461-58-5

Basic information

• Product Name: Dicyandiamide
• Synonyms: acr-h3636;aralditeht986;aralditexb2879b;aralditexb2979b;bakeliteve2560;cyano-guanidin;dicyandiamido;Dicyandiamin
• CAS NO: 461-58-5
• Molecular Formula: C2H4N4
• Molecular Weight: 84.08
• EINECS: 207-312-8
• Product Categories: Pharmaceutical Intermediates;INORGANIC & ORGANIC CHEMICALS;Intermediates;Organics;Dyestuff Intermediates;Amines;Intermediates & Fine Chemicals;Pharmaceuticals;amine series
• Mol File: 461-58-5.mol

Chemical Properties

• Melting Point: 208-211 °C(lit.)
• Boiling Point: 144.35°C (rough estimate)
• Flash Point: 92.8 °C
• Appearance: White/Crystalline Powder
• Density: 1.40
• Vapor Pressure: 0.068mmHg at 25°C
• Refractive Index: 1.6260 (estimate)
• Storage Temp.: 2-8°C
• Solubility: H2O: 0.1 g/mL, clear
• PKA: 0.73±0.70(Predicted)
• Water Solubility: 32 g/L (20 ºC)
• Stability: Stable. Incompatible with strong acids, strong oxidizing agents, strong bases.
• Merck: 14,3092
• BRN: 605637
• CAS DataBase Reference: Dicyandiamide(CAS DataBase Reference)
• NIST Chemistry Reference: Dicyandiamide(461-58-5)
• EPA Substance Registry System: Dicyandiamide(461-58-5)

Safety Data

• Hazard Codes: Xn,T
• Statements: 20/21/22-43-36/38-25
• Safety Statements: 22-24/25-45-36-3
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 1
• RTECS: ME9950000
• TSCA: Yes
• Hazardous Substances Data: 461-58-5(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Uses

Different sources of media describe the Uses of 461-58-5 differently. You can refer to the following data:
1. Dicyandiamide is a guanidine derivative used in the synthesis of barbiturates,it is also used in the plastics industry (manufacture of melamine).
2. In the plastics industry (manufacture of melamine). In the pharmaceutical industry (barbiturates, guanidine derivatives).
3. Dicyandiamide is used in the synthesis of barbiturates. It is used as a stabilizer of ammonium dinitramide melt. It is used as hardener.

Application

Dicyanodiammonia, abbreviated as dicy or DCD. It is an organic substance with the chemical formula of c2h4n4. It is a dimer of cyanamide and a cyano derivative of guanidine. Chemical formula c2h4n4. White crystalline powder. Soluble in water, alcohol, ethylene glycol and dimethylformamide, almost insoluble in ether and benzene. Stable when dry. It is a guanidine in which one of the amino hydrogens of guanidine itself is substituted by a cyano group. It is used in the manufacture of fertilizers, pharmaceuticals, explosives, oil well drilling muds, and dyestuffs. It has a role as a curing agent, a flame retardant, a fertilizer, an explosive and a nitrification inhibitor. It is a member of guanidines and a nitrile. The application of nitrification inhibitors has been used as a strategy to promote N utilization efficacy and reduce N2O emissions in paddy Dicyandiamide (DCD) as a widely used nitrification inhibitor inhibits the activity of ammonium-oxidizing bacteria which results in longer ammonium retention and reduces the production of NO2?in soils. DCD efficacy was found to be related to DCD concentration, temperature, moisture, pH, and organic matter content. Studies have shown that leaching DCD from agricultural soils into aquatic ecosystems can strongly change the community composition of benthic stream bacteria and algae and influence stream nutrient cycling stoichiometry. Literature on the mechanisms and benefits of nitrification inhibitors is extensive but there are very few studies focused on the influence of DCD application on other microbes in paddy system.

Production Methods

Dicyanodiamide is manufactured by dimerization of cyanamide in aqueous solution. The 25% cyanamide solution produced is adjusted to pH 8–9 and held at approximately 80C for 2 h to give complete conversion. The hot liquor is filtered and transferred to a vacuum crystallizer, where it is cooled. The crystals or dicyanodiamide are separated in continuous centrifuges and passed to rotary driers. In 1990, the total worldwide production of dicyanodiamide was about 30,000 tons.

General Description

Dicyandiamide is commonly used for the curing of epoxy resins. It is a nitrification inhibitor that is said to be capable of reducing nitrate (NO3-) leaching and nitrous oxide (N2O) emissions from grazed pasture soils.

Flammability and Explosibility

Nonflammable

Synthesis

The calcium hydrogen cyanide suspension obtained from the hydrolysis of calcium cyanamide is filtered under reduced pressure to remove the calcium hydroxide filter residue, and then carbon dioxide is introduced into the filtrate to precipitate the calcium in the form of calcium carbonate to obtain the cyanamide solution. It is polymerized under alkaline conditions, then filtered, cooled, crystallized, separated and dried to obtain dimer cyanamide. The temperature at the maximum rate of dicyandiamide formation is related to pH: pH is 9.7 at 50 ℃; PH 9.1 at 80 ℃; The pH is 8.8 at 100 ℃. After controlled polymerization under these conditions, the finished dicyandiamide is obtained by cooling, crystallization, separation and drying. The content of dicyandiamide in industrial products is 99%, and 4239kg of lime nitrogen (more than 21% nitrogen) is consumed per ton of products.

Purification Methods

Recrystallise cyanoguanidine from water or EtOH. [Beilstein 3 IV 160.]

InChI:InChI=1/C2H4N4/c3-1-6-2(4)5/h(H4,4,5,6)/p+1

Upstream product

• 88905-87-7 azido-N-cyanoformamidinate 
• 67880-22-2 dicyandiazide 
• 420-04-2 CYANAMID 
• 674-81-7 nitrosoguanidine 
• 556-90-1 pseudothiohydantoin 
• 17356-08-0 thiourea 
• 5901-56-4 N-4-nitrophenylguanidine 
• 67-64-1 acetone 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 621-85-2 S-benzyl isothiocarbamide 
• 6051-53-2 (E)-4-(2-hydroxyphenyl)but-3-en-2-one 
• 76299-86-0 N⁶-<(Dimethylamino)methylene>-9-(1-ethoxyethyl)adenine 
• 29181-66-6 2-amino-thiazole-4,5-dione-5-oxime 
• 3084-00-2 N-carbethoxy cyanamide 

Downstream Products

• 5606-32-6 6-piperidino-[1,3,5]-triazine-2,4-diamine 
• 102-02-3 1-phenylbiguanide 
• 4685-18-1 2,4-diamino-6-(2-furyl)-1,3,5-triazine 
• 25007-79-8 2,4-diamino-6-(2′-pyridyl)-1,3,5-triazine 
• 2827-42-1 2,4-diamino-6-morpholino-1,3,5-triazine 
• 16827-13-7 Isonicotinoylamino-diguanid 
• 98488-77-8 N²-furfuryl-[1,3,5]triazine-2,4-diyldiamine 
• 63071-29-4 N¹-acetyl-N³-cyanoguanidine 
• 16352-06-0 6-methyl-5-azacytosine 
• 106837-88-1 N-carbamimidoyl-N'-(4-hydroxy-phenyl)-urea 
• 99548-38-6 1-carbamimidamido-N-(4-hydroxyphenyl)methanimidamide 
• 7152-19-4 N-(4-methyl-6-oxo-1,6-dihydropyrimidin-2-yl)cyanamide 
• 77747-40-1 6-Methyl-2-ureido-4(3H)-pyrimidinone 
• 68216-08-0 1-(3-methoxy-phenyl)-biguanide 

Relevant articles and documents

Nitrosation of Cyanamide: Preparation and Properties of the Elusive E- and Z-N'-Cyanodiazohydroxides

Nitrosation of cyanamide leads to unstable E/Z-cyanodiazohydroxides that easily deprotonate to E/Z-cyanodiazotates. Pursuing observations of E. Drechsel 145 years ago, the structure and reactivity of those products was determined, mainly in aqueous solution. Depending on the pH, three different thermal decomposition pathways give either N2O + HCN or N2 + HNCO. They were evaluated experimentally and by quantum mechanical calculations.

Novel method for synthesis of sulphaguanidine

The microwave-enhanced synthesis of sulphaguanidine is achieved rapidly and in good yield via the step-wise reaction of cyanamide with sulphonamide in the presence of acidic alumina or montmorillonite clays (KSF and K10).

Formation of pyrimidin-2-ylcyanamide and 2-aminopyrimidine in the reaction of aniline derivatives with cyanamide and dimethylamino-1-pyridyl-2-propenone

Substituted o- and p-nitroanilines and m-benzylaminoanilines in the reaction with cyanamide failed to yield the corresponding arylguanidines, and in the presence of 3-dimethylamino-1-(3-pyridyl)-2-propen-1-one formed 4-pyridyl-substituted pyrimidin-2-ylcyanamides and 2-amino-pyrimidines.

Reaction of N-(carbamimidoyl)thiourea with 1-benzoyl-2-phenylacetylene

1-Benzoyl-2-phenylacetylene reacted with N-(carbamimidoyl)thiourea in glacial acetic acid saturated with 20% HBr to give (4,6-diphenyl-2H-1,3-thazin- 2-ylidene)guanidine hydrobromide. The reaction of the same compounds in anhydrous ethanol in the presence

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CRF receptor antagonists and methods relating thereto

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Bis(trimesitylgermylcarbodiimido)germylene, trimesitylgermylcyanamide and trimesitylgermylcarbodiimide

Bis(trimesitylgermylcarbodiimido)germylene (1), isolated as a white precipitate from the reaction of lithium trimesitylgermylcyanamide with dichlorogermylene, is stable at room temperature in the absence of water and oxygen. The germylene structure is pre

Kinetics of the reaction of β-methoxy-α-nitrostilbene with cyanamide in 50% DMSO-50% water. Failure to detect the S(N)V intermediate

A kinetic study of the reaction of β-methoxy-α-nitrostilbene (1-OMe) with cyanamide (CNA) over a pH range from 8.5 to 12.4 shows that it is the anion (CNA-, pK(a) = 11.38) rather than the neutral amine that is the reactive species. Attempts at monitoring the reaction with the neutral CNA at low pH were unsuccessful because of competing hydrolysis. It is shown that the nucleophilic reactivity of CNA is abnormally low, probably because of a resonance effect, and that the reactivity of CNA- is high, higher than that of strongly basic oxyanion because of relatively weak solvation. The high reactivity of both 1-OMe and CNA- appeared to constitute favorable conditions conducive to the detection of the S(N)V intermediate, as has been the case in the reactions of 1-OMe with thiolate ions, alkoxide ions, and some amines. However, no intermediate was observed. Reasons for this failure are discussed.

Formation of Oxygen-bridged Heterocycles in the Hantzsch Synthesis with 4-(2-Hydroxyphenyl)but-3-en-2-one

Condensations of 4-(2-hydroxyphenyl)but-3-en-2-one with methyl acetoacetate, pentane-2,4-dione, dimedone, and methyl cyanoacetate under the conditions of the Hantzsch synthesis lead to 9-methyl-8-oxa-10-azatricyclo2,7>trideca-2,4,6,11-tetraene derivatives and related heterocycles.An analogous condensation with 2-aminopropene-1,1,3-triscarbonitrile yields stereoselectively 11-dicyanomethylene-9-methyl-8-oxa-10-azatricyclo2,7>trideca-2,4,6-triene-12α-carbonitrile.Under suitable reaction conditions, the condensation of 4-(2-hydroxyphenyl)but-3-en-2-one with cyanamide affords various products with the 9-methyl-8-oxa-10,12-diazatricyclo2,7>trideca-2,4,6,11-tetraene skeleton.Condensation products of salicylaldehyde with acetone, 2-aminopropene-1,1,3-triscarbonitrile, and 3-aminocrotononitrile have been identified.

Heterocyclic amidino substituted ureas and their pharmaceutical uses

This invention relates to methods for the prophylactic and curative treatment of gastrointestinal and cardiovascular disorders and parasitic infections in humans and animals, using a class of hetrocyclic amidino substituted urea and thiourea compounds, a novel class of heterocyclic amidino substituted urea and thiourea compounds and pharmaceutical compositions and animal feed additives including the same.