136507-15-8

Basic information

• Product Name: 2-METHOXY-4-NITROBENZALDEHYDE
• Synonyms: 2-METHOXY-4-NITROBENZALDEHYDE;2-FORMYL-5-NITROANISOLE;4-Nitro-2-Methoxybenzaldehyde;2-Methoxy-4-nitrobenzaldehyde 97%;Benzaldehyde, 2-methoxy-4-nitro-
• CAS NO: 136507-15-8
• Molecular Formula: C₈H₇NO₄
• Molecular Weight: 181.15
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Aldehydes;C8;Carbonyl Compounds
• Mol File: 136507-15-8.mol

Chemical Properties

• Melting Point: 120-124 °C
• Boiling Point: 354.728 °C at 760 mmHg
• Flash Point: 184.222 °C
• Appearance: /
• Density: 1.323 g/cm³
• Vapor Pressure: 3.28E-05mmHg at 25°C
• Refractive Index: 1.59
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2-METHOXY-4-NITROBENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHOXY-4-NITROBENZALDEHYDE(136507-15-8)
• EPA Substance Registry System: 2-METHOXY-4-NITROBENZALDEHYDE(136507-15-8)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• WGK Germany: 3
• Hazardous Substances Data: 136507-15-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-METHOXY-4-NITROBENZALDEHYDE is used as a key intermediate for the preparation of N-((oxazolyl)phenyl)chromanecarboxamide derivatives. These derivatives are therapeutically active substances for the treatment of retinal diseases, such as age-related macular degeneration and diabetic retinopathy. The compound plays a crucial role in the development of these therapeutic agents due to its ability to be chemically modified and incorporated into the final drug molecules.

InChI:InChI=1/C8H7NO4/c1-13-8-4-7(9(11)12)3-2-6(8)5-10/h2-5H,1H3

Upstream product

• 13120-77-9 2-methyl-5-nitroanisole 
• 5428-54-6 2-methyl-5-nitrophenol 
• 16855-08-6 2-hydroxy-6-nitrobenzaldehyde 
• 74-88-4 methyl iodide 
• 619-19-2 2-hydroxy-4-nitrobenzoic acid 
• 39106-79-1 methyl 2-methoxy-4-nitrobenzoate 
• 201230-82-2 carbon monoxide 
• 97-52-9 2-methoxy-4-nitrophenylamine 
• 858213-45-3 α'-acetoxy-2,2'-dimethoxy-4,4'-dinitro-bibenzyl-α-ol 
• 101118-65-4 α,α'-dibromo-2,2'-dimethoxy-4,4'-dinitro-bibenzyl 
• 136507-13-6 acetic acid 2-methoxy-4-nitro-benzyl ester 
• 90434-16-5 1-(bromomethyl)-2-methoxy-4-nitrobenzene 
• 136507-14-7 (2-methoxy-4-nitrophenyl)methanol 
• 112689-80-2 α,α'-diacetoxy-2,2'-dimethoxy-4,4'-dinitro-bibenzyl 

Downstream Products

• 198821-78-2 5-(2-methoxy-4-nitrophenyl)-oxazole 
• 497854-58-7 (2-methoxy-4-nitrophenyl)(pyridin-2-yl)methanol 
• 1027140-01-7 2-(2-methoxy-4-nitro-phenyl)-1H-benzoimidazole-5-carboxylic acid 
• 878199-39-4 1-(2-methoxy-4-nitro-phenyl)-3-phenyl-propynone 
• 198821-79-3 3-methoxy-4-(1,3-oxazol-5-yl)aniline 

Relevant articles and documents

Novel amide-based inhibitors of inosine 5′-monophosphate dehydrogenase

A series of novel amide-based small molecule inhibitors of inosine monophosphate dehydrogenase (IMPDH) was explored. The synthesis and the structure-activity relationships (SARs) derived from in vitro studies are described.

Preparation of 5-(2-methoxy-4-nitrophenyl)oxazole: A key intermediate for the construction of VX-497

A process for the multigram preparation of 5-(2-methoxy-4-nitrophenyl)oxazole, a key intermediate for the preparation of the hepatitis C drug candidate VX-497 (merimepodib), has been achieved in good yield from a commercially available dye. Early studies focused on the preparation of the requisite aldehyde by the Beech reaction. A second approach utilized a palladium (0)-catalyzed formylation of an aryl diazonium species, which was followed by condensation of the aldehyde with tosylmethyl isocyanide (TosMIC) to provide the required oxazole. This two-step method has been carried out to provide multigram samples of this key intermediate in 75% overall yield and >95% purity from the commercially available Fast Red B tetrafluoroborate salt.

Substitution Effect on 2-(Oxazolinyl)-phenols and 1,2,5-Chalcogenadiazole -Annulated Derivatives: Emission-Color-Tunable, Minimalistic Excited-State Intramolecular Proton Transfer (ESIPT)-Based Luminophores

Minimalistic 2-(oxazolinyl)-phenols substituted with different electron-donating and -withdrawing groups as well as 1,2,5-chalcogenadiazole-annulated derivatives thereof were synthesized and investigated in regard to their emission behavior in solution as well as in the solid state. Depending on the nature of the incorporated substituent and its position, emission efficiencies were increased or diminished, resulting in AIE or ACQ characteristics. Single-crystal analysis revealed J- and H-type packing motifs and a so-far undescribed isolation of ESIPT-based fluorophores in the keto form.

Vinyl-Fluorene Molecular Wires for Voltage Imaging with Enhanced Sensitivity and Reduced Phototoxicity

Fluorescent voltage indicators are an attractive alternative for studying the electrical activity of excitable cells; however, the development of indicators that are both highly sensitive and low in toxicity over long-term experiments remains a challenge.

Effect of aldehyde and methoxy substituents on nucleophilic aromatic substitution by [18F]fluoride

For a series of benzaldehydes only with a leaving group or with both a leaving group and a single methoxy substituent 18F-fluorination via nucleophilic aromatic substitution (SNAr) was studied in DMF and Me2SO. In general, the radiochemical yields were clearly higher in DMF than in Me2SO. In the fluorodehalogenation reaction (leaving group: halogen = Br, Cl), extremely low radiochemical yields were observed in Me2SO (2SO (within 3 min reaction time, 90% of the precursor was consumed; radiochemical yield = 1.0 ± 0.5%); however, in DMF oxidation was always kept at a low level during the entire reaction (13C-NMR ppm values of the aromatic carbon atom bearing the leaving group.

Orally active CCR5 antagonists as anti-HIV-1 agents 2: Synthesis and biological activities of anilide derivatives containing a pyridine N-oxide moiety

In order to develop orally active CCR5 antagonists, we investigated 1-benzoxepine derivatives containing new polar substituents, such as phosphonate, phosphine oxide or pyridine N-oxide moieties, as replacements for the previoiusly reported quaternary ammonium moiety. Among these compounds, the 2-(α-hydroxybenzyl)pyridine N-oxide 5e exhibited moderate CCR5 antagonistic activity and had an acceptable pharmacokinetic profile in rats. Subsequent chemical modification was performed and compound (S)-5f possessing the (S)-configuration hydroxy group was found to be more active than the (R)-isomer. Replacement of the 1-benzoxepine ring with a 4-methylphenyl group by a 1-benzazepine ring with a 4-[2-(butoxy)ethoxy]phenyl group enhanced the activity in the binding assay. In addition, introduction of a 3-trifluoromethyl group on the phenyl group of the anilide moiety led to greatly increased activity in the HIV-1 envelope-mediated membrane fusion assay. In particular, compound (S)-5s showed the most potent CCR5 antagonistic activity (IC 50=7.2 nM) and inhibitory effect (IC50=5.4 nM) in the fusion assay, together with good pharmacokinetic properties in rats.

USE OF COMPOUNDS HAVING AN AMINE NUCLEUS IN MANUFACTURE OF A MEDICAMENT USEFUL FOR TREATING FACTOR VIIA-ASSOCIATED CONDITIONS

Use of at least one compound having the formula (I), or a pharmaceutically-acceptable salt, hydrate or prodrug thereof, in the manufacture of a medicament useful for treating conditions associated with the activity of Factor VIIa is described.

Compounds derived from an amine nucleus and pharmaceutical compositions comprising same

Compounds having the formula (I), are effective as inhibitors of IMPDH enzyme and/or serine protease Factor VIIa, wherein B is a monocyclic or bicyclic carbocyclic or heterocyclic ring, D is a monocyclic or bicyclic carbocyclic or heterocyclic ring except when A is a heterocyclic ring, then D is a heterocyclic ring system, R is hydrogen or C1-4alkyl, and A, R1, R2and R4are as defined in the specification.

Amide and diamide inhibitors of IMPDH enzyme for use in treating IMPDH-associated disorders

The present invention discloses the identification of the inhibitors of IMPDH (inosine-5′-monophosphate dehydrogenase). The compounds and pharmaceutical compositions disclosed herein are useful in treating or preventing IMPDH associated disorders, such as transplant rejection and autoimmune diseases.

Vanilloid receptor ligands and their use in treatments

Compounds having the general structure and compositions containing them, for the treatment of acute, inflammatory and neuropathic pain, dental pain, general headache, migraine, cluster headache, mixed-vascular and non-vascular syndromes, tension headache, general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, inflammatory eye disorders, inflammatory or unstable bladder disorders, psoriasis, skin complaints with inflammatory components, chronic inflammatory conditions, inflammatory pain and associated hyperalgesia and allodynia, neuropathic pain and associated hyperalgesia and allodynia, diabetic neuropathy pain, causalgia, sympathetically maintained pain, deafferentation syndromes, asthma, epithelial tissue damage or dysfunction, herpes simplex, disturbances of visceral motility at respiratory, genitourinary, gastrointestinal or vascular regions, wounds, burns, allergic skin reactions, pruritis, vitiligo, general gastrointestinal disorders, gastric ulceration, duodenal ulcers, diarrhea, gastric lesions induced by necrotising agents, hair growth, vasomotor or allergic rhinitis, bronchial disorders or bladder disorders.