3316-24-3

Basic information

• Product Name: 1-(2-Methoxyphenyl)-2-nitroethene
• Synonyms: TRANS-2-METHOXY-BETA-NITROSTYRENE;AKOS BBS-00006782;2-METHOXY-B-NITROSTYRENE;2'-METHOXY-BETA-NITROSTYRENE;2-METHOXY-BETA-NITROSTYRENE;2-Methoxy-alpha-nitrostyrene;2-(2-METHOXYPHENYL)NITROETHENE;1-(2-METHOXYPHENYL)-2-NITROETHANE
• CAS NO: 3316-24-3
• Molecular Formula: C₉H₉NO₃
• Molecular Weight: 179.17
• Product Categories: Ethanes/ethenes
• Mol File: 3316-24-3.mol

Chemical Properties

• Melting Point: 46-50 °C(lit.)
• Boiling Point: 311.69°C (rough estimate)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.2822 (rough estimate)
• Vapor Pressure: 0.00208mmHg at 25°C
• Refractive Index: 1.5600 (estimate)
• Storage Temp.: Keep Cold
• CAS DataBase Reference: 1-(2-Methoxyphenyl)-2-nitroethene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-Methoxyphenyl)-2-nitroethene(3316-24-3)
• EPA Substance Registry System: 1-(2-Methoxyphenyl)-2-nitroethene(3316-24-3)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• RTECS: DA5341500
• HazardClass: IRRITANT, KEEP COLD
• Hazardous Substances Data: 3316-24-3(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
1-(2-Methoxyphenyl)-2-nitroethene is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a versatile building block for the development of new drugs with potential applications in the treatment of various diseases, including cancer.
2. Used in Chemical Synthesis:
In the chemical industry, 1-(2-Methoxyphenyl)-2-nitroethene serves as a valuable reagent for the preparation of a wide range of organic compounds. Its functional groups can be further modified or reacted with other molecules to produce a diverse array of products with different properties and applications.
3. Used in the Synthesis of Focal Adhesion Kinase Inhibitors:
1-(2-Methoxyphenyl)-2-nitroethene is used as a reagent in the preparation of pyridine compounds, which act as focal adhesion kinase inhibitors. These inhibitors may be useful in the treatment of diseases such as cancer in warm-blooded animals, as they can help regulate cellular processes and prevent uncontrolled cell growth.
4. Used in the Synthesis of Purine Derivatives:
1-(2-Methoxyphenyl)-2-nitroethene is also used as a reagent in the synthesis of purine derivatives, which may act as inhibitors of mutant EGF (Epidermal Growth Factor) receptors. By targeting these receptors, these derivatives could potentially play a role in the treatment of various types of cancer and other diseases related to abnormal cell growth.

Safety Profile

Moderately toxic by ingestion.When heated to decomposition it emits toxic vapors ofNOx.

InChI:InChI=1/C9H9NO3/c1-13-9-5-3-2-4-8(9)6-7-10(11)12/h2-7H,1H3/b7-6+

Upstream product

• 625-75-2 nitroacetic acid 
• 135-02-4 ortho-anisaldehyde 
• 612-15-7 o-methoxystyrene 
• 75-52-5 nitromethane 
• 1011-54-7 2-methoxycinnamic acid 
• 6099-03-2 3-(2'-methoxyphenyl)propenoic acid 
• 38316-04-0 1-(2-methoxy-phenyl)-2-nitro-ethanol 

Downstream Products

• 46270-50-2 1-(2-methoxyphenyl)-2-nitroethan-1-one 
• 329969-53-1 (4-Methoxy-phenyl)-[(Z)-(3S,4R)-4-(2-methoxy-phenyl)-5-nitro-3-phenyl-pent-1-enyl]-carbamic acid tert-butyl ester 

Relevant articles and documents

Catalytic Asymmetric Construction of Tertiary Carbon Centers Featuring an α-Difluoromethyl Group with CF2H-CH2-NH2as the "building Block"

We report here for the first time a novel difluoromethylated ketimine building block condensed by thioisatin and difluoroethylamine, offering efficient access to a broad range of enantioenriched products bearing difluoroethylamine units (27 examples, ≤98% yield, >99% ee) in the presence of quinine-derived squaramide. Further transformation of the intermediate would generate a variety of versatile functional blocks like α-difluoromethyl amines, β-amino acid, and β-diamine with retention of the enantiomeric excess at the difluoromethyl-bound carbon.

Dipolar HCP materials as alternatives to DMF solvent for azide-based synthesis

Hypercrosslinked polymers HCP-DMF and HCP-DMF-SO3H containing abundant and flexible DMF moieties were designed and synthesized. Benefitting from the solvation microenvironment provided by the pseudo-DMF moities, the polar HCPs manifested outstanding performances in the conversions of NaN3 to benzylic azides and 1,2,3-triazoles in EtOH (95%), respectively, avoiding the use of risky DMF and improving the separation processes of the products.

Palladium-Catalyzed Formal (3 + 2) Cycloaddition Reactions of 2-Nitro-1,3-enynes with Vinylaziridines, -epoxides, and -cyclopropanes

A two-step Pd-catalyzed (3 + 2) cycloaddition/HNO2 elimination reaction sequence has been developed to give novel cyclic 1,3-dien-5-yne systems from Pd-stabilized zwitterionic 1,3-dipoles and 2-nitro-1,3-enyne substrates. The process is highly atom-efficient and tolerates the reaction of 2-vinyloxirane, 1-tosyl-2-vinylaziridine, and diethyl 2-vinylcyclopropane-1,1-dicarboxylate derived 1,3-dipoles with a variety of 2-nitro-1,3-enyne substrates. The stereochemistry of the intermediate (3 + 2) cycloadducts was determined by single crystal X-ray analysis. Furthermore, a selective kinetic elimination of the cycloadduct with an antiperiplanar relationship between the NO2 group and the participating hydrogen was demonstrated, allowing for efficient isolation of a single diastereoisomer of the cycloadduct.

Geometrically Selective Denitrative Trifluoromethylthiolation of β-Nitrostyrenes with AgSCF3for (E)-Vinyl Trifluoromethyl Thioethers

An efficient copper(II)-promoted denitrative trifluoromethylthiolation under mild reaction conditions has been developed for vinyl trifluoromethyl thioethers to construct Cvinyl-SCF3 bonds with stable AgSCF3 as a source of the trifluoromethylthio. This reaction system tolerates a broad range of functional groups to commendably achieve a high product yield and excellent stereoselectivity of E/Z.

Molecular Engineering of β-Substituted Oxoporphyrinogens for Hydrogen-Bond Donor Catalysis

A new class of bifunctional hydrogen-bond donor organocatalyst using oxoporphyrinogens having increased intramolecular hydrogen-bond donor distances is reported. Oxoporphyrinogens are highly non-planar rigid macrocycles containing a multiple hydrogen bond-forming binding site. In this work, we describe the first example of non-planar OxPs as hydrogen-bond donor catalysts prepared using a molecular engineering approach of the binding site for dual activation of substrates. The introduction of β-substituents is key to the catalytic activity and the catalysts are able to catalyze 1,4-conjugate additions and sulfa-Michael additions, as well as, Henry and aza-Henry reactions at low catalyst loadings (≤ 1 mol-%) under mild conditions. Preliminary mechanistic studies have been carried out and a possible reaction mechanism has been proposed based on the bi-functional activation of both substrates through hydrogen-bonding interactions.

Asymmetric synthesis of tetrahydropyran[3,2-c]quinolinones via an organocatalyzed formal [3 + 3] annulation of quinolinones and MBH 2-naphthoates of nitroolefin

An efficient asymmetric and enantio-swithchable organocatalytic [3 + 3] annulation reaction using MBH-2-naphthoates of nitroalkenes and 4-hydroxyquinolin-2(1H)-ones has been developed. Densely substituted tetrahydropyrano[3,2-c]quinolinones scaffolds with two adjacent stereogenic centers are obtained with high yield (up to 95% yield) and good stereoselectivities (up to >20:1 dr and 96% ee) in an enantio-switchable manner. Furthermore, gram scale synthesis was achieved and the nitro group could easily transform into an amino group without any appreciable loss in the diastereo- and enantioselectivity.

NCC Pincer Ni (II) Complexes Catalyzed Hydrophosphination of Nitroalkenes with Diphenylphosphine

An efficient NCC pincer Ni (II)-catalyzed hydrophosphination of nitroalkenes with diphenylphosphine has been developed. Under the optimized conditions, both (hetero)aromatic and aliphatic nitroalkenes were well tolerated, irrespective of electronic effect, to provide the corresponding products in up to 99% yield.

Phosphorus-containing thienopyrimidine derivative

The invention belongs to the field of medicinal chemistry, relates to a phosphorus-containing thienopyrimidine derivative, in particular to a compound shown as a formula I or pharmaceutically acceptable salt thereof, a preparation method of the compound,

Novel approach in the synthesis of imidazo [1, 2-a] pyridine from phenyl acrylic acids

This paper describes highly efficient concise method for the synthesis of imidazo[1,2-a] pyridine. It is a first report employing, amino pyridines, copper nitrate, and phenyl acrylic acids in the synthesis of imidazo[1,2-a] pyridine. The silent features of the devised protocol include the high yield, milder reaction conditions, and shorter reaction time.

Preparation method of nitroolefin derivative with nitrate as nitro source

The invention relates to a nitroolefin derivative with nitrate as nitro source and a preparation method thereof. Under the atmosphere of nitrogen, an olefin compound, nitrate, trimethylchlorosilane (TMSC1) and copper salt are stirred in acetonitrile at 0-30 DEG C; in addition, the reaction degree is monitored by using a TLC point plate; after the olefin compound is completely consumed, alkali is added to an obtained mixture to be stirred for 20-30 min; then after a solvent is removed from an obtained mixture by using a rotary evaporator, the nitroolefin derivative can be obtained through silicagel column purification. Compared with the prior art, the nitroolefin derivative with the nitrate as the nitro source, provided by the invention, has the advantages of mild reaction condition, high yield, high E type selectivity and the like.