Thiobarbituric acid supplier

Name
4,6-Dihydroxy-2-mercaptopyrimidine
EINECS 207-985-8
CAS No. 504-17-6
Article Data21
CAS DataBase
Density 1.69 g/cm³
Solubility water: <6 g/L (20 °C)
Melting Point 245 °C (dec.)(lit.)
Formula C₄H₄N₂O₂S
Boiling Point 463.4 °C at 760 mmHg
Molecular Weight 144.154
Flash Point 234 °C
Transport Information
Appearance off-white to yellow powder
Safety 22-24/25-37/39-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Barbituricacid, 2-thio- (8CI);1,2,3,4,5,6-Hexahydro-4,6-dioxopyrimidine-2-thione;2-Mercapto-4,6-dihydroxypyrimidine;2-Mercaptobarbituric acid;2-Mercaptopyrimidine-4,6-diol;2-Thio-4,6-dioxypyrimidine;2-Thiobarbituricacid;2-Thiopyrimidine-4,6-diol;Austranal;Bathyran;Hexahydropyrimidine-4,6-dione-2-thione;NSC 4733;Thiobarbituric acid;4,6-Dihydroxy-2-mercaptopyrimidine;
PSA 90.29000
LogP -0.43500

Synthetic route

: 17356-08-0
thiourea

: 105-53-3
diethyl malonate

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

Conditions

Conditions	Yield
With sodium In ethanol for 6h; Reflux;	80%
With ethanol; sodium In neat liquid at 60℃; for 0.5h; Reagent/catalyst; Sonication;	79%
With sodium methylate In methanol at 65℃; for 8h;	72%

: 624-67-9
Propargylic aldehyde

: 54-42-2
5-Iodo-2'-deoxyuridine

A: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

B: 3-(5'-Iodo-2'-deoxyuridin-3'-yl)prop-2-enal

Conditions

Conditions	Yield
With triethylamine In N-methyl-acetamide; ethyl acetate	A n/a B 25%

...Expand

: 996-82-7, 34727-00-9, 73177-21-6
sodium diethylmalonate

: 17356-08-0
thiourea

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

Conditions

Conditions	Yield
With ethanol at 80℃;

: 17356-08-0
thiourea

: 108-59-8
malonic acid dimethyl ester

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

Conditions

Conditions	Yield
In dimethylsulfoxide-d6 at 22 - 28℃; Mechanism; pH = 1-2;

: 1004-40-6
6-Amino-2-thiouracil

: 7664-93-9
sulfuric acid

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: 1004-39-3
4,6-diaminopyrimidine-2(1H)-thione

: 7664-93-9
sulfuric acid

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

2-thio-barbituric acid diimide-(4.6): 2-thio-barbituric acid diimide-(4.6)

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

Conditions

Conditions	Yield
With sulfuric acid

2-thiobarbituric acid imide-(4): 2-thiobarbituric acid imide-(4)

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

Conditions

Conditions	Yield
With sulfuric acid

: 996-82-7
sodium diethylmalonate

: 17356-08-0
thiourea

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

Conditions

Conditions	Yield
In water

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: 575499-16-0
N-(3, 5-dichlorophenyl)-2-(4-formylphenoxy)acetamide

: 1310561-77-3
N-(3,5-dichlorophenyl)-2-(4-((4,6-dioxo-2-thioxotetrahydropyrimidin-5(6H)-ylidene)methyl)phenoxy)acetamide

Conditions

Conditions	Yield
In ethanol; water at 80℃;	99.1%

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: 100-52-7
benzaldehyde

: 27470-61-7
5-benzylidene-2-thio-barbituric acid

Conditions

Conditions	Yield
With triethylamine In ethanol for 0.25h; Reflux;	99%
With ethylammonium nitrate at 20℃; for 0.5h; Knoevenagel condensation;	94%
In water at 20℃; for 1h; Knoevenagel condensation;	93%

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: 4397-53-9
p-benzyloxybenzaldehyde

: 143034-05-3
5-(4-(benzyloxy)benzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione

Conditions

Conditions	Yield
With morpholine In acetic acid; benzene for 15h; Heating;	99%
In ethanol; water at 80℃; for 2h;	98.1%
In ethanol; water at 80℃; for 2h;	98.1%

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: 53278-43-6
DL-2-<(Diethylamino)thioxomethylthio>propionsaeure

: 100515-84-2
5-<2-(Diethylamino)-5-methyl-1,3-dithiol-4-ylio>hexahydro-4,6-dioxo-2-thioxo-5-pyrimidinid

Conditions

Conditions	Yield
With sodium acetate In acetic anhydride at 90℃;	99%

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: 66-77-3
1-naphthaldehyde

: 143034-06-4
5-(1-naphthylidene)-2-thiobarbituric acid

Conditions

Conditions	Yield
With morpholine In acetic acid; benzene for 15h; Heating;	99%

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: 555-16-8
4-nitrobenzaldehdye

: C15H11N5O6S2

Conditions

Conditions	Yield
In ethanol at 20℃; for 0.5h; Condensation;	99%
In water at 25℃; for 0.333333h;

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: 331962-59-5
N-(4-acetylphenyl)-2-(4-formylphenoxy)acetamide

: 1310561-74-0
N-(4-acetylphenyl)-2-(4-((4,6-dioxo-2-thioxotetrahydropyrimidin-5(6H)-ylidene)methyl)phenoxy)acetamide

Conditions

Conditions	Yield
In ethanol; water at 80℃;	99%

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: 122-51-0
orthoformic acid triethyl ester

: 1829-84-1
sulfamethoxazole

: 1345551-62-3
4-{[(4,6-dioxo-2-thioxotetrahydropyrimidin-5(2H)-ylidene)methyl]amino}-N-(4-methylisoxazol-3-yl)benzenesulfonamide

Conditions

Conditions	Yield
In iso-butanol for 3h; Reflux;	99%

...Expand

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: 555-16-8
4-nitrobenzaldehdye

: 1219456-24-2
5-(4-nitrophenyl)-2,8-dithioxo-2,3,7,8,9,10-hexahydropyrido[2,3-d:6,5-d′]dipyrimidine 4,6(1H,5H)-dione

Conditions

Conditions	Yield
With copper(II) ferrite; ammonium acetate In water for 0.166667h; Sonication; Green chemistry;	99%
With copper(II) ferrite; ammonium acetate In water for 0.0166667h; Microwave irradiation;	98%
With copper(II) ferrite; ammonium acetate In water at 20℃; for 0.416667h; Hantzsch Dihydropyridine Synthesis; Green chemistry;	98%
With 1-methyl-2-oxopyrrolidinium hydrogen sulfate; ammonium acetate In water at 20℃; for 0.133333h; Irradiation; Green chemistry;	98%
With ammonium acetate In neat (no solvent) at 110℃; for 0.0833333h;	91%

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: 104-88-1
4-chlorobenzaldehyde

: 5-(4-chlorophenyl)-2,8-dithioxo-2,3,7,8,9,10-hexahydropyrido[2,3-d:6,5-d′]dipyrimidine-4,6(1H,5H)-dione

Conditions

Conditions	Yield
With copper(II) ferrite; ammonium acetate In water at 20℃; for 0.416667h; Catalytic behavior; Solvent; Hantzsch Dihydropyridine Synthesis; Green chemistry;	99%
With copper(II) ferrite; ammonium acetate In water for 0.0666667h; Sonication; Green chemistry;	98%
With copper(II) ferrite; ammonium acetate In water for 0.0166667h; Microwave irradiation;	98%
With 1-methyl-2-oxopyrrolidinium hydrogen sulfate; ammonium acetate In water at 20℃; for 0.0833333h; Catalytic behavior; Solvent; Irradiation; Green chemistry;	98%
With ammonium acetate In neat (no solvent) at 110℃; for 0.0833333h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature;	90%

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: C13H16N2O4

: 2',4'-dimethyl-8'-nitro-2-thioxo-1',2,2',3,4',4a'-hexahydro-4H,6'H-spiro[pyrimidine-5,5'-[1,4]oxazino[4,3-a]quinoline]-4,6(1H)-dione

Conditions

Conditions	Yield
With morpholine In ethanol at 80℃; for 36h; Knoevenagel Condensation; Green chemistry;	99%

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: 88951-64-8
p-formylphenyl p-bromophenylcarbamoylmethyl ether

: 358980-92-4
N-(4-bromophenyl)-2-(4-((4,6-dioxo-2-thioxotetrahydropyrimidin-5(6H)-ylidene)methyl)phenoxy)acetamide

Conditions

Conditions	Yield
In ethanol; water at 80℃;	98.9%

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: 95-55-6
2-amino-phenol

: 6-(2-hydroxyphenylimine)-2-thioxotetrahydropyrimidin-4(1H)-one

Conditions

Conditions	Yield
With acetic acid In ethanol for 8h; Reflux;	98.8%

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: 85803-62-9
2-(4-methylpiperazin-1-yl)benzaldehyde

: C16H18N4O2S

Conditions

Conditions	Yield
In isopropyl alcohol for 8h; Knoevenagel Condensation; Reflux;	98.7%

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: 120-57-0
piperonal

: 74051-76-6
5-(benzo[d][1,3]dioxol-5-ylmethylene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione

Conditions

Conditions	Yield
With ethylammonium nitrate at 20℃; for 0.166667h; Knoevenagel condensation;	98%
for 0.0333333h; Irradiation;	96%
With 1-butyl-3-methylimidazolium Tetrafluoroborate at 20℃; for 2h;	94.2%

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: 123-11-5
4-methoxy-benzaldehyde

: 60045-61-6
5-(4-methoxybenzylidene)-2-thiobarbituric acid

Conditions

Conditions	Yield
With ethylammonium nitrate at 20℃; for 0.166667h; Knoevenagel condensation;	98%
With morpholine In acetic acid; benzene for 15h; Heating;	97%
With triethylamine In ethanol for 0.25h; Reflux;	97%

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: 121-33-5
vanillin

: 73681-14-8
5-(3-methoxyl-4-hydroxybenzylidene)-2-thioxodihyropyrimidine-4,6(1H,5H)-dione

Conditions

Conditions	Yield
In ethanol; water at 80℃; Knoevenagel condensation;	98%
In ethanol at 80℃; for 2h; Knoevenagel Condensation;	74%
With hydrogenchloride

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: 100-10-7
4-dimethylamino-benzaldehyde

: 27430-15-5
5-[4-(N,N-dimethylamino)benzylidene]-2-thiobarbituric acid

Conditions

Conditions	Yield
With ethylammonium nitrate at 20℃; for 0.166667h; Knoevenagel condensation;	98%
In water for 1h; Heating;	96%
In ethanol at 20 - 60℃;	95%

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: 67-52-7
BARBITURIC ACID

Conditions

Conditions	Yield
With quinolinium monofluorochromate(VI) In acetonitrile for 1.5h; Heating;	98%
With bismuth(III) nitrate In acetonitrile for 0.25h; Heating;	94%
With 2,2'-bipyridinium chlorochromate In acetonitrile for 0.0333333h; Product distribution; Further Variations:; Reagents; Temperatures; without microwave irradiation; solvent-free; microwave irradiation;	93%

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: 4,6-dimethyl-1H-pyrazolo[3,4-b]pyridine-3-diazonium nitrate

: 5-{(4,6-dimethyl-1H-pyrazolo[3,4-b]pyridin-3-yl)hydrazono}-2-thioxopyrimidine-4,6(1H,3H,5H)-dione

Conditions

Conditions	Yield
With trimethylamine at 20℃; under 375.03 Torr; for 12h;	98%

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: 104-55-2
3-phenyl-propenal

: 5-(3-Phenyl-allylidene)-2-thioxo-dihydro-pyrimidine-4,6-dione

Conditions

Conditions	Yield
With ethylammonium nitrate at 20℃; for 0.333333h; Knoevenagel condensation;	98%
With 1-butyl-3-methylimidazolium Tetrafluoroborate microwave irradiation;	96.1%
With PVP-Ni nanoparticle In ethylene glycol at 50℃; Knoevenagel condensation;	85%

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: 100-52-7
benzaldehyde

: 5-phenyl-2,8-dithioxo-2,3,7,8,9,10-hexahydropyrido[2,3-d:6,5-d′]dipyrimidine-4,6(1H,5H)-dione

Conditions

Conditions	Yield
With copper(II) ferrite; ammonium acetate In water for 0.0166667h; Microwave irradiation;	98%
With copper(II) ferrite; ammonium acetate In water at 20℃; for 0.333333h; Reagent/catalyst; Temperature; Hantzsch Dihydropyridine Synthesis; Green chemistry;	98%
With copper(II) ferrite; ammonium acetate In water for 0.166667h; Sonication; Green chemistry;	95%

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: 85378-39-8
2-(2,4-dichlorobenzylideneamino)naphthalene

: 3-(2,4-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydrobenzo[f]quinolin-3-carbonyl thiourea

Conditions

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride In water at 100℃; for 6h;	98%

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: 932-52-5
5-Aminouracil

: 459-57-4
4-fluorobenzaldehyde

: 1210058-14-2
10-(4-fluorophenyl)-1,3,6,8-tetrahydro-7-thioxo-pyrido[3,2-d:6,5-d']dipyrimidine-2,4,9-trione

Conditions

Conditions	Yield
In N,N-dimethyl-formamide Microwave irradiation;	98%

...Expand

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: 207129-05-3
4,4'-(butylazanediyl)dibenzaldehyde

: 1417732-28-5
5,5'-(4,4'-(hexylazanediyl)bis(4,1-phenylene)bis(methyliden-1-yl))bis(2-thioxopyrimidine-4,6(1H,3H)-dione)

Conditions

Conditions	Yield
With deep eutectic solvent at 40 - 45℃; for 1h; Knoevenagel Condensation;	98%

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: 552-89-6
2-nitro-benzaldehyde

: 5-(2-nitrophenyl)-2,8-dithioxo-2,3,7,8,9,10-hexahydropyrido[2,3-d:6,5-d′]dipyrimidine-4,6(1H,5H)-dione

Conditions

Conditions	Yield
With copper(II) ferrite; ammonium acetate In water at 20℃; for 0.633333h; Hantzsch Dihydropyridine Synthesis; Green chemistry;	98%
With copper(II) ferrite; ammonium acetate In water for 0.2h; Sonication; Green chemistry;	95%
With copper(II) ferrite; ammonium acetate In water for 0.0333333h; Microwave irradiation;	95%
With 1-methyl-2-oxopyrrolidinium hydrogen sulfate; ammonium acetate In water at 20℃; for 0.166667h; Irradiation; Green chemistry;	95%
With ammonium acetate In neat (no solvent) at 110℃; for 0.166667h;	88%

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: 591-31-1
3-methoxy-benzaldehyde

: 5-(3-methoxyphenyl)-2,8-dithioxo-2,3,7,8,9,10-hexahydropyrido[2,3-d:6,5-d′]dipyrimidine-4,6(1H,5H)-dione

Conditions

Conditions	Yield
With copper(II) ferrite; ammonium acetate In water for 0.133333h; Sonication; Green chemistry;	98%
With copper(II) ferrite; ammonium acetate In water at 20℃; for 0.5h; Hantzsch Dihydropyridine Synthesis; Green chemistry;	98%
With 1-methyl-2-oxopyrrolidinium hydrogen sulfate; ammonium acetate In water at 20℃; for 0.133333h; Irradiation; Green chemistry;	98%
With copper(II) ferrite; ammonium acetate In water for 0.0333333h; Microwave irradiation;	95%
With ammonium acetate In neat (no solvent) at 110℃; for 0.166667h;	90%

: 1121-60-4
pyridine-2-carbaldehyde

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: 5-(pyridin-2-yl)-2,8-dithioxo-2,3,7,8,9,10-hexahydropyrido[2,3-d:6,5-d′]dipyrimidine-4,6(1H,5H)-dione

Conditions

Conditions	Yield
With copper(II) ferrite; ammonium acetate In water for 0.0333333h; Microwave irradiation;	98%
With 1-methyl-2-oxopyrrolidinium hydrogen sulfate; ammonium acetate In water at 20℃; for 0.133333h; Irradiation; Green chemistry;	96%
With copper(II) ferrite; ammonium acetate In water for 0.2h; Sonication; Green chemistry;	95%
With copper(II) ferrite; ammonium acetate In water at 20℃; for 0.416667h; Hantzsch Dihydropyridine Synthesis; Green chemistry;	95%

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: 16588-34-4
4-chloro-3-nitro-benzaldehyde

: 5-(4-chloro-3-nitrophenyl)-2,8-dithioxo-2,3,7,8,9,10-hexahydropyrido[2,3-d:6,5-d′]dipyrimidine-4,6(1H,5H)-dione

Conditions

Conditions	Yield
With copper(II) ferrite; ammonium acetate In water for 0.2h; Sonication; Green chemistry;	98%
With copper(II) ferrite; ammonium acetate In water at 20℃; for 0.416667h; Hantzsch Dihydropyridine Synthesis; Green chemistry;	98%
With copper(II) ferrite; ammonium acetate In water for 0.0166667h; Microwave irradiation;	97%
With 1-methyl-2-oxopyrrolidinium hydrogen sulfate; ammonium acetate In water at 20℃; for 0.166667h; Irradiation; Green chemistry;	95%

: 504-17-6
4,6-dihydroxy-2-mercaptopyrimidine

: C16H11N5O3S2

: 5,5′-(1,4-phenylene)bis(2,8-dithioxo-2,3,7,8,9,10-hexahydropyrido[2,3-d:6,5-d']dipyrimidine-4,6(1H,5H)-dione)

Conditions

Conditions	Yield
With copper(II) ferrite; ammonium acetate In water for 0.2h; Sonication; Green chemistry;	98%
With copper(II) ferrite; ammonium acetate In water at 20℃; for 0.333333h; Hantzsch Dihydropyridine Synthesis; Green chemistry;	95%

Thiobarbituric acid Consensus Reports

Reported in EPA TSCA Inventory.

Thiobarbituric acid Specification

Thiobarbituric acid, with the CAS number 504-17-6, is an organic compound and a heterocycle. It has many Synonyms of TBA; TIMTEC-BB SBB004132; THIOBARBITURIC ACID; 5h)-pyrimidinedione,dihydro-2-thioxo-6(1h; 6(1H,5H)-Pyrimidinedione,dihydro-2-thioxo-4; austranal; 2-mercaptobarbituricacid; 2-thio-barbituricaci. It is used to quantitate lipopolysaccharides, carrageenan, and sialic acids. Used to detect lipid hydroperoxides and lipid oxidation.

Physical properties about Thiobarbituric acid are: (1)ACD/LogP: -0.518; (2)ACD/LogD (pH 5.5): -0.86; (3)ACD/LogD (pH 7.4): -2.37; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 5.63; (7)ACD/KOC (pH 7.4): 1.00; (8)#H bond acceptors: 4; (9)#H bond donors: 2; (10)Index of Refraction: 1.645; (11)Molar Refractivity: 33.166 cm³; (12)Molar Volume: 91.445 cm³; (13)Polarizability: 13.148 10-24cm³; (14)Surface Tension: 80.661003112793 dyne/cm; (15)Density: 1.576 g/cm³

When you are using Thiobarbituric acid, please be cautious about it as the following:
1. Do not breathe dust;
2. Avoid contact with skin and eyes;
3. Wear suitable gloves and eye/face protection;
4. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;

You can still convert the following datas into molecular structure:
(1)InChI=1S/C4H4N2O2S/c7-2-1-3(8)6-4(9)5-2/h1H2,(H2,5,6,7,8,9);
(2)InChIKey=RVBUGGBMJDPOST-UHFFFAOYSA-N;
(3)SmilesC1(CC(NC(N1)=S)=O)=O;

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
guinea pig	LD50	unreported	4650mg/kg (4650mg/kg)	Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 25(5), Pg. 50, 1981.
mouse	LD50	intraperitoneal	600mg/kg (600mg/kg)	National Technical Information Service. Vol. AD277-689,
mouse	LD50	unreported	829mg/kg (829mg/kg)	Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 25(5), Pg. 50, 1981.
rat	LD50	oral	> 5gm/kg (5000mg/kg)	Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 25(5), Pg. 50, 1981.
rat	LD50	unreported	5060mg/kg (5060mg/kg)	Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 25(5), Pg. 50, 1981.

Product Name

4,6-Dihydroxy-2-mercaptopyrimidine

Synthetic route

Thiobarbituric acid Consensus Reports

Thiobarbituric acid Specification

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