Urea

Urea
Names
Pronunciation urea /jʊəˈrə/, carbamide /ˈkɑːrbəmd/
Preferred IUPAC name
Urea
Systematic IUPAC name
Carbonyl diamide
Other names
  • Carbamide
  • Carbonyldiamide
  • Carbonyldiamine
  • Diaminomethanal
  • Diaminomethanone
Identifiers
3D model (JSmol)
635724
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.286
E number E927b (glazing agents, ...)
1378
KEGG
RTECS number
  • YR6250000
UNII
  • 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
  • C(=O)(N)N
Properties
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
545 g/L (at 25 °C)
Solubility 500 g/L glycerol

  50 g/L ethanol
  ~4 g/L acetonitrile

Basicity (pKb) 13.9
−33.4·10−6 cm3/mol
Structure
4.56 D
ThermochemistryCRC Handbook
−333.19 kJ/mol
−197.15 kJ/mol
Pharmacology
B05BC02 (WHO) D02AE01 (WHO)
Hazards
GHS labelling:
NFPA 704 (fire diamond)
1
1
0
Flash point Non-flammable
Lethal dose or concentration (LD, LC):
8500 mg/kg (oral, rat)
Safety data sheet (SDS) ICSC 0595
Related compounds
Related ureas
Thiourea
Hydroxycarbamide
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

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 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). 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.

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