2'-Hydroxy-3'-nitro-[1,1'-biphenyl]-3-carboxylic acid

Name: 2'-Hydroxy-3'-nitro-[1,1'-biphenyl]-3-carboxylic acid
Brand: ChemScene
Availability: OutOfStock
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CAS No. 376591-95-6
Cat. No. CS-0570200
Molecule weight259.21
Purity≥97%
MDL No.MFCD11558889

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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2'-Hydroxy-3'-nitro-[1,1'-biphenyl]-3-carboxylic acid|CS-0570200

Structure of 376591-95-6

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General Information

CAS No. 376591-95-6
Cat. No. CS-0570200
Purity ≥97%
MDL No. MFCD11558889
Storage RT, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₉NO₅
Molecular Weight 259.21
Synonym(s) 2-Hydroxy-3''-Nitro-Biphenyl-3-Carboxylic Acid
SMILES C1=CC(=CC(=C1)C(=O)O)C2=C(C(=CC=C2)[N+](=O)[O-])O

Description

This biphenyl-based carboxylic acid features a hydroxyl group at the 2'-position and a nitro substituent at the 3'-position, creating an electron-deficient aryl system with enhanced solubility and reactivity. The ortho-hydroxy and para-nitro arrangement enables intramolecular hydrogen bonding, stabilizing reactive intermediates in transition metal-catalyzed transformations. This scaffold serves as a key building block for bioactive heterocycles and functional materials.

Application

2'-Hydroxy-3'-nitro-[1,1'-biphenyl]-3-carboxylic acid serves as a versatile building block for the synthesis of biologically relevant biphenyl scaffolds. The ortho-hydroxyl and meta-nitro groups enable directed metalation and facilitate subsequent functionalization via cross-coupling or nitro reduction. Its stability under standard bench conditions and compatibility with common protecting group strategies make it well-suited for iterative synthetic sequences in medicinal chemistry and materials science applications.

Synthesis

Route1
- In-stock
  
  893736-72-6
- ~%
- 376591-95-6
References
- LIGAND PHARMACEUTICALS, INC. Patent: WO2006/47344 A1, 2006 ; Location in patent: Page/Page column 45; 155 ;
Route2
- In-stock
  
  376591-94-5
- ~76%
- 376591-95-6
References
- Erickson-Miller, Connie J; Eppley, Daniel F.; Jenkins, Julian; Luengo, Juan I.; Liu, Nannan; Price, Alan T.; Shaw, Anthony N.; Visonneau, Sophie; Wiggall, Kenneth Patent: US2004/19190 A1, 2004 ; Location in patent: Page 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 : H315-H319
Precautionary Statements : P264-P280-P302+P352-P362+P364

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Computational Chemistry Data

TPSA 100.67
LogP 2.6656
H_Acceptors 4
H_Donors 2
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Carboxylic Acid

Building Blocks Functional Group Nitro compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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2'-Hydroxy-3'-nitro-[1,1'-biphenyl]-3-carboxylic acid

CAS No. 376591-95-6

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