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carbonyldiamine diaminomethanal diaminomethanone identifiers cas number 57 13 6 y 3d model jsmol interactive image beilstein reference 635724 chebi chebi 16199 y chembl chembl985 y chemspider 1143 y drugbank db03904 y echa infocard 100 000 286 e number e927b glazing agents gmelin reference 1378 iuphar bps 4539 kegg d00023 y pubchem cid 1176 rtecs number yr6250000 unii 8w8t17847w y comptox dashboard epa dtxsid4021426 inchi inchi 1s ch4n2o c2 1 3 4 h h4 2 3 4 y key xsqukjjjfzcrtk uhfffaoysa n y inchi 1 ch4n2o c2 1 3 4 h h4 2 3 4 key xsqukjjjfzcrtk uhfffaoyaf smiles c o n n properties chemical formula co nh 2 2 molar mass 60 056 g mol 1 appearance white solid density 1 32 g cm 3 melting point 132 4 c 270 3 f 405 5 k 2 boiling point decomposes solubility in water 790 g l 5 c 41 f 278 k 1200 g l 25 c 77 f 298 k 2 solubility in acetonitrile 4 g l 3 solubility in ethanol 50 g l citation needed solubility in glycerol 500 g l 4 log p 1 73 22 c 72 f 295 k 5 vapor pressure 1 25 mmhg 167 pa 6 acidity p k a 0 1 2 conjugate acid basicity p k b 13 9 a conjugate acid uronium magnetic susceptibility χ 33 5 10 6 cm 3 mol 2 refractive index n d 1 484 2 structure crystal structure tetragonal prisms from alcohol 2 dipole moment 4 56 d citation needed thermochemistry 2 std enthalpy of formation δ f h 298 333 19 kj mol pharmacology atc code b05bc02 who d02ae01 who hazards nfpa 704 fire diamond 6 1 0 0 lethal dose or concentration ld lc ld 50 median dose 8500 mg kg oral rat safety data sheet sds fisher scientific 6 related compounds related ureas thiourea hydroxycarbamide related compounds carbamide peroxide nitrourea urea nitrate urea perchlorate urea phosphate except where otherwise noted data are given for materials in their standard state at 25 c 77 f 100 kpa y verify what is y n infobox references chemical compound urea also called carbamide because it is a diamide of carbonic acid is an organic compound with chemical formula co nh 2 2 this amide has two amino groups nh 2 joined by a carbonyl functional group c o it is thus the simplest amide of carbamic acid 7 urea serves an important role in the cellular metabolism of nitrogen containing compounds by animals and is the main nitrogen containing substance in the urine of mammals the word urea is neo latin from french urée from ancient greek οὖρον oûron urine it is a colorless odorless solid highly soluble in water and practically non toxic dissolved in water it is neither acidic nor alkaline the body uses it in many processes most notably nitrogen excretion in the liver it forms by the condensation of ammonia nh 3 and carbon dioxide co 2 in the urea cycle urea is widely used in fertilizers as a source of nitrogen n in 1828 friedrich wöhler showed that urea can be produced from inorganic starting materials an important conceptual milestone in chemistry this showed for the first time that a substance previously known only as a byproduct of life could be synthesized in the laboratory from non biological starting materials thereby contradicting the widely held doctrine of vitalism which stated that organic compounds could only be derived from living organisms molecular and crystal structure edit the structure of the molecule of urea is o c nh 2 2 the urea molecule is planar when in a solid crystal because of sp 2 hybridization of the n orbitals 8 9 it is non planar with c 2 symmetry when in the gas phase or in aqueous solution with c n h and h n h bond angles that are intermediate between the trigonal planar angle of 120 and the tetrahedral angle of 109 5 10 9 in solid urea the oxygen center is engaged in two n h o hydrogen bonds the resulting hydrogen bond network is probably established at the cost of efficient molecular packing the structure is quite open the ribbons forming tunnels with square cross section the carbon in urea is described as sp 2 hybridized the c n bonds have significant double bond character and the carbonyl oxygen is relatively basic citation needed urea s high aqueous solubility reflects its ability to engage in extensive hydrogen bonding with water by virtue of its tendency to form porous frameworks urea has the ability to trap many organic compounds in these so called clathrates the organic guest molecules are held in channels formed by interpenetrating helices composed of hydrogen bonded urea molecules in this way urea clathrates have been well investigated for separations 11 reactions edit structure of fe urea 6 2 showing intramolecular hydrogen bonds 12 color code blue n red o basicity edit urea is a weak base with a p k b of 13 9 a when combined with strong acids it undergoes protonation at oxygen to form uronium salts 13 14 15 it is a lewis base forming metal complexes of the type m urea 6 n 16 n functionalization edit as an electron rich amide urea readily undergoes n functionalization by electrophilic reagents this property gives rise to several reagents nitration occurs at the amine to give n nitrourea 17 chlorination similarly gives n chlorourea 18 transamination edit urea undergoes transamination for example treatment with anilinium gives both n phenylurea and n n diphenylurea 19 20 n methylurea can be prepared by a similar acid catalyzed pathway 21 heterocyclization edit urea being a multifunctional is a versatile precursor to heterocycles it reacts with malonic esters to make barbituric acids 22 with hydroxyketones urea condenses to give glyoxalones 23 it is a precursor to pyrimidines 24 thermolysis edit molten urea decomposes into ammonium cyanate at about 152 c 306 f and into ammonia and isocyanic acid above 160 c 320 f 25 co nh 2 2 nh 4 ocn nh 3 hnco heating above 160 c 320 f yields biuret nh 2 conhconh 2 and triuret nh 2 conhconhconh 2 via reaction with isocyanic acid 26 25 co nh 2 2 hnco nh 2 conhconh 2 nh 2 conhconh 2 hnco nh 2 conhconhconh 2 at higher temperatures it converts to a range of condensation products including cyanuric acid cnoh 3 guanidine hnc nh 2 2 and melamine 26 25 hydrolysis edit in aqueous solution urea slowly equilibrates with ammonium cyanate this elimination reaction 27 cogenerates isocyanic acid which can carbamylate proteins in particular the n terminal amino group the side chain amino of lysine and to a lesser extent the side chains of arginine and cysteine 28 29 each carbamylation event adds 43 daltons to the mass of the protein which can be observed in protein mass spectrometry 29 for this reason pure urea solutions should be freshly prepared and used as aged solutions may develop a significant concentration of cyanate 20 mm in 8 m urea 29 dissolving urea in ultrapure water followed by removing ions i e cyanate with a mixed bed ion exchange resin and storing that solution at 4 c 39 f is a recommended preparation procedure 30 however cyanate will build back up to significant levels within a few days 29 alternatively adding 25 50 mm ammonium chloride to a concentrated urea solution decreases formation of cyanate because of the common ion effect 29 31 analysis edit urea is readily quantified by a number of different methods such as the diacetyl monoxime colorimetric method and the berthelot reaction after initial conversion of urea to ammonia via urease these methods are amenable to high throughput instrumentation such as automated flow injection analyzers 32 and 96 well micro plate spectrophotometers 33 related compounds edit main article ureas urea is the parent for a class of chemical compounds that share the same functional group namely such compounds have a carbonyl group attached to two organic amine residues r 1 r 2 n c o nr 3 r 4 where r 1 r 2 r 3 and r 4 groups are hydrogen h organyl or other groups examples include carbamide peroxide allantoin and hydantoin ureas are closely related to biurets and related in structure to amides carbamates carbodiimides and thiocarbamides uses edit agriculture edit a plant in bangladesh that produces urea fertilizer more than 90 of world industrial production of urea is for use as a nitrogen release fertilizer 26 urea has the highest nitrogen content of all solid nitrogenous fertilizers in common use therefore it has a low transportation cost per unit of nitrogen nutrient urea breaks down in the soil to give ammonium ions nh 4 the ammonium is taken up by the plant through its roots in some soils the ammonium is oxidized by bacteria to give nitrate no 3 which is also a nitrogen rich plant nutrient the loss of nitrogenous compounds to the atmosphere and runoff is wasteful and environmentally damaging so urea is sometimes modified to enhance the efficiency of its agricultural use techniques to make controlled release fertilizers that slow the release of nitrogen include the encapsulation of urea in an inert sealant and conversion of urea into derivatives such as urea formaldehyde compounds which degrade into ammonia at a pace matching plants nutritional requirements the most common impurity of synthetic urea is biuret which impairs plant growth 34 resins edit urea is a raw material for the manufacture of formaldehyde based resins such as uf muf and mupf used mainly in wood based panels for instance particleboard fiberboard osb and plywood 35 explosives edit urea can be used in a reaction with nitric acid to make urea nitrate a high explosive that is used industrially and as part of some improvised explosive devices automobile systems edit urea is used in selective non catalytic reduction sncr and selective catalytic reduction scr reactions to reduce the no x pollutants in exhaust gases from diesel dual fuel and lean burn natural gas engines the bluetec system for example injects a water based urea solution into the exhaust system ammonia nh 3 produced by the hydrolysis of urea reacts with nitrogen oxides no x and is converted into nitrogen gas n 2 and water within the catalytic converter the conversion of noxious no x to innocuous n 2 is described by the following simplified global equation 36 4 no 4 nh 3 o 2 4 n 2 6 h 2 o when urea is used a pre reaction hydrolysis occurs to first convert it to ammonia co nh 2 2 h 2 o 2 nh 3 co 2 being a solid highly soluble in water 1200 g l at 25 c 77 f 2 urea is much easier and safer to handle and store than the more irritant caustic and hazardous ammonia so it is the reactant of choice trucks and cars using these catalytic converters need to carry a supply of diesel exhaust fluid also sold as adblue a solution of urea in water laboratory uses edit urea in concentrations up to 10 m is a protein denaturant as it disrupts the noncovalent bonds in the proteins this property can be exploited to increase the solubility of some proteins a mixture of urea and choline chloride is used as a deep eutectic solvent des a substance similar to ionic liquid when used in a deep eutectic solvent urea gradually denatures the proteins that are solubilized 37 urea in concentrations up to 8 m can be used to make fixed brain tissue transparent to visible light while still preserving fluorescent signals from labeled cells this allows for much deeper imaging of neuronal processes than previously obtainable using conventional one photon or two photon confocal microscopes 38 medical use edit urea containing creams are used as topical dermatological products to promote rehydration of the skin urea 40 is indicated for psoriasis xerosis onychomycosis ichthyosis eczema keratosis keratoderma corns and calluses if covered by an occlusive dressing 40 urea preparations may also be used for nonsurgical debridement of nails urea 40 dissolves the intercellular matrix of the nail plate 39 40 only diseased or dystrophic nails are removed as there is no effect on healthy portions of the nail 41 urea has been studied as a diuretic it was first used by dr w friedrich in 1892 42 in a 2010 study of icu patients urea was used to treat euvolemic hyponatremia and was found safe inexpensive and simple 43 like saline urea has been injected into the uterus to induce abortion although this method is no longer in widespread use 44 the blood urea nitrogen bun test is a measure of the amount of nitrogen in the blood that comes from urea it is used as a marker of renal function though it is inferior to other markers such as creatinine because blood urea levels are influenced by other factors such as diet dehydration 45 and liver function urea has also been studied as an excipient in drug coated balloon dcb coating formulations to enhance local drug delivery to stenotic blood vessels 46 47 urea when used as an excipient in small doses 3 μg mm 2 to coat dcb surface was found to form crystals that increase drug transfer without adverse toxic effects on vascular endothelial cells 48 urea labeled with carbon 14 or carbon 13 is used in the urea breath test which is used to detect the presence of the bacterium helicobacter pylori h pylori in the stomach and duodenum of humans associated with peptic ulcers the test detects the characteristic enzyme urease produced by h pylori by a reaction that produces ammonia from urea this increases the ph reduces the acidity of the stomach environment around the bacteria similar bacteria species to h pylori can be identified by the same test in animals such as apes dogs and cats including big cats citation needed miscellaneous edit this section needs more citations please help improve this section by adding citations to reliable sources unsourced material may be challenged and removed find sources urea news newspapers books scholar jstor april 2026 learn how and when to remove this message an ingredient in diesel exhaust fluid def which is 32 5 urea and 67 5 de ionized water def is sprayed into the exhaust stream of diesel vehicles to break down dangerous no x emissions into harmless nitrogen and water a component of animal feed providing a relatively cheap source of non protein nitrogen to promote growth a non corroding alternative to rock salt for road de icing it is often the main ingredient of pet friendly salt substitutes although it is less effective than traditional rock salt or calcium chloride 49 50 a main ingredient in hair removers such as nair and veet a browning agent in factory produced pretzels an ingredient in some skin cream moisturizers hair conditioners and shampoos a cloud seeding agent along with other salts 51 a flame proofing agent commonly used in dry chemical fire extinguisher charges such as the urea potassium bicarbonate mixture along with diammonium phosphate as a yeast nutrient for fermentation of sugars into ethanol a nutrient used by plankton in ocean nourishment experiments for climate engineering purposes as an additive to extend the working temperature and open time of hide glue as a solubility enhancing and moisture retaining additive to dye baths for textile dyeing or printing 52 as an optical parametric oscillator in nonlinear optics 53 importance to help prepare an alpine skiing course by hardening the snow into a icier surface to maintain the integrity of the course physiology edit amino acids e g from ingested food can be oxi...