4-Hydroxy-5-methoxy-2-nitrobenzaldehyde

Name: 4-Hydroxy-5-methoxy-2-nitrobenzaldehyde
Brand: ChemScene
Availability: InStock
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CAS No. 2454-72-0
Cat. No. CS-0030147
Purity≥98%
MDL No.MFCD00034536

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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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4-Hydroxy-5-methoxy-2-nitrobenzaldehyde|CS-0030147

Structure of 2454-72-0

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General Information

CAS No. 2454-72-0
Cat. No. CS-0030147
Purity ≥98%
MDL No. MFCD00034536
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₈H₇NO₅
Molecular Weight 197.14
Synonym(s) 6-Nitrovanillin; Entacapone Impurity 68
SMILES O=CC1=CC(OC)=C(O)C=C1[N+]([O-])=O

Description

4-Hydroxy-5-methoxy-2-nitrobenzaldehyde features a nitro group at the para position relative to the aldehyde, enhancing electrophilicity for nucleophilic additions. The phenolic hydroxyl and methoxy substituents provide polar functionality, improving solubility in protic solvents. This compound serves as a key intermediate in the synthesis of bioactive heterocycles and fluorescent probes due to its electron-deficient aromatic core and orthogonal functional handles.

Application

4-Hydroxy-5-methoxy-2-nitrobenzaldehyde serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling efficient access to substituted benzimidazoles, quinoline derivatives, and other heterocyclic scaffolds. Its ortho-dihydroxy and nitro-aldehyde functionalities provide orthogonal reactivity for sequential transformations, while the methoxy group enhances solubility and modulates electronic properties. Bench-stable and readily purified by recrystallization, it facilitates reliable use in multi-step syntheses.

Synthesis

Route1
- 2426-84-8
- ~58%
- In-stock
  
  2454-72-0
References
- Tsai, Shiou-Chuan; Klinman, Judith P. Bioorganic Chemistry, 2003 , vol. 31, # 2 p. 172 - 190
Route2
- In-stock
  
  712-97-0
- ~66%
- In-stock
  
  2454-72-0
- In-stock
  
  58749-47-6
References
- Imakura; Okimoto; Konishi; Hisazumi; Yamazaki; Kobayashi; Yamashita Chemical and Pharmaceutical Bulletin, 1992 , vol. 40, # 7 p. 1691 - 1696
Route3
- 121-33-5
- ~5%
- In-stock
  
  2454-72-0
- In-stock
  
  6635-20-7
- In-stock
  
  2450-26-2
References
- Kaupp, Gerd; Schmeyers, Jens Journal of Organic Chemistry, 1995 , vol. 60, # 17 p. 5494 - 5503

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

Quality Control

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Computational Chemistry Data

TPSA 89.67
LogP 1.1215
H_Acceptors 5
H_Donors 1
Rotatable_Bonds 3

Other Classifications

Building Blocks Functional Group Aldehyde

Building Blocks Functional Group Nitro compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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4-Hydroxy-5-methoxy-2-nitrobenzaldehyde

CAS No. 2454-72-0

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