Lot numbers can be found on the outside label of a product:
4-Hydroxy-3-methoxy-5-nitrobenzoic acid
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CAS No. 15785-54-3
- Cat. No. CS-0010503
- Purity≥98%
- MDL No.MFCD06203146
*For research and further manufacturing use only, not for direct human use.
Structure of 15785-54-3
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General Information
- CAS No. 15785-54-3
- Cat. No. CS-0010503
- Purity ≥98%
- MDL No. MFCD06203146
- Storage 4°C, stored under nitrogen
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₈H₇NO₆
- Molecular Weight 213.15
- Synonym(s) 3-Nitro-4-hydroxy-5-methoxybenzoic acid; 5-Nitrovanillic acid; 3-Methoxy-4-hydroxy-5-nitrobenzoic acid
- SMILES OC(C1=CC([N+]([O-])=O)=C(O)C(OC)=C1)=O
Description
4-Hydroxy-3-methoxy-5-nitrobenzoic acid features a strategically positioned nitro group that enhances electrophilic reactivity, while the hydroxyl and methoxy substituents provide orthogonal functional handles for derivatization. This electron-deficient aromatic core enables efficient coupling in synthetic sequences requiring controlled reactivity under standard conditions.
Application
4-Hydroxy-3-methoxy-5-nitrobenzoic acid serves as a versatile building block for heterocyclic synthesis and medicinal chemistry campaigns, offering orthogonal functional groups for sequential derivatization. The carboxylic acid enables amide or ester formation, while the phenolic hydroxyl and methoxy groups provide sites for selective protection or coupling. Its nitro group facilitates reduction to an amino derivative, enabling access to diverse scaffold classes. Bench-stable and readily purified by recrystallization, it supports scalable synthesis in API development workflows.
Synthesis
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Route1
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In-stock
121-34-6 - ~55%
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In-stock
15785-54-3
References
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Kiss, Laszlo E.; Ferreira, Humberto S.; Torrao, Leonel; Bonifacio, Maria Joao; Palma, P. Nuno; Soares-Da-Silva, Patricio; Learmonth, David A. Journal of Medicinal Chemistry, 2010 , vol. 53, # 8 p. 3396 - 3411
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Route2
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In-stock
3943-74-6 - ~%
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In-stock
15785-54-3
References
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Journal of the American Chemical Society, , vol. 117, # 16 p. 4722 - 4723
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Route3
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In-stock
6635-20-7 - ~%
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In-stock
15785-54-3
References
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Journal of the American Chemical Society, , vol. 20, p. 316 American Chemical Journal, , vol. 24, p. 176
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Safety Information
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GHS Pictogram :
N/A
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GHS No : N/A
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Signal Word : N/A
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UN#: N/A
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Class : N/A
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Packing Group : N/A
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Hazard Statements : N/A
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Precautionary Statements : N/A
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Quality Control
Computational Chemistry Data
- TPSA 109.9
- LogP 1.0072
- H_Acceptors 5
- H_Donors 2
- Rotatable_Bonds 3
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Key Words
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