5153-71-9

Usage

Uses

Used in Chemical Synthesis:
TRANS-4-BROMO-BETA-NITROSTYRENE is used as a Michael acceptor for the organocatalytic asymmetric Michael addition of protected 3-hydroxypropanal to β-nitrostyrenes. This application is significant because it allows for the creation of new compounds with potential applications in various industries, such as pharmaceuticals, materials science, and agrochemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, TRANS-4-BROMO-BETA-NITROSTYRENE is used as a key intermediate in the synthesis of various drug molecules. Its unique chemical structure enables the development of new drugs with improved efficacy and selectivity, contributing to the advancement of medical treatments for various diseases and conditions.
Used in Materials Science:
TRANS-4-BROMO-BETA-NITROSTYRENE is also utilized in the field of materials science for the development of novel materials with specific properties. Its halogenated hydrocarbon nature allows for the creation of materials with enhanced stability, reactivity, or other desirable characteristics, which can be applied in various technological applications.
Used in Agrochemicals:
In the agrochemical industry, TRANS-4-BROMO-BETA-NITROSTYRENE is employed as a building block for the synthesis of new pesticides or other agrochemicals. Its unique structure can be exploited to develop more effective and environmentally friendly products, contributing to sustainable agricultural practices and food security.

InChI:InChI=1/C8H6BrNO2/c9-8-3-1-7(2-4-8)5-6-10(11)12/h1-6H/b6-5+

Upstream product

• 75-52-5 nitromethane 
• 1122-91-4 4-bromo-benzaldehyde 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 17104-98-2 1-(4-bromophenyl)-2-nitroethanol 
• 1200-07-3 trans-4-bromocinnamic acid 
• 1200-07-3 3-(4-bromophenyl)acrylic acid 
• 1402933-44-1 C₁₁H₈BrN₃O₂ 
• 2826-24-6 4-bromobenzylidenemalononitrile 

Downstream Products

• 75-52-5 nitromethane 
• 137521-07-4 1-bromo-4-(2-nitroethyl)benzene 
• 92-52-4 biphenyl 
• 73918-56-6 4-Bromophenethylamine 
• 41441-38-7 methyl 2-carbomethoxy-4-nitro-3-(4-bromo-phenyl)-butyrate 

Relevant academic research and scientific papers

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.

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.

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.

Chlorination of Conjugated Nitroalkenes with PhICl 2and so 2Cl 2for the Synthesis of α-Chloronitroalkenes

Chlorination of conjugated nitroalkenes with iodobenzene dichloride or sulfuryl chloride to give target α-chloronitroalkenes in good yields is described. Details of the procedure depend on the donating ability of the nitroalkene substituents. The activity of the described chlorinating agents increases in order 'PhICl 2/Py' 2Cl 2' 2Cl 2/HCl' with the former producing the best yields for highly donating substrates and the latter for non-activated groups. An autocatalytic role of hydrogen chloride and the chemoselectivity of chlorination were also demonstrated.

A photocatalyst-free photo-induced denitroalkylation of β-nitrostyrenes with 4-alkyl substituted Hantzsch esters at room temperature

A photocatalyst-free stereoselectively photo-induced strategy for the denitroalkylation of β-nitrostyrenes using 4-alkyl substituted Hantzsch esters as the alkyl source under xenon lamp irradiation is developed. The reaction proceeds at room temperature and affords the corresponding products in moderate to excellent yields. The oxidant di-t-butyl peroxide serves as an efficient radical initiator under irradiation of a Xenon lamp, initiating alkyl radicals from the 4-alkyl substituted Hantzsch esters.

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.

tert-Butyl Nitrite Mediated Nitro-Nitratosation of Internal Alkenes

In an oxygen atmosphere tert-butyl nitrite (TBN) reacts with unsymmetrical internal benzylic alkenes giving nitro-nitratosation product exclusively. The γ-diaryl-substituted styrenes provided better yields compared to γ-alkyl-aryl-substituted styrenes. The higher yields for the former type of substrates is possibly dictated by the additional stability of benzylic radical due to the anchimeric assistance imparted by the γ-substituted phenyl ring. During oxidative nitration, the nitro (NO2) group adds at the non-benzylic site, whereas the nitrato group (ONO2) is attached at the relatively stable benzylic position. Under similar reaction conditions, α,β-unsaturated carboxylic acids, afforded nitroalkenes as the sole product.

Preparation method of beta-trans-nitroolefin

The invention relates to a preparation method of beta-trans-nitroolefin. The method comprises: sequentially adding an olefin compound, a nitration reagent and a solvent into a reaction container, mixing the substances uniformly, and carrying out constant temperature reaction for 18h under an illumination condition to obtain a reaction solution; and sequentially carrying out drying, concentration and column chromatography treatment on the reaction solution to obtain the beta-trans-nitroolefin compound. The method is simple and practicable, low in cost and high in product yield, can realize large-scale production, and has good industrial application prospects in the aspects of functional organic material, bioactive compound and drug synthesis.