Basic information
- Standard SMILES
O=C1CC(=O)NC(=S)N1- InChIKey
RVBUGGBMJDPOST-UHFFFAOYSA-N- Molecular formula
- C4H4N2O2S
- Average molar mass
- 144.15 g/mol
- Monoisotopic mass
- 143.99934837
Overview
2-thiobarbituric acid is a barbiturate, the structure of which is that of barbituric acid in which the oxygen at C-2 is replaced by sulfur. It has a role as a reagent and an allergen.
Names & identifiers
- Preferred name
- Thiobarbituric acid
- IUPAC
- 2-sulfanylidene-1,3-diazinane-4,6-dione
- English name
- 2-Thiobarbituric acid
- Molecular formula
- C4H4N2O2S
- Molecular weight
- 144.15
Names & synonyms
2-THIOBARBITURIC ACID504-17-6Thiobarbituric acidBathyranAustranal2-Mercaptobarbituric acid4,6(1H,5H)-Pyrimidinedione, dihydro-2-thioxo-2-sulfanylidene-1,3-diazinane-4,6-dioneBarbituric acid, 2-thio-Dihydro-2-thioxo-4,6(1H,5H)-pyrimidinedione2-Mercapto-4,6-dihydroxypyrimidineM1YZW5SS7C
Show more names
TBA2-sulfanylpyriMidine-4,6-diol4,6-DIHYDROXY-2-MERCAPTOPYRIMIDINEusafek-6602-Mercapto-4Thiobarbituric
CHEBI:33202NSC-47332-sulfanylidenedihydropyrimidine-4,6(1H,5H)-dioneDTXSID7060124RefChem:483744DTXCID5040831207-985-82-thioxodihydropyrimidine-4,6(1H,5H)-dione
Database identifiers
- CAS
504-17-6- PubChem CID
- 2723628
- DTXSID
DTXSID7060124- ChEMBL
CHEMBL584805- ChEBI
CHEBI:33202- UNII
- M1YZW5SS7C
- EC Number
- 207-985-8
- Nikkaji
- J12.869D
Properties
Computed structural properties
- XLogP
- -0.9
- Topological polar surface area
- 90.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 171
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Pyrimidines
SpringerMaterials PropertiesCrystal structure
Physical DescriptionOff-white powder; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 245 °C · 245 °C (dec.)(lit.)
- Density
- 1.451 · 1.451 (estimate)
- bulk density
- 210 kg/m3 · 210kg/m3
- refractive index
- 1.769 · 1.7690 (estimate)
- storage temp.
- 2 · Inert atmosphere,2-8°C
- solubility
- 50 g/l · 50g/l slightly soluble
- pka
- 3.96 · 3.96±0.20(Predicted)
- form
- Liquid
- color
- Clear colorless
- PH
- 1.7 · 1.7-1.9 (10g/l, H2O, 20℃)
- Water Solubility
- 6 g/L · <6 g/L (20 ºC)
- BRN
- 120663 · 120663
- Stability
- Stable. Incompatible with strong oxidizing agents.
- InChI
- 1S/C4H4N2O2S/c7-2-1-3(8)6-4(9)5-2/h1H2,(H2,5,6,7,8,9)
- InChIKey
- RVBUGGBMJDPOST-UHFFFAOYSA-N
- SMILES
- O=C1CC(=O)NC(=S)N1
- CAS DataBase Reference
- 504 · 504-17-6(CAS DataBase Reference)
- FDA UNII
- 1 YZW5SS7C · M1YZW5SS7C
- NIST Chemistry Reference
- 4 · 4,6(1H,5h)-pyrimidinedione, dihydro-2-thioxo-(504-17-6)
- EPA Substance Registry System
- 4 · 4,6(1H,5H)-Pyrimidinedione, dihydro-2-thioxo- (504-17-6)
- UNSPSC Code
- 12352115 · 12352115
- NACRES
- 21 · NB.21
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P280a-P304+P340-P305+P351+P338-P405-P501a
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 22 · 22-24/25-37/39-26
- RIDADR
- 3335 · UN 3335
- WGK Germany
- 2 · 2
- RTECS
- 7700000 · CQ7700000
- F
- 13 · 13-23
- TSCA
- TSCA listed
- HS Code
- 29335995 · 29335995
- Storage Class
- 11 · 11 - Combustible Solids
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 5.3% (1 of 19) of reports.
Warning
H315 (94.7%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 19 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 4,6(1H,5H)-Pyrimidinedione, dihydro-2-thioxo-
REACH registered substance: 2-thiobarbituric acid (EC: 207-985-8)
2-Thiobarbituric acid: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryA skin and strong eye irritant; [Alfa Aesar MSDS] See Terbacil and 5-Diazouracil.
Hazard Classes and CategoriesSkin Irrit. 2 (94.7%)
Safety data
- F
- 13-23
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- CQ7700000
- ridadr
- UN 3335
- hs_code
- 29335995
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 22-24/25-37/39-26
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
- Precautionary statements
- P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Chemistry & industry
Uses & manufacturing
General Manufacturing Information4,6(1H,5H)-Pyrimidinedione, dihydro-2-thioxo-: ACTIVE
Applications
Uses2-Thiobarbituric acid has been used to measure malondialdehyde (MDA) in lipid peroxidation assay.
Uses4,6-Dihydroxy-2-mercaptopyrimidine can be used to quantitate lipopolysaccharides, carrageenan, and sialic acids, and to detect lipid hydroperoxides and lipid oxidation.
General Description2-Thiobarbituric acid is a molecule made up of heteroatoms: nitrogen, sulphur and oxygen.
Preparation methods
Preparation2-thiobarbituric acid was synthesized by the reaction of diethyl malonate with thiourea. Dissolve thiourea in methanol, add sodium methoxide and diethyl malonate, heat under reflux for 4-5h, then distill under reduced pressure to recover methanol to the end, and add hydrochloric acid to acidify to pH 1-2 after cooling. After standing overnight, thiobarbituric acid crystals were precipitated, filtered, and recrystallized with water to obtain the pure product.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: 2-thiobarbituric acid is a barbiturate, the structure of which is that of barbituric acid in which the oxygen at C-2 is replaced by sulfur. It has a role as a reagent and an allergen.
Related reactions
18 records
Linked notes
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