6299-25-8

Basic information

• Product Name: 4,6-Dichloro-2-(methylthio)pyrimidine
• Synonyms: 4,6-dichloropyrimidine methyl sulphide;2-Methylthio-4,6-dichloropyrimidine;4,6-DICHLORO-2-(METHYLTHIO)PYRIMIDINE, 9 8%;Dichloro-2-methylmercaptopyrimidine,4,6-;4,6-Dichloro-2-(Methylthio)Pyr;4,6-DICHLORO-2-METHYLTHIOPYRIMIDINE 98%;4,6-Dichloro-2-(methylthio)pyrimidine ,99%;4,6-Dichloro-2-Methythiopyrimidine
• CAS NO: 6299-25-8
• Molecular Formula: C₅H₄Cl₂N₂S
• Molecular Weight: 195.07
• EINECS: 228-577-6
• Product Categories: Halides;Pyrazines, Pyrimidines & Pyridazines;Nucleotides and Nucleosides;Pyrimidine;Bases & Related Reagents;Nucleotides;Sulfur & Selenium Compounds;Pyrazines, Pyrimidines & Pyridazines;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyrimidines;PyrimidinesHeterocyclic Building Blocks;Heterocycle-Pyrimidine series
• Mol File: 6299-25-8.mol
• Article Data: 16

Chemical Properties

• Melting Point: 38-42 °C(lit.)
• Boiling Point: 135-136 °C14 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: White to yellow or orange/Powder or Crystals
• Density: 1.502 (estimate)
• Vapor Pressure: 0.00553mmHg at 25°C
• Refractive Index: 1.6300 (estimate)
• Storage Temp.: Freezer
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate
• PKA: -4.86±0.30(Predicted)
• BRN: 127664
• CAS DataBase Reference: 4,6-Dichloro-2-(methylthio)pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6-Dichloro-2-(methylthio)pyrimidine(6299-25-8)
• EPA Substance Registry System: 4,6-Dichloro-2-(methylthio)pyrimidine(6299-25-8)

Safety Data

• Hazard Codes: C
• Statements: 34-36/37
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3263 8/PG 2
• WGK Germany: 3
• F: 10-19
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 6299-25-8(Hazardous Substances Data)

Usage

Description

4,6-Dichloro-2-(methylthio)pyrimidine, with the CAS number 6299-25-8, is a white crystalline solid that is primarily utilized in the field of organic synthesis. 4,6-Dichloro-2-(methylthio)pyrimidine is known for its ability to react with (η5-C5H5)Fe(CO)2, leading to the formation of monometallic and bimetallic complexes. Its unique chemical properties make it a valuable component in various chemical reactions and processes.

Uses

Used in Organic Synthesis:
4,6-Dichloro-2-(methylthio)pyrimidine is used as a key intermediate in the synthesis of various organic compounds. Its reactivity with (η5-C5H5)Fe(CO)2 allows for the creation of monometallic and bimetallic complexes, which can be further utilized in the development of new molecules with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4,6-Dichloro-2-(methylthio)pyrimidine is used as a building block for the development of new drugs. Its unique chemical structure and reactivity make it a promising candidate for the synthesis of novel therapeutic agents, particularly those targeting specific biological pathways or receptors.
Used in Chemical Research:
4,6-Dichloro-2-(methylthio)pyrimidine is also employed in chemical research, where it serves as a model compound for studying the properties and behavior of similar molecules. Its ability to form complexes with (η5-C5H5)Fe(CO)2 provides valuable insights into the mechanisms of complex formation and the factors influencing the stability and reactivity of these complexes.
Used in Material Science:
In the field of material science, 4,6-Dichloro-2-(methylthio)pyrimidine can be used to develop new materials with specific properties. The formation of monometallic and bimetallic complexes with (η5-C5H5)Fe(CO)2 can lead to the creation of materials with unique electronic, optical, or magnetic properties, which can be applied in various technological applications.

InChI:InChI=1/C5H4Cl2N2S/c1-2-8-4(6)3(10)5(7)9-2/h10H,1H3

Upstream product

• 504-17-6 4,6-dihydroxy-2-mercaptopyrimidine 
• 74-88-4 methyl iodide 
• 29639-68-7 2,4-dihydroxy-2-methylmercaptopyrimidine (keto tautomer) 
• 10025-87-3 trichlorophosphate 
• 10026-13-8 phosphorus pentachloride 
• 1979-98-2 4,6-dihydroxy-2-methylmercaptopyrimidine 
• 77-78-1 dimethyl sulfate 
• 120978-01-0 bis(4,6-dichloropyrimidin-2-yl) disulfide 

Downstream Products

• 30117-02-3 6-chloro-2-(piperidin-1-yl)pyrimidin-4-amine 
• 89466-42-2 4-chloro-6-methoxy-2-(methylsulfanyl)pyrimidine 
• 86627-01-2 2-Methylsulfonyl-4-chloro-6-(N-methyl-2,3-xylidino)-pyrimidine 
• 91759-36-3 4-chloro-2-(methylsulfonyl)-6-<(2,3-dimethylphenyl)oxy>pyrimidine 
• 86627-00-1 6-chloro-N-(2,3-dimethylphenyl)-2-methylsulfonylpyrimidin-4-amine 
• 569684-16-8 6-[3,5-bis(trifluoromethyl)phenylmethyl]-4-(2-methylphenyl)-2-methanesulfonyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,5]oxazocin-5-one 
• 569684-04-4 6-[3,5-bis(trifluoromethyl)phenylmethyl]-4-(2-methylphenyl)-2-methylthio-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,5]oxazocin-5-one 
• 569683-98-3 6-[3,5-bis(trifluoromethyl)benzyl]-4-chloro-2-methylthio-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,5]oxazocin-5-one 
• 569684-18-0 6-[3,5-bis(trifluoromethyl)benzyl]-4-(2-methoxyphenyl)-2-methylsulfonyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,5]oxazocin-5-one 
• 606971-58-8 N-[3,5-bis(trifluoromethyl)benzyl]-N-[3-(t-butoxycarbonylamino)propyl]-4,6-dichloro-2-(methylthio)pyrimidine-5-carboxylic acid amide 
• 606971-80-6 6-[3,5-bis(trifluoromethyl)benzyl]-4-(2-methylphenyl)-2-methylsulfonyl-5,6,7,8,9,10-hexahydropyrimido[4,5-b][1,5]diazocin-5-one 
• 865368-03-2 6-[3,5-bis(trifluoromethyl)benzyl]-4-(2-fluorophenyl)-2-methylsulfonyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,5]oxazocin-5-one 
• 606971-81-7 6-[3,5-bis(trifluoromethyl)benzyl]-4-(2-methylphenyl)-2-methylsulfonyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-e][1,4]diazepin-5-one 
• 606971-60-2 N-[3,5-bis(trifluoromethyl)benzyl]-N-[2-(t-butoxycarbonylamino)ethyl]-4,6-dichloro-2-(methylthio)pyrimidine-5-carboxylic acid amide 

Relevant articles and documents

Production process of 4, 6-dimethoxy-2-methylsulfonyl pyrimidine

The invention belongs to the field of organic synthesis, and discloses a production process of 4, 6-dimethoxy-2-methanesulfonyl pyrimidine. According to the production process, dimethyl malonate, thiourea and sodium methoxide are used as raw materials, and cyclization, methylation, chlorination, methoxylation, oxidation and recrystallization are performed to prepare the product. According to the process provided by the invention, the yield of the 4, 6-dimethoxy-2-methylsulfonyl pyrimidine is greater than 90%. Compared with the prior art, methanol, phosphorus oxychloride, methylbenzene and sodium tungstate are repeatedly utilized, so that the wastewater treatment difficulty is reduced, and the production cost is reduced; moreover, sodium sulfate, hydrochloric acid, sodium phosphate and sodium chloride can be co-produced while 4, 6-dimethoxy-2-methylsulfonyl pyrimidine is produced, so that pollutants generated in the production process are greatly reduced, and the economic benefit and environmental benefit of the production process are further improved.

Preparation method of 4, 6-dichloro-2-methylthiopyrimidine

The invention provides a preparation method of 4, 6-dichloro-2-methylthiopyrimidine. According to the method, 4,6-dihydroxy-2-methylthiopyrimidine is employed as a raw material and oxalyl chloride isemployed as a chlorination reagent to chlorinate the raw material, and then a reaction is carried out in a solvent to prepare the 4,6-dichloro-2-methylthiopyrimidine. The method has the beneficial effects that the whole technological process is simple, no phosphorus-containing waste liquid or waste solid is generated, the yield is high, the product quality can be stably controlled, and the methodis suitable for industrial production.

A Strategy for the Triarylation of Pyrrolopyrimidines by Using Microwave-Promoted Cross-Coupling Reactions

New pyrrolo[2,3-d]pyrimidines that have aryl groups at the 2-, 4-, and 6-positions were prepared by the arylation reaction of 4-chloro-7-methyl-2-(methylthio)-6-phenylpyrrolo[2,3-d]pyrimidine (6) and the corresponding arylboronic acid under Suzuki-Miyaura conditions followed by a second arylation under Liebeskind-Srogl cross-coupling conditions. A parallel study that began with the C-2 chemoselective arylation of 6 under Liebeskind-Srogl conditions followed by a Suzuki-Miyaura coupling at C-4 was carried out, and the results of each route were compared. All of the tranformations were performed under microwave irradiation. Several triarylpyrrolopyrimidines were readily prepared from 4,6-dichloro-2-(methylthio)pyrimidine (2) in excellent yields by using effective cross-coupling reactions. An advantage of this method is its tolerance towards various substituted aryl groups.