2-Mercaptopyrimidine

Base Information

• Chemical Name: 2-Mercaptopyrimidine
• CAS No.: 1450-85-7
• Deprecated CAS: 107646-94-6,19351-11-2,847778-89-6,19351-11-2,847778-89-6
• Molecular Formula: C4H4N2S
• Molecular Weight: 112.155
• Hs Code.: 29335995
• European Community (EC) Number: 215-917-3,258-741-2
• NSC Number: 193522,48073
• UNII: T72Z5M7P5T
• DSSTox Substance ID: DTXSID6049220
• Nikkaji Number: J208.747B
• Wikidata: Q27124108
• Metabolomics Workbench ID: 58658
• ChEMBL ID: CHEMBL1688952
• Mol file: 1450-85-7.mol

Synonyms:2-mercapto pyrimidine;2-mercaptopyrimidine;pyrimidine-2-thiol;pyrimidine-2-thiol, lithium salt

Chemical Property of 2-Mercaptopyrimidine

Chemical Property:

• Appearance/Colour: yellow powder
• Vapor Pressure: 0.519mmHg at 25°C
• Melting Point: 230 °C (dec.)(lit.)
• Refractive Index: 1.662
• Boiling Point: 191.3 °C at 760 mmHg
• PKA: 7.11±0.10(Predicted)
• Flash Point: 69.5 °C
• PSA: 64.58000
• Density: 1.3 g/cm³
• LogP: 0.76530
• Storage Temp.: -20°C
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 112.00951931
• Heavy Atom Count: 7
• Complexity: 137

Purity/Quality:

99% ^*data from raw suppliers

2-Mercaptopyrimidine 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-63-20/21/22
• Safety Statements: 22-24/25-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CNC(=S)N=C1
• General Description: 2-Mercaptopyrimidine is a sulfur-containing heterocyclic compound that serves as a key intermediate in the synthesis of various N,S-heterocycles, including thiazolopyrimidines and antipyrine-containing derivatives. It reacts with substituted acetonitriles to form thiazolo[3,2-a]pyrimidinium salts, which are further utilized in the development of polymethine dyes. Additionally, it acts as a nucleophile in reactions with chloroacetyl or cyanoacetyl antipyrine derivatives to produce biologically relevant sulfur-containing heterocycles. The compound's versatility in forming diverse heterocyclic structures highlights its importance in medicinal chemistry and dye synthesis.

Technology Process of 2-Mercaptopyrimidine

There total 12 articles about 2-Mercaptopyrimidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

2-(tert-butylthio)pyrimidine (84358-82-7) → 2-thioxopyrimidine (1450-85-7)

Guidance literature:

Heating;

Reference yield: 56.0%

→ 2-thioxopyrimidine (1450-85-7) + ethyl 6-methyl-4-(3-nitrophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-carboxylate (914915-59-6)

Guidance literature:

Reference yield:

malonaldehydebis(dimethylacetal) (102-52-3) + 1-(methyl)-thiourea (598-52-7) → 2-thioxopyrimidine (1450-85-7)

Guidance literature:

With potassium carbonate; In ethanol; water;

upstream raw materials:

2-chloropyrimidine

thiourea

malondialdehyde bis(diethyl acetal)

(E)-3-(diethylamino)acrylaldehyde

Downstream raw materials:

2-(carboxymethylthio)pyrimidine

2-(methylsulfanyl)pyrimidine

pyrimidine-2-sulfonamide

2-(4-chloro-phenyl)-3-oxo-2,3-dihydro-thiazolo[3,2-a]pyrimidinylium betaine

Refernces

Cyclazines and their Analogs. 1. Thiazolopyrimidopyrimidines

10.1007/BF00475264

The research focuses on synthesizing derivatives of a new heterocyclic system, specifically formyl-substituted thiazolopyrimidopyrimidines, with the aim of developing new classes of polymethine dyes. The study involves reacting 3-amino-5-methyl-thiazolo[3,2-a]pyrimidinium salts, prepared from 2-mercaptopyrimidines and substituted acetonitriles, with the Vilsmeier reagent. Key chemicals used include 2-mercaptopyrimidines, various nitriles such as α-cyanobenzylbenzenesulfonate and α-bromopropionitrile, and phosphoryl chloride. The synthesized compounds exhibit strong UV absorption bands and a broad band near 600 nm, indicating potential for use in dyes. The study concludes that the position and intensity of these bands are significantly influenced by the nature of the substituents, suggesting that these new heterocyclic derivatives can be tailored for specific applications in dye synthesis.

Versatile synthesis of N,S-heterocycles containing the antipyrine moiety

10.1080/104265090969054

The study, titled "Versatile Synthesis of N,S-Heterocycles Containing the Antipyrine Moiety" focuses on synthesizing novel sulfur derivatives with potential biological activity, incorporating the antipyrine moiety. The primary chemicals involved include 4-(chloroacetyl)antipyrine (1) and 4-(cyanoacetyl)antipyrine (14), which serve as key starting materials. Compound 1 reacts with various sulfur nucleophiles, such as O-ethyl xanthic acid potassium salt, 4,5-dihydrothiazole-2-thiol, and pyrimidine-2-thiol, to produce corresponding sul?de derivatives (2–5). Additionally, compound 1 reacts with 2-aminobenzothiazole to form the imidazo[2,1-b]benzothiazole derivative (7). The 2-aminothiazole derivatives (10 and 11) are synthesized via a waste-free, solid-state reaction of compound 1 with thiourea derivatives (8 and 9). These aminothiazole products are then coupled with pyrazolopyridinyl and aromatic diazonium salts to create a series of azo dyes (12 and 13). Furthermore, compound 14 reacts with phenyl isothiocyanate to form a nonisolable adduct (15), which is used as a precursor for synthesizing ketene N,S-acetal (16), dihydrothiazole (17), and thiazolidinone (18) derivatives. The study explores the reactivity of these compounds and their potential applications in medicine and pharmacology, leveraging the known pharmacological properties of antipyrine derivatives.