Dichloroacetylene

Base Information

• Chemical Name: Dichloroacetylene
• CAS No.: 7572-29-4
• Molecular Formula: C2Cl2
• Molecular Weight: 94.928
• European Community (EC) Number: 620-404-6
• ICSC Number: 1426
• UNII: 95I833JV4S
• DSSTox Substance ID: DTXSID7020429
• Nikkaji Number: J33.811G
• Wikipedia: Dichloroacetylene
• Wikidata: Q20963653
• Mol file: 7572-29-4.mol

Synonyms:dichloroacetylene;dichloroethyne

Chemical Property of Dichloroacetylene

Chemical Property:

• Vapor Pressure: 122mmHg at 25°C
• Melting Point: -1.8oC
• Refractive Index: 1.4279
• Boiling Point: 74.1°Cat760mmHg
• Flash Point: 7.3°C
• PSA: 0.00000
• Density: 1.403g/cm³
• LogP: 1.38240
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 93.9377054
• Heavy Atom Count: 4
• Complexity: 46.9

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s): Confirmed carcinogen. TLV: ceiling 0.1 ppm.
• Hazard Codes: E,Xn
• Statements: 2-40-48/20
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Halogenated Aliphatics, Unsaturated
• Canonical SMILES: C(#CCl)Cl
• Inhalation Risk: A harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance may cause effects on the nervous system and kidneys. This may result in tissue lesions, impaired functions and kidney impairment.
• General Description: Dichloroethyne (dichloroacetylene, ClC≡CCl) serves as a key intermediate in the elimination-addition mechanism of enolate dichlorovinylation, where it reacts with enols to form α-dichlorovinyl ketones. Its reactivity is influenced by the competition between unimolecular chloride elimination and bimolecular proton abstraction, highlighting its role as a versatile Michael acceptor in haloacetylene chemistry. The study underscores its synthetic utility in ethynylation and vinylation reactions involving enol systems.

Technology Process of Dichloroacetylene

There total 14 articles about Dichloroacetylene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

Trichloroethylene (79-01-6) → dichloroethyne (7572-29-4) + chloroacetylene (593-63-5) + 1,2-Dichloro-ethyne; hydrochloride (73787-88-9)

Guidance literature:

In various solvent(s); at -258.2 ℃; for 18h; Irradiation; vacuum-UV photolysis in argon matrix; IR examination of the product mixture;

DOI:10.1021/ja00529a004

Reference yield:

Trichloroethylene (79-01-6) → dichloroethyne (7572-29-4) + 1,2-Dichloroethylene (540-59-0,43695-79-0) + chloroacetylene (593-63-5) + 1,1-Dichloroethylene (75-35-4,9002-85-1)

Guidance literature:

With H; at 776.9 ℃; Mechanism; Rate constant;

DOI:10.1021/j100010a028

Reference yield:

Trichloroethylene (79-01-6) → dichloroethyne (7572-29-4) + chloroacetylene (593-63-5)

Guidance literature:

Mechanism; Thermodynamic data; Irradiation; translational energy;

DOI:10.1063/1.476568

upstream raw materials:

Trichloroethylene

tetrachloromethane

1,1,2,2-tetrachloroethylene

1,2-dichlorofluoroethylene

Downstream raw materials:

1,2-di(1-hydroxycyclohexyl)acetylene

hexachlorobenzene

1-chloro-2-cyclohexylethyne

(E)-1,2-dichloro-1-ethoxy-ethene

Refernces

CHLOROACETYLENES AS MICHAEL ACCEPTORS. I. MECHANISM OF ENOLATE DICHLOROVINYLATION.

10.1016/S0040-4039(00)87344-X

The study aimed to elucidate the mechanism of the condensation of enol dichloroacetylene with trichloroethylene to form α-dichlorovinyl ketone, which was previously unclear. The study concluded that the reaction proceeds via dichloroacetylene as an essential intermediate and the mechanism is elimination-addition. The fate of the initial adduct of dichloroacetylene and enol depends on the competition between unimolecular elimination of Cl- and bimolecular proton abstraction. The key chemicals used in the process include trichloroethylene, dichloroacetylene (ClC≡CCl), lithium diisopropylamide (LDA), hexamethylphosphoramide (HMPA) and lithium bis(trimethylsilyl)amide (LiN(SiMe3)2). The study also involved the use of deuterated trichloroethylene to study the isotope effect, supporting the proposed mechanism. This work has important implications for the synthetic scope of haloacetylene chemistry in the ethynylation and vinylation of enol systems.

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