18984-21-9

Basic information

• Product Name: 2,4-DICHLORO-OMEGA-NITROSTYRENE
• Synonyms: TRANS-2,4-DICHLORO-BETA-NITROSTYRENE;2,4-DICHLORO-OMEGA-NITROSTYRENE;2,4-DICHLORO-BETA-NITROSTYRENE;1-(2,4-DICHLOROPHENYL)-2-NITROETHENE;1-(2,4-DICHLOROPHENYL)-2-NITROETHYLENE;trans-2,4-dichloro-β-nitrostyrene;1-(2,4-Dichlorophenyl)-2-nitroethylene 98%;2,4-DICHLORO-BETA-NITROSTYRENE 97%
• CAS NO: 18984-21-9
• Molecular Formula: C₈H₅Cl₂NO₂
• Molecular Weight: 218.04
• Product Categories: Alkenyl;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 18984-21-9.mol

Chemical Properties

• Melting Point: 115-119 °C(lit.)
• Boiling Point: 334.1 °C at 760 mmHg
• Flash Point: 155.9 °C
• Appearance: /
• Density: 1.447 g/cm³
• Vapor Pressure: 0.000253mmHg at 25°C
• Refractive Index: 1.626
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2,4-DICHLORO-OMEGA-NITROSTYRENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DICHLORO-OMEGA-NITROSTYRENE(18984-21-9)
• EPA Substance Registry System: 2,4-DICHLORO-OMEGA-NITROSTYRENE(18984-21-9)

Safety Data

• Hazard Codes: Xn,N,Xi
• Statements: 22-36-50/53
• Safety Statements: 26-36-60-61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 18984-21-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2,4-Dichloro-omega-nitrostyrene is used as a valuable intermediate for the synthesis of other complex organic compounds. Its unique combination of functional groups allows for the creation of a wide range of chemical products, making it an essential component in the field of organic chemistry.
Used in Chemical Research:
In the chemical research industry, 2,4-dichloro-omega-nitrostyrene is used as a model compound to study the reactivity and properties of various functional groups. This helps researchers understand the behavior of similar compounds and develop new synthetic strategies and applications.
Used in Pharmaceutical Industry:
2,4-Dichloro-omega-nitrostyrene is used as a building block in the synthesis of pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications, contributing to the advancement of medicine and healthcare.
Used in Material Science:
In the field of material science, 2,4-dichloro-omega-nitrostyrene is used as a precursor for the development of new materials with specific properties. Its versatility in organic synthesis enables the creation of materials with tailored characteristics, such as improved strength, flexibility, or conductivity, for various applications.

InChI:InChI=1/C8H5Cl2NO2/c9-7-2-1-6(8(10)5-7)3-4-11(12)13/h1-5H/b4-3+

Upstream product

• 75-52-5 nitromethane 
• 874-42-0 2,4-dichlorobenzaldeyhde 
• 2972-76-1 2-(2,4-dichlorobenzylidene)malononitrile 

Downstream Products

• 138964-43-9 4-(2,4-dichlorophenyl)-3-nitropyrrole 
• 90798-35-9 (1-<2,4-Dichlor-phenyl>-2-nitro-ethylmercapto)-essigsaeure 
• 92546-35-5 3-(1-<2,4-Dichlor-phenyl>-2-nitro-ethylmercapto)-propionsaeure 
• 92023-55-7 6-Nitro-5-<2,4-dichlorphenyl>-bicyclo<2.2.1>hepten-(2) 
• 95195-33-8 5-Nitro-4-<2.4-dichlor-phenyl>-cyclohexen 
• 138964-48-4 2-formyl-3-(2,4-dichlorophenyl)-4-nitropyrrole 
• 1073917-20-0 (R)-3-(1-(2,4-dichlorophenyl)-2-nitroethyl)pentane-2,4-dione 
• 1145659-14-8 2-(2,4-dichlorophenyl)-1-nitro-3-phenylpropane 
• 1073794-56-5 2,4-dichloro-1-((2R,3R)-1,3-dinitrobutan-2-yl)lbenzene 
• 1174340-53-4 (4S)-5-nitro-4-(2,4-dichlorophenyl)-pentan-2-one 
• 1170773-42-8 (R)-diethyl 2-[1-(2,4-dichlorophenyl)-2-nitroethyl]malonate 
• 1021394-84-2 (2S,3R)-3-(2,4-dichlorophenyl)-2-ethyl-4-nitrobutyraldehyde 

Relevant articles and documents

Exploiting the chiral ligands of bis(Imidazolinyl)-and bis(oxazolinyl)thiophenes—Synthesis and application in Cu-catalyzed friedel–crafts asymmetric alkylation

Five new C2-symmetric chiral ligands of 2,5-bis(imidazolinyl)thiophene (L1–L3) and 2,5-bis(oxazolinyl)thiophene (L4 and L5) were synthesized from thiophene-2,5-dicarboxylic acid (1) with enantiopure amino alcohols (4a–c) in excellent optical purity and chemical yield. The util-ity of these new chiral ligands for Friedel–Crafts asymmetric alkylation was explored. Subse-quently, the optimized tridentate ligand L5 and Cu(OTf)2 catalyst (15 mol%) in toluene for 48 h promoted Friedel–Crafts asymmetric alkylation in moderate to good yields (up to 76%) and with good enantioselectivity (up to 81% ee). The bis(oxazolinyl)thiophene ligands were more potent than bis(imidazolinyl)thiophene analogues for the asymmetric induction of the Friedel–Crafts asymmetric alkylation.

Synthesis method of lifitegrast intermediate 5,7-dichloro-1,2,3,4-tetrahydroisoquinoline

The invention discloses a synthesis method of a lifitegrast intermediate 5,7-dichloro-1,2,3,4-tetrahydroisoquinoline, wherein the synthesis method comprises the steps: by using 2,4-dichlorobenzaldehyde as a starting material, carrying out nitro-alcohol co

Cinnamic acid derivative and preparation method and application thereof

The invention provides a cinnamic acid derivative. The cinnamic acid derivative is of the structure as shown in the formula I. The invention also provides two methods for preparing the cinnamic acid derivative. The two methods depend on a single bond or double bonds in the structure shown in the formula I. The invention further provides a pesticide. The pesticide comprises the cinnamic acid derivative. In addition, the invention provides a sterilization method. The sterilization method includes the step of applying the cinnamic acid derivative or the pesticide to crops. The crops include rice,wheat, fruit trees and vegetables. The low-toxicity, low-residue-content and high-activity environment-friendly cinnamic acid derivative is developed, and the cinnamic acid derivative pesticide can replace traditional high-toxicity and high-residue-content pesticides.

Synthesis, antiproliferative and pro-apoptotic effects of nitrostyrenes and related compounds in Burkitt’s lymphoma

Background: Cancers of the lymphatic cells (lymphomas) account for approximately 12% of malignant diseases worldwide. The nitrostyrene scaffold is identified as a lead target structure for the development of particularly effective compounds targeting Burkitt’s lymphoma (BL). Objectives: The aims of the curent study were to synthesise a panel of nitrostyrene compounds and to evaluate their activity in Burkitt’s lymphoma (BL). Methods: A panel of structurally varied compounds were designed and synthesised using Henry Knoevenagel condensation reactions. Single crystal X-Ray analysis confirmed the E configuration for six examples of these novel structures. A number of nitrostyrene-related compounds were also investigated including 1,3-bis(aryl)-2-nitropropenes together with heterocyclic scaffolds containing the nitrovinyl pharmacophore such as 3-nitro-2-phenyl-2H-chromenes. The antiproliferative activities of the compounds were evaluated using the BL cell lines EBV- MUTU-1 and EBV+ DG-75 (chemoresistant) to establish preliminary structure-activity relationships. Results: Lead compounds with optimized nitrostyrene scaffolds and 3-nitro-2-phenyl-2Hchromene structures were successfully established with typical IC50 values of 0.45 μM and 0.47 μM in MUTU-1 cells and 1.41 μM and 1.92 μM, respectively, in DG-75 cells. The mechanism of cell death was identified as apoptotic and the lead compound was found to elicit comparable apoptotic effects to Taxol in Burkitt’s lymphoma cell lines MUTU-1 and DG-75. Conclusion: This class of pharmaceutically active compounds with potential for the treatment of Burkitt’s lymphoma suggest a potential role for nitrostyrene based agents in chemotherapy.

A thiourea-functionalized metal-organic macrocycle for the catalysis of Michael additions and prominent size-selective effect

A discrete tetranuclear thiourea-based metal-organic macrocycle (MOM) with a large size was constructed by a well-designed organic ligand and nickel(ii) ions via self-assembly. Incorporating thiourea groups as hydrogen-bond donors into a metal-organic com

Cinchona alkaloid and di-: Tert -butyldicarbonate-DMAP promoted efficient synthesis of (E)-nitroolefins

The synthesis of nitroolefins from aldehydes and olefins is generally limited by the formation of a mixture of cis and trans compounds. Here we report an alternative, metal-free protocol for the synthesis of β-nitroolefins from arylidinemalononitrile using cinchona alkaloid along with di-tert-butyldicarbonate-DMAP in high yields with total selectivity.

Benzo-hexatomic ring derivative used as DPP-4 inhibitor and application of benzo-hexatomic ring derivative

The invention relates to a benzo-hexatomic ring derivative used as a DPP-4 inhibitor and application of the benzo-hexatomic ring derivative, in particular to compounds shown as in formula I, medicine compositions with the compounds shown as in the formula I and application of the compounds in preparing medicines for treating diseases related to DPP-4 or inhibiting the DPP-4.

Silver(I)-catalyzed denitrative trifluoromethylation of β-nitrostyrenes with CF3SO2Na

A novel and convenient approach to the synthesis of substituted β-trifluoromethyl styrenes via a silver(I)-catalyzed denitrative trifluoromethylation with CF3SO2Na under relatively mild conditions has been developed. This protocol delivered excellent stereoselectivity and showed wide substrate tolerance.

Synthesis of pyrimidine-2,4,6-trione derivatives: Anti-oxidant, anti-cancer, α-glucosidase, β-glucuronidase inhibition and their molecular docking studies

This paper describes a facile protocol, efficient, and environmentally benign for the synthesis a series of barbiturate acid substituted at C5 position 3a–o. The desired compounds subjected in vitro for different set of bioassays including against anti-oxidant (DPPH and super oxide scavenger assays), anti-cancer, α-glucosidase and β-glucuronidase inhibitions. Compound 3m (IC50?=?22.9?±?0.5?μM) found to be potent α-glucosidase enzyme inhibitors and showed more activity than standard acarbose (IC50?=?841?±?1.73?μM). Compound 3f (IC50?=?86.9?±?4.33?μM) found to be moderate β-Glucuronidase enzyme inhibitors and showed activity comparatively less than the standard D-saccharic acid 1,4-lactone (IC50?=?45.75?±?2.16?μM). Furthermore, in sillico investigation was carried out to investigate bonding mode of barbiturate acid derivatives.