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Basic Information

Molecular Structure:
CAS No.:	66-22-8
Name:	Uracil
Article Data:	251

Formula:	C₄H₄N₂O₂
Molecular Weight:	114.089
Synonyms:	SQ 7726;Urazil;pyrimidine-2,4(1H,3H)-dione;2,4-Pyrimidinediol;2,4-Pyrimidinedione;2,4-Dihydroxypyrimidine;4-hydroxy-2(1H)-pyrimidinone;2,4-Dihydroxypyrimidine(Uracil);BMS 205603-01;2,4(1H,3H)-Pyrimidinedione (9CI);2,4-(1H,3H)-pyrimidinedione (9CI);RU 12709;Uracil (8CI);SQ 6201;2,4(1H,3H)-pyrimidinedione;2, 4 (1H,3H)-Pyrimidinedione;2-hydroxy-4(1H)-pyrimidinone;Uracil (JAN/USAN);2,4-Dioxopyrimidine;Hybar X;Pyrod;Ura;Pirod;SQ 8493;1H-pyrimidine-2,4-dione;2, 4-Dioxopyrimidine;Pyrimidine-2,4-diol;
EINECS:	200-621-9
Density:	1.322 g/cm³
Melting Point:	>300 °C(lit.)
Boiling Point:	440.5°C at 760 mmHg
Flash Point:	220.2oC
Solubility:	soluble in hot water
Appearance:	white powder
Hazard Symbols:	Xi
Risk Codes:	Xi
Safety:	22-24/25
PSA:	65.72000
LogP:	-0.93680

Synthetic route

: 141-90-2
2-thiouracil

: 66-22-8
uracil

Conditions

Conditions	Yield
With sodium hydroxide; methyloxirane In water at 20℃;	100%
With dihydrogen peroxide; potassium hydroxide In ethanol at 0 - 60℃; for 4h;	65.3%
With iodosylbenzene In acetone for 15h; Ambient temperature;	62%

: 879499-38-4
[1-(4-isopropoxypyrimidin-2-yl)piperidin-2-yl]-methanol

: 66-22-8
uracil

Conditions

Conditions	Yield
With hydrogenchloride In water at 90℃; for 0.333333h;	100%

: 178047-66-0
3-Phenyl-5,7a-dihydro-1-oxa-2,3a,5-triaza-inden-4-one

: 66-22-8
uracil

Conditions

Conditions	Yield
In methanol for 24h;	100%

: 35551-31-6
4-methylsulfanylpyrimidin-2(1H)-one

: 66-22-8
uracil

Conditions

Conditions	Yield
With ferrous(II) sulfate heptahydrate In water at 80℃; for 72h;	100%

: 951-78-0
2'-deoxyuridine

: 66-22-8
uracil

Conditions

Conditions	Yield
With 18-crown-6 ether In dimethyl sulfoxide at 50℃; for 36h;	97.3%
With Lactobacillus animalis ATCC 35046 2’-N-deoxyribosyltransferase immobilized in DEAE-Sepharose; water for 1h; Enzymatic reaction;	22%
With potassium phosphate; 5'-amino-5'-deoxyuridine phosphorylase In Tris HCl buffer at 30℃; for 3h; pH=9; Kinetics; Concentration; Time; Enzymatic reaction;

: 58-96-8
uridine

A: α-D-ribofuranose-1-O-phosphate barium salt

B: 66-22-8
uracil

Conditions

Conditions	Yield
Stage #1: uridine With magnesium(II) chloride hexahydrate; recombinant E. coli uridine phosphorylase In aq. phosphate buffer at 23℃; pH=7.0; Stage #2: With ammonium hydroxide; barium(II) acetate In aq. phosphate buffer at 4℃; pH=8.0;	A 96% B n/a

: 3083-77-0
araU

A: α-D-arabinofuranosyl-1-phosphate barium salt

B: 66-22-8
uracil

Conditions

Conditions	Yield
Stage #1: araU With magnesium(II) chloride hexahydrate; recombinant E. coli uridine phosphorylase In aq. phosphate buffer at 40℃; for 72h; pH=7.0; Stage #2: With ammonium hydroxide; barium(II) acetate In aq. phosphate buffer at 4℃; pH=8.0;	A 96% B n/a

: 34846-90-7
methyl 3-methoxyprop-2-enoate

: 57-13-6
urea

: 66-22-8
uracil

Conditions

Conditions	Yield
Stage #1: urea With sodium methylate In 5,5-dimethyl-1,3-cyclohexadiene at 60℃; for 4h; Stage #2: methyl 3-methoxyprop-2-enoate In 5,5-dimethyl-1,3-cyclohexadiene at 80 - 110℃; for 6h; Temperature; Time; Solvent; Reagent/catalyst;	95.2%

: 139705-96-7
3',5'-di-O-acetyl-2'-deoxy-2'-<(4-methoxyphenyl)sulfonyl>uridine

A: [4-[(4-methoxyphenyl)sulfonyl]furan-2-yl]methyl acetate

B: 66-22-8
uracil

Conditions

Conditions	Yield
With N1,N1,N12,N12-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a:2,1'-c][1,4]diazepine-2,12-diamine In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere;	A 95% B n/a

: 51-20-7
5-bromouracil

: 66-22-8
uracil

Conditions

Conditions	Yield
With N,N-dimethyl acetamide at 180℃; for 7h;	93.8%
With isopropyl alcohol Product distribution; Mechanism; Quantum yield; Irradiation; deuterated 2-propanol solvents;
In ethanol Product distribution; Quantum yield; Mechanism; Irradiation; further solvent;

Raw Materials

952-92-1

109-72-8

147-94-4

Downstream Products

65-86-1

585-05-7

31448-54-1

71-43-2

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History

Uracil (CAS NO.66-22-8) is Originally discovered in 1900, and was isolated by hydrolysis of yeast nuclein which found in bovine thymus and spleen, herring sperm, and wheat germ.

Consensus Reports

EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

Specification

The Uracil, with the CAS registry number 66-22-8 and EINECS registry number 200-621-9, has the IUPAC name of 1H-pyrimidine-2,4-dione. It is a kind of white powder, and belongs to the following product categories: Heterocyclic Compounds; Pyrimidines; Biochemistry; Nucleobases and their analogs; Nucleosides, Nucleotides & Related Reagents; Nutritional Supplements; Nucleic acids. It is very stable, and incompatible with strong oxidizing agents. The molecular formula of the chemical is C₄H₄N₂O₂. What's more, while dealing with this chemical, you should not breathe dust and then try to avoid contacting with skin and eyes.

The Uracil is a common and naturally occurring pyrimidine derivative, and can be found in RNA. It was isolated by hydrolysis of yeast nuclein that was found in bovine thymus and spleen, herring sperm, and wheat germ. And it can be used for drug delivery and as a pharmaceutical.

The physical properties of Uracil are as followings: (1)ACD/BCF (pH 5.5): 1; (2)ACD/BCF (pH 7.4): 1; (3)ACD/KOC (pH 5.5): 6.494; (4)ACD/KOC (pH 7.4): 5.915; (5)#H bond acceptors: 4; (6)#H bond donors: 2; (7)#Freely Rotating Bonds: 0; (8)Polar Surface Area: 58.2 Å²; (9)Index of Refraction: 1.502; (10)Molar Refractivity: 25.008 cm³; (11)Molar Volume: 84.809 cm³; (12)Polarizability: 9.914×10^-24cm³; (13)Surface Tension: 41.304 dyne/cm; (14)Density: 1.322 g/cm³.

Preparation: This chemical can be prepared by Malic acid, sulfuric acid and urea. The reaction equation is as follows:

You should be cautious while dealing with this chemical. It irritates to eyes, respiratory system and skin. Therefore, you had better take the following instructions: Do not breathe dust and avoid contacting with skin and eyes; Wear suitable protective clothing, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: c1c[nH]c(=O)[nH]c1=O
(2)InChI: InChI=1/C4H4N2O2/c7-3-1-2-5-4(8)6-3/h1-2H,(H2,5,6,7,8)
(3)InChIKey: ISAKRJDGNUQOIC-UHFFFAOYAV

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LD50	oral	> 5gm/kg (5000mg/kg)		Medicamentos de Actualidad. Vol. 21, Pg. 125, 1985.
mouse	LD50	intraperitoneal	1513mg/kg (1513mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)	Journal of Pharmacology and Experimental Therapeutics. Vol. 207, Pg. 504, 1978.
mouse	LD50	oral	> 8gm/kg (8000mg/kg)		Oyo Yakuri. Pharmacometrics. Vol. 20, Pg. 1009, 1980.
rabbit	LD50	oral	> 10gm/kg (10000mg/kg)		Medicamentos de Actualidad. Vol. 21, Pg. 125, 1985.
rat	LD50	oral	> 6gm/kg (6000mg/kg)		Medicamentos de Actualidad. Vol. 21, Pg. 125, 1985.

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