3-Amino-5,6-dichloropyrazine-2-carboxylic acid

Name: 3-Amino-5,6-dichloropyrazine-2-carboxylic acid
Brand: ChemScene
Availability: InStock
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CAS No. 4853-52-5
Cat. No. CS-0005633
Purity≥98%
MDL No.MFCD16657584

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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+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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3-Amino-5,6-dichloropyrazine-2-carboxylic acid|CS-0005633

Structure of 4853-52-5

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General Information

CAS No. 4853-52-5
Cat. No. CS-0005633
Purity ≥98%
MDL No. MFCD16657584
Storage 4°C, sealed storage, away from moisture and light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₅H₃Cl₂N₃O₂
Molecular Weight 208.00
Synonym(s) NSC 382681; 3-Amino-5,6-dichloro-2-pyrazinecarboxylic acid
SMILES O=C(C1=NC(Cl)=C(Cl)N=C1N)O

Description

3-Amino-5,6-dichloropyrazine-2-carboxylic acid features a pyrazine core with complementary electron-deficient and nucleophilic functional groups, enabling direct incorporation into heterocyclic scaffolds. The amino and carboxylic acid moieties facilitate conjugation in medicinal chemistry applications, while the dichloro substitution enhances reactivity under standard coupling conditions. This compound serves as a key building block for bioactive molecule synthesis.

Application

3-Amino-5,6-dichloropyrazine-2-carboxylic acid serves as a versatile building block in medicinal chemistry, enabling the synthesis of pyrazine-based heterocycles through standard amide coupling and electrophilic substitution reactions. Its orthogonal functional groups—amino, carboxylic acid, and two chloro substituents—facilitate sequential derivatization, offering high stability for bench handling and ease of purification. The molecule functions effectively in multi-step syntheses targeting kinase inhibitors and antimicrobial agents, with demonstrated compatibility in both solution-phase and solid-phase workflows.

Synthesis

Route1
- In-stock
  
  1458-18-0
- ~37%
- In-stock
  
  4853-52-5
References
- SCHERING CORPORATION; PHARMACOPEIA DRUG DISCOVERY, INC. Patent: WO2006/88920 A1, 2006 ; Location in patent: Page/Page column 147 ; WO 2006/088920 A1

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-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 89.1
LogP 1.0638
H_Acceptors 4
H_Donors 2
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Aromatic heterocycle compounds Pyrazine compounds

Key Words

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3-Amino-5,6-dichloropyrazine-2-carboxylic acid

CAS No. 4853-52-5

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