Methyl 2-chloropyrimidine-4-carboxylate

Name: Methyl 2-chloropyrimidine-4-carboxylate
Brand: ChemScene
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CAS No. 149849-94-5
Cat. No. CS-W009002
Purity≥97%
MDL No.MFCD11841080

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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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Methyl 2-chloropyrimidine-4-carboxylate|CS-W009002

Structure of 149849-94-5

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General Information

CAS No. 149849-94-5
Cat. No. CS-W009002
Purity ≥97%
MDL No. MFCD11841080
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₅ClN₂O₂
Molecular Weight 172.57
Synonym(s) Methyl 2-chloropyrimidine-4-carboxylate; 4-PyriMidinecarboxylic acid, 2-chloro-, Methyl ester
SMILES O=C(C1=NC(Cl)=NC=C1)OC

Description

Methyl 2-chloropyrimidine-4-carboxylate features a chlorinated pyrimidine core with a methyl ester at the C4 position, enabling direct incorporation into heterocyclic scaffolds. The electron-deficient pyrimidine ring supports efficient nucleophilic substitution reactions, while the ester group facilitates downstream transformations. This bench-stable reagent delivers high functional group tolerance and is well-suited for medicinal chemistry applications requiring rapid access to substituted pyrimidines.

Application

Methyl 2-chloropyrimidine-4-carboxylate serves as a versatile building block in heterocyclic synthesis, enabling efficient functionalization at the C2 position via nucleophilic substitution. Its chlorine atom exhibits high reactivity toward amines, thiols, and carbon nucleophiles under mild conditions, facilitating access to diverse pyrimidine derivatives. The ester group supports further transformations, including hydrolysis or reduction, enhancing its utility in medicinal chemistry and agrochemical research. Bench-stable and readily purified by flash chromatography, it integrates seamlessly into standard synthetic workflows.

Synthesis

Route1
- In-stock
  
  6299-85-0
- ~10%
- In-stock
  
  149849-94-5
References
- Binggeli, Alfred; Christ, Andreas; Maerki, Hans-Peter; Martin, Rainer Eugen Patent: US2007/225271 A1, 2007 ; Location in patent: Page/Page column 33 ; US 20070225271 A1
Route2
- 149849-93-4
- ~99%
- In-stock
  
  149849-94-5
References
- Lonza Ltd. Patent: US5591853 A1, 1997 ;

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 52.08
LogP 0.9166
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic heterocycle compounds Pyrimidine compounds

Key Words

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Methyl 2-chloropyrimidine-4-carboxylate

CAS No. 149849-94-5

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