Product Name

  • Name

    6-Chloro-3-methyluracil

  • EINECS 610-113-2
  • CAS No. 4318-56-3
  • Article Data25
  • CAS DataBase
  • Density 1.51 g/cm3
  • Solubility
  • Melting Point 278-280°C (dec.)
  • Formula C5H5ClN2O2
  • Boiling Point 268.7 °C at 760 mmHg
  • Molecular Weight 160.56
  • Flash Point 116.3 °C
  • Transport Information UN 1992
  • Appearance
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 4318-56-3 (6-Chloro-3-methyluracil)
  • Hazard Symbols IrritantXi
  • Synonyms Uracil,6-chloro-3-methyl- (7CI,8CI);3-Methyl-6-chlorouracil;6-Chloro-3-methylpyrimidine-2,4(1H,3H)-dione;NSC55976;6-Chloro-3-methyl uracil;
  • PSA 54.86000
  • LogP -0.27300

Synthetic route

1-methyl-2,4,6(1H,3H,5H)-pyrimidinetrione sodium salt

1-methyl-2,4,6(1H,3H,5H)-pyrimidinetrione sodium salt

3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

Conditions
ConditionsYield
With trichlorophosphate In water; acetonitrile at 8 - 80℃; for 2h; Temperature;85.3%
1-methyl-2,4,6-pyrimidinetrione
2565-47-1

1-methyl-2,4,6-pyrimidinetrione

3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

Conditions
ConditionsYield
With water; trichlorophosphate at 80℃; for 4h;81%
With water; trichlorophosphate at 80℃; for 2h;80%
With trichlorophosphate at 0 - 80℃;71.6%
6-hydroxy-3-methylpyrimidine-2,4(1H,3H)-dione
882872-13-1

6-hydroxy-3-methylpyrimidine-2,4(1H,3H)-dione

3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

Conditions
ConditionsYield
With trichlorophosphate In acetonitrile at 120℃; for 0.333333h; Microwave irradiation;80%
malonic acid
141-82-2

malonic acid

N-Methylurea
598-50-5

N-Methylurea

3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

Conditions
ConditionsYield
Stage #1: malonic acid; N-Methylurea With acetic anhydride; acetic acid
Stage #2: With trichlorophosphate
1-methyl-1H-imidazole
616-47-7

1-methyl-1H-imidazole

3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

3-methyl-1-(3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-6-yl)imidazolium chloride

3-methyl-1-(3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-6-yl)imidazolium chloride

Conditions
ConditionsYield
In chlorobenzene for 7h; Heating;100%
3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

6-hydrazinyl-3-methylpyrimidine-2,4(1H,3H)-dione
123506-41-2

6-hydrazinyl-3-methylpyrimidine-2,4(1H,3H)-dione

Conditions
ConditionsYield
With hydrazine hydrate In ethanol at 20 - 80℃;100%
With hydrazine hydrate In ethanol at 80℃; for 1h;100%
With hydrazine hydrate In ethanol at 80℃; for 1h; Inert atmosphere;100%
3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

2-(bromomethyl)-4-fluorobenzonitrile
421552-12-7

2-(bromomethyl)-4-fluorobenzonitrile

2-[(6-chloro-3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)methyl]-4-fluorobenzonitrile
865759-24-6

2-[(6-chloro-3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)methyl]-4-fluorobenzonitrile

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 20 - 55℃; for 4h; Time; Temperature;98.9%
Stage #1: 3-methyl-6-chlorouracil; 2-(bromomethyl)-4-fluorobenzonitrile In tetrahydrofuran at 40℃; for 0.25h;
Stage #2: With sodium hydrogencarbonate; copper(II) acetylacetonate In tetrahydrofuran at 60℃; for 3h; Temperature; Reagent/catalyst;		98.93%
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 107℃; for 2h; Solvent; Temperature; Reagent/catalyst;96.6%
4-amino-N,N-dimethylaniline
99-98-9

4-amino-N,N-dimethylaniline

3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

6-(4-Dimethylamino-anilino)-3-methyl-2,4(1H,3H)-pyrimidindion
83983-31-7

6-(4-Dimethylamino-anilino)-3-methyl-2,4(1H,3H)-pyrimidindion

Conditions
ConditionsYield
With sodium hydroxide for 0.5h;98%
Heating;92%
3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

para-fluorobenzylamine
140-75-0

para-fluorobenzylamine

6-(4-fluoro-benzylamino)-3-methyl-1H-pyrimidine-2,4-dione

6-(4-fluoro-benzylamino)-3-methyl-1H-pyrimidine-2,4-dione

Conditions
ConditionsYield
In butan-1-ol for 3h; Substitution; Heating;97%
3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

2-(bromomethyl)benzonitrile
22115-41-9

2-(bromomethyl)benzonitrile

2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)methyl)benzonitrile
865758-96-9

2-((6-chloro-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)methyl)benzonitrile

Conditions
ConditionsYield
Stage #1: 3-methyl-6-chlorouracil With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 23℃; for 0.25h; Schlenk technique; Inert atmosphere;
Stage #2: 2-(bromomethyl)benzonitrile In tetrahydrofuran at 65℃; for 2h; Schlenk technique; Inert atmosphere;		96%
With 1-methyl-pyrrolidin-2-one; N-ethyl-N,N-diisopropylamine at 60 - 65℃; for 3h; Large scale;96.42%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 40 - 45℃; Solvent; Temperature;95.8%
benzyl bromide
100-39-0

benzyl bromide

3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

1-benzyl-6-chloro-3-methyl-1H-pyrimidine-2,4-dione
66400-16-6

1-benzyl-6-chloro-3-methyl-1H-pyrimidine-2,4-dione

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 65℃; for 12h; Reagent/catalyst; Temperature;96%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 40℃; for 6h;
m-Anisidine
536-90-3

m-Anisidine

3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

6-(3-Methoxy-anilino)-3-methyl-2,4(1H,3H)-pyrimidindion
59776-23-7

6-(3-Methoxy-anilino)-3-methyl-2,4(1H,3H)-pyrimidindion

Conditions
ConditionsYield
With sodium hydroxide for 0.5h;95%
Heating;69%
thiophenol
108-98-5

thiophenol

3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

3-methyl-6-(phenylthio)pyrimidine-2,4(1H,3H)-dione
69139-08-8

3-methyl-6-(phenylthio)pyrimidine-2,4(1H,3H)-dione

Conditions
ConditionsYield
With potassium hydroxide In ethanol for 2h; Heating;95%
Stage #1: 3-methyl-6-chlorouracil With (1,3,5-triaza-7-phosphaadamantan-1-ium-1-yl)butane-1-sulfonate; palladium diacetate In N,N-dimethyl-formamide for 0.0833333h; Schlenk technique; Inert atmosphere;
Stage #2: thiophenol With potassium phosphate In N,N-dimethyl-formamide at 50℃; for 2h; Schlenk technique; Inert atmosphere;		72%
C5H14N2*2ClH

C5H14N2*2ClH

3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

C10H18N4O2
1186491-87-1

C10H18N4O2

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In ethanol at 100℃;95%
(4-fluorobenzyl)hydrazine dihydrochloride

(4-fluorobenzyl)hydrazine dihydrochloride

3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

C12H13FN4O2
1186491-91-7

C12H13FN4O2

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In ethanol at 100℃;95%
2-methylpropylhydrazine dihydrochloride
145295-89-2

2-methylpropylhydrazine dihydrochloride

3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

C9H16N4O2
1186491-89-3

C9H16N4O2

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In ethanol at 100℃;95%
benzylhydrazine dihydrochloride
20570-96-1

benzylhydrazine dihydrochloride

3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

3-methyl-6-(1-benzylhydrazino)uracil
58695-90-2

3-methyl-6-(1-benzylhydrazino)uracil

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In ethanol at 100℃;95%
3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

ethyl hydrazine dihydrochloride

ethyl hydrazine dihydrochloride

6-(1-ethylhydrazinyl)-3-methylpyrimidine-2,4(1H,3H)-dione
144294-61-1

6-(1-ethylhydrazinyl)-3-methylpyrimidine-2,4(1H,3H)-dione

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In ethanol at 100℃;95%
3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

1-propylhydrazine dihydrochloride

1-propylhydrazine dihydrochloride

C8H14N4O2
1186491-90-6

C8H14N4O2

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In ethanol at 100℃;95%
3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

1-butylhydrazine dihydrochloride

1-butylhydrazine dihydrochloride

6-(N-Butylhydrazino)-3-methyl-1H-pyrimidine-2,4-dione
729599-02-4

6-(N-Butylhydrazino)-3-methyl-1H-pyrimidine-2,4-dione

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In ethanol at 100℃;95%
3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

para-methylbenzylamine
104-84-7

para-methylbenzylamine

3-methyl-6-(4-methyl-benzylamino)-1H-pyrimidine-2,4-dione

3-methyl-6-(4-methyl-benzylamino)-1H-pyrimidine-2,4-dione

Conditions
ConditionsYield
In butan-1-ol for 3h; Substitution; Heating;94%
4-chlorobenzylamine
104-86-9

4-chlorobenzylamine

3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

6-<(4-chlorobenzyl)amino>-3-methyluracil
73908-18-6

6-<(4-chlorobenzyl)amino>-3-methyluracil

Conditions
ConditionsYield
In butan-1-ol for 3h; Substitution; Heating;93%
In butan-1-ol for 4h; Heating;60%
N-methyl-p-aminophenol
150-75-4

N-methyl-p-aminophenol

3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

6-(4-Hydroxy-N-methyl-anilino)-3-methyl-2,4(1H,3H)-pyrimidindion
76837-72-4

6-(4-Hydroxy-N-methyl-anilino)-3-methyl-2,4(1H,3H)-pyrimidindion

Conditions
ConditionsYield
at 145℃; for 0.5h;93%
4-methoxy-benzylamine
2393-23-9

4-methoxy-benzylamine

3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

6-(4-Methoxy-benzylamino)-3-methyl-1H-pyrimidine-2,4-dione
73908-17-5

6-(4-Methoxy-benzylamino)-3-methyl-1H-pyrimidine-2,4-dione

Conditions
ConditionsYield
In butan-1-ol for 3h; Substitution; Heating;93%
3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

p-methoxybenzyl chloride
824-94-2

p-methoxybenzyl chloride

6-chloro-1-(4-methoxybenzyl)-3-methylpyrimidine-2,4(1H,3H)-dione
916764-89-1

6-chloro-1-(4-methoxybenzyl)-3-methylpyrimidine-2,4(1H,3H)-dione

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 1h; Inert atmosphere;93%
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 16h;70%
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 16h;66.7%
4-amino-o-xylene
95-64-7

4-amino-o-xylene

3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

6-(3,4-Dimethyl-anilino)-3-methyl-2,4(1H,3H)-pyrimidindion
59776-24-8

6-(3,4-Dimethyl-anilino)-3-methyl-2,4(1H,3H)-pyrimidindion

Conditions
ConditionsYield
With sodium hydroxide for 0.5h;92%
at 160 - 170℃; for 0.166667h;89%
With acetic acid; N,N-diethylaniline at 190℃; for 0.416667h;88%
at 180 - 200℃; for 0.166667 - 0.25h;
n-Dodecylamine
124-22-1

n-Dodecylamine

3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

6-(Dodecylamino)-3-methyluracil
83797-71-1

6-(Dodecylamino)-3-methyluracil

Conditions
ConditionsYield
In butan-1-ol for 5h; Heating;92%
3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

4-chlorobenzohydroximoyl chloride
28123-63-9

4-chlorobenzohydroximoyl chloride

3-(4-chlorophenyl)-6-methyl-5H-[1,2,4]oxadiazolo[4,5-c]pyrimidine-5,7(6H)-dione

3-(4-chlorophenyl)-6-methyl-5H-[1,2,4]oxadiazolo[4,5-c]pyrimidine-5,7(6H)-dione

Conditions
ConditionsYield
With triethylamine In methanol at 20℃; for 5h;92%
3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

propargyl bromide
106-96-7

propargyl bromide

6-chloro-3-methyl-1-(prop-2-yn-1-yl)pyrimidine-2,4(1H,3H)-dione

6-chloro-3-methyl-1-(prop-2-yn-1-yl)pyrimidine-2,4(1H,3H)-dione

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide for 4h; Reflux;92%
N-hydroxy-4-methylbenzenecarboximidoyl chloride
36288-37-6

N-hydroxy-4-methylbenzenecarboximidoyl chloride

3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

6-methyl-3-(p-tolyl)-5H-[1,2,4]oxadiazolo[4,5-c]pyrimidine-5,7(6H)-dione

6-methyl-3-(p-tolyl)-5H-[1,2,4]oxadiazolo[4,5-c]pyrimidine-5,7(6H)-dione

Conditions
ConditionsYield
With triethylamine In methanol at 20℃; for 5h;91%
(R)-piperidin-3-ylcarbamic acid tert-butyl ester
309956-78-3

(R)-piperidin-3-ylcarbamic acid tert-butyl ester

3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

(R)-1-(1-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)-3-tert-butoxycarbonylaminopiperidine

(R)-1-(1-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)-3-tert-butoxycarbonylaminopiperidine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 78 - 82℃; for 10h; Reagent/catalyst; Solvent;91%
dmap
1122-58-3

dmap

3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

4-(dimethylamino)-1-(3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-6-yl)pyridinium chloride

4-(dimethylamino)-1-(3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-6-yl)pyridinium chloride

Conditions
ConditionsYield
In various solvent(s) for 5h; Heating;90%
methyl bromide
74-83-9

methyl bromide

3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

1,3-Dimethyl-6-chlorouracil
6972-27-6

1,3-Dimethyl-6-chlorouracil

Conditions
ConditionsYield
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane; water at 40℃; Alkylation;90%
3-methyl-6-chlorouracil
4318-56-3

3-methyl-6-chlorouracil

allyl bromide
106-95-6

allyl bromide

1-allyl-6-chloro-3-methyl-1H-pyrimidine-2,4-dione
66400-17-7

1-allyl-6-chloro-3-methyl-1H-pyrimidine-2,4-dione

Conditions
ConditionsYield
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane; water at 40℃; Alkylation;90%

6-Chloro-3-methyluracil Chemical Properties

IUPAC Name: 6-Chloro-3-methyl-1H-pyrimidine-2,4-dione 
Following is the structure of 2,4(1H,3H)-Pyrimidinedione,6-chloro-3-methyl- (CAS NO.4318-56-3):
                        
Empirical Formula: C5H5ClN2O2
Molecular Weight: 160.5584 g/mol
Molar Refractivity: 35.42 cm3
Molar Volume: 106.3 cm3
Density: 1.51 g/cm3
Flash Point: 116.3 °C
Index of Refraction: 1.58
Surface Tension: 54.1 dyne/cm
Melting point: 278-280 °C (dec.)
Enthalpy of Vaporization: 58.85 kJ/mol
Boiling Point: 268.7 °C at 760 mmHg
Vapour Pressure of 2,4(1H,3H)-Pyrimidinedione,6-chloro-3-methyl- (CAS NO.4318-56-3): 0.00101 mmHg at 25 °C
Product Categories of 2,4(1H,3H)-Pyrimidinedione,6-chloro-3-methyl- (CAS NO.4318-56-3): Pyrimidine; Biochemistry; Nucleobases and their analogs; Nucleosides, Nucleotides & Related Reagents
Canonical SMILES: CN1C(=O)C=C(NC1=O)Cl
InChI: InChI=1S/C5H5ClN2O2/c1-8-4(9)2-3(6)7-5(8)10/h2H,1H3,(H,7,10)
InChIKey: SGLXGFAZAARYJY-UHFFFAOYSA-N

6-Chloro-3-methyluracil Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing.
RIDADR: UN 1992
Hazard Note: Irritant

6-Chloro-3-methyluracil Specification

 2,4(1H,3H)-Pyrimidinedione,6-chloro-3-methyl- , its cas register number is 4318-56-3. It also can be called 6-Chloro-3-methyluracil ; 6-Chloro-3-methylpyrimidine-2,4(1H,3H)-dione ; and 3-Methyl-6-chlorouracil .

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