3,5-Dibromoisonicotinaldehyde

Name: 3,5-Dibromoisonicotinaldehyde
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CAS No. 70201-42-2
Cat. No. CS-W003286
Purity≥97%
MDL No.MFCD06410681

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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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3,5-Dibromoisonicotinaldehyde|CS-W003286

Structure of 70201-42-2

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General Information

CAS No. 70201-42-2
Cat. No. CS-W003286
Purity ≥97%
MDL No. MFCD06410681
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₃Br₂NO
Molecular Weight 264.90
Synonym(s) 3,5-Dibromo-4-pyridine carboxaldehyde
SMILES O=Cc1c(Br)cncc1Br

Description

3,5-Dibromoisonicotinaldehyde features a pyridine core bearing two bromine substituents at the 3- and 5-positions and an aldehyde group at the 2-position. This electron-deficient scaffold enables direct incorporation into cross-coupling reactions and serves as a building block for functionalized heterocycles in medicinal chemistry and materials science.

Application

3,5-Dibromoisonicotinaldehyde serves as a versatile building block in heterocyclic synthesis, enabling direct functionalization at the 3- and 5-positions of the pyridine ring. Its aldehyde functionality facilitates nucleophilic additions, reductive aminations, and condensation reactions with amines or hydrazines under mild conditions. The ortho-bromine substituents provide complementary sites for palladium-catalyzed cross-coupling, supporting the construction of complex biaryl scaffolds. Bench-stable and readily purified by column chromatography, it functions efficiently in multi-step synthetic sequences requiring high regiocontrol and functional group compatibility.

Synthesis

Route1
- In-stock
  
  625-92-3
- 109-94-4
- ~63%
- In-stock
  
  70201-42-2
References
- GENENTECH,INC.; FORMA TM, LLC; YUEN, Po-Wai; BAIR, Kenneth, W.; BAUMEISTER, Timm, R.; DRAGOVICH, Peter; LIU, Xiongcai; PATEL, Snahel; ZAK, Mark; ZHAO, Guiling; ZHANG, Yamin; ZHENG, Xiaozhang Patent: WO2013/127269 A1, 2013 ; Location in patent: Page/Page column 148 ;
Route2
- In-stock
  
  625-92-3
- 107-31-3
- ~%
- In-stock
  
  70201-42-2
References
- Bioorganic and Medicinal Chemistry Letters, , vol. 17, # 10 p. 2789 - 2794

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS06
Signal Word : Danger	UN#: 2811
Class : 6.1	Packing Group : Ⅲ
Hazard Statements : H301-H315-H317-H319-H335
Precautionary Statements : P280-P302+P352-P330

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Computational Chemistry Data

TPSA 29.96
LogP 2.4191
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Bromide

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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3,5-Dibromoisonicotinaldehyde

CAS No. 70201-42-2

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