37629-59-7

Basic information

• Product Name: 2-[(1E)-2-nitroprop-1-en-1-yl]thiophene
• Synonyms: 2-[(1E)-2-Nitro-1-propen-1-yl]thiophene; 2-[(1E)-2-Nitroprop-1-en-1-yl]thiophene; thiophene, 2-[(1E)-2-nitro-1-propen-1-yl]-
• CAS NO: 37629-59-7
• Molecular Formula: C₇H₇NO₂S
• Molecular Weight: 169.201
• Mol File: 37629-59-7.mol

Chemical Properties

• Boiling Point: 273.5°C at 760 mmHg
• Flash Point: 119.2°C
• Density: 1.277g/cm³
• Vapor Pressure: 0.00957mmHg at 25°C
• Refractive Index: 1.617
• CAS DataBase Reference: 2-[(1E)-2-nitroprop-1-en-1-yl]thiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(1E)-2-nitroprop-1-en-1-yl]thiophene(37629-59-7)
• EPA Substance Registry System: 2-[(1E)-2-nitroprop-1-en-1-yl]thiophene(37629-59-7)

Safety Data

• Hazardous Substances Data: 37629-59-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-[(1E)-2-nitroprop-1-en-1-yl]thiophene is used as a raw material for the production of pharmaceuticals, contributing to the development of new drugs and medicinal compounds. Its unique chemical structure allows it to be a key component in the synthesis of various therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, 2-[(1E)-2-nitroprop-1-en-1-yl]thiophene serves as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides. Its reactivity and functional groups make it suitable for creating effective and targeted agricultural products.
Used in Organic Synthesis:
2-[(1E)-2-nitroprop-1-en-1-yl]thiophene is utilized as a building block in organic synthesis, enabling the creation of a wide range of organic compounds with diverse applications. Its versatility in chemical reactions makes it a valuable intermediate in the synthesis of various organic molecules.
Used in Dye and Pigment Manufacturing:
2-[(1E)-2-nitroprop-1-en-1-yl]thiophene is employed in the manufacturing of dyes and pigments, where its chemical properties contribute to the color and stability of the final products. Its use in this industry highlights its potential in creating vibrant and long-lasting colors for various applications.
Used as a Flavoring Agent:
2-[(1E)-2-nitroprop-1-en-1-yl]thiophene is also used as a flavoring agent in the food and beverage industry. Its unique chemical structure allows it to impart specific flavors and aromas to products, enhancing their sensory qualities.
It is crucial to handle 2-[(1E)-2-nitroprop-1-en-1-yl]thiophene with caution and in accordance with safety guidelines due to its hazardous nature. Proper handling and storage measures should be implemented to minimize risks associated with its flammability and potential for irritation.

Upstream product

• 98-03-3 thiophene-2-carbaldehyde 
• 79-24-3 Nitroethane 
• 15022-18-1 1-(thiophen-2-yl)propan-2-one 

Downstream Products

• 30433-93-3 (+/-)-1-(methyl-2-thien-2-yl)ethylamine 
• 15022-18-1 1-(thiophen-2-yl)propan-2-one 
• 91461-95-9 ((4R,5R)-3-Methyl-2-oxy-4-thiophen-2-yl-4,5-dihydro-isoxazol-5-yl)-phenyl-methanone 

Relevant articles and documents

Guanidine-containing compound as well as preparation method and application thereof

The invention discloses a cyanoguanidine-containing compound as well as a preparation method and application thereof. The invention also discloses a composition containing the cyanoguanidine-structured compound (I) or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier. The invention also discloses application thereof in preparation of analgesic drugs. The compounds of the invention are useful in the treatment of various pain.

Synthesis of N-Heterocycles by Reductive Cyclization of Nitroalkenes Using Molybdenum Hexacarbonyl as Carbon Monoxide Surrogate

The development of a method that uses molybdenum hexacarbonyl [Mo(CO)6] as carbon monoxide (CO) surrogate for the palladium-catalyzed reductive cyclization of nitroalkenes into indoles or thienopyrroles is reported. Several types of nitroalkenes could be transformed into the desired products in excellent yields and in most cases with complete regioselectivities and higher yields than those previously reported with palladium/CO system.

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.

Palladium-Catalyzed Intramolecular Cyclization of Nitroalkenes: Synthesis of Thienopyrroles

In the presence of carbon monoxide, the palladium/phenanthroline system catalyzes the intramolecular amination of thiophene rings following the reduction of a nitroalkene moiety directly attached to the S-heterocyclic ring. Optimization of the ligand and reaction conditions allowed the synthesis of a series of thienopyrroles aryl/alkyl-substituted at either the 2- or 3-position of the pyrrole ring. By using low pressures of carbon monoxide (5 bars), high yields of fused bicyclic compounds have been obtained (up to 98 % yield).

Enantioselective hydrogenation of α,β-disubstituted nitroalkenes

The first highly chemo- and enantioselective hydrogenation of α,β-disubstituted nitroalkenes was accomplished with rhodium/JosiPhos-J2 as a catalyst, with the yield and enantioselectivity of up to 95% and 94%, respectively. The α-chiral nitroalkanes will provide an entry to valuable chiral amphetamines which are otherwise not so easily accessed. This journal is the Partner Organisations 2014.

Palladium-catalyzed synthesis of substituted nitroolefins

A one-pot protocol toward several substituted nitroolefins 4 and 6 starting with substituted acetones 2 and 5 was described. A facile process was carried out for the triflation of substituted acetones 2 and 5 with triflic anhydride (Tf2O) under the basic condition (Cs2CO3) and then palladium-catalyzed cross-coupling of enol triflates 3 with NaNO 2 and BINAP in the presence of phase-transfer reagents (n-Bu 4NBr) under the refluxing 1,2-dimethoxyethane (DME) in acceptable yields.

Heteroarylisopropylamines as MAO inhibitors

The in vitro monoamine oxidase inhibitory (MAOI) activities of 11 heteroarylisopropylamines vis-a-vis MAO-A and MAO-B were described and interpreted in terms of possible interactions with the enzyme active site. Molecular dynamics simulations allowed a comparison between the most active MAO-A inhibitor of the series, the 1-(2-benzofuryl)-2-aminopropane, and the specific, analogous MAO-A substrate serotonin.

Thieno tetrahydropyridines useful as class III antiarrhythmic agents

This invention relates to thieno tetrahydropyridine and isoquinoline derivative compounds which are useful as antiarrhythmic agents, pharmaceutical compositions comprising such compounds, novel intermediates for their preparation and their methods of use. More particularly these thieno tetrahydropyridine and isoquinoline derivative compounds have been demonstrated to increase the effective refractory period (ERP) of isolated perfused cardiac tissue in vitro.

Aminoethylthiophene derivatives

This invention relates to aminoethylthiophene derivatives and more particularly 2-and 3-aminoethylthiophene derivatives which are useful as antiarrhythmic agents, their methods of use as antiarrhythmic agents, and novel intermediate compounds useful for preparation of the aminoethylthiophene derivatives of the invention.

Synthesis and evaluation of radioiodinated 2-(2(RS)-aminopropyl)-5- iodothiophenes as brain imaging agents

Methods have been developed for the preparation of 2-(2(RS)-aminopropyl)- 5-iodothiophenes. The syntheses and physical properties of 2-(2(RS)- aminopropyl)-5-iodothiophene and N-isopropyl-2-(2(RS)-aminopropyl)-5- iodothiophene are described. The radioiodinated agents are of interest because of the high expected uptake and prolonged brain retention that may result from binding to high-capacity, relatively nonspecific amine binding sites. Radioiodine was introduced into the 5-position of 2-(2(RS)- aminopropyl)-5-iodothiophene and N-isopropyl-2-(2(RS)-aminopropyl)-5- iodothiophene by radioiodination of the corresponding 5-boronic acid or 5- (trimethylstannyl) derivatives. Tissue distribution studies in rats with 2- (2(RS)-aminopropyl)-5-[125I]iodothiophene showed high brain uptake (5 min, 2.77% dose/g; 30 min, 2.51% dose/g) and good brain/blood (B/B) ratios (5 min, 6/1; 30 min 3.8/1. A comparison of the brain uptake of the N-isopropyl derivative with the 2(RS)-aminopropyl analogue demonstrated higher initial brain uptake and brain to blood ratios (5 min, 3.2% dose/g; 10.3/1) but more rapid washout (30 min, 1.37% dose; 2.8/1). These data suggest that radiolabeled 2-(2(RS)-aminopropyl)-5-iodothiophenes are potentially useful agents for cerebral perfusion imaging by single-photon-emission computerized tomography (SPECT).