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| | guanidine Basic information |
| | guanidine Chemical Properties |
| Melting point | ~50° | | Boiling point | 82.3°C (rough estimate) | | density | 1.6000 (rough estimate) | | refractive index | 1.5950 (estimate) | | storage temp. | -20°C Freezer | | solubility | DMSO (Slightly), Methanol (Slightly) | | pka | pKa ~12.5(at 25℃) | | form | Solid | | color | White | | EPA Substance Registry System | Guanidine (113-00-8) |
| | guanidine Usage And Synthesis |
| Chemical Properties | Colorless crystals. Soluble inwater and alcohol. Combustible. | | Uses | Organic synthesis | | Uses | Guanidine is an intermediate in synthesizing N-Formylguanidine (F700505), which is used in the preparation of Amiloride (A578700), a sodium channel blocker used as a diuretic drug. | | Definition | ChEBI: Guanidine is an aminocarboxamidine, the parent compound of the guanidines. It is a one-carbon compound, a member of guanidines and a carboxamidine. It is a conjugate base of a guanidinium. | | Production Methods | Guanidine is formed (1) by heating ammonium thiocyanate to 180 °C, (2) by ammonolysis of orthocarbonates, C(OC2H5)4 + 3NH3 → (NH2)2C=NH + 4C2H5OH, (3) by ammonolysis of chloropicrin, Cl3CNO2 + 7NH3 → NH2)2 C=NH + 3NH4Cl + N2 + 3H2O, (4) by ammonolysis of cyanogen chloride, ClCN + NH3 → ClC(NH2)=NH → HN=C=NH → (NH2)2 C=NH.
Guanidine forms salts with acids, e.g., guanidine nitrate, HNC(NH2)2 · HNO3. By heating at 120 °C for several hours, a mixture of ammonium thiocyanate and dicyanodiamide, guanidine thiocyanate solution is obtained by extracting with water. Treating guanidine with a mixture of nitric and sulfuric acids forms nitroguanidine which is reduced by zinc and acetic acid to aminoguanidine.
By treating aminoguanidine (1) with dilute acid or alkali, there is obtained, first, semicarbazide, finally hydrazine; (2) with nitrous acid, diazoguanidine which is decomposed by alkali into alkali azide (e.g., NaN3) plus cyanamide (H2N·CN) plus water. | | Agricultural Uses | Carbamidine is another name for guanidine. It is a
crystalline basic compound related to urea. It forms a
number of salts which are used as fertilizers. Guanidine
phosphate is an example. | | Purification Methods | Crystallise it from water/EtOH under nitrogen. It is very deliquescent and absorbs CO2 from the air readily. [Jones Trans Faraday Soc 55 524 1959, Beilstein 3 H 82, 3 I 39, 3 II 69, 3 III 154, 3 IV 148.] |
| | guanidine Preparation Products And Raw materials |
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