Dicyanoacetylene

Base Information

• Chemical Name: Dicyanoacetylene
• CAS No.: 1071-98-3
• Molecular Formula: C4N2
• Molecular Weight: 76.0574
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID50147919
• Nikkaji Number: J43.493K
• Wikipedia: Dicyanoacetylene
• Wikidata: Q903293
• Mol file: 1071-98-3.mol

Synonyms:Dicyanoacetylene;2-Butynedinitrile;but-2-ynedinitrile;Dicyanoethyne;1071-98-3;ACETYLENEDICARBONITRILE;Sous-azote de carbone;Sous-azote de carbone [French];BRN 1735267;C4N2;dicyanovinylene;1,2-Dicyanoacetylene;NCC.$.CCN;DTXSID50147919;C4-N2;Q903293

Chemical Property of Dicyanoacetylene

Chemical Property:

• Vapor Pressure: 101mmHg at 25°C
• Melting Point: 20.5°C
• Refractive Index: 1.4647
• Boiling Point: 76.5°Cat760mmHg
• Flash Point: °C
• PSA: 47.58000
• Density: 1.176g/cm³
• LogP: 0.03696
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 76.006148008
• Heavy Atom Count: 6
• Complexity: 163

Purity/Quality:

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

2-BUTYNEDINITRILE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: C(#CC#N)C#N

Technology Process of Dicyanoacetylene

There total 9 articles about Dicyanoacetylene 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: 60.0%

Cellocidin (543-21-5) → 2-butynedinitrile (1071-98-3)

Guidance literature:

With phosphorus pentoxide; In sulfolane; at 110 ℃; for 3h; Inert atmosphere;

DOI:10.1021/acs.chemmater.7b01446

Reference yield: 33.0%

Cellocidin (543-21-5) → propiolonitrile (1070-71-9) + 2-butynedinitrile (1071-98-3)

Guidance literature:

With phosphorus pentoxide; at 100 - 370 ℃; self-propagating stationary heat wave mode;

Reference yield:

propiolonitrile (1070-71-9) → 2-butynedinitrile (1071-98-3) + cyanoacetylene-d (6922-94-7) + Dicyanodiacetylene (16419-78-6) + penta-2,4-diynenitrile (59866-32-9) + cyanoethynyl radical (62435-43-2) + acetylene (74-86-2,25067-58-7)

Guidance literature:

With deuterium; under 1.5 Torr; Quantum yield; Irradiation; various pressures of D₂;

DOI:10.1021/jp952787z

upstream raw materials:

Cellocidin

propiolonitrile

ethenetetracarbonitrile

cyanogen chloride

Downstream raw materials:

2,3-dicyanonorbornadiene

3-methylphthalonitrile

1.2-Dicyan-3.4-dihydro-4-methyl-4-(α.α-dimethyl-benzyl)-naphthalin

3-hydroxy-6-pentyl-1,2-benzenedicarbonitrile

Refernces

• 1、 Saggiomo. "-". . p. 1171,1174. Retrieved 1957.
• 2、 Gou, Huiyang,Zhu, Li,Huang, Haw-Tyng,Biswas, Arani,Keefer, Derek W.,Chaloux, Brian L.,Prescher, Clemens,Yang, Liuxiang,Kim, Duck Young,Ward, Matthew D.,Lerach, Jordan,Wang, Shengnan,Oganov, Artem R.,Epshteyn, Albert,Badding, John V.,Strobel, Timothy A.. "From Linear Molecular Chains to Extended Polycyclic Networks: Polymerization of Dicyanoacetylene". . p. 6706 - 6718. Retrieved 2017.
• 3、 Seki, Kanekazu,Yagi, Mikio,He, Maoqi,Halpern, Joshua B.,Okabe, Hideo. "Reaction rates of the CN radical with diacetylene and dicyanoacetylene". . p. 657 - 662. Retrieved 1996.
• 4、 Khlifi,Paillous,Bruston,Guillemin,Benilan,Daoudi,Raulin. "Gas infrared spectra, assignments, and absolute IR band intensities of C4N2 in the 250-3500 cm-1 region: Implications for Titan's stratosphere". . p. 707 - 712. Retrieved 1997.
• 5、 Winther, F.,Ketelsen, M.,Guarnieri, A.. "The infrared and Raman spectrum of dicyanoacetylene. The ν9 fundamental". . p. 65 - 74. Retrieved 1994.
• 6、 -. "NOVEL COMPOUND AND METHOD OF PRODUCING ORGANIC SEMICONDUCTOR DEVICE". . . Retrieved 2008/12/06.