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51-52-5

Basic Information
CAS No.: 51-52-5
Name: 4(1H)-Pyrimidinone,2,3-dihydro-6-propyl-2-thioxo-
Molecular Structure:
Molecular Structure of 51-52-5 (4(1H)-Pyrimidinone,2,3-dihydro-6-propyl-2-thioxo-)
Formula: C7H10N2OS
Molecular Weight: 170.23 .
Synonyms: Uracil,6-propyl-2-thio- (7CI,8CI);2-Mercapto-4-hydroxy-6-n-propylpyrimidine;2-Mercapto-4-hydroxy-6-propylpyrimidine;2-Mercapto-6-propylpyrimidin-4-ol;2-Thio-4-oxo-6-propyl-1,3-pyrimidine;2-Thio-6-propyl-1,3-pyrimidin-4-one;6-Propyl-2-thio-2,4(1H,3H)pyrimidinedione;6-Propyl-2-thiouracil;6-Propylthiouracil;6-n-Propyl-2-thiouracil;6-n-Propylthiouracil;NSC 6498;NSC 70461;PTU (thyreostatic);Procasil;Propacil;Propycil;Propyl-Thiorist;Propyl-Thyracil;Propylthiorit;Propylthiouracil;Prothiucil;Prothiurone;Prothycil;Prothyran;Protiural;Thiuragyl;Thyreostat II;
EINECS: 200-103-2
Density: 1.24 g/cm3
Melting Point: 218-220 °C(lit.)
Boiling Point: 355.2 °C at 760 mmHg
Flash Point: 168.6 °C
Solubility: 1.1 g/L in water
Appearance: white crystalline powder
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 22-40
Safety: 36/37-45
Transport Information:
PSA: 80.74000
LogP: 1.38500
Synthetic route
3249-68-1

ethyl butyroyl acetate

17356-08-0

thiourea

51-52-5

propylthiouracil

Conditions
ConditionsYield
Reflux;81%
With potassium hydroxide In ethanol at 80℃; for 5h;41%
With sodium ethanolate
17356-08-0

thiourea

30414-54-1

methyl 3-oxohexanoate

51-52-5

propylthiouracil

Conditions
ConditionsYield
With potassium carbonate In water at 70 - 105℃; for 3h;78%
With sodium ethanolate In ethanol at 100℃; Inert atmosphere;33%
Heating;
51-52-5

propylthiouracil

931-53-3

Cyclohexyl isocyanide

762-42-5

dimethyl acetylenedicarboxylate

dimethyl 2-(cyclohexylamino)-4,8-dihydro-8-oxo-6-propylpyrimido[2,1-b][1,3]thiazine-3,4-dicarboxylate

Conditions
ConditionsYield
In toluene for 1h; Reflux;94%
51-52-5

propylthiouracil

14542-93-9

1,1,3,3-tetramethylbutane isonitrile

762-42-5

dimethyl acetylenedicarboxylate

dimethyl 2-(2,4,4-trimethylpentan-2-ylamino)-4,8-dihydro-8-oxo-6-propylpyrimido[2,1-b][1,3]thiazine-3,4-dicarboxylate

Conditions
ConditionsYield
In toluene for 1h; Reflux;93%
51-52-5

propylthiouracil

119072-54-7, 2769-71-3

2,6-dimethylphenyl isonitrile

762-21-0

acetylenedicarboxylic acid diethyl ester

diethyl 2-(2,6-dimethylphenylamino)-2,8-dihydro-8-oxo-6-propylpyrimido[2,1-b][1,3]thiazine-3,4-dicarboxylate

Conditions
ConditionsYield
In toluene for 1h; Reflux;93%
51-52-5

propylthiouracil

119072-54-7, 2769-71-3

2,6-dimethylphenyl isonitrile

762-42-5

dimethyl acetylenedicarboxylate

dimethyl 2-(2,6-dimethylphenylamino)-2,8-dihydro-8-oxo-6-propylpyrimido[2,1-b][1,3]thiazine-3,4-dicarboxylate

Conditions
ConditionsYield
In toluene for 1h; Reflux;92%
51-52-5

propylthiouracil

119072-55-8, 7188-38-7

tert-butylisonitrile

79-11-8

chloroacetic acid

67-64-1

acetone

100-46-9

benzylamine

1379463-56-5

2-(N-benzyl-2-((6-oxo-4-propyl-1,6-dihydropyrimidin-2-yl)thio)acetamido)-N-(tert-butyl)-2-methylpropanamide

Conditions
ConditionsYield
Stage #1: propylthiouracil; chloroacetic acid at 20℃; for 0.5h; Ionic liquid;
Stage #2: acetone; benzylamine at 20℃; for 0.25h; Ugi condensation; Ionic liquid;
Stage #3: tert-butylisonitrile at 20℃; for 5h; Ugi condensation; Ionic liquid;
90%
51-52-5

propylthiouracil

931-53-3

Cyclohexyl isocyanide

79-11-8

chloroacetic acid

67-64-1

acetone

100-46-9

benzylamine

1379463-51-0

2-(N-benzyl-2-((6-oxo-4-propyl-1,6-dihydropyrimidin-2-yl)thio)acetamido)-N-cyclohexyl-2-methylpropanamide

Conditions
ConditionsYield
Stage #1: propylthiouracil; chloroacetic acid at 20℃; for 0.5h; Ionic liquid;
Stage #2: acetone; benzylamine at 20℃; for 0.25h; Ugi condensation; Ionic liquid;
Stage #3: Cyclohexyl isocyanide at 20℃; for 5h; Ugi condensation; Ionic liquid;
89%
51-52-5

propylthiouracil

931-53-3

Cyclohexyl isocyanide

79-11-8

chloroacetic acid

67-64-1

acetone

1-(cyclohexylamino)-2-methyl-1-oxopropan-2-yl 2-([4-oxo-6-propyl-1,4-dihydropyrimidin-2-yl]thio)acetate

Conditions
ConditionsYield
With octyl methyl imidazolium bromide for 6h; Heating; Green chemistry;89%
51-52-5

propylthiouracil

452-86-8

4-methyl-1,2-dihydroxybenzene

2-(4,5-dihydroxy-2-methylphenylthio)-6-propylpyrimidin-4(3H)-one

Conditions
ConditionsYield
With laccase from Agaricus bisporus In aq. phosphate buffer; ethanol at 20℃; for 13h; pH=6; Green chemistry; Enzymatic reaction; chemoselective reaction;88%
51-52-5

propylthiouracil

931-53-3

Cyclohexyl isocyanide

762-21-0

acetylenedicarboxylic acid diethyl ester

diethyl 2-(cyclohexylamino)-4,8-dihydro-8-oxo-6-propylpyrimido[2,1-b][1,3]thiazine-3,4-dicarboxylate

Conditions
ConditionsYield
In toluene for 1h; Reflux;87%
51-52-5

propylthiouracil

448224-88-2

2-bromo-N-[4-(4-chloro-phenyl)-1,3-thiazol-2-yl]-acetamide

C18H17ClN4O2S2

Conditions
ConditionsYield
With potassium phosphate; sodium iodide In N,N-dimethyl-formamide at 60℃; for 1h;87%
51-52-5

propylthiouracil

931-53-3

Cyclohexyl isocyanide

4755-72-0, 39266-56-3

Chloro-phenyl-acetic acid

67-64-1

acetone

1-(cyclohexylamino)-2-methyl-1-oxopropan-2-yl 2-([4-oxo-6-propyl-1,4-dihydropyrimidin-2-yl]thio)-2-phenylacetate

Conditions
ConditionsYield
With octyl methyl imidazolium bromide at 30℃; for 6h; Green chemistry;87%
51-52-5

propylthiouracil

13345-08-9

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

Conditions
ConditionsYield
With chloroacetic acid In water for 5h; Heating;86%
With chloroacetic acid
With chloroacetic acid Heating;
With chloroacetic acid
51-52-5

propylthiouracil

116302-66-0

Iodoselane

C17H36N2OSSeSi3

Conditions
ConditionsYield
With triethylamine In toluene at 20℃; for 0.166667h;85%
51-52-5

propylthiouracil

931-53-3

Cyclohexyl isocyanide

108-94-1

cyclohexanone

79-11-8

chloroacetic acid

100-46-9

benzylamine

1379463-54-3

1-(N-benzyl-2-((6-oxo-4-propyl-1,6-dihydropyrimidin-2-yl)thio)acetamido)-N-cyclohexylcyclohexanecarboxamide

Conditions
ConditionsYield
Stage #1: propylthiouracil; chloroacetic acid at 20℃; for 0.5h; Ionic liquid;
Stage #2: cyclohexanone; benzylamine at 20℃; for 0.25h; Ugi condensation; Ionic liquid;
Stage #3: Cyclohexyl isocyanide at 20℃; for 5h; Ugi condensation; Ionic liquid;
85%
51-52-5

propylthiouracil

14542-93-9

1,1,3,3-tetramethylbutane isonitrile

762-21-0

acetylenedicarboxylic acid diethyl ester

diethyl 2-(2,4,4-trimethylpentan-2-ylamino)-4,8-dihydro-8-oxo-6-propylpyrimido[2,1-b][1,3]thiazine-3,4-dicarboxylate

Conditions
ConditionsYield
In toluene for 1h; Reflux;85%
119-65-3

isoquinoline

51-52-5

propylthiouracil

762-42-5

dimethyl acetylenedicarboxylate

dimethyl 2-(2-methoxy-2-oxoethylidene)-5-oxo-7-propyl-2H,5H,11b'H-spiro[thiazolo[3,2-a]pyrimidine-3,2'-[1,3]oxazino[2,3-a]isoquinoline]-3',4'-carboxylate

Conditions
ConditionsYield
In toluene at 110℃; for 5h;85%
51-52-5

propylthiouracil

119072-55-8, 7188-38-7

tert-butylisonitrile

79-11-8

chloroacetic acid

67-64-1

acetone

1-(tert-butylamino)-2-methyl-1-oxopropan-2-yl 2-([4-oxo-6-propyl-1,4-dihydropyrimidin-2-yl]thio)acetate

Conditions
ConditionsYield
With octyl methyl imidazolium bromide at 30℃; for 6h; Green chemistry;85%
51-52-5

propylthiouracil

931-53-3

Cyclohexyl isocyanide

75-04-7

ethylamine

79-11-8

chloroacetic acid

67-64-1

acetone

1379463-49-6

N-cyclohexyl-2-(N-ethyl-2-((6-oxo-4-propyl-1,6-dihydropyrimidin-2-yl)thio)acetamido)-2-methylpropanamide

Conditions
ConditionsYield
Stage #1: propylthiouracil; chloroacetic acid at 20℃; for 0.5h; Ionic liquid;
Stage #2: ethylamine; acetone at 20℃; for 0.25h; Ugi condensation; Ionic liquid;
Stage #3: Cyclohexyl isocyanide at 20℃; for 5h; Ugi condensation; Ionic liquid;
83%
51-52-5

propylthiouracil

931-53-3

Cyclohexyl isocyanide

79-11-8

chloroacetic acid

96-22-0

pentan-3-one

3-(cyclohexylcarbamoyl)pentan-3-yl 2-([4-oxo-6-propyl-1,4-dihydropyrimidin-2-yl]thio)acetate

Conditions
ConditionsYield
With octyl methyl imidazolium bromide at 30℃; for 6h; Green chemistry;83%
51-52-5

propylthiouracil

931-53-3

Cyclohexyl isocyanide

4755-72-0, 39266-56-3

Chloro-phenyl-acetic acid

96-22-0

pentan-3-one

3-(cyclohexylcarbamoyl)pentan-3-yl 2-([4-oxo-6-propyl-1,4-dihydropyrimidin-2-yl]thio)-2-phenylacetate

Conditions
ConditionsYield
With octyl methyl imidazolium bromide at 30℃; for 6h; Green chemistry;83%
51-52-5

propylthiouracil

74-88-4

methyl iodide

5751-17-7

2-(methylthio)-6-propylpyrimidin-4(3H)-one

Conditions
ConditionsYield
With sodium hydroxide In water at 20 - 40℃; for 4h;82%
With potassium hydroxide
With sodium hydroxide In water at 20℃;
51-52-5

propylthiouracil

37746-78-4

4-bromo-trans-crotonic acid ethyl ester

(5-oxo-7-propyl-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidin-3-yl)-acetic acid ethyl ester

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h;82%
51-52-5

propylthiouracil

931-53-3

Cyclohexyl isocyanide

67-64-1

acetone

598-78-7

(R,S)-2-chloropropionic acid

1-(cyclohexylamino)-2-methyl-1-oxopropan-2-yl 2-([4-oxo-6-propyl-1,4-dihydropyrimidin-2-yl]thio)propanoate

Conditions
ConditionsYield
With octyl methyl imidazolium bromide at 30℃; for 6h; Green chemistry;82%
51-52-5

propylthiouracil

119072-55-8, 7188-38-7

tert-butylisonitrile

4755-72-0, 39266-56-3

Chloro-phenyl-acetic acid

67-64-1

acetone

1-(tert-butylamino)-2-methyl-1-oxopropan-2-yl 2-([4-oxo-6-propyl-1,4-dihydropyrimidin-2-yl]thio)-2-phenylacetate

Conditions
ConditionsYield
With octyl methyl imidazolium bromide at 30℃; for 6h; Green chemistry;81%
51-52-5

propylthiouracil

3,3-dichloroallyl halide

3,3-dichloroallyl halide

C10H12Cl2N2OS

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide81%
51-52-5

propylthiouracil

123-31-9

hydroquinone

1611453-74-7

2-(2,5-dihydroxyphenylsulfanyl)-6-propyl-1H-pyrimidin-4-one

Conditions
ConditionsYield
In aq. phosphate buffer; water; N,N-dimethyl-formamide at 25℃; pH=6; Michael Addition; Electrolysis;80%
119-65-3

isoquinoline

51-52-5

propylthiouracil

762-21-0

acetylenedicarboxylic acid diethyl ester

diethyl 2-(2-ethoxy-2-oxoethylidene)-5-oxo-7-propyl-2H,5H,11b'H-spiro[thiazolo[3,2-a]pyrimidine-3,2'-[1,3]oxazino[2,3-a]isoquinoline]-3',4'-carboxylate

Conditions
ConditionsYield
In toluene at 110℃; for 5h;80%
51-52-5

propylthiouracil

119072-55-8, 7188-38-7

tert-butylisonitrile

75-04-7

ethylamine

79-11-8

chloroacetic acid

67-64-1

acetone

1379463-57-6

N-(tert-butyl)-2-(N-ethyl-2-((6-oxo-4-propyl-1,6-dihydropyrimidin-2-yl)thio)acetamido)-2-methylpropanamide

Conditions
ConditionsYield
Stage #1: propylthiouracil; chloroacetic acid at 20℃; for 0.5h; Ionic liquid;
Stage #2: ethylamine; acetone at 20℃; for 0.25h; Ugi condensation; Ionic liquid;
Stage #3: tert-butylisonitrile at 20℃; for 5h; Ugi condensation; Ionic liquid;
79%
51-52-5

propylthiouracil

38838-06-1

methyl 5-deoxy-5-iodo-2,3-isopropylidene-β-D-ribofuranoside

676557-71-4

methyl 5-deoxy-2,3-O-isopropylidene-5-(6-propyluracil-2-yl)thio-β-D-ribofuranoside

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 60℃; for 1h;78%
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    Propylthiouracil Basic information Product Name: Propylthiouracil Synonyms: 2,3-dihydro-6-propyl-2-thioxo-4(1h)-pyrimidinon;2,3-dihydro-6-propyl-2-thioxo-4(1h)pyrimidinone;2,3-Dihydro-6-propyl-2-thioxo-4(1H)-pyrimidinone;2-Mercapt

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Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 2B IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 329.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1974,p. 67.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory.

Specification

The Propylthiouracil, with the CAS registry number 51-52-5, is also known as 6-n-Propylthiouracil. It belongs to the product categories of Pyridines, Pyrimidines, Purines and Pteredines; Intermediates & Fine Chemicals; Pharmaceuticals; API's. Its EINECS registry number is 200-103-2. This chemical's molecular formula is C7H10N2OS and molecular weight is 170.2321. Its IUPAC name is called 6-propyl-2-sulfanylidene-1H-pyrimidin-4-one. What's more, this chemical's classification codes are Antimetabolites; Antithyroid Agents; Drug / Therapeutic Agent; Hormone Antagonists; Hormones, Hormone Substitutes, and Hormone Antagonists; Human Data; Mutation Data; Noxae; Reproductive Effect; Thyroid Inhibitor; Tumor Data. Meanwhile, it can be used as anti-thyroid drugs and in biochemical research. Propylthiouracil is a thioamide drug used to treat hyperthyroidism (including Graves' disease) by decreasing the amount of thyroid hormone produced by the thyroid gland.

Physical properties of Propylthiouracil: (1)ACD/LogP: 1.37; (2)ACD/LogD (pH 5.5): 1.37; (3)ACD/LogD (pH 7.4): 1.3; (4)ACD/BCF (pH 5.5): 6.49; (5)ACD/BCF (pH 7.4): 5.48; (6)ACD/KOC (pH 5.5): 132.69; (7)ACD/KOC (pH 7.4): 111.93; (8)#H bond acceptors: 3; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 2; (11)Index of Refraction: 1.596; (12)Molar Refractivity: 46.62 cm3; (13)Molar Volume: 137 cm3; (14)Surface Tension: 54.9 dyne/cm; (15)Density: 1.24 g/cm3; (16)Flash Point: 168.6 °C; (17)Enthalpy of Vaporization: 62.4 kJ/mol; (18)Boiling Point: 355.2 °C at 760 mmHg; (19)Vapour Pressure: 1.56E-05 mmHg at 25°C.

Preparation of Propylthiouracil: this chemical can be prepared by β-oxo-hexanoate with thiourea via condensation reaction. Meanwhile, it can also be prepared by butyryl ethyl acetate and thiourea via condensation reaction.

Uses of Propylthiouracil: it can be used to produce 2-methylsulfanyl-6-propyl-1H-pyrimidin-4-one with iodomethane at temperature of 60 °C. This reaction will need reagent aq. NaOH and solvent ethanol. The yield is about 55%.

Propylthiouracil can be used to produce 2-methylsulfanyl-6-propyl-1H-pyrimidin-4-one with iodomethane

When you are using this chemical, please be cautious about it. This chemical is harmful and irritant. Harmful if swallowed. Whenever you will contact it, please wear suitable protective clothing and gloves. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CCCC1=CC(=O)NC(=S)N1
(2)InChI: InChI=1S/C7H10N2OS/c1-2-3-5-4-6(10)9-7(11)8-5/h4H,2-3H2,1H3,(H2,8,9,10,11)
(3)InChIKey: KNAHARQHSZJURB-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 165mg/kg/2W-I (165mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE" Drug Intelligence and Clinical Pharmacy. Vol. 19, Pg. 669, 1985.
child TDLo oral 900mg/kg/60D- (900mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"

LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"
Annals of Internal Medicine. Vol. 82, Pg. 228, 1975.
child TDLo oral 1785mg/kg/17W (1785mg/kg) LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"

KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION
Journal of Pediatric Gastroenterology and Nutrition. Vol. 7, Pg. 776, 1988.
man TDLo oral 42857ug/kg/10 (42.857mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS

KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED
American Journal of Kidney Diseases. Vol. 24, Pg. 575, 1994.
man TDLo oral 116mg/kg/11W- (116mg/kg) LIVER: OTHER CHANGES Archives of Internal Medicine. Vol. 135, Pg. 319, 1975.
man TDLo oral 257mg/kg (257mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) Postgraduate Medical Journal. Vol. 73, Pg. 445, 1997.
mouse LDLo unreported 750ug/kg (0.75mg/kg)   Drugs in Japan Vol. 6, Pg. 732, 1982.
rat LD50 oral 1250mg/kg (1250mg/kg)   Nature. Vol. 157, Pg. 659, 1946.
rat LDLo intraperitoneal 400mg/kg (400mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 97, Pg. 478, 1949.
rat LDLo unreported 750ug/kg (0.75mg/kg)   Drugs in Japan Vol. 6, Pg. 732, 1982.
women LDLo oral 84mg/kg/2W-I (84mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE" Archives of Internal Medicine. Vol. 142, Pg. 838, 1982.
women LDLo oral 480mg/kg/9W-I (480mg/kg) VASCULAR: OTHER CHANGES

BLOOD: AGRANULOCYTOSIS
Southern Medical Journal. Vol. 75, Pg. 1297, 1982.
women LDLo unreported 6mg/kg (6mg/kg) VASCULAR: SHOCK

BLOOD: CHANGES IN SPLEEN

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL"
New England Journal of Medicine. Vol. 249, Pg. 814, 1953.
women TDLo oral 693mg/kg/11W- (693mg/kg) LIVER: "HEPATITIS, FIBROUS (CIRRHOSIS, POST-NECROTIC SCARRING)"

LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"
Southern Medical Journal. Vol. 87, Pg. 943, 1994.
women TDLo oral 900mg/kg/21W- (900mg/kg) LIVER: OTHER CHANGES Archives of Internal Medicine. Vol. 140, Pg. 1184, 1980.

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