17354-63-1

Basic information

• Product Name: 1-(P-METHOXYPHENYL)2-NITROPROPENE
• Synonyms: 1-(P-METHOXYPHENYL)2-NITROPROPENE;p-(2-nitropropenyl)anisole;1-(4-METHOXYPHENYL)-2-NITROPROPENE, >95%;2-Nitro-1-(4-methoxyphenyl)-1-propene;1-Methoxy-4-(2-nitro-1-propenyl)benzene;4-Methoxy-β-methyl-β-nitrostyrene;Ai3-63172;Benzene, 1-methoxy-4-(2-nitro-1-propenyl)-
• CAS NO: 17354-63-1
• Molecular Formula: C₁₀H₁₁NO₃
• Molecular Weight: 193.2
• EINECS: 241-381-5
• Product Categories: API intermediates
• Mol File: 17354-63-1.mol

Chemical Properties

• Boiling Point: 321.7°Cat760mmHg
• Flash Point: 147.4°C
• Appearance: /
• Density: 1.156g/cm³
• Vapor Pressure: 0.000551mmHg at 25°C
• Refractive Index: 1.568
• CAS DataBase Reference: 1-(P-METHOXYPHENYL)2-NITROPROPENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(P-METHOXYPHENYL)2-NITROPROPENE(17354-63-1)
• EPA Substance Registry System: 1-(P-METHOXYPHENYL)2-NITROPROPENE(17354-63-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• Hazardous Substances Data: 17354-63-1(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Synthesis:
1-(P-METHOXYPHENYL)2-NITROPROPENE is used as an intermediate in the synthesis of 4-Methoxyamphetamine Hydrochloride (M261015), which is a designer drug belonging to the amphetamine class. This designer drug is known for its ability to release 5-hydroxytryptamine (serotonin) in brain tissue, making it a subject of interest for researchers and pharmaceutical companies.
2. Used in the Amphetamine Industry:
In the amphetamine industry, 1-(P-METHOXYPHENYL)2-NITROPROPENE is used as a key component in the production of 4-Methoxyamphetamine Hydrochloride. 1-(P-METHOXYPHENYL)2-NITROPROPENE is valuable for its potential effects on the central nervous system, particularly its influence on serotonin levels. The development and study of such designer drugs can lead to a better understanding of the mechanisms underlying various neurological and psychiatric disorders, as well as the discovery of new therapeutic approaches.
3. Used in Research and Development:
1-(P-METHOXYPHENYL)2-NITROPROPENE is also utilized in research and development for its potential applications in the creation of new drugs and pharmaceuticals. Its unique molecular structure allows for further modification and exploration of its properties, which could lead to the discovery of novel compounds with specific therapeutic effects.

InChI:InChI=1/C10H11NO3/c1-8(11(12)13)7-9-3-5-10(14-2)6-4-9/h3-7H,1-2H3

Upstream product

• 110-86-1 pyridine 
• 509-14-8 tetranitromethane 
• 67-64-1 acetone 
• 104-46-1 anethole 
• 60-29-7 diethyl ether 
• 918-37-6 hexanitroethane 
• 79-24-3 Nitroethane 
• 123-11-5 4-methoxy-benzaldehyde 
• 148527-35-9 1-(4-methoxyphenyl)-2-nitropropyl acetate 
• 135711-43-2 Butyl-[1-(4-methoxy-phenyl)-2-nitro-propyl]-amine 
• 148527-33-7 2-nitro-1-hydroxy-1-(4-methoxy-phenyl)-propane 
• 2393-23-9 4-methoxy-benzylamine 

Downstream Products

• 52271-41-7 4-methoxyphenylacetone oxime 
• 29865-49-4 2-nitro-1-(4-methoxylphenyl) propane 
• 3027-13-2 1-(3-methoxyphenyl)propan-2-one 
• 64-13-1 2-amino-1-(4-methyoxyphenyl)propane 
• 95838-53-2 2-Acetyl-3-(4-methoxyphenyl)-4-aci-nitropentansaeure-tert-butylester 
• 95838-95-2 5-<(Acetyl)(tert-butoxycarbonyl)methylenamino>-4,5-dihydro-4-(4-methoxyphenyl)-2,5-dimethyl-3-furancarbonsaeure-tert-butylester 
• 53235-90-8 tetraethyl 2-(4-methoxyphenyl)ethene-1,1-diyldiphosphonate 
• 51146-36-2 aci-nitroethane trimethylsilyl ester 
• 142840-13-9 (4S,4aR,9aR)-4-(4-Methoxy-phenyl)-3-methyl-4,4a,5,6,7,8,9,9a-octahydro-cyclohepta[e][1,2]oxazine 2-oxide 
• 124901-14-0 ethyl 4-methyl-3-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate 
• 133088-91-2 2-(p-Toluenesulphonyl)-3-(4-methoxy-phenyl)-4-methylpyrrole 
• 99290-10-5 [(4S,5S)-4-(4-Methoxy-phenyl)-3-methyl-2-oxy-4,5-dihydro-isoxazol-5-yl]-phenyl-methanone 
• 100780-39-0 t-Butyl 3-(p-methoxy-phenyl)-4-methylpyrrole-2-carboxylate 
• 122-84-9 4-methoxybenzyl methyl ketone 

Relevant articles and documents

A diversity-oriented synthesis of polyheterocycles: Via the cyclocondensation of azomethine imine

Pd-Catalyzed sequential reactions to afford skeletally diverse molecules are described. The reaction involved azomethine imine formation and a cyclocondensation reaction as individual steps. The methodology provides excellent regio- and stereocontrol. Skeletal diversity was ensured by changing the electrophilic counterpart of azomethine imine. Due to its broader diversity and complexity, the DOS methodology is likely to benefit drug discovery and development in the future.

Substrate promiscuity of ortho-naphthoquinone catalyst: Catalytic aerobic amine oxidation protocols to deaminative cross-coupling and n-nitrosation

ortho-Naphthoquinone-based organocatalysts have been identified as versatile aerobic oxidation catalysts. Primary amines were readily cross-coupled with primary nitroalkanes via deaminative pathway to give nitroalkene derivatives in good to excellent yields. Secondary and tertiary amines were inert to ortho-naphthoquinone catalysts; however, secondary nitroalkanes were readily converted by ortho-naphthoquinone catalysts to the corresponding nitrite species that in situ oxidized the amines to the corresponding N-nitroso compounds. Without using harsh oxidants in a stoichiometric amount, the present catalytic aerobic oxidation protocol utilizes the substrate promiscuity feature to provide a facile access to amine oxidation products under mild reaction conditions.

Discovery of a PCAF Bromodomain Chemical Probe

The p300/CBP-associated factor (PCAF) and related GCN5 bromodomain-containing lysine acetyl transferases are members of subfamily I of the bromodomain phylogenetic tree. Iterative cycles of rational inhibitor design and biophysical characterization led to the discovery of the triazolopthalazine-based L-45 (dubbed L-Moses) as the first potent, selective, and cell-active PCAF bromodomain (Brd) inhibitor. Synthesis from readily available (1R,2S)-(?)-norephedrine furnished L-45 in enantiopure form. L-45 was shown to disrupt PCAF-Brd histone H3.3 interaction in cells using a nanoBRET assay, and a co-crystal structure of L-45 with the homologous Brd PfGCN5 from Plasmodium falciparum rationalizes the high selectivity for PCAF and GCN5 bromodomains. Compound L-45 shows no observable cytotoxicity in peripheral blood mononuclear cells (PBMC), good cell-permeability, and metabolic stability in human and mouse liver microsomes, supporting its potential for in vivo use.

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The invention provides novel compounds having the general formula: wherein R1, R2, R3, R4, R5 and R6 are as described herein, compositions including the compounds and methods of using the compounds.

NOVEL DIHYDROQUINOLIZINONES FOR THE TREATMENT AND PROPHYLAXIS OF HEPATITIS B VIRUS INFECTION

The invention provides novel compounds having the general formula (I) wherein R1, R2 R3, R4, R5 and R6 are as described herein, compositions including the compounds and methods of using the compounds in the treatment of the hepatitis B virus.

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Provided herein are methods and compositions for selective and targeted cancer therapy, in particular certain benzothiophenes, benzothiazoles, oxalamides, N-acyl ureas and chromones, and their use in selectively treating certain adenocarcinomas. In some embodiments, the selective toxicity of the compounds may be mediated through SCD1 and/or CYP450 such as CYP4F11.

Iron-catalyzed tandem one-pot addition and cyclization of the blaise reaction intermediate and nitroolefins: Synthesis of substituted NH-pyrroles from nitriles

The iron-catalyzed addition and cyclization of the Blaise reaction intermediate and nitroolefins to synthesize highly functionalized NH-pyrroles in a tandem one-pot manner from nitriles has been developed. This reaction shows good functional group tolerance and affords a broad spectrum of substituted NH-pyrroles in good yields. Copyright

Highly enantioselective reduction of α-methylated nitroalkenes

Highly selective: The reduction of α-methyl-substituted nitroalkenes succeeds in a highly enantioselective fashion with an ene reductase from Gluconobacter oxydans. Under optimized reaction conditions the desired nitroalkanes are formed with enantiomeric excesses of up to 95% in these biotransformations. Copyright

Enzymatic enantiomeric resolution of phenylethylamines structurally related to amphetamine

Both enantiomers of several phenylethylamines, structurally related to amphetamine, have been prepared in good yields and excellent enantiomeric purity by enzymatic kinetic resolution using CAL-B and ethyl methoxyacetate as the acyl donor. In the case of the 4-hydroxyderivative of amphetamine (compound 4i), the S enantiomer racemized possibly in a dynamic kinetic resolution (DKR) under the enzymatic conditions used. The Royal Society of Chemistry 2011.

Straightforward synthesis of nitroolefins by microwave- or ultrasound-assisted Henry reaction

β-Nitroalcohol or nitroethylene derivatives can be obtained from aryl aldehydes and nitromethane under Henry condensation conditions. We present a new modification using microwave irradiation or ultrasound as the energy source. Microwave irradiation allowed a novel one-pot synthesis of nitroolefins from aryl aldehydes using ammonium acetate as a catalyst without solvent. Different reaction conditions, such as base, solvent, and reaction time were studied. Only small amounts of β-hydroxyl nitro compounds were isolated, using microwave irradiation for less than 25 min. In contrast, the use of ultrasound increased the yield of the nitroalcohols.