3216-50-0

Basic information

• Product Name: 2-(DIMETHYLAMINO)THIOPHENE
• Synonyms: 2-N,N-DIMETHYLAMINO-THIOPHENE;2-(DIMETHYLAMINO)THIOPHENE
• CAS NO: 3216-50-0
• Molecular Formula: C₆H₉NS
• Molecular Weight: 127.21
• Mol File: 3216-50-0.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(DIMETHYLAMINO)THIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(DIMETHYLAMINO)THIOPHENE(3216-50-0)
• EPA Substance Registry System: 2-(DIMETHYLAMINO)THIOPHENE(3216-50-0)

Safety Data

• Hazardous Substances Data: 3216-50-0(Hazardous Substances Data)

Usage

General Description

2-(Dimethylamino)thiophene is a chemical compound with the molecular formula C6H9NS. It is a heterocyclic organic compound containing a thiophene ring with a dimethylamino group attached at the 2-position. 2-(DIMETHYLAMINO)THIOPHENE is commonly used as a building block in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. It has also been studied for its potential use in materials science, as it exhibits interesting electronic and optical properties. 2-(Dimethylamino)thiophene is a versatile and useful chemical with a variety of applications in the field of organic chemistry.

Upstream product

• 7774-74-5 Thiophene-2-thiol 
• 124-40-3 dimethyl amine 
• 556-61-6 methyl thioisocyanate 
• 74-99-7 prop-1-yne 
• 74-88-4 methyl iodide 

Downstream Products

• 163928-43-6 5-N,N-dimethylamino-2,2'-bithiophene 

Relevant articles and documents

One-pot syntheses of 2-N-Alkylamino-, 2-N-Phenylamino-2-N,N-Dialkylamino-, and 2-N-Alkyl-N-phenylaminothiophenes

A number of 2-N-alkylamino- or 2-N-phenylamino-, 2-N,N-dialkylamino-, and 2-N-alkyl-N-phenylaminothiophenes have been prepared in good yields by adding a solution of tert-butylalcohol and potassium tert-butoxide in dimethylsulfoxide to a solution of the adduct from a lithiated 1-alkyne, RCH2C≡CLi, or the lithiated allene, tBuCH=C=CHLi, and isothiocyanate, R′N=C=S, in tetrahydrofuran and subsequently hydrolyzing the reaction mixture or quenching it with methyl iodide.

THE RATES OF BASE CLEAVAGE OF SUBSTITUTED 2-THIENYLTRIMETHYLSILANES. AB INITIO CALCULATIONS OF THE ACIDITIES OF MONOSUBSTITUTED THIOPHENS

Rates of cleavage in NaOMe-MeOH at 50 deg C have been determined for the mono-substituted 2-trimethylsilylthiophens X*C4H2S*SiMe3-2 with X = H, 3-NO2, 3-Br, 4-Br-, and 5-NO2, -CN, -COPh, -Me, -OMe and -NMe2, and for one disubstituted compound, 4,5-Br2*C4HS*SiMe3-2.For several compounds the rate and product isotope effects have also been determined.The energies involved in the process X*C4H3S X*C4H2S- for deprotonation at the 2-position have been calculated by an ab initio method (STO-3G), and the results used in analysis of the substituent effects in the cleavage of the XC4H2S*SiMe3-2 compounds.The results are consistent with the view the aryl anions separate in the rate-determining step of the cleavage.The isotope effects are all close to unity, whereas by comparison with results for XC6H4CH2SiMe3 and related species of similar reactivity, values in the region of 10 would be expected for the 3- and 5-NO2 compounds if the product isotope effect for a carbanion R depended only in the pKa of RH.The difference between the thienyl- and benzyl-type anions is attributed to the absence of conjugative delocalization of the charge in the former. Approximate pKa values are derived for the 2-positions of the X*C4H3S compounds.