15690-25-2

Basic information

• Product Name: 3-(2-THIENYL)ACRYLIC ACID 98
• Synonyms: 3-(2-THIENYL)ACRYLIC ACID 98;(2E)-3-(2-Thienyl)-2-propenoic acid;(E)-3-(2-Thienyl)acrylic acid;2-Thiopheneacrylic acid, (E)-;3-(Thien-2-yl)acrylic acid;trans-2-Thiopheneacrylic acid;3-(Thien-2-yl)acrylic acid 98%;3-(2-Thienyl)propenoic acid, GC 98%
• CAS NO: 15690-25-2
• Molecular Formula: C₇H₆O₂S
• Molecular Weight: 154.18634
• EINECS: 214-402-0
• Product Categories: Aromatic Cinnamic Acids, Esters and Derivatives
• Mol File: 15690-25-2.mol

Chemical Properties

• Melting Point: 145-148 °C(lit.)
• Boiling Point: 247.55°C (rough estimate)
• Flash Point: 134.6oC
• Appearance: Slightly beige powder
• Density: 1.2950 (rough estimate)
• Vapor Pressure: 0.000551mmHg at 25°C
• Refractive Index: 1.5100 (estimate)
• Storage Temp.: 2-8°C(protect from light)
• Solubility: Chloroform, Methanol
• PKA: 4.34±0.10(Predicted)
• BRN: 112053
• CAS DataBase Reference: 3-(2-THIENYL)ACRYLIC ACID 98(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-THIENYL)ACRYLIC ACID 98(15690-25-2)
• EPA Substance Registry System: 3-(2-THIENYL)ACRYLIC ACID 98(15690-25-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 15690-25-2(Hazardous Substances Data)

Usage

Uses

1. Pharmaceutical Industry:
3-(2-Thienyl)acrylic acid 98 is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its application in this industry is primarily due to its ability to form essential building blocks for the development of new drugs.
a. Anti-HIV Applications:
In the fight against HIV, 3-(2-Thienyl)acrylic acid 98 is used as a starting material for the synthesis of HEPT analogs. These analogs have shown potential in inhibiting the replication of the HIV virus, making them a crucial component in the development of anti-HIV medications.
b. Monoamine Oxidase B Inhibition:
3-(2-Thienyl)acrylic acid 98 is also used in the synthesis of benzimidazole and caffeine (C080100) analogs, which act as inhibitors of monoamine oxidase B (MAO-B). These inhibitors are essential in the treatment of various neurodegenerative disorders, such as Parkinson's disease, by preventing the breakdown of dopamine in the brain.
2. Chemical Synthesis:
3-(2-Thienyl)acrylic acid 98 is used as a versatile building block in the synthesis of various organic compounds. Its unique chemical properties allow it to be a valuable component in the creation of new molecules with potential applications in various industries, including pharmaceuticals, materials science, and agrochemicals.

InChI:InChI=1/C7H6O2S/c8-7(9)4-3-6-2-1-5-10-6/h1-5H,(H,8,9)/p-1/b4-3+

Upstream product

• 98-03-3 thiophene-2-carbaldehyde 
• 141-82-2 malonic acid 
• 13979-15-2 ethyl (E)-3-(thiophen-2-yl)acrylate 
• 57502-38-2 methyl (E)-3-(2-thienyl)propenoate 
• 65946-59-0 (trimethylsilyl)ketene bis(trimethylsilyl) acetal 
• 3437-95-4 2-Iodothiophene 
• 79-10-7 acrylic acid 
• 201230-82-2 carbon monoxide 
• 477727-73-4 2-(thiophen-2-yl)vinyl bromide 
• 91228-44-3 2-thienylphenyliodonium tosylate 
• 2021-58-1 rac-3-(2-thienyl)alanine 
• 292638-85-8 acrylic acid methyl ester 
• 15875-50-0 2,2-dimethyl-5-thiophen-2-ylmethylene-[1,3]dioxane-4,6-dione 
• 874-83-9 (E)-4-(2-thienyl)but-3-en-2-one 

Downstream Products

• 57502-38-2 methyl (E)-3-(2-thienyl)propenoate 
• 100725-80-2 N-benzoyl-O-(3t-[2]thienyl-acryloyl)-hydroxylamine 
• 71447-46-6 4-(ξ-2-[2]thienyl-vinyl)-benzoic acid 
• 42970-79-6 (E)-2-[2-(4-nitrophenyl)ethenyl]thiophene 
• 95415-03-5 2-(4-nitro-phenyl)-5-(4-nitro-styryl)-thiophene 
• 50626-17-0 2-(4-nitro-phenyl)-3t-[2]thienyl-acrylic acid 
• 36650-39-2 trans-β-(2-thienyl)acrylamide 
• 28424-61-5 (2E)-3-(2-thiophenyl)-2-propenoyl chloride 
• 5871-68-1 2,3-dihydro-2-(2-thienyl)-1,5-benzothiazepin-4(5H)-one 
• 98-03-3 thiophene-2-carbaldehyde 
• 1026861-91-5 (E)-1-(4-{2-[Bis-(4-fluoro-phenyl)-methoxy]-ethyl}-piperazin-1-yl)-3-thiophen-2-yl-propenone 
• 111-14-8 oenanthic acid 
• 16862-05-8 methyl 3-(2-thienyl)propanoate 
• 251999-62-9 (E)-p-nitrophenyl 3-(2-thienyl)acrylate 

Relevant articles and documents

Discovery of Novel Benzothiazepinones as Irreversible Covalent Glycogen Synthase Kinase 3β Inhibitors for the Treatment of Acute Promyelocytic Leukemia

Recently, irreversible inhibitors have attracted great interest in antitumors due to their advantages of forming covalent bonds to target proteins. Herein, some benzothiazepinone compounds (BTZs) have been designed and synthesized as novel covalent GSK-3β inhibitors with high selectivity for the kinase panel. The irreversible covalent binding mode was identified by kinetics and mass spectrometry, and the main labeled residue was confirmed to be the unique Cys14 that exists only in GSK-3β. The candidate 4-3 (IC50 = 6.6 μM) showed good proliferation inhibition and apoptosis-inducing ability to leukemia cell lines, low cytotoxicity on normal cell lines, and no hERG inhibition, which hinted the potential efficacy and safety. Furthermore, 4-3 exhibited decent pharmacokinetic properties in vivo and remarkably inhibited tumor growth in the acute promyelocytic leukemia (APL) mouse model. All the results suggest that these newly irreversible BTZ compounds might be useful in the treatment of cancer such as APL.

Chlorination Reaction of Aromatic Compounds and Unsaturated Carbon-Carbon Bonds with Chlorine on Demand

Chlorination with chlorine is straightforward, highly reactive, and versatile, but it has significant limitations. In this Letter, we introduce a protocol that could combine the efficiency of electrochemical transformation and the high reactivity of chlorine. By utilizing Cl3CCN as the chloride source, donating up to all three chloride atom, the reaction could generate and consume the chlorine in situ on demand to achieve the chlorination of aromatic compounds and electrodeficient alkenes.

Dual Nickel/Ruthenium Strategy for Photoinduced Decarboxylative Cross-Coupling of α,β-Unsaturated Carboxylic Acids with Cycloketone Oxime Esters

Herein, a dual nickel/ruthenium strategy is developed for photoinduced decarboxylative cross-coupling between α,β-unsaturated carboxylic acids and cycloketone oxime esters. The reaction mechanism is distinct from previous photoinduced decarboxylation of α,β-unsaturated carboxylic acids. This reaction might proceed through a nickelacyclopropane intermediate. The C(sp2)-C(sp3) bond constructed by the aforementioned reaction provides an efficient approach to obtaining various cyanoalkyl alkenes, which are synthetically valuable organic skeletons in organic and medicinal chemistry, under mild reaction conditions. The protocol tolerates many critical functional groups and provides a route for the modification of complex organic molecules.

Iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabled aldehyde C-H methylation

A practical and general iron-catalyzed domino decarboxylation-oxidation of α,β-unsaturated carboxylic acids enabling aldehyde C-H methylation for the synthesis of methyl ketones has been developed. This mild, operationally simple method uses ambient air as the sole oxidant and tolerates sensitive functional groups for the late-stage functionalization of complex natural-product-derived and polyfunctionalized molecules.

Enantioselective Rauhut–Currier Reaction with β-Substituted Acrylamides Catalyzed by N-Heterocyclic Carbenes

β-Substituted acrylamides have low electrophilicity and are yet to be exploited in the enantioselective Rauhut–Currier reaction. By exploiting electron-withdrawing protection of the amide and moderate nucleophilicity N-heterocyclic carbenes, such substrates have been converted to enantioenriched quinolones. The reaction proceeds with complete diastereoselectivity, good yield, and modest enantioselectivity. Derivatizations are reported, as are computational studies, supporting decreased amide bond character with electron-withdrawing protection of the nitrogen.

Organic metal compound and organic light-emitting device

Organic metal compounds and organic light-emitting devices employing the same are provided. The organic metal compound has a chemical structure of Formula (I) or Formula (II): In particular, one of the following two conditions (1) and (2) is met: (1) R1 is deuterium or C1-6 deuterated alkyl group, when R3 and R4 are independently hydrogen, halogen, C1-6 alkyl group, C1-6 fluoroalkyl or C3-12 heteroaryl group; and (2) R1 is hydrogen, deuterium, C1-6 alkyl group, C1-6 deuterated alkyl group, C3-12 heteroaryl group, or C6-12 aryl group, when at least one of R3 and R4 is C6-12 aryl group or C6-12 fluoroaryl group.

Photocatalytic decarboxylative alkenylation of α-amino and α-hydroxy acid-derived redox active esters by NaI/PPh3 catalysis

Herein, we report the photocatalytic decarboxylative alkenylation reactions of N-(acyloxy)phthalimide derived from α-amino and α-hydroxy acids with 1,1-diarylethene, and with cinnamic acid derivatives through double decarboxylation, using sodium iodide and triphenylphosphine as redox catalysts. The reaction proceeds under mild irradiation conditions with visible blue light (440 nm or 456 nm) in an acetone solvent without recourse to transition-metal or organic dye based photoredox catalysts. The reaction proceeds via photoactivation of a transiently self-assembled chromophore from N-(acyloxy)phthalimide and NaI/PPh3. Solvation plays a crucial role in the reactivity.

Piperine derivative as well as preparation method and application thereof

The invention provides a piperine derivative as well as a preparation method and an application thereof. The piperine derivative is a compound shown as a formula (I), or a salt thereof, or a stereoisomer thereof, or a hydrate thereof. The compound provided by the invention can effectively protect nerve cells and improve the survival rate of the nerve cells, so that the compound provided by the invention can effectively treat neurodegenerative diseases and can be used for preparing medicines for treating the neurodegenerative diseases.

Introducing of potent cytotoxic novel 2-(aroylamino)cinnamamide derivatives against colon cancer mediated by dual apoptotic signal activation and oxidative stress

Curcumin and trans-cinnamaldehyde are acrolein-based Michael acceptor compounds that are commonly found in domestic condiments, and known to cause cancer cell death via redox mechanisms. Based on the structural features of these compounds we designed and synthesized several 2-cinnamamido-N-substituted-cinnamamide (bis-cinnamamide) compounds. One of the derivatives, (Z)-2-[(E)-cinnamamido]-3-phenyl-N-propylacrylamide 8 showed a moderate antiproliferative potency (HCT-116 cell line inhibition of 32.0 μM), no inhibition of normal cell lines C-166, and proven cellular activities leading to apoptosis. SAR studies led to more than 10-fold increase in activity. Our most promising compound, [(Z)-3-(1H-indol-3-yl)-N-propyl-2-[(E)-3-(thien-2-yl)propenamido)propenamide] 45 killed colon cancer cells at IC50 = 0.89 μM (Caco-2), 2.85 μM (HCT-116) and 1.65 μM (HT-29), while exhibiting much weaker potency on C-166 and BHK normal cell lines (IC50 = 71 μM and 77.6 μM, respectively). Cellular studies towards identifying the compounds mechanism of cytotoxic activities revealed that apoptotic induction occurs in part as a result of oxidative stress. Importantly, the compounds showed inhibition of cancer stem cells that are critical for maintaining the potential for self-renewal and stemness. The results presented here show discovery of covalently acting Michael addition compounds that potently kill cancer cells by a defined mechanism, with prominent selectivity profile over non-cancerous cell lines.

Radical-Cation Vinylcyclopropane Rearrangements by TiO2Photocatalysis

Radical cation vinylcyclopropane rearrangements by TiO2 photocatalysis in lithium perchlorate/nitromethane solution are described. The reactions are triggered by oxidative single electron transfer, which is followed by immediate ring-opening of the cyclopropanes to generate distonic radical cations as unique reactive intermediates. This approach can also be applied to vinylcyclobutane, leading to the construction of six-membered rings. A stepwise mechanism via distonic radical cations is proposed based on preliminary mechanistic studies, which is supported by density functional theory calculations.