Methyl 5-bromo-2-fluoronicotinate

Name: Methyl 5-bromo-2-fluoronicotinate
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CAS No. 931105-37-2
Cat. No. CS-W022862
Purity≥98%
MDL No.MFCD11617316

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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+
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Methyl 5-bromo-2-fluoronicotinate|CS-W022862

Structure of 931105-37-2

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General Information

CAS No. 931105-37-2
Cat. No. CS-W022862
Purity ≥98%
MDL No. MFCD11617316
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₅BrFNO₂
Molecular Weight 234.02
Synonym(s) 3-pyridinecarboxylic acid, 5-bromo-2-fluoro-, methyl ester
SMILES BrC1=CC(=C(N=C1)F)C(=O)OC

Description

Methyl 5-bromo-2-fluoronicotinate is a fluorinated heterocyclic ester featuring complementary halogen substituents at the 5- and 2-positions of the nicotinate core. This electron-deficient scaffold enables direct functionalization in cross-coupling reactions, offering high regioselectivity and stability under standard conditions. The molecule integrates readily into synthetic sequences requiring precise substitution patterns.

Application

Methyl 5-bromo-2-fluoronicotinate serves as a versatile building block in heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions due to its orthogonal halogen reactivity. The bromine at C5 facilitates Suzuki, Stille, or Negishi couplings, while the fluorine at C2 enhances electrophilicity for nucleophilic substitution. Its bench-stable nature and ease of purification make it well-suited for iterative synthesis of substituted nicotinates and pharmaceutical intermediates.

Synthesis

Route1
- In-stock
  
  78686-79-0
- ~58%
- In-stock
  
  931105-37-2
References
- Bristol-Myers Squibb Company Patent: US2007/78140 A1, 2007 ; Location in patent: Page/Page column 35-36 ; US 20070078140 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 : H315-H319-H335
Precautionary Statements : P260-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 39.19
LogP 1.7698
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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Methyl 5-bromo-2-fluoronicotinate

CAS No. 931105-37-2

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