78468-34-5

Basic information

• Product Name: 2-AMINO-4-NITROBENZENEMETHANOL
• Synonyms: 2-amino-4-nitro-benzylalcoho;2-AMINO-4-NITROBENZYL ALCOHOL;2-AMINO-4-NITROBENZENEMETHANOL;(2-amino-4-nitrophenyl)methanol;(2-Amino-4-nitrophenyl)methanol, 2-(Hydroxymethyl)-5-nitroaniline
• CAS NO: 78468-34-5
• Molecular Formula: C₇H₈N₂O₃
• Molecular Weight: 168.15
• Product Categories: Benzhydrols, Benzyl & Special Alcohols
• Mol File: 78468-34-5.mol

Chemical Properties

• Melting Point: 178-180 °C
• Boiling Point: 424.1°C at 760 mmHg
• Flash Point: 210.3°C
• Appearance: /
• Density: 1.432g/cm³
• Vapor Pressure: 6.01E-08mmHg at 25°C
• Refractive Index: 1.663
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 13.46±0.10(Predicted)
• CAS DataBase Reference: 2-AMINO-4-NITROBENZENEMETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-4-NITROBENZENEMETHANOL(78468-34-5)
• EPA Substance Registry System: 2-AMINO-4-NITROBENZENEMETHANOL(78468-34-5)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 78468-34-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-4-nitrobenzenemethanol is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its role in drug development is crucial due to its ability to be incorporated into the structures of different medicinal compounds, enhancing their therapeutic effects.
Used in Dye Industry:
In the dye industry, 2-amino-4-nitrobenzenemethanol is utilized as an intermediate in the production of dyes. Its chemical properties allow it to contribute to the color-fastness and stability of the dyes, making it an important component in the formulation of various dye products.
Used in Antimicrobial Applications:
2-Amino-4-nitrobenzenemethanol is used as an antimicrobial agent for its inherent antibacterial and antifungal properties. It is particularly valuable in the development of new drugs to combat infectious diseases, providing a foundation for creating effective treatments against a range of microbial infections.
Used in Research and Development:
In research and development settings, 2-amino-4-nitrobenzenemethanol is used as a key compound in the exploration of new chemical reactions and the synthesis of novel organic compounds. Its unique structure and reactivity make it a valuable tool for scientists working in organic chemistry and related fields.

InChI:InChI=1/C7H8N2O3/c8-7-3-6(9(11)12)2-1-5(7)4-10/h1-3,10H,4,8H2

Upstream product

• 651733-13-0 2-acetamido-4-nitrobenzyl alcohol 
• 619-17-0 4-Nitroanthranilic acid 
• 3558-19-8 methyl 2-amino-4-nitrobenzoate 
• 651733-07-2 2-acetamido-4-nitrobenzyl bromide 
• 121-14-2 2,4-dinitrotoluene 
• 2879-79-0 N-(2-methyl-5-nitrophenyl)acetamide 

Downstream Products

• 571186-90-8 C₂₉H₃₁N₇O₂ 
• 1613505-52-4 C₂₄H₁₈N₂O₅S 
• 1453169-02-2 7-nitro-2-phenylquinazoline 
• 109466-84-4 4-nitro-2-aminobenzaldehyde 
• 1042972-63-3 7-nitro-1H-benzo[d][1,3]oxazin-2-(4H)-one 
• 1172621-16-7 methyl 2-(hydroxymethyl)-5-nitrophenylcarbamate 
• 262863-79-6 (Z)-3-(2-Azido-4-nitro-phenyl)-2-[(2-chloro-pyridine-3-carbonyl)-amino]-acrylic acid methyl ester 

Relevant articles and documents

Selective sodium channel regulator as well as preparation and application thereof

The invention provides a compound serving as a selective sodium channel regulator and a synthesis and use method, and particularly provides a compound shown as a formula (I), a preparation method of the compound and application of the compound serving as the selective sodium channel regulator. The compounds exhibit excellent activity as a regulator of sodium channels.

Investigations into the potential role of metabolites on the anti-leukemic activity of imatinib, nilotinib and midostaurin

The efficacy and side-effects of drugs do not just reflect the biochemical and pharmacodynamic properties of the parent compound, but often comprise of cooperative effects between the properties of the parent and active metabolites. Metabolites of imatinib, nilotinib and midostaurin have been synthesised and evaluated in assays to compare their properties as protein kinase inhibitors with the parent drugs. The N-desmethylmetabolite of imatinib is substantially less active than imatinib as a BCR-ABL1 kinase inhibitor, thus providing an explanation as to why patients producing high levels of this metabolite show a relatively low response rate in chronic myeloid leukaemia (CML) treatment. The hydroxymethylphenyl and N-oxide metabolites of imatinib and nilotinib are only weakly active as BCR-ABL1 inhibitors and are unlikely to play a role in the efficacy of either drug in CML. The 3-(R)-HO-metabolite of midostaurin shows appreciable accumulation following chronic drug administration and, in addition to mutant forms of FLT3, potently inhibits the PDPK1 and VEGFR2 kinases (IC50 values 100 nM), suggesting that it might contribute to drug efficacy in acute myeloid leukaemia patients. The case studies discussed here provide further examples of how the synthesis and characterisation of metabolites can make important contributions to understanding the clinical efficacy of drugs.

ARYL AMIDE KINASE INHIBITORS

The present disclosure is generally directed to compounds which can inhibit AAK1 (adaptor associated kinase 1), compositions comprising such compounds, and methods for inhibiting AAK1.

TETRAHYDRONAPHTHYRIDINE, BENZOXAZINE, AZA-BENZOXAZINE, AND RELATED BICYCLIC COMPOUNDS FOR INHIBITION OF RORgamma ACTIVITY AND THE TREATMENT OF DISEASE

The invention provides certain bicylic heterocyclic compounds of the Formula (I) or pharmaceutically acceptable salts thereof, wherein X1, X2, R1, R2, R3, R4, and Cy are as defined herein. The invention also provides pharmaceutical compositions comprising such compounds of the Formula (I) or pharmaceutically acceptable salts thereof, and methods of using the compounds of the Formula (I) or pharmaceutically acceptable salts thereof or pharmaceutical compositions comprising the same for treating diseases or conditions mediated by RORgammaT.

Synthesis of quinolinomorphinan derivatives as highly selective δ opioid receptor ligands

We have reported previously the novel δ opioid agonist KNT-127 which showed high affinity and selectivity for the δ receptor. Moreover, the analgesic effect of subcutaneously administered KNT-127 was more potent than that of a prototypical δ agonist (-)-TAN-67 in the acetic acid writhing test. This study of the structure-activity relationship of KNT-127 derivatives focused on the introduction of substituents onto the 5′-, 6′-, 7′- or 8′-position of the quinoline ring and revealed that many derivatives with 5′- or 8′-substituents showed high affinities and selectivities for the δ receptor. Especially, SYK-153 with an 8′-OH group showed the highest affinity and the most balanced and highest selectivity for the δ receptor among the synthesized compounds.

Synthesis of substituted indole from 2-aminobenzaldehyde through [1,2]-aryl shift

A mild, efficient, and simple method for the synthesis of 3-ethoxycarbonylindoles has been developed. Addition of ethyl diazoacetate (EDA) to 2-aminobenzaldehydes cleanly affords the indole core. As opposed to other common approaches for the synthesis of indole, this method displays both excellent functional group tolerance and perfect regiochemical control. This allowed the synthesis of a variety of useful indole building blocks from 2-aminobenzaldehydes derived from readily available anthranilic acids.

Nonpeptide inhibitors of measles virus entry

Measles virus (MV) is one of the most infectious pathogens known. Despite the existence of a vaccine, over 500 000 deaths/year result from MV or associated complications. Anti-measles compounds could conceivably reverse these statistics. Previously, we described a homology model of the MV fusion protein trimer and a putative binding site near the head-neck region. The resulting model permitted the identification of two nonpeptidic entry inhibitors. Here, we present the design, synthesis, and bioevaluation of several series of fusion inhibitors and describe their structure-activity relationships (SAR). Five simply substituted anilides show low-μM blockade of the MV, one of which (AS-48) exhibits IC50 = 0.6-3.0 μM across a panel of wild-type MV strains found in the field. Molecular field topology analysis (MFTA), a 2D QSAR approach based on local molecular properties (atomic charges, hydrogen-bonding capacity and local lipophilicity), applied to the anilide series suggests structural modifications to improve potency.

Nitroaryl phosphoramide compositions and methods for targeting and inhibiting undesirable cell growth or proliferation

The present invention relates to nitroaryl-substituted phosphoramide prodrug compounds and methods of producing the same for use in targeting and inhibiting undesirable cell growth or proliferation.

Nitrobenzocyclophosphamides as potential prodrugs for bioreductive activation: Synthesis, stability, enzymatic reduction, and antiproliferative activity in cell culture

In efforts to obtain potential anticancer prodrugs for gene-directed enzyme prodrug therapy using Eschericia coli nitroreductase, a series of four benzocyclophosphamide analogues were designed and synthesized incorporating a strategically placed nitro group in a position para to the benzylic carbon for reductive activation. All four analogues were found to be stable in phosphate buffer at pH 7.4 and 37 °C and were good substrates of E. coli nitroreductase with half lives between 7 and 24 min at pH 7.0 and 37 °C. However, only two analogues 6a and 6c, both with a benzylic oxygen in the phosphorinane ring para to the nitro group, showed a modest 33-36-fold enhanced cytotoxicity in E. coli nitroreductase-expressing cells. These results suggest that good substrate activity and the para benzylic oxygen are required for activation by E. coli nitroreductase. Compounds 6a and 6c represent a new structure type for reductive activation and a lead for further modification in the development of better analogues with improved selective toxicity to be used in gene-directed enzyme prodrug therapy.

Nitroaryl Phosphoramides as Novel Prodrugs for E. coli Nitroreductase Activation in Enzyme Prodrug Therapy

Cyclic and acyclic nitroaryl phosphoramide mustard analogues were activated by E. coli nitroreductase, an enzyme explored in GDEPT. The more active acyclic 4-nitrobenzyl phosphoramide mustard (7) showed 167 500x selective cytotoxicity toward nitroreductase-expressing V79 cells with an IC50 as low as 0.4 nM. This is about 100x more active and 27x more selective than CB1954 (1). The superior activity was attributed to its better substrate activity (kcat/Km 19x better than 1) and/or excellent cytotoxicity of phosphoramide mustard released.