306935-74-0

Basic information

• Product Name: 4-(4-CHLOROANILINO)-4-OXOBUT-2-ENOIC ACID
• Synonyms: TIMTEC-BB SBB000655;4-OXO-4-(4-CHLOROPHENYLAMINO)-2-BUTENOIC ACID;4-(4-CHLOROANILINO)-4-OXOBUT-2-ENOIC ACID
• CAS NO: 306935-74-0
• Molecular Formula: C₁₀H₈ClNO₃
• Molecular Weight: 225.63
• Mol File: 306935-74-0.mol
• Article Data: 10

Chemical Properties

• Melting Point: 200 °C
• Boiling Point: 466.2°Cat760mmHg
• Flash Point: 235.7°C
• Appearance: /
• Density: 1.448g/cm³
• Vapor Pressure: 1.72E-09mmHg at 25°C
• Refractive Index: 1.642
• PKA: 3.44±0.10(Predicted)
• CAS DataBase Reference: 4-(4-CHLOROANILINO)-4-OXOBUT-2-ENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-CHLOROANILINO)-4-OXOBUT-2-ENOIC ACID(306935-74-0)
• EPA Substance Registry System: 4-(4-CHLOROANILINO)-4-OXOBUT-2-ENOIC ACID(306935-74-0)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:Irritating to eyes, respiratory system and skin.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S37/39:Wear suitable g
• Hazardous Substances Data: 306935-74-0(Hazardous Substances Data)

Usage

General Description

4-(4-chloroanilino)-4-oxobut-2-enoic acid is a chemical compound with the molecular formula C10H9ClNO3. It is also known by the systematic name 4-(4-chlorophenylamino)-3-oxo-2-butenoic acid. 4-(4-CHLOROANILINO)-4-OXOBUT-2-ENOIC ACID is a derivative of 4-aminobenzoic acid and belongs to the class of aromatic amides. It is commonly used as a building block in organic synthesis and pharmaceutical research. The presence of a chlorine atom and an amino group in its chemical structure suggests potential applications in medicinal chemistry and drug development. Its main chemical properties and functional groups make it a versatile intermediate for the development of new compounds with various biological activities.

InChI:InChI=1/C10H8ClNO3/c11-7-1-3-8(4-2-7)12-9(13)5-6-10(14)15/h1-6H,(H,12,13)(H,14,15)/b6-5+

Upstream product

• 108-31-6 maleic anhydride 
• 106-47-8 4-chloro-aniline 

Downstream Products

• 1631-29-4 N-(4-chlorophenyl)maleimide 
• 485826-47-9 C₂₆H₁₆ClNO₅ 

Relevant articles and documents

Identification of two arylimides as cholinesterase inhibitors and testing of propranolol addition on impaired rat memory

Alzheimer's disease (AD) is clearly linked to the decline of acetylcholine (ACh) effects in the brain. These effects are regulated by the hydrolytic action of acetylcholinesterase (AChE). Therefore, a central palliative treatment of AD is the administration of AChE inhibitors although additional mechanisms are currently described and tested for generating advantageous therapeutic strategies. In this work, we tested new arylamides and arylimides as potential inhibitors of AChE using in silico tools. Then, these compounds were tested in vitro, and two selected compounds, C7 and C8, as well as propranolol showed inhibition of AChE. In addition, they demonstrated an advantageous acute toxicity profile compared to that of galantamine as a reference AChE inhibitor. in vivo evaluation of memory performance enhancement was performed in an animal model of cognitive disturbance with each of these compounds and propranolol individually as well as each compound combined with propranolol. Memory improvement was observed in each case, but without a significant additive effect with the combinations.

The discovery, design and synthesis of potent agonists of adenylyl cyclase type 2 by virtual screening combining biological evaluation

Adenylate cyclases (ACs), play a critical role in the conversion of adenosine triphosphate (ATP) into the second messenger cyclic adenosine monophosphate (cAMP). Studies have indicated that adenylyl cyclase type 2 (AC2) is potential drug target for many diseases, however, up to now, there is no AC2-selective agonist reported. In this research, docking-based virtual screening with the combination of cell-based biological assays have been performed for discovering novel potent and selective AC2 agonists. Virtual screening disclosed a novel hit compound 8 as an AC2 agonist with EC50 value of 8.10 μM on recombinant human hAC2 + HEK293 cells. The SAR (structure activity relationship) based on the derivatives of compound 8 was further explored on recombinant AC2 cells and compound 73 was found to be the most active agonist with the EC50 of 90 nM, which is 160-fold more potent than the reported agonist Forskolin and could selectively activate AC2 to inhibit the expression of Interleukin-6. The discovery of a new class of AC2-selective agonists would provide a novel chemical probe to study the physiological function of AC2.

Alizarin red S-TiO2-catalyzed cascade C(sp3)-H to C(sp2)-H bond formation/cyclization reactions toward tetrahydroquinoline derivatives under visible light irradiation

A very low amount of organic dye (Alizarin red S) sensitized TiO2 and it was successfully used to catalyze cascade C(sp3)-H to C(sp2)-H bond formation/cyclization reactions under visible light irradiation. The modified TiO2 photocatalyst efficiently, for the first time, advanced [4+2] cyclization of N,N-dimethylanilines and maleimides to the corresponding tetrahydroquinolines in air atmosphere. The reaction proceeds through α-amino radicals without additional oxidant at ambient temperature to afford products in good to excellent yields.