Not to be confused with uric acid, urate, or urine.
"Carbonic diamide" redirects here. For the azide, see carbonyl diazide.
Urea
Names
Pronunciation
urea /jʊəˈriːə/, carbamide /ˈkɑːrbəmaɪd/
Preferred IUPAC name
Urea[1]
Systematic IUPAC name
Carbonic diamide[1]
Other names
Carbamide
Carbonyldiamide
Carbonyldiamine
Diaminomethanal
Diaminomethanone
Identifiers
CAS Number
57-13-6Y
3D model (JSmol)
Interactive image
Beilstein Reference
635724
ChEBI
CHEBI:16199Y
ChEMBL
ChEMBL985Y
ChemSpider
1143Y
DrugBank
DB03904Y
ECHA InfoCard
100.000.286
E number
E927b (glazing agents, ...)
Gmelin Reference
1378
IUPHAR/BPS
4539
KEGG
D00023Y
PubChem CID
1176
RTECS number
YR6250000
UNII
8W8T17847WY
CompTox Dashboard (EPA)
DTXSID4021426
InChI
InChI=1S/CH4N2O/c2-1(3)4/h(H4,2,3,4)Y
Key: XSQUKJJJFZCRTK-UHFFFAOYSA-NY
InChI=1/CH4N2O/c2-1(3)4/h(H4,2,3,4)
Key: XSQUKJJJFZCRTK-UHFFFAOYAF
SMILES
C(=O)(N)N
Properties
Chemical formula
CO(NH2)2
Molar mass
60.06 g/mol
Appearance
White solid
Density
1.32 g/cm3
Melting point
133 to 135 °C (271 to 275 °F; 406 to 408 K)
Boiling point
decomposes
Solubility in water
545 g/L (at 25 °C)[2]
Solubility
500 g/L glycerol[3]
50 g/L ethanol
~4 g/L acetonitrile[4]
Basicity (pKb)
13.9[5]
Magnetic susceptibility (χ)
−33.4·10−6 cm3/mol
Structure
Dipole moment
4.56 D
ThermochemistryCRC Handbook
Std enthalpy of formation (ΔfH⦵298)
−333.19 kJ/mol
Gibbs free energy (ΔfG⦵)
−197.15 kJ/mol
Pharmacology
ATC code
B05BC02 (WHO) D02AE01 (WHO)
Hazards
GHS labelling:
Pictograms
NFPA 704 (fire diamond)
1
1
0
Flash point
Non-flammable
Lethal dose or concentration (LD, LC):
LD50 (median dose)
8500 mg/kg (oral, rat)
Safety data sheet (SDS)
ICSC 0595
Related compounds
Related ureas
Thiourea Hydroxycarbamide
Related compounds
Carbamide peroxide
Urea phosphate
Acetone
Carbonic acid
Carbonyl fluoride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yverify (what is YN ?)
Infobox references
Chemical compound
Urea, also called carbamide (because it is a diamide of carbonic acid), is an organic compound with chemical formula CO(NH2)2. This amide has two amino groups (–NH2) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest amide of carbamic acid.
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. Urea is Neo-Latin, from French urée, from Ancient Greek οὖρον (oûron) 'urine', itself from Proto-Indo-European *h₂worsom.
It is a colorless, odorless solid, highly soluble in water, and practically non-toxic (LD50 is 15 g/kg for rats).[6] Dissolved in water, it is neither acidic nor alkaline. The body uses it in many processes, most notably nitrogen excretion. The liver forms it by combining two ammonia molecules (NH3) with a carbon dioxide (CO2) molecule in the urea cycle. Urea is widely used in fertilizers as a source of nitrogen (N) and is an important raw material for the chemical industry.
In 1828, Friedrich Wöhler discovered that urea can be produced from inorganic starting materials, which was 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 without biological starting materials, thereby contradicting the widely held doctrine of vitalism, which stated that only living organisms could produce the chemicals of life.
^ abNomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 416, 860–861. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. The compound H2N-CO-NH2 has the retained name 'urea', which is the preferred IUPAC name, with locants N and N′, as shown above the structure below. The systematic name is 'carbonic diamide', (…).
^Yalkowsky, Samuel H.; He, Yan; Jain, Parijat (19 April 2016). Handbook of Aqueous Solubility Data. CRC Press. ISBN 9781439802465.
^"Solubility of Various Compounds in Glycerine" (PDF). msdssearch.dow.com. Archived from the original (PDF) on 13 April 2014. Retrieved 12 April 2014.
^Loeser E, DelaCruz M, Madappalli V (9 June 2011). "Solubility of Urea in Acetonitrile–Water Mixtures and Liquid–Liquid Phase Separation of Urea-Saturated Acetonitrile–Water Mixtures". Journal of Chemical & Engineering Data. 56 (6): 2909–2913. doi:10.1021/je200122b.
^Calculated from 14−pKa. The value of pKa is given as 0.10 by the CRC Handbook of Chemistry and Physics, 49th edition (1968–1969). A value of 0.18 is given by Williams, R. (24 October 2001). "pKa Data" (PDF). Archived from the original (PDF) on 24 August 2003.
Urea, also called carbamide (because it is a diamide of carbonic acid), is an organic compound with chemical formula CO(NH2)2. This amide has two amino...
Blood urea nitrogen (BUN) is a medical test that measures the amount of urea nitrogen found in blood. The liver produces urea in the urea cycle as a waste...
The urea cycle (also known as the ornithine cycle) is a cycle of biochemical reactions that produces urea (NH2)2CO from ammonia (NH3). Animals that use...
created by a diesel engine. Specifically, DEF is an aqueous urea solution made with 32.5% urea and 67.5% deionized water. DEF is consumed in a selective...
Urea phosphate is a 1:1 combination of urea and phosphoric acid that is used as a fertilizer. It has an NPK formula 17-44-0, and is soluble in water,...
In enzymology, a urea carboxylase (EC 6.3.4.6) is an enzyme that catalyzes the chemical reaction ATP + urea + HCO3- ⇌ {\displaystyle \rightleftharpoons...
Urea nitrate is a fertilizer-based high explosive that has been used in improvised explosive devices in Afghanistan, Pakistan, Iraq, and various terrorist...
Diazolidinyl urea is an antimicrobial preservative used in cosmetics. It is chemically related to imidazolidinyl urea which is used in the same way. Diazolidinyl...
Imidazolidinyl urea is an antimicrobial preservative used in cosmetics [citation needed]. It is chemically related to diazolidinyl urea which is used in...
Coated urea fertilizers are a group of controlled release fertilizers consisting of prills of urea coated in less-soluble chemicals such as sulfur, polymers...
In chemistry, ureas are a class of organic compounds with the formula (R2N)2CO where R = H, alkyl, aryl, etc. Thus, in addition to describing the specific...
Uremia is the term for high levels of urea in the blood. Urea is one of the primary components of urine. It can be defined as an excess in the blood of...
The urea breath test is a rapid diagnostic procedure used to identify infections by Helicobacter pylori, a spiral bacterium implicated in gastritis, gastric...
A urea transporter is a membrane transport protein, transporting urea. Humans and other mammals have two types of urea transport proteins, UT-A and UT-B...
UAN is a solution of urea and ammonium nitrate in water used as a fertilizer. The combination of urea and ammonium nitrate has an extremely low critical...
catalyze the hydrolysis of urea into carbon dioxide and ammonia: (NH2)2CO + H2O urease→ CO2 + 2NH3 The hydrolysis of urea occurs in two stages. In the...
explosive compound synthesized by the nitration of urea or by way of a dehydration reaction of urea nitrate. "Nitrourea". CAMEO Chemicals. NOAA. 2.4. Ingersoll...
within living things. Friedrich Wöhler's conversion of ammonium cyanate into urea in 1828 is often cited as the starting point of modern organic chemistry...
Urine urea nitrogen (UUN) refers to a test that measures the urine urea to assess nitrogen balance. Urea nitrogen is the end product of breakdown of proteins...
chloride byproduct: NH2Cl + NH3 → N2H4 + HCl Related to the Raschig process, urea can be oxidized instead of ammonia. Again sodium hypochlorite serves as the...
of urea:In 2020, worldwide production capacity was approximately 180 million tonnes. As a fertilizer, it is a source of nitrogen for plants. Urea production...
Methylol urea is the organic compound with the formula H2NC(O)NHCH2OH. It is a white, water-soluble solid that decomposes near 110 °C. Methylolurea is...
Urea can crystallise with other compounds. These can be called urea adducts or if a solvent is involved, a urea solvate, and the process is called urea...