Diacetylene

Base Information

• Chemical Name: Diacetylene
• CAS No.: 460-12-8
• Molecular Formula: C4H2
• Molecular Weight: 50.0599
• Hs Code.: 2901299090
• European Community (EC) Number: 207-303-9
• UNII: 6389J044O5
• DSSTox Substance ID: DTXSID8060036
• Nikkaji Number: J401D
• Wikipedia: Diacetylene
• Wikidata: Q422802
• Metabolomics Workbench ID: 55690
• Mol file: 460-12-8.mol

Synonyms:Butadiyne(8CI); Biacetylene; Biethynyl; Diacetylene

Chemical Property of Diacetylene

Chemical Property:

• Appearance/Colour: gas
• Vapor Pressure: 1270mmHg at 25°C
• Melting Point: -35.99°C
• Refractive Index: 1.4189
• Boiling Point: 10.3°Cat760mmHg
• Flash Point: °C
• PSA: 0.00000
• Density: 0.806g/cm³
• LogP: 0.25280
• Water Solubility.: 1g/L(25 oC)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 50.0156500638
• Heavy Atom Count: 4
• Complexity: 67.1

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Chemical Classes: Other Classes -> Aliphatics, Unsaturated
• Canonical SMILES: C#CC#C

Technology Process of Diacetylene

There total 139 articles about Diacetylene 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: 93.0%

1,4-Dichloro-2-butyne (821-10-3) → Butadiyne (460-12-8,27987-87-7)

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide; at 70 - 75 ℃; into -78 deg C cooling trap;

DOI:10.1021/ol034258g

Reference yield: 67.5%

ethynylmagnesium chloride (65032-27-1) → Butadiyne (460-12-8,27987-87-7)

Guidance literature:

With 1,2-dichloro-ethane; manganese(ll) chloride; In tetrahydrofuran; at 25 ℃; for 12h; Inert atmosphere;

DOI:10.1016/j.jorganchem.2008.12.021

Reference yield:

3-buten-1-yne (689-97-4) → styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + Butadiyne (460-12-8,27987-87-7) + naphthalene (91-20-3,71998-51-1,72931-45-4) + phenylacetylene (536-74-3) + 1-indene (95-13-6) + acetylene (74-86-2,25067-58-7)

Guidance literature:

at 800 ℃; for 8.33333E-05h; Product distribution; Mechanism;

DOI:10.1016/0040-4039(95)00629-Q

upstream raw materials:

2-bromofuran

2,7-dimethyl-octa-3,5-diyne-2,7-diol

2-methyl-but-2-ene

diphenylether

Downstream raw materials:

3-ethynyl-1⁽²⁾H-pyrazole

3,3'-bi(1H-pyrazole)

1-methoxy-buten-3-yne

1-ethoxybut-1-en-3-yne

Refernces

Trithiocarbonate Anion as a Sulfur Source for the Synthesis of 2,5-Disubstituted Thiophenes and 2-Substituted Benzo[ b]thiophenes

10.1021/acs.joc.0c01516

The study focuses on the synthesis of 2,5-disubstituted thiophenes and 2-substituted benzo[b]thiophenes using the trithiocarbonate anion (CS32-) as a sulfur source. This anion was generated in situ from carbon disulfide (CS2) and potassium hydroxide (KOH) in dimethyl sulfoxide (DMSO). The purpose of these chemicals is to serve as a novel synthetic equivalent of the S2- synthon, which is used for the cyclization of 1,3-butadiynes and 2-haloalkynyl (hetero)arenes. The study aims to provide a cheap and readily available method for the synthesis of these compounds, which have applications in various fields such as biochemistry, materials chemistry, and organic synthesis. The use of CS32- allows for metal-free cyclization reactions, offering a moderate to good yield of the target compounds with good functional group tolerance.

Synthesis and evaluation of high-birefringence polymethacrylate having a diphenyl-diacetylene LC moiety in the side chain

10.1039/c2jm32489j

The research primarily focuses on the synthesis and evaluation of a high-birefringence polymethacrylate with a diphenyl-diacetylene (DPDA) moiety in the side chain. The polymer was designed to form a nematic liquid crystal (LC) phase with a wide temperature range and exhibit high birefringence, which is crucial for applications in optical devices such as flat panel displays, optical fibers, and photostorage devices. The synthesis involved Negishi cross-coupling of an asymmetric diacetylene protected with a tert-butyldimethylsilyl (TBDMS) group and 2,2-dibromoalkene, followed by E2 reaction and deprotection with tetra-n-butylammonium fluoride (TBAF), and esterification with methacrylate chloride. Anion polymerization using n-butyllithium (n-BuLi) was employed to obtain the final polymer. The thermal properties were analyzed using differential scanning calorimetry (DSC) and polarizing optical microscopy (POM), while the optical properties, specifically the birefringence, were determined through UV-visible spectroscopy and a microscope spectroscopic method with a Nikon LV100 Pol optical microscope and a USB4000 spectrometer. The polymer showed a high birefringence of 0.3 at 550 nm at room temperature, indicating its potential for use in optical applications.