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Thiobarbituric acid

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Name

Thiobarbituric acid

EINECS 207-985-8
CAS No. 504-17-6 Density 1.69 g/cm3
PSA 90.29000 LogP -0.43500
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 N/A Appearance off-white to yellow powder
Safety 22-24/25-37/39-26 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 504-17-6 (4,6-Dihydroxy-2-mercaptopyrimidine) Hazard Symbols IrritantXi
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;

Article Data 21

Thiobarbituric acid Synthetic route

17356-08-0

thiourea

105-53-3

diethyl malonate

504-17-6

4,6-dihydroxy-2-mercaptopyrimidine

Conditions
ConditionsYield
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
ConditionsYield
With triethylamine In N-methyl-acetamide; ethyl acetateA n/a
B 25%
996-82-7, 34727-00-9, 73177-21-6

sodium diethylmalonate

17356-08-0

thiourea

504-17-6

4,6-dihydroxy-2-mercaptopyrimidine

Conditions
ConditionsYield
With ethanol at 80℃;
17356-08-0

thiourea

108-59-8

malonic acid dimethyl ester

504-17-6

4,6-dihydroxy-2-mercaptopyrimidine

Conditions
ConditionsYield
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
ConditionsYield
With sulfuric acid
2-thiobarbituric acid imide-(4)

2-thiobarbituric acid imide-(4)

504-17-6

4,6-dihydroxy-2-mercaptopyrimidine

Conditions
ConditionsYield
With sulfuric acid
996-82-7

sodium diethylmalonate

17356-08-0

thiourea

504-17-6

4,6-dihydroxy-2-mercaptopyrimidine

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

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) Effect 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.

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