74395-18-9

Basic information

• Product Name: 4-METHYLTHIOPHENE 2-YLMETHANOL
• Synonyms: 4-METHYLTHIOPHENE-2-HYDROXYMETHYL;4-METHYLTHIOPHENE 2-YLMETHANOL;2-(Hydroxymethyl)-4-methylthiophene;4-Methylthiophen-2-ylmethanol;(4-Methylthien-2-yl)methanol;(4-Methylthiophen-2-yl)
• CAS NO: 74395-18-9
• Molecular Formula: C6H8OS
• Molecular Weight: 128.19
• Mol File: 74395-18-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 60 °C
• Flash Point: 86 °C
• Appearance: /
• Density: 1.176 g/cm³
• Vapor Pressure: 0.0726mmHg at 25°C
• Refractive Index: 1.572
• Storage Temp.: 2-8°C
• PKA: 13.90±0.10(Predicted)
• CAS DataBase Reference: 4-METHYLTHIOPHENE 2-YLMETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHYLTHIOPHENE 2-YLMETHANOL(74395-18-9)
• EPA Substance Registry System: 4-METHYLTHIOPHENE 2-YLMETHANOL(74395-18-9)

Safety Data

• Hazardous Substances Data: 74395-18-9(Hazardous Substances Data)

Usage

General Description

4-Methylthiophene-2-ylmethanol is a chemical compound with the molecular formula C9H10OS. It is a colorless to pale yellow liquid with a slightly fruity odor. 4-METHYLTHIOPHENE 2-YLMETHANOL is used as a building block in the synthesis of pharmaceuticals, agrochemicals, and fragrance ingredients. 4-Methylthiophene-2-ylmethanol is commonly used as an intermediate in the production of chemicals and is a versatile starting material for the preparation of various functionalized thiophene derivatives. It is important to handle this chemical with care, as it may be harmful if ingested, inhaled, or in contact with the skin.

InChI:InChI=1/C6H8OS/c1-5-2-6(3-7)8-4-5/h2,4,7H,3H2,1H3

Upstream product

• 28686-90-0 4-methyl-thiophene-2-carboxylic acid methyl ester 
• 14282-78-1 4-methylthiophene-2-carboxylic acid 
• 50-00-0 formaldehyd 
• 616-44-4 3-Methylthiophene 
• 6030-36-0 4-methylthiophene-2-carbaldehyde 

Downstream Products

• 1085941-51-0 (R)-2-(1-amino-2-methylpropyl)-8-fluoro-3-((4-methylthiophen-2-yl)methyl)benzofuro[3,2-d]pyrimidin-4(3H)-one 
• 913828-93-0 {4-methyl-5-[5-(4-phenoxyphenyl)-1,2,4-oxadiazol-3-yl]-2-thienyl }methanol 
• 1028947-16-1 C₂₆H₃₀N₂O₃SSi 
• 1309207-77-9 1-benzhydryl-3-(4-methylthiophen-2-ylmethoxy)azetidine 

Relevant articles and documents

MUSCARINIC AGONISTS AS NON-STEROIDAL AND NON-OPIOID ANALGESICS AND METHODS OF USE THEREOF

Novel Gi/o-biased muscarinic agonists selectively activate only one specific signaling pathway and are novel pharmacophores for development of new painkillers (analgesics). Methods of making and using these agonists are also described.

Discovery of CS-2100, a potent, orally active and S1P3-sparing S1P1 agonist

S1P3-sparing S1P1 agonists have attracted attention as a suppressant of autoimmunity with reduced side effects. Our synthetic efforts and extensive SAR studies led to the discovery of 10b named CS-2100 with the EC50 value of 4.0 nM for human S1P1 and over 5000-fold selectivity against S1P3. The in vivo immunosuppressive efficacy was evaluated in rats on host versus graft reaction and the ID 50 value was determined at 0.407 mg/kg. The docking studies of CS-2100 with the homology model of S1P1 and S1P3 showed that the ethyl group on the thiophene ring of CS-2100 was sterically hindered by Phe263 in S1P3, not in the case of Leu276 in S1P1. This observation gives an explanation for the excellent S1P3-sparing characteristic of CS-2100.

Practical access to metallo thiophenes: Regioselective synthesis of 2,4-disubstituted thiophenes

This report describes a protocol for functionalization of thiophenes, utilizing a regioselective magnesiation mediated by commercial Grignard reagents and catalytic 2,2,6,6-tetramethylpiperidine. This metalation provides practical access to metallo thiophenes, avoiding cryogenic conditions, prolonged reaction times, and prohibitively expensive reagents. Application to a target thiophene-phthalazinone 6 was accomplished by addition of 2-magnesio-4- methylthiophene to phthalic anhydride, providing the product with >40:1 regioselectivity. This also solved a chemoselectivity issue encountered with analogous lithio-thiophene reagents and cyclic anhydrides, or with magnesio-thiophene generated by simultaneous lithium-to-magnesium transmetalation/anhydride acylation. These alternative in situ transmetalation sequences were plagued by an age effect dictated by the kinetic solubility of MgCl2/THF complexes.