58069-82-2

Basic information

• Product Name: UREA-13C
• Synonyms: UREA- 13C 99%;UREA (13C, 99%, 15N2, 98%);UREA-13C USP(CRM STANDARD);UREA (13C, 99%);Urea-13C - Research Grade;Urea-13C ,99 atom % 13C [99 atom % 13C];Urea C 13 (150 mg);Aquacare-13C
• CAS NO: 58069-82-2
• Molecular Formula: CH₄N₂O
• Molecular Weight: 61.06
• Product Categories: Carbon-13 Salts;cGMPStable Isotopes;Alphabetical Listings;Stable Isotopes;U-Z;Aliphatics;Amines;Intermediates & Fine Chemicals;Isotope Labelled Compounds;Pharmaceuticals
• Mol File: 58069-82-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 132-135 °C(lit.)
• Appearance: /
• Density: 1.212 g/cm³
• Refractive Index: 1.468
• Storage Temp.: 15-25°C
• Solubility: DMSO (Soluble), Methanol (Slightly)
• CAS DataBase Reference: UREA-13C(CAS DataBase Reference)
• NIST Chemistry Reference: UREA-13C(58069-82-2)
• EPA Substance Registry System: UREA-13C(58069-82-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 58069-82-2(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Labelled Urea. Physiological regulator of nitrogen excretion in mammals; synthesized in the liver as an end-product of protein catabolism and excreted in urine. Also occurs normally in skin. Emollient; diuretic.

InChI:InChI=1/CH4N2O/c2-1(3)4/h(H4,2,3,4)/i1+1

Synthetic route

potassium <13C>cyanate → 13C urea (58069-82-2)

Conditions	Yield
With ammonium sulfate; ammonium hydroxide at 70℃; for 4h;	87%

trichloro[13C]methyl phenyl sulfide (1071435-30-7) → 13C urea (58069-82-2) + (13C)-guanidine hydrochloride (286013-04-5)

Conditions	Yield
Stage #1: trichloro[13C]methyl phenyl sulfide With ammonia In ethanol; dichloromethane; water at -80 - 20℃; for 72.5h; Stage #2: With hydrogenchloride; water	A 49% B 47%

<13CO>-N-methyl-N-nitrosourea (MNU) → diazomethane (186581-53-3, 908094-01-9) + 13C urea (58069-82-2) + carbonic acid monomethyl ester (7456-87-3) + [13C]cyanic acid (118832-13-6) + carbonate ion + (13)CH2NO5P(2-)

Conditions	Yield
With sodium hydroxide; phosphate buffer In methanol; water at 22℃; Product distribution; other reagents, temperature;

ammonium sulfate + potassium <13C>cyanate → 13C urea (58069-82-2)

Conditions	Yield
recrystn. from ethanol;

phenylethane 1,2-diol (93-56-1) + 13C urea (58069-82-2) → 4-phenyl (2-13C)-1,3-dioxolan-2-one

Conditions	Yield
With iron(II) bromide In 1,4-dioxane at 150℃; for 18h; Inert atmosphere; Sealed tube;	90%

13C urea (58069-82-2) → 13C3-cyanuric acid (201996-37-4)

Conditions	Yield
In sulfolane at 205℃; under 100 Torr; for 2h;	88.4%
In sulfolane; cyclohexanol at 50 - 200℃;	87%
With sulfolane; cyclohexanol at 60 - 210℃; for 3h;

13C urea (58069-82-2) + [13C2,15N3]5,6-diaminopyrimidine-2,4(1H,3H)-dione hemisulfate → [13C3,15N3]uric acid

Conditions	Yield
at 190℃; for 2h;	80%

13C urea (58069-82-2) + Glyoxal (131543-46-9) → C2(13)C2H6O2N4

Conditions	Yield
With hydrogenchloride In water at 85 - 90℃;	78%

13C urea (58069-82-2) + methyl (2RS)-2-(6-chloro-9H-carbazol-2-yl)propanoate (52263-88-4) → C16(13)CH16N2O2

Conditions	Yield
With nickel(II) acetylacetonate; potassium fluoride; phenylsilane; zinc; bis(2-diphenylphosphinoethyl)phenylphosphine In 1-methyl-pyrrolidin-2-one at 90 - 140℃; for 20h;	75%

13C urea (58069-82-2) + ethyl 2-cyanoacetate (105-56-6) → 6-amino[2-13C]uracil

Conditions	Yield
With sodium ethanolate In ethanol for 5h; Heating;	74%

13C urea (58069-82-2) + Propiolic acid (471-25-0) → [2-13C]-pyrimidine-2,4(1H,3H)-dione (35803-45-3)

Conditions	Yield
With PPA at 85℃; for 6h;	66%
Stage #1: 13C urea; Propiolic acid at 95 - 110℃; Stage #2: With water; sodium hydroxide	64%

13C urea (58069-82-2) + benzil (134-81-6) → [2-13C]phenytoin

Conditions	Yield
With potassium hydroxide at 100℃; for 3h;	65%

5,6-diaminouracil (3240-72-0) + 13C urea (58069-82-2) → <8-13C>uric acid (139290-36-1)

Conditions	Yield
at 170℃;	60%

13C urea (58069-82-2) + methyl p-toluene sulfonate (80-48-8) → O-methyl-[13C]isourea p-methylsulfonate salt (88597-10-8)

Conditions	Yield
Methylation; Heating;	60%
1.) 100 deg C, 5 h; 2.) acetone, RT, 1 h; Yield given. Multistep reaction;

13C urea (58069-82-2) + 2-bromo-3-methyl-butyryl bromide (26464-05-1) → C5(13)CH11BrN2O2

Conditions	Yield
In tetrahydrofuran for 15h; Heating;	48%

13C urea (58069-82-2) → 6-chlorouracil-(13)C2

13C urea (58069-82-2) + diethyl diethylmalonate (77-25-8) → [2-13C]barbital

Conditions	Yield
With sodium ethanolate 1.) EtOH, RT, 10 min, 2.) EtOH, reflux, 12 h; Yield given. Multistep reaction;

13C urea (58069-82-2) + ethyl 2-hydroxy-2,2-dimethylethanoate (80-55-7) → [2-13C]dimethadione

Conditions	Yield
With sodium ethanolate 1.) ETOH, 0 deg C, 2.) EtOH, reflux, 30 h; Yield given. Multistep reaction;

13C urea (58069-82-2) + [13C](methoxy) chloroformic acid methyl ester → [13C]2(urea,methoxy) methoxycarbonyl urea

Conditions	Yield
at 100℃; for 1h;

13C urea (58069-82-2) + DL-5-chlorohydantoin (32282-43-2) → DL-2-(13)C-allantoin + DL-[H2N(13)CO]allantoin

Conditions	Yield
In nitromethane for 1h; Reflux;

13C urea (58069-82-2) + [13C,15N]5,6-diaminopyrimidine-2,4(1H,3H)-dione → [13C2,15N2]uric acid

Conditions	Yield
at 185℃; for 1h;	296 mg

13C urea (58069-82-2) → carbon dioxide (1111-72-4)

Conditions	Yield
With carbon dioxide; urease In water for 1h; Catalytic behavior; Solvent; Concentration; Sealed tube; Enzymatic reaction;

Upstream product

• 1071435-30-7 trichloro[13C]methyl phenyl sulfide 

Downstream Products

• 1111-72-4 carbon dioxide 
• 201996-37-4 [¹³C]cyanuric acid 
• 35803-45-3 [2-13C]-uracil 

Relevant articles and documents

THE MEASUREMENT OF SYNTHESIS RATES OF ALBUMIN AND FIBRINOGEN IN RABBITS.

1. A formula is proposed for calculating fractional synthesis rates of

SINGLE CARBON PRECURSOR SYNTHONS

The chemistry of [13C]methyl phenyl sulfide is exploited to produce new isotopically labeled precursors that allow for the facile assembly of a wide range of labeled molecules from simple and relatively inexpensive starting materials. These compounds are applicable to a variety of research areas such as quantum computing, metabolism and materials science.

Concomitant oxygen-18 enrichment in commercial carbon-13 labelled urea

By mass spectroscopy, 50-fold oxygen-18 enrichment over natural abundance was observed in commercial 13C-urea (99 atom % 13C) synthesized from 13C-carbon monoxide that had been 13C-enriched by cryogenic distillation. in contrast, 13C-urea synthesized from 13C-potassium cyanide (a 13C-labened compound having no oxygen atom) showed the natural abundance level of oxygen-18 .