arthur M. Journal of Medicinal Chemistry, 1988 , vol. 31, # 11 p. 2136 - 2145
Route3
- In-stock
  
  5326-47-6
- 74-88-4
- ~%
- In-stock
  
  77317-55-6
References
- WO2013/116786 A1, ; Page/Page column 18 ;

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-5-iodobenzoate

CAS No. 77317-55-6

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