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Basic Information
CAS No.: 1820-81-1
Name: 5-Chlorouracil
Article Data: 26
Molecular Structure:
Molecular Structure of 1820-81-1 (5-Chlorouracil)
Formula: C4H3ClN2O2
Molecular Weight: 146.533
Synonyms: 2,4 (1H,3H)-Pyrimidinedione, 5-chloro-;2,4(1H,3H)-Pyrimidinedione, 5-chloro-;Uracil, 5-chloro- (VAN) (8CI);Uracil, 5-chloro-;5-Chloro-2,4-pyrimidinedione;5-Chlorouracil,5-Chloro-2,4-dihydroxypyrimidine;
EINECS: 217-339-7
Density: 1.61 g/cm3
Melting Point: >300 °C(lit.)
Boiling Point: 413.6 °C at 760 mmHg
Flash Point: 203.9 °C
Solubility: slightly soluble in water
Appearance: white to light beige crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 22-24/25-36-26
PSA: 65.72000
LogP: -0.28340
Synthetic route
66-22-8

uracil

1820-81-1

5-chlorouracil

Conditions
ConditionsYield
With 1,2-Dichloro-3-iodobenzene In water; acetic acid at 80℃; for 0.25h;92%
With hydrogenchloride; ammonium cerium(IV) nitrate In methanol at 70℃; for 5.5h;82%
With sodium hydrogencarbonate; lithium chloride In acetonitrile Ambient temperature; electrolysis (Pt electrodes, SCE reference, LiClO4 as supporting electrolyte);77%
With potassium phosphate; potassium chloride; dihydrogen peroxide; chloroperoxidase pH 3;7%
123551-49-5

5-chloro-2,4-dimethoxypyrimidine

1820-81-1

5-chlorouracil

Conditions
ConditionsYield
With hydrogenchloride69%

5-methoxycarbonyluracil

1820-81-1

5-chlorouracil

Conditions
ConditionsYield
With hydrogenchloride; chlorine In water for 16h; Heating;63%
66-22-8

uracil

A

1820-81-1

5-chlorouracil

B

2072-83-5

5,5-dichloro-6-hydroxy-5,6-dihydrouracil

Conditions
ConditionsYield
With sodium persulfate; water; sodium chloride In acetic acid at 100 - 105℃;A 20%
B 53%
With sodium persulfate; water; sodium chloride In acetic acid at 100 - 105℃;A 20%
B 53%
65906-87-8

5-chloro-6-hydroxy-5-methoxycarbonyl-5,6-dihydrouracil

1820-81-1

5-chlorouracil

Conditions
ConditionsYield
With hydrogenchloride In water for 15h; Heating;27%
In hydrogenchloride
128-09-6

N-chloro-succinimide

108-24-7

acetic anhydride

64-19-7

acetic acid

66-22-8

uracil

1820-81-1

5-chlorouracil

128-09-6

N-chloro-succinimide

66-22-8

uracil

1820-81-1

5-chlorouracil

106146-79-6

2-ethylmercapto-5-chloro-3H-pyrimidin-4-one

1820-81-1

5-chlorouracil

Conditions
ConditionsYield
With hydrogenchloride

1-α-D-arabinopyranosyl-5-chloro-1H-pyrimidine-2,4-dione

1820-81-1

5-chlorouracil

Conditions
ConditionsYield
With hydrogenchloride
40338-28-1

1-acetyl-1H-pyrimidine-2,4-dione

1820-81-1

5-chlorouracil

Conditions
ConditionsYield
Yield given. Multistep reaction;
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  • 1820-81-1  CAS NO.1820-81-1

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    1820-81-1 CAS NO.1820-81-1

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Specification

The 5-Chlorouracil, with the CAS registry number 1820-81-1 and EINECS registry number 217-339-7, has the IUPAC name of 5-chloro-1H-pyrimidine-2,4-dione. It is a kind of white to light beige crystalline powder, and belongs to the following product categories: Pyridines, Pyrimidines, Purines and Pteredines; Pyrimidine series; Heterocyclic Compounds; Biochemistry; Nucleobases and their analogs; Nucleosides, Nucleotides & Related Reagents; Nucleic acids; Bases & Related Reagents; Heterocycles; Nucleotides. The molecular formula of the chemical is C4H3ClN2O2. What's more, it is always used for the experimental and clinical treatment of neoplastic and viral diseases.

The physical properties of 5-Chlorouracil are as followings: (1)ACD/LogP: -0.52; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.52; (4)ACD/LogD (pH 7.4): -0.78; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 12.35; (8)ACD/KOC (pH 7.4): 6.76; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 40.62 Å2; (13)Index of Refraction: 1.587; (14)Molar Refractivity: 30.56 cm3; (15)Molar Volume: 90.9 cm3; (16)Polarizability: 12.11×10-24cm3; (17)Surface Tension: 57.3 dyne/cm; (18)Density: 1.61 g/cm3; (19)Flash Point: 203.9 °C; (20)Enthalpy of Vaporization: 69.22 kJ/mol; (21)Boiling Point: 413.6 °C at 760 mmHg; (22)Vapour Pressure: 1.98E-07 mmHg at 25°C. 

Uses of 5-Chlorouracil: It can react with chloro-trimethyl-silane to produce 5-Chloro-2,4-bis(trimethylsiloxy)pyrimidine. This reaction will need reagent hexamethylsilazane, and the yield is about 99%.   

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: Cl/C1=C/NC(=O)NC1=O
(2)InChI: InChI=1/C4H3ClN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
(3)InChIKey: ZFTBZKVVGZNMJR-UHFFFAOYAS