90905-31-0

Basic information

• Product Name: 2-METHYLSULFANYL-PYRIMIDINE-5-CARBALDEHYDE
• Synonyms: ASINEX-REAG BAS 05215236;ASISCHEM C63389;CHEMBRDG-BB 4010269;2-METHYLSULFANYL-PYRIMIDINE-5-CARBALDEHYDE;2-Methylsulfonylpyrimidine-5-carbaldehyde;2-Methylsulfanyl-pyrimidine-5-carbaldehyde ,95%;2-(Methylthio)pyrimidine-5-carboxaldehyde;2-(Methylsulfanyl)-5-pyrimidinecarbaldehyde
• CAS NO: 90905-31-0
• Molecular Formula: C₆H₆N₂OS
• Molecular Weight: 154.19
• Product Categories: Pyrimidines
• Mol File: 90905-31-0.mol

Chemical Properties

• Melting Point: 83-84 °C(Solv: cyclohexane (110-82-7))
• Boiling Point: 301.214 °C at 760 mmHg
• Flash Point: 135.97 °C
• Appearance: /
• Density: 1.29 g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.583
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -0.75±0.22(Predicted)
• CAS DataBase Reference: 2-METHYLSULFANYL-PYRIMIDINE-5-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYLSULFANYL-PYRIMIDINE-5-CARBALDEHYDE(90905-31-0)
• EPA Substance Registry System: 2-METHYLSULFANYL-PYRIMIDINE-5-CARBALDEHYDE(90905-31-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-43
• Safety Statements: 36/37
• HazardClass: IRRITANT
• Hazardous Substances Data: 90905-31-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-METHYLSULFANYL-PYRIMIDINE-5-CARBALDEHYDE is used as an intermediate in the synthesis of various pharmaceuticals for its role in the production of drugs with potential therapeutic effects.
Used in Agrochemical Industry:
2-METHYLSULFANYL-PYRIMIDINE-5-CARBALDEHYDE is used as an intermediate in the synthesis of agrochemicals, contributing to the development of agricultural chemicals that can enhance crop protection and yield.
Used in Research and Development:
2-METHYLSULFANYL-PYRIMIDINE-5-CARBALDEHYDE is utilized in research and development for exploring its potential applications in medicine and agriculture, driving innovation in these fields.

InChI:InChI=1/C6H6N2OS/c1-10-6-7-2-5(4-9)3-8-6/h2-4H,1H3

Upstream product

• 18655-47-5 triformylmethane 
• 4338-95-8 S-methylthiouronium iodide 
• 53114-57-1 S-methylisothiourea hydrochloride 
• 867-44-7 S-Methylisothiourea sulfate 

Downstream Products

• 55551-49-0 2-N,N-Dimethylaminopyrimidine-5-carboxaldehyde 
• 130161-49-8 2-methylthiopyrimidine-5-carbaldehyde phenylhydrazone 
• 1029052-80-9 (1-benzenesulfonyl-5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)(2-methylsulfanylpyrimidin-5-yl)methanol 
• 1344664-08-9 [5-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyrimidin-2-yl]-cyclohexyl-amine 
• 1344664-09-0 [5-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-pyrimidin-2-yl]-(4-methyl-cyclohexyl)-amine 
• 130161-46-5 2-phenylpyrimidine-5-carbaldehyde 
• 1119398-70-7 2-(3-methoxyphenyl)pyrimidine-5-carbaldehyde 
• 915919-99-2 2-(naphthalen-2-yl)pyrimidine-5-carbaldehyde 
• 921939-12-0 2-(thiophen-2-yl)pyrimidine-5-carbaldehyde 
• 1102229-83-3 2-[4-(trifluoromethyl)phenyl]pyrimidine-5-carbaldehyde 
• 944904-93-2 2-(4-fluorophenyl)pyrimidine-5-carbaldehyde 
• 928713-84-2 2-(4-chlorophenyl)pyrimidine-5-carbaldehyde 
• 928713-22-8 2-(3-chlorophenyl)pyrimidine-5-carbaldehyde 
• 1433404-01-3 tert-butyl N-[(1R)-1-(4-chloro-2-fluoro-3-{hydroxy[2-(methylsulfanyl)pyrimidin-5-yl]methyl}phenyl)propyl]carbamate 

Relevant articles and documents

Synthesis of Soai Type 2-Arylpyrimidine-5-carbaldehydes through Desulfurative Cross-Coupling with Arylboronic Acids

A two-step synthesis of 2-arylpyrimidine-5-carbaldehydes, which are of relevance as substrates for Soai's asymmetric autocatalysis, was realized by exploiting a hidden threefold symmetry in the target core structure. Condensation of Arnold's C 3-symmetric vinamidinium cation with S-methylisothiouronium sulfate provides 2-methylsulfanyl-pyrimidine-5-carbaldehyde; introduction of aryl groups at C-2 of the latter was accomplished by a Liebeskind-Srogl palladium-catalyzed desulfurative (de-methylsulfanylative) coupling with aryl boronic acids to obtain the target compounds 1 (14 examples, 60-95 % yield). 2-Arylpyrimidine-5-carbaldehydes, which are of relevance as substrates in Soai's asymmetric autocatalysis, are prepared through Liebeskind-Srogl coupling of aryl boronic acids with 2-methylthiopyrimidine-5-carbaldehyde; the latter is obtained in a hydrolytic condensation of two symmetric amidinium salts.

Formation of Pyrimidine-5-carboxaldehydes, 1-Aminoethylene-2,2-dicarboxaldehyde and 2-Amino-4-anilino-1,3,5-triazine from Triformylmethane and Amidines

Triformylmethane (1) reacted with benzamidine, guanidine and S-methylisothiourea to give the corresponding 2-substituted pyrimidines-5-carboxaldehydes.However reactions of 1 with acetamidine (or formamidine) and phenylbiguanide gave the unexpected 1-aminoethylene-2,2-dicarboxaldehyde (5) and 2-amino-4-anilino-1,3,5-triazine (9), respectively.

DIRECT SYNTHESIS OF 2-SUBSTITUTED 5-FORMYLPYRIMIDINES AND RING TRANSFORMATION OF THEIR PHENYLHYDRAZONES INTO 4-FORMYL-1-PHENYLPYRAZOLE

Triformylmethane (1) reacted with benzamidine, guanidine and S-methylisothiourea to give 2-substituted 5-formylpyrimidines (2a-c), whose phenylhydrazones (3a-c) readily underwent ring transformation into 4-formyl-1-phenylpyrazole (4) on heating in acidic methanol.

Direct syntheses of pyrazole-4-carbaldehydes and pyrimidine-5-carbaldehydes starting from triformylmethane.

Triformylmethane is transformed into the pyrazole-4-carbaldehydes 2, 4, 6, 7, 9, 11 and the pyrazole-4-carbaldehydes 8, 10, 12 by corresponding hydrazines, and into the pyrimidine-5-carbaldehydes 13, 14, 15 by appropriate amidines.