543-21-5

Basic information

• Product Name: ACETYLENEDICARBOXAMIDE
• Synonyms: Acetylendicarbonsaeureamid;Acetylenedicarboxylic acid diamide;acetylenedicarboxylicaciddiamide;Aquamycin;Lenamycin;Renamycin;2-BUTYNEDIAMIDE;ACETYLENEDICARBOXAMIDE
• CAS NO: 543-21-5
• Molecular Formula: C₄H₄N₂O₂
• Molecular Weight: 112.09
• EINECS: 200-816-9
• Mol File: 543-21-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 179 °C
• Boiling Point: 209.98°C (rough estimate)
• Flash Point: 131.6°C
• Appearance: Cream to beige/Fine Crystalline Powder
• Density: 1.4421 (rough estimate)
• Vapor Pressure: 0.00167mmHg at 25°C
• Refractive Index: 1.4610 (estimate)
• PKA: 13.01±0.50(Predicted)
• CAS DataBase Reference: ACETYLENEDICARBOXAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ACETYLENEDICARBOXAMIDE(543-21-5)
• EPA Substance Registry System: ACETYLENEDICARBOXAMIDE(543-21-5)

Safety Data

• Hazard Codes: T
• Statements: 25-21
• Safety Statements: 45-36/37-28A
• Hazardous Substances Data: 543-21-5(Hazardous Substances Data)

Usage

Description

ACETYLENEDICARBOXAMIDE, also known as Cellocidin, is a dicarboxylic acid diamide derived from the formal condensation of both carboxy groups of butynedioic acid with ammonia. It is an antibiotic originally isolated from Streptomyces chibaensis and is characterized by its cream to beige fine crystalline powder appearance. Cellocidin possesses a broad antibacterial, antifungal, and antitumor profile due to its ability to react with endogenous thiols like cysteine and glutathione.

Uses

Used in Pharmaceutical Applications:
ACETYLENEDICARBOXAMIDE is used as an antibiotic for its activity against various bacterial strains, including M. tuberculosis, and against the trypanosomes T. brucei and T. rhodesiense. It also inhibits the proliferation of LCL1 and LCL2 cells transformed by Epstein-Barr virus (EBV), activates the c-Myc and NF-κB pathways in BC3 and LCL1 cells, and induces necrotic cell death in B cells infected with gammaherpes virus.
Used in Agricultural Applications:
ACETYLENEDICARBOXAMIDE is used as a protective agent against bacterial leaf blight in rice plants. It inhibits α-ketoglutarate oxidation in X. oryzae, the bacterium that causes leaf blight, when used at a concentration of 1 ppm, suggesting that it inhibits the citric acid cycle. Formulations containing ACETYLENEDICARBOXAMIDE have been used as agricultural pesticides.

Purification Methods

Acetylenedicarboxamide crystallises from MeOH and H2O [m 190-192o(dec) as hemihydrate]. When prepared from the ester + NH3 it has m 213o(dec). Also a melting point of 290-292o(dec) has been reported. [Saggimo J Org Chem 22 1171 1857, Kharash et al. J Org Chem 10 392 1945, Blomquist & Winslow J Org Chem 10 156 1945, Beilstein 2 I 317, 2 III 1995, 2 IV 2295.]

InChI:InChI=1/C4H4N2O2/c5-3(7)1-2-4(6)8/h(H2,5,7)(H2,6,8)

Upstream product

• 363-59-7 dimethyl α,α'-difluorosuccinate 
• 762-42-5 dimethyl acetylenedicarboxylate 

Downstream Products

• 1071-98-3 2-butynedinitrile 
• 38066-72-7 C₅₄H₄₄N₂ 
• 18352-46-0 (E)-2-[Bis-(2-chloro-ethyl)-amino]-but-2-enedioic acid diamide 
• 83341-05-3 2-(1,3-Diphenyl-2-imidazolidinyliden)-1,3-dithiol-4,5-dicarbonsaeure-diamid 
• 1070-71-9 propiolonitrile 
• 436084-20-7 5-(4-methoxy-phenyl)-1,4,6,7,7-pentamethyl-bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid diamide 
• 1416133-74-8 1-[2-(phenylsulfonamido)ethyl]-1H-1,2,3-triazole-4,5-dicarboxylamide 

Relevant articles and documents

From Linear Molecular Chains to Extended Polycyclic Networks: Polymerization of Dicyanoacetylene

Dicyanoacetylene (C4N2) is an unusual energetic molecule with alternating triple and single bonds (think miniature, nitrogen-capped carbyne), which represents an interesting starting point for the transformation into extended carbon-nitrogen solids. While pressure-induced polymerization has been documented for a wide variety of related molecular solids, precise mechanistic details of reaction pathways are often poorly understood and the characterization of recovered products is typically incomplete. Here, we study the high-pressure behavior of C4N2 and demonstrate polymerization into a disordered carbon-nitrogen network that is recoverable to ambient conditions. The reaction proceeds via activation of linear molecules into buckled molecular chains, which spontaneously assemble into a polycyclic network that lacks long-range order. The recovered product was characterized using a variety of optical spectroscopies, X-ray methods, and theoretical simulations and is described as a predominately sp2 network comprising "pyrrolic" and "pyridinic" rings with an overall tendency toward a two-dimensional structure. This understanding offers valuable mechanistic insights into design guidelines for next-generation carbon nitride materials with unique structures and compositions.

The infrared and Raman spectrum of dicyanoacetylene. The ν9 fundamental

The Raman spectrum of liquid dicyanoacetylene, NC-CC-CN, was reinvestigated and ν3 found at 617 cm-1.The Fermi resonance between ν1 and 2ν5 is explained, considering the isotopic species NC-13CC-CN.The high resolution infrared spectrum of the lowest frequency fundamental ν9 has been recorded for the first time, and the rotational constants for several states with v9 /= 9 have been determied.