5465-37-2

Basic information

• Product Name: (2E)-1,4-bis(4-chlorophenyl)but-2-ene-1,4-dione
• Synonyms: (2E)-1,4-Bis(4-chlorophenyl)-2-butene-1,4-dione
• CAS NO: 5465-37-2
• Molecular Formula: C₁₆H₁₀Cl₂O₂
• Molecular Weight: 305.1554
• Mol File: 5465-37-2.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 443.7°C at 760 mmHg
• Flash Point: 187°C
• Density: 1.321g/cm³
• Vapor Pressure: 4.55E-08mmHg at 25°C
• Refractive Index: 1.612
• CAS DataBase Reference: (2E)-1,4-bis(4-chlorophenyl)but-2-ene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-1,4-bis(4-chlorophenyl)but-2-ene-1,4-dione(5465-37-2)
• EPA Substance Registry System: (2E)-1,4-bis(4-chlorophenyl)but-2-ene-1,4-dione(5465-37-2)

Safety Data

• Hazardous Substances Data: 5465-37-2(Hazardous Substances Data)

Usage

General Description

The chemical (2E)-1,4-bis(4-chlorophenyl)but-2-ene-1,4-dione, also known as tetrachlorobenzoquinone, is an organic compound with the molecular formula C16H10Cl4O2. It is a yellow, crystalline solid that is commonly used as a dye intermediate and in the production of pharmaceuticals. Tetrachlorobenzoquinone is also known for its strong oxidizing properties, and it is often used as a reagent in organic synthesis. Additionally, it has been studied for its potential as an anti-tumor agent due to its ability to induce cell death in cancer cells. However, it is important to note that tetrachlorobenzoquinone is considered to be toxic and should be handled with proper precautions.

Upstream product

• 859811-17-9 1,4-bis-(4-chloro-phenyl)-2-methoxy-butane-1,4-dione 
• 627-63-4 fumaryl dichloride 
• 108-90-7 chlorobenzene 
• 3282-33-5 1-(4-chlorophenyl)-2-diazoethanone 
• 103-26-4 Methyl cinnamate 
• 110-83-8 cyclohexene 
• 4998-15-6 4-chlorophenylglyoxal 
• 1777-56-6 4-chlorobenzoylmethylenetriphenylphosphorane 
• 873-73-4 4-n-chlorophenylacetylene 
• 24314-35-0 1,4-bis(4-chlorophenyl)butane-1,4-dione 
• 536-38-9 4-chlorobenzoylmethyl bromide 
• 99-91-2 para-chloroacetophenone 
• 7647-01-0 hydrogenchloride 
• 7446-08-4 selenium(IV) oxide 

Downstream Products

• 24314-35-0 1,4-bis(4-chlorophenyl)butane-1,4-dione 
• 5465-45-2 (+/-)-1.2-dimethyl-4r.5t-bis-(4-chloro-benzoyl)-cyclohexene-⁽¹⁾ 
• 859811-17-9 1,4-bis-(4-chloro-phenyl)-2-methoxy-butane-1,4-dione 
• 34102-86-8 3,6-bis-(4-chlorophenyl)-pyridazine 
• 74103-65-4 2,3-dibromo-1,4-bis-(4-chloro-phenyl)-butane-1,4-dione 
• 1426129-78-3 5-(4-chlorophenyl)-4-[2-(4-chlorophenyl)-2-oxoethyl]-2-methyl-1H-pyrrole-3-carboxylic acid methyl ester 
• 1426129-79-4 5-(4-chlorophenyl)-4-[2-(4-chlorophenyl)-2-oxoethyl]-2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester 
• 1426129-80-7 2-[4-acetyl-2-(4-chlorophenyl)-5-methyl-1H-pyrrol-3-yl]-1-(4-chlorophenyl)ethanone 
• 36710-36-8 2,5-bis-(4-chlorophenyl)furan 

Relevant articles and documents

Visible-Light-Driven Stereoselective Annulation of Alkyl Anilines and Dibenzoylethylenes via Electron Donor-Acceptor Complexes

A catalyst-free, stereoselective visible-light-driven annulation reaction between alkenes and N,N-substituted dialkyl anilines for the synthesis of substituted tetrahydroquinolines is presented. The reaction is driven by the photoexcitation of an electron donor-acceptor (EDA) complex, and the resulting products are obtained in good to high yields with complete diastereoselectivity. Mechanistic rationale and photochemical characterization of the EDA-complex are provided.

Visible-light-mediated oxidative dimerization of arylalkynes in the open air: Stereoselective synthesis of (Z)-1,4-enediones

An organic photoredox catalytic one-pot protocol is developed for the highly stereoselective synthesis of (Z)-1,4-enediones. The reaction starts directly from alkyne precursors, using 4-(4-cyanophenyl)-2,6-diphenylpyrylium tetrafluoroborate (CN-TPT) as an efficient photosensitizer and dioxygen in the air as a green oxidant. A Csp-Csp oxidative coupling/[4 + 2] cyclization (with dioxygen)/fragmentive isomerization cascade mechanism was proposed. The predominant formation of (Z)-1,4-enediones is attributed to the efficient visible-light illumination from blue LEDs, along with possible energy transfer from the photosensitizer CN-TPT to the E-isomers.

Asymmetric organocatalytic aza-michael reactions of isatin derivatives

Isatin was activated by derivatization to a Schiff base with aniline and used as an aza-Michael donor in organocatalytic asymmetric reactions with symmetric and nonsymmetric unsaturated 1,4-diketones. After hydrolysis (in situ), the N-substituted isatins were obtained in high yields (up to >95%) with high enantioselectivity (up to 95%).