37888-03-2

Basic information

• Product Name: TRANS-3-CHLORO-BETA-NITROSTYRENE
• Synonyms: trans-3-chloro-β-nitrostyrene;Trans-1-Chloro-3-(2-nitrovinyl)benzene;trans-M-Chloro-β-nitrostyrene;(E)-1-Chloro-3-(2-nitrovinyl)benzene;trans-1-(3-Chlorophenyl)-2-nitroethene
• CAS NO: 37888-03-2
• Molecular Formula: C₈H₆ClNO₂
• Molecular Weight: 183.59
• Product Categories: Alkenyl;Halogenated Hydrocarbons;Organic Building Blocks;Building Blocks;Chemical Synthesis;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 37888-03-2.mol
• Article Data: 55

Chemical Properties

• Melting Point: 48-52 °C(lit.)
• Boiling Point: 299.9°Cat760mmHg
• Flash Point: 135.2°C
• Appearance: Pale yellow/Powder
• Density: 1.324g/cm³
• Vapor Pressure: 0.00207mmHg at 25°C
• Refractive Index: 1.615
• Storage Temp.: 2-8°C
• CAS DataBase Reference: TRANS-3-CHLORO-BETA-NITROSTYRENE(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-3-CHLORO-BETA-NITROSTYRENE(37888-03-2)
• EPA Substance Registry System: TRANS-3-CHLORO-BETA-NITROSTYRENE(37888-03-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36/37
• WGK Germany: 3
• Hazardous Substances Data: 37888-03-2(Hazardous Substances Data)

Usage

Description

TRANS-3-CHLORO-BETA-NITROSTYRENE is an organic compound that serves as an essential intermediate in the synthesis of various chemical compounds. It is characterized by its unique molecular structure, which features a nitro group and a chloro group attached to a styrene backbone. TRANS-3-CHLORO-BETA-NITROSTYRENE plays a crucial role in the development of pharmaceuticals and other chemical products.

Uses

Used in Pharmaceutical Industry:
TRANS-3-CHLORO-BETA-NITROSTYRENE is used as a key intermediate for the synthesis of thiazolones and nitroalkenes, which are essential in the preparation of compounds with anti-cancer properties. These compounds have shown potential in targeting and inhibiting the growth of cancer cells, making them valuable in the development of novel cancer treatments.
In the field of organic chemistry, TRANS-3-CHLORO-BETA-NITROSTYRENE is used as a versatile building block for the creation of various complex molecules with potential applications in different industries. Its unique structure allows for further functionalization and modification, enabling the development of new compounds with specific properties and functions.

InChI:InChI=1/C8H6ClNO2/c9-8-3-1-2-7(6-8)4-5-10(11)12/h1-6H/b5-4+

Upstream product

• 1866-38-2 m-Chlorocinnamic acid 
• 75-52-5 nitromethane 
• 587-04-2 m-Chlorobenzaldehyde 
• 2039-85-2 3-Chlorostyrene 
• 1866-38-2 3-chlorocinnamic acid 
• 79-24-3 Nitroethane 
• 108-90-7 chlorobenzene 
• 39220-98-9 1-(3-chlorophenyl)-2-nitroethanol 
• 4152-90-3 m-chlorobenzylamine 

Downstream Products

• 10125-47-0 3-Chlor-1-<1,3,3,3-tetranitro-propyl-2>-benzol 
• 10125-45-8 3-Chlor-1-<1,3,3-trinitro-butyl-2>-benzol 
• 10125-46-9 3-Chlor-1-(1,3,3-trinitropentyl-2)-benzol 
• 13078-79-0 2-(3-chlorophenyl)ethylamine 
• 637780-49-5 2,4,6-triamino-5-[2-nitro-1-(3-chlorophenyl)ethyl]pyrimidine 
• 637780-48-4 2,6-diamino-5-[2-nitro-1-(3-chlorophenyl)ethyl]-3H-pyrimidin-4-one 
• 1020270-23-8 (S)-3-(3-chlorophenyl)-4-nitrobutanal 
• 1092380-02-3 C₂₃H₂₂ClF₃N₂O₆ 
• 1073794-51-0 1-chloro-3-((2R,3R)-1,3-dinitrobutan-2-yl)lbenzene 
• 1186386-18-4 (R)-3-(3-chlorophenyl)-2,2-dimethyl-4-nitrobutanal 
• 1173374-28-1 ethyl1-(1-(3-chlorophenyl)-2-nitroethyl)-2-oxocyclopentanecarboxylate 
• 1020665-79-5 3-((R)-1-(3-chlorophenyl)-2-nitroethyl)pentane-2,4-dione 
• 1173398-69-0 (S)-3-[1-(3-chlorophenyl)-2-nitroethyl]-pentane-2, 4-dione 

Relevant articles and documents

Metal-free Synthesis of β-Nitrostyrenes via DDQ-Catalyzed Nitration

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Biological evaluation and SAR analysis of novel covalent inhibitors against fructose-1,6-bisphosphatase

Fructose-1,6-bisphosphatase (FBPase) is an attractive target for affecting the GNG pathway. In our previous study, the C128 site of FBPase has been identified as a new allosteric site, where several nitrovinyl compounds can bind to inhibit FBPase activity. Herein, a series of nitrostyrene derivatives were further synthesized, and their inhibitory activities against FBPase were investigated in vitro. Most of the prepared nitrostyrene compounds exhibit potent FBPase inhibition (IC50 3, CF3, OH, COOH, or 2-nitrovinyl were installed at the R2 (meta-) position of the benzene ring, the FBPase inhibitory activities of the resulting compounds increased 4.5–55 folds compared to those compounds with the same groups at the R1 (para-) position. In addition, the preferred substituents at the R3 position were Cl or Br, thus compound HS36 exhibited the most potent inhibitory activity (IC50 = 0.15 μM). The molecular docking and site-directed mutation suggest that C128 and N125 are essential for the binding of HS36 and FBPase, which is consistent with the C128-N125-S123 allosteric inhibition mechanism. The reaction enthalpy calculations show that the order of the reactions of compounds with thiol groups at the R3 position is Cl > H > CH3. CoMSIA analysis is consistent with our proposed binding mode. The effect of compounds HS12 and HS36 on glucose production in primary mouse hepatocytes were further evaluated, showing that the inhibition was 71% and 41% at 100 μM, respectively.

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.