5-Chlorouracil supplier | CasNO.1820-81-1

Name
5-Chlorouracil
EINECS 217-339-7
CAS No. 1820-81-1
Article Data26
CAS DataBase
Density 1.61 g/cm³
Solubility slightly soluble in water

Melting Point >300 °C(lit.)

Formula C₄H₃ClN₂O₂

Boiling Point 413.6 °C at 760 mmHg

Molecular Weight 146.533

Flash Point 203.9 °C

Transport Information

Appearance white to light beige crystalline powder

Safety 22-24/25-36-26

Risk Codes 36/37/38

Molecular Structure

Hazard Symbols Xi

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;

PSA 65.72000

LogP -0.28340

Synthetic route

66-22-8
uracil

1820-81-1
5-chlorouracil

Conditions

Conditions Yield

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

Conditions Yield

With hydrogenchloride 69%

5-methoxycarbonyluracil

1820-81-1
5-chlorouracil

Conditions

Conditions Yield

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

Conditions Yield

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

Conditions Yield

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

...Expand

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

Conditions Yield

With hydrogenchloride

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

1820-81-1
5-chlorouracil

Conditions

Conditions Yield

With hydrogenchloride

40338-28-1
1-acetyl-1H-pyrimidine-2,4-dione

1820-81-1
5-chlorouracil

Conditions

Conditions Yield

Yield given. Multistep reaction;

5-Chloro-6-hydroxyamino-dihydro-pyrimidine-2,4-dione

1820-81-1
5-chlorouracil

Conditions

Conditions Yield

With hydroxylamine at 25℃; Equilibrium constant; var. pH;

(+-)-5,5-dichloro-6-methoxy-dihydro-pyrimidine-2,4-dione

(+-)-5,5-dichloro-6-methoxy-dihydro-pyrimidine-2,4-dione

1820-81-1
5-chlorouracil

Conditions

Conditions Yield

With hydrogenchloride; tin

5.5-dichloro-4-oxy-dihydrouracil

5.5-dichloro-4-oxy-dihydrouracil

1820-81-1
5-chlorouracil

Conditions

Conditions Yield

With hydrogenchloride; tin

66-22-8
uracil

A

1820-81-1
5-chlorouracil

B
5.5-dichloro-4-oxy-dihydrouracil

5.5-dichloro-4-oxy-dihydrouracil

Conditions

Conditions Yield

With chlorine

50-90-8
5-chloro-2'-deoxyuridine

1820-81-1
5-chlorouracil

Conditions

Conditions Yield

With phosphate buffer; thymidine phosphorylase from Escherichia coli at 37℃; pH=7; Enzyme kinetics; Further Variations:; concentration of reagent;

42821-92-1
methyl 2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

1820-81-1
5-chlorouracil

Conditions

Conditions Yield

With hydrogenchloride In water

1820-81-1
5-chlorouracil

65094-55-5
C4H4ClN2O2

Conditions

Conditions Yield

With H2SO4 glasses Product distribution; Irradiation; 100%

75-77-4
chloro-trimethyl-silane

1820-81-1
5-chlorouracil

58990-53-7
5-chloro-2,4-bis-O-trimethylsilyluracil

Conditions

Conditions Yield

With 1,1,1,3,3,3-hexamethyl-disilazane Ambient temperature; 99%

1820-81-1
5-chlorouracil

930-69-8
sodium thiophenolate

1137-90-2
5-(phenylsulfanyl)-2,4(1H,3H)-pyrimidinedione

Conditions

Conditions Yield

In N,N,N,N,N,N-hexamethylphosphoric triamide at 150℃; for 0.0833333h; microwave irradiation; 97%

1820-81-1
5-chlorouracil

140-88-5
ethyl acrylate

1370413-72-1
3-(5-chloro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)propionic acid ethyl ester

Conditions

Conditions Yield

With triethylamine In N,N-dimethyl-formamide at 60℃; Aza-Micheal reaction; 96%

1820-81-1
5-chlorouracil

5750-76-5
2,4,5-trichloropyrimidine

Conditions

Conditions Yield

With phosphorus pentachloride; trichlorophosphate Neat (no solvent); Heating / reflux; 95%

With phosgene; Triphenylphosphine oxide In nitrobenzene at -5 - 125℃; for 0.833333h; Inert atmosphere; 93%

With N,N-diethylaniline; trichlorophosphate at 110℃; for 24h; 81%

1820-81-1
5-chlorouracil

999-97-3
1,1,1,3,3,3-hexamethyl-disilazane

58990-53-7
5-chloro-2,4-bis-O-trimethylsilyluracil

Conditions

Conditions Yield

With ammonium sulfate for 5h; Heating; 95%

With chloro-trimethyl-silane Heating;

With ammonium sulfate for 3h; Heating;

1820-81-1
5-chlorouracil

292638-85-8
acrylic acid methyl ester

1256346-76-5
3-(5-chloro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)propionic acid methyl ester

Conditions

Conditions Yield

With triethylamine In N,N-dimethyl-formamide at 60℃; for 4h; Michael Addition; 95%

With triethylamine In N,N-dimethyl-formamide at 20℃; Michael-type addition; regioselective reaction; 88%

1820-81-1
5-chlorouracil

141-32-2
acrylic acid n-butyl ester

1370413-75-4
3-(5-chloro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)propionic acid butyl ester

Conditions

Conditions Yield

With triethylamine In N,N-dimethyl-formamide at 60℃; Aza-Micheal reaction; 95%

1820-81-1
5-chlorouracil

97-00-7
1-chloro-2,4-dinitro-benzene

1-(2,4-dinitro-phenyl)-5-chloro-1H-pyrimidine-2,4-dione

Conditions

Conditions Yield

With zinc(II) oxide at 130℃; for 0.1h; Ionic liquid; Microwave irradiation; 92%

1820-81-1
5-chlorouracil

63331-62-4
5-Chloro-4-thiouracil

Conditions

Conditions Yield

With diphosphorus pentasulfide; sodium hydrogencarbonate In diethylene glycol dimethyl ether at 110℃; for 3h; 90%

1820-81-1
5-chlorouracil

604-68-2
α-D-glucopyranose peracetylate

379218-39-0
5-chloro-1-(2,3,4,6-tetra-O-acetyl-β-D-gluco-hexopyranosyl)uracil

Conditions

Conditions Yield

Stage #1: 5-chlorouracil With 1,1,1,3,3,3-hexamethyl-disilazane; saccharin In acetonitrile for 3h; Heating;
Stage #2: α-D-glucopyranose peracetylate With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 20 - 85℃; 90%

1820-81-1
5-chlorouracil

100-46-9
benzylamine

28485-19-0
5-(benzylamino)dihydropyrimidine-2,4(1H,3H)-dione

Conditions

Conditions Yield

at 150℃; for 0.333333h; microwave irradiation; 88%

1820-81-1
5-chlorouracil

6674-22-2
1,8-diazabicyclo[5.4.0]undec-7-ene

2,3,4,6,7,8,9,10-octahydro-pyrimido[1,2-a]azepine; compound with 5-chloro-1H-pyrimidine-2,4-dione

Conditions

Conditions Yield

In acetonitrile at 20℃; 87%

1820-81-1
5-chlorouracil

58-61-7
adenosine

1369492-08-9
C4H3ClN2O2*C10H13N5O4

Conditions

Conditions Yield

In ethanol; chloroform; water for 8h; Reflux; 84%

1820-81-1
5-chlorouracil

[Zn(OH)(hydrotris(3-tert-butyl-5-isopropyl-1-pyrazolyl)borate)]

[Zn(hydrotris(3-tert-butyl-5-isopropyl-1-pyrazolyl)borate)(5-chlorouracilate)]

Conditions

Conditions Yield

In methanol; dichloromethane (N2); using Schlenk techniques; addn. of suspn. of 5-chlorouracil in methanol to soln. of Zn(HB(Me3CC3HN2CHMe2)3)(OH) in CH2Cl2; stirring overnight; filtration, evapn. of solvent, drying under vac., elem. anal.; 81%

1820-81-1
5-chlorouracil

36288-37-6
N-hydroxy-4-methylbenzenecarboximidoyl chloride

6-chloro-3-(p-tolyl)-5H-[1,2,4]oxadiazolo[4,5-a]pyrimidin-5-one

Conditions

Conditions Yield

With dmap In 1,4-dioxane for 5h; Reflux; 80%

1820-81-1
5-chlorouracil

27607-77-8
trimethylsilyl trifluoromethanesulfonate

121654-00-0
3,4,6-tris-O-tert-butyldimethylsilyl-1,2-anhydro-α-D-glucopyranose

1-[3′,4′,6′-tri-O-(tert-butyldimethylsilyl)-2-O-trimethylsilyl-β-D-glucopyranosyl]-5-chloro-2,4(1H,3H)-pyrimidinedione

Conditions

Conditions Yield

Stage #1: 5-chlorouracil With 1,1,1,3,3,3-hexamethyl-disilazane at 120℃; for 1.5h; Inert atmosphere;
Stage #2: trimethylsilyl trifluoromethanesulfonate; 3,4,6-tris-O-tert-butyldimethylsilyl-1,2-anhydro-α-D-glucopyranose at 60℃; for 3h; Inert atmosphere; 80%

...Expand

1820-81-1
5-chlorouracil

61946-91-6
4-ethyl-N-hydroxybenzene-1-carboximidoyl chloride

6-chloro-3-(4-ethylphenyl)-5H-[1,2,4]oxadiazolo[4,5-a]pyrimidin-5-one

Conditions

Conditions Yield

With dmap In 1,4-dioxane for 5h; Reflux; 79%

1820-81-1
5-chlorouracil

27607-77-8
trimethylsilyl trifluoromethanesulfonate

74372-90-0, 112289-38-0, 135202-48-1, 148888-66-8, 71696-32-7
1,2-anhydro-3,4,6-tri-O-benzyl-β-D-mannopyranose

1-[3′,4′,6′-tri-O-(benzyl)-2-O-trimethylsilyl-glucopyranosyl]-5-chloro-2,4(1H,3H)-pyrimidinedione

Conditions

Conditions Yield

Stage #1: 5-chlorouracil With 1,1,1,3,3,3-hexamethyl-disilazane at 120℃; for 1.5h; Inert atmosphere;
Stage #2: trimethylsilyl trifluoromethanesulfonate; 1,2-anhydro-3,4,6-tri-O-benzyl-β-D-mannopyranose at 60℃; for 3h; Inert atmosphere; 79%

...Expand

848644-37-1
1,2,3,5-tetra-O-acetyl-3-C-ethynyl-D-ribo-pentofuranose

1820-81-1
5-chlorouracil

848644-41-7
1-[2,3,5-tri-O-acetyl-3-C-ethynyl-β-D-ribo-pentofuranosyl]-5-chlorouracil

Conditions

Conditions Yield

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate In acetonitrile at 50℃; for 29h; 78%

1820-81-1
5-chlorouracil

107-13-1
acrylonitrile

C7H6ClN3O2

Conditions

Conditions Yield

With triethylamine In water at 100℃; for 0.0833333h; Michael addition; microwave irradiation; 78%

1820-81-1
5-chlorouracil

1765-40-8
(bromomethyl)pentafluorobenzene

N1,N3-bis(pentafluorobenzyl)-5-chlorouracil

Conditions

Conditions Yield

With N-ethyl-N,N-diisopropylamine In methanol at 42℃; for 2h; 77%

1820-81-1
5-chlorouracil

chromium chloride hexahydrate

4998-57-6
His

203308-39-8
Cr(3+)*C4H2N2O2Cl(1-)*C6H8N3O2(1-)*H2O*Cl(1-) = Cr(C4H2N2O2Cl)(C6H8N3O2)(H2O)Cl

Conditions

Conditions Yield

With triethyl formate; aq. NaOH In ethanol; water addn. aq. histidine to pptd. (pH 5-6, aq. NaOH) suspn. of metal/5-chlorouracil complex in ethanol; pptn. on concn. and ether addn., drying (vac., 50°C); elem. anal.; 75%

...Expand

1820-81-1
5-chlorouracil

106-95-6
allyl bromide

N-allyl 5-chlorouracil

Conditions

Conditions Yield

With sodium hydroxide In water at 100℃; for 0.166667h; Microwave irradiation; regioselective reaction; 75%

1820-81-1
5-chlorouracil

5-chloro-6-deuteropyrimidine-2,4(1H,3H)-dione

Conditions

Conditions Yield

With [D]-sodium hydroxide; sodium In water-d2 at 0 - 120℃; Inert atmosphere; 75%

1820-81-1
5-chlorouracil

350-46-9
4-Fluoronitrobenzene

5-chloro-1-(4-nitro-phenyl)-1H-pyrimidine-2,4-dione

Conditions

Conditions Yield

Stage #1: 5-chlorouracil With potassium carbonate In dimethyl sulfoxide at 80℃; for 0.5h;
Stage #2: 4-Fluoronitrobenzene In dimethyl sulfoxide at 70 - 80℃; 74%

1820-81-1
5-chlorouracil

108-98-5
thiophenol

1137-90-2
5-(phenylsulfanyl)-2,4(1H,3H)-pyrimidinedione

Conditions

Conditions Yield

With potassium carbonate In ethylene glycol at 130 - 140℃; for 2h; 71%

iron(III) chloride hexahydrate

1820-81-1
5-chlorouracil

4998-57-6
His

203308-40-1
Fe(3+)*C4H2N2O2Cl(1-)*C6H8N3O2(1-)*H2O*Cl(1-) = Fe(C4H2N2O2Cl)(C6H8N3O2)(H2O)Cl

Conditions

Conditions Yield

With triethyl formate; aq. NaOH In ethanol; water addn. aq. histidine to pptd. (pH 5-6, aq. NaOH) suspn. of metal/5-chlorouracil complex in ethanol; pptn. on concn. and ether addn., drying (vac., 50°C); elem. anal.; 70%

...Expand

1820-81-1
5-chlorouracil

chromium chloride hexahydrate

Cr(3+)*C4H2N2O2Cl(1-)*OH(1-)*Cl(1-) = Cr(C4H2N2O2Cl)(OH)Cl

Conditions

Conditions Yield

With triethyl orthoformate In ethanol refluxing (2-3 h); pptn. (pH 5-6, aq. NaOH), washing (ethanol), drying (vac., 50°C);elem. anal.; 70%

5-Chlorouracil 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

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Conditions	Yield
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%

Conditions	Yield
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%

Conditions	Yield
With hydrogenchloride In water for 15h; Heating;	27%
In hydrogenchloride

Conditions	Yield
With phosphorus pentachloride; trichlorophosphate Neat (no solvent); Heating / reflux;	95%
With phosgene; Triphenylphosphine oxide In nitrobenzene at -5 - 125℃; for 0.833333h; Inert atmosphere;	93%
With N,N-diethylaniline; trichlorophosphate at 110℃; for 24h;	81%

Conditions	Yield
With ammonium sulfate for 5h; Heating;	95%
With chloro-trimethyl-silane Heating;
With ammonium sulfate for 3h; Heating;

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 60℃; for 4h; Michael Addition;	95%
With triethylamine In N,N-dimethyl-formamide at 20℃; Michael-type addition; regioselective reaction;	88%

Product Name

5-Chlorouracil

Synthetic route

5-Chlorouracil Specification

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