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Benzene, 1,1-(1,2-ethynediyl)bis(4-chloro-, also known as 1,4-dichlorobenzene, is a chemical compound that features a benzene ring with two chlorine atoms and an ethynediyl bridge. Benzene, 1,1-(1,2-ethynediyl)bis(4-chlorois highly reactive due to the presence of the ethynediyl group, which facilitates the formation of various derivatives and functional groups. The chloro substituents enhance its utility in the synthesis of chlorinated compounds. However, it is essential to handle this chemical with care due to its toxic nature and potential hazards to human health and the environment.

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  • 1820-42-4 Structure
  • Basic information

    1. Product Name: Benzene, 1,1-(1,2-ethynediyl)bis(4-chloro-
    2. Synonyms:
    3. CAS NO:1820-42-4
    4. Molecular Formula: C14H8Cl2
    5. Molecular Weight: 247.124
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 1820-42-4.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 352.3°Cat760mmHg
    3. Flash Point: 163.1°C
    4. Appearance: N/A
    5. Density: 1.3g/cm3
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: Benzene, 1,1-(1,2-ethynediyl)bis(4-chloro-(CAS DataBase Reference)
    10. NIST Chemistry Reference: Benzene, 1,1-(1,2-ethynediyl)bis(4-chloro-(1820-42-4)
    11. EPA Substance Registry System: Benzene, 1,1-(1,2-ethynediyl)bis(4-chloro-(1820-42-4)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 1820-42-4(Hazardous Substances Data)

1820-42-4 Usage

Uses

Used in Organic Synthesis:
Benzene, 1,1-(1,2-ethynediyl)bis(4-chlorois utilized as a reagent in organic synthesis for the production of various chemicals and materials. Its high reactivity allows for the formation of numerous derivatives and functional groups, making it a valuable component in the synthesis process.
Used in Chemical Production:
Benzene, 1,1-(1,2-ethynediyl)bis(4-chloroserves as a building block in the manufacturing of a wide range of chemicals and materials. Its unique structure and reactivity contribute to the development of new products and innovations in the chemical industry.
Used in Chlorinated Compound Preparation:
The presence of chloro substituents in Benzene, 1,1-(1,2-ethynediyl)bis(4-chloromakes it useful in the preparation of various chlorinated compounds. These chlorinated products find applications in different industries, such as pharmaceuticals, agrochemicals, and polymers.
Used in Pharmaceutical Industry:
Benzene, 1,1-(1,2-ethynediyl)bis(4-chlorois employed as an intermediate in the synthesis of certain pharmaceutical compounds. Its reactivity and functional group compatibility make it suitable for the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
Benzene, 1,1-(1,2-ethynediyl)bis(4-chlorois also used in the agrochemical industry for the synthesis of various agrochemical products, such as pesticides and herbicides. Its reactivity and chlorinated nature contribute to the effectiveness of these products in controlling pests and weeds.
Used in Polymer Industry:
Benzene, 1,1-(1,2-ethynediyl)bis(4-chlorois utilized in the polymer industry for the production of specific polymers and polymer additives. Its unique structure and reactivity enable the development of new polymer materials with improved properties and performance.

Check Digit Verification of cas no

The CAS Registry Mumber 1820-42-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,8,2 and 0 respectively; the second part has 2 digits, 4 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 1820-42:
(6*1)+(5*8)+(4*2)+(3*0)+(2*4)+(1*2)=64
64 % 10 = 4
So 1820-42-4 is a valid CAS Registry Number.

1820-42-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-chloro-4-[2-(4-chlorophenyl)ethynyl]benzene

1.2 Other means of identification

Product number -
Other names p,p'-Dichlorobenzil

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1820-42-4 SDS

1820-42-4Relevant articles and documents

Rhodium(III)-catalysed decarbonylative annulation through C-H activation: Expedient access to aminoisocoumarins by weak coordination

Mayakrishnan, Sivakalai,Arun, Yuvaraj,Maheswari, Narayanan Uma,Perumal, Paramasivan Thirumalai

, p. 11889 - 11892 (2018)

Rhodium-catalysed decarbonylative annulation of isatoic anhydrides with alkynes through C-H activation for the synthesis of aminoisocoumarins was developed. This enables the gram-scale transformation to iodoisocoumarin which is a vital building block in transition-metal-catalysed cross couplings. These compounds exhibit blue-emitting luminescence properties.

Direct coupling reactions of alkynylsilanes catalyzed by palladium(II) chloride and a di(2-pyridyl)methylamine-derived palladium(II) chloride complex in water and in NMP

Gil-Molto, Juan,Najera, Carmen

, p. 1874 - 1882 (2006)

Symmetrical internal alkynes can be prepared either by diarylation of mono- and bis(trimethylsilyl)acetylene (TMSA and BTMSA) catalyzed by ligand-less palladium(II) chloride or by a di(2-pyridyl) methylamine-derived palladium(II) chloride complex 1 (typic

Synthesis of α,α-Dichloroketones through Sequential Reaction of Decarboxylative Coupling and Chlorination

Cho, Eunjeong,Kim, Myungjin,Jayaraman, Aravindan,Kim, Jimin,Lee, Sunwoo

, p. 781 - 784 (2018)

2,2-Dichloro-1,2-diarylethanones were synthesized from diarylalkynes and trichloroisocyanuric acid. The reaction was conducted in CH3CN/H2O at room temperature for 12 h. In addition, the desired 2,2-dichloro-1,2-diarylethanones could be prepared from aryl bromides and propiolic acid through sequential Pd-catalyzed decarboxylative coupling and chlorination. This method showed moderate to good yields and good tolerance toward functional groups such as chlorides, bromides, aldehydes, and ketones.

Poly(phenylene-carborane) for boron-carbide/carbon ceramic precursor synthesized via nickel catalysis

Cheng, Shengli,Yuan, Kuanyu,Wang, Xin,Han, Jianhua,Jian, Xigao,Wang, Jinyan

, p. 224 - 231 (2017)

High thermally and thermo-oxidatively stable poly(phenylene-carborane) (PPB) was synthesized via Ni(0)-catalyzed polymerization of bis(aryl chloride) monomer containing carborane. This polymer was soluble in THF and NMP at room temperature, thus allowing

Extensive Substituent Scrambling in Substituted Diphenylacetylenes on Electron Impact

Ramana. D. V.,Krishna, N. V. S. Rama

, p. 903 - 908 (1989)

Extensive randomization of the substituents is found in mono- and disubstituted diphenylacetylenes under electron impact conditions.The study of diphenylacetylenes with a variety of substituents indicates that the electron-withdrawing groups favour the substituent scrambling.All the substituted diphenylaceetylenes give an ion at m/z 176, having a common ion-structure, arising as a result of the expulsion of a hydrogen radical and the substituent in monosubstituted diphenylacetylenes and the expulsion of both the substituents in disubstituted diphenylacetylenes.A ring-expanded structure is postulated for this common fragment.

Pd-Catalyzed Alkyne Insertion/C-H Activation/[4 + 2] Carboannulation of Alkenes to the Synthesis of Polycyclics

Guo, Songjin,Li, Panpan,Guan, Zhe,Cai, Libo,Chen, Siwei,Lin, Aijun,Yao, Hequan

, p. 921 - 925 (2019)

An unprecedented Pd-catalyzed alkyne insertion/C-H activation/intramolecular [4 + 2] carboannulation of alkenes has been reported. In this transformation, the C-H activation was triggered by an in situ generated alkenylpalladium species via the Pd-catalyzed cross-coupling reaction of aryl iodides and alkynes. Subsequently, the resulting five-membered C, C-palladacycle intermediates were added across the alkenes, providing a unique approach to access diversified polycyclics in good efficiency. Two new rings and three C-C bonds were formed in one pot.

Synthesis and Photophysical Study of Heteropolycyclic and Carbazole Motif: Nickel-Catalyzed Chelate-Assisted Cascade C-H Activations/Annulations

Prusty, Namrata,Banjare, Shyam Kumar,Mohanty, Smruti Ranjan,Nanda, Tanmayee,Yadav, Komal,Ravikumar, Ponneri C.

supporting information, p. 9041 - 9046 (2021/11/30)

Herein, nickel-catalyzed synthesis of polyarylcarbazole through sequential C-H bond activations has been described. Regioselective indole C2/C3 functionalization has been achieved in the presence of indole C7-H, which is quite challenging. In addition, this approach also gives easy access to building a heteropolycyclic motif through C6/C7 C-H functionalization of indoline. This methodology is not limited to aromatic internal alkynes as coupling partners; aliphatic alkynes have also shown good tolerance. Notably, during the optimization the catalytic enhancement with sodium iodide as an additive has been observed. We have also studied the photophysical properties of these highly conjugated molecules.

Palladium-Catalyzed Cascade Dearomative Spirocyclization and C?H Annulation of Aromatic Halides with Alkynes

Liao, Xingrong,Zhou, Fulin,Bin, Zhengyang,Yang, Yudong,You, Jingsong

supporting information, p. 5203 - 5207 (2021/07/19)

Described herein is a palladium-catalyzed intermolecular dearomative annulation of aryl halides with alkynes, which provides a rapid approach to a class of structurally unique spiroembedded polycyclic aromatic compounds. The cascade process is accomplished by a sequential alkyne migratory insertion, Heck-type dearomatization, and C-H bond annulation. Further optoelectronic study indicated this fused spirocyclic scaffold could be a potential host material for OLEDs, as exemplified by a fabricated red PhOLED device with a maximum external quantum efficiency of 23.0%.

Selective Synthesis of Non-Aromatic Five-Membered Sulfur Heterocycles from Alkynes by using a Proton Acid/N-Chlorophthalimide System

Yu, Wentao,Zhu, Baiyao,Shi, Fuxing,Zhou, Peiqi,Wu, Wanqing,Jiang, Huanfeng

supporting information, p. 1313 - 1322 (2020/12/01)

A multicomponent strategy to achieve two different regioselectivities from alkynes, isothiocyanates and H2O with a proton acid/N-chlorophthalimide (NCPI) system is described to selectively obtain non-aromatic five-membered sulfur heterocycles (1,3-oxathiol-2-imines/thiazol-2(3H)-one derivatives) through multiple bond formations. The process features readily available starting materials, mild reaction conditions, broad substrate scope, good functional-group tolerance, high regio- and chemo- selectivities, gram-scale synthesis and late-stage modifications. Mechanistic studies support the proposal that the transformation process includes a combination of H2O and isothiocyanate, free-radical formation, carbonation and intramolecular cyclization to give the products. Furthermore, the 1,3-oxathiol-2-imine derivatives possess unique fluorescence characteristics and can be used as Pd2+ sensors with a “turn-off” response, demonstrating potential applications in environmental and biological fields.

Rhodium-Catalyzed Regioselective Hydroformylation of Alkynes to α,β-Unsaturated Aldehydes Using Formic Acid

Fan, Chao,Hou, Jing,Chen, Yu-Jia,Ding, Kui-Ling,Zhou, Qi-Lin

supporting information, p. 2074 - 2077 (2021/04/05)

A rhodium-catalyzed hydroformylation of alkynes with formic acid was developed. The method provides α,β-unsaturated aldehydes in high yield and E-selectivity without the need to handle toxic CO gas.

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