4623-55-6

Basic information

• Product Name: 2-amino-3-cyano-5-methylthiophene
• Synonyms: 2-Amino-4-methyl-3-thiophenecarbonitrile;2-azanyl-4-methyl-thiophene-3-carbonitrile
• CAS NO: 4623-55-6
• Molecular Formula: C₆H₆N₂S
• Molecular Weight: 138.1902
• Product Categories: API intermediates
• Mol File: 4623-55-6.mol

Chemical Properties

• Melting Point: 118-119 °C
• Boiling Point: 311.4 °C at 760 mmHg
• Flash Point: 142.1 °C
• Appearance: /
• Density: 1.26 g/cm³
• Vapor Pressure: 0.000565mmHg at 25°C
• Refractive Index: 1.605
• PKA: -0.15±0.10(Predicted)
• CAS DataBase Reference: 2-amino-3-cyano-5-methylthiophene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-3-cyano-5-methylthiophene(4623-55-6)
• EPA Substance Registry System: 2-amino-3-cyano-5-methylthiophene(4623-55-6)

Safety Data

• Hazardous Substances Data: 4623-55-6(Hazardous Substances Data)

Usage

Uses

Used in Scientific Research:
2-amino-3-cyano-5-methylthiophene is used as a research compound for [application reason] in the field of organic chemistry. It is utilized as an intermediate building block to synthesize more complex compounds, including certain drugs and pharmaceuticals.
Used in Pharmaceutical Industry:
2-amino-3-cyano-5-methylthiophene is used as a chemical intermediate for [application reason] in the synthesis of drugs and pharmaceuticals. Its reactive groups, such as amino and cyano, enable it to participate in various chemical reactions, making it a valuable component in the development of new medications.
Used in Organic Chemistry:
2-amino-3-cyano-5-methylthiophene is used as a key component for [application reason] in the synthesis of complex organic compounds. Its versatility in engaging in chemical reactions due to its reactive groups makes it an essential tool in the field of organic chemistry.

InChI:InChI=1/C6H6N2S/c1-4-3-9-6(8)5(4)2-7/h3H,8H2,1H3

Upstream product

• 67-64-1 acetone 
• 109-77-3 malononitrile 
• 55704-78-4 2,5-dihydroxy-2,5-dimethyl-1,4-dithiane 
• 75-07-0 acetaldehyde 
• 110-89-4 piperidine 

Downstream Products

• 85487-09-8 2-benzamido-3-cyano-4-methylthiophene 
• 1030377-48-0 C₂₂H₂₄N₈OS 
• 1030377-70-8 5-methyl-2-{(5R)-5-methyl-4-[5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoyl]-1,4-diazepan-1-yl}thieno[2,3-d]pyrimidine 
• 43088-64-8 5-Methyl-3,4-dihydrothieno<2,3-d>pyrimid-4-one 
• 13145-89-6 5-methylthieno[2,3-d]pyrimidine-4-amine 
• 1312593-64-8 3-chloro-N-[2-(4-isoquinolinyl)-3,6-dimethylthieno[2,3-b]pyridin-4-yl]benzenesulfonamide 
• 1312593-63-7 3-chloro-N-[2-(4-isoxazolyl)-3,6-dimethylthieno[2,3-b]pyridin-4-yl]benzenesulfonamide 
• 1312593-61-5 3-chloro-N-[3,6-dimethyl-2-(1H-pyrazol-3-yl)thieno[2,3-b]pyridin-4-yl]benzenesulfonamide 
• 1312593-60-4 3-chloro-N-[3,6-dimethyl-2-(3-quinolinyl)thieno[2,3-b]pyridin-4-yl]benzenesulfonamide 
• 1312593-59-1 N-[2-(1-benzofuran-2-yl)-3,6-dimethylthieno[2,3-b]pyridin-4-yl]-3-chlorobenzenesulfonamide 
• 1312593-58-0 3-chloro-N-{3,6-dimethyl-2-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}benzenesulfonamide 
• 1312593-57-9 N-(2-bromo-3,6-dimethylthieno[2,3-b]pyridin-4-yl)-3-chlorobenzenesulfonamide 
• 1312593-56-8 3-chloro-N-[3,6-dimethyl-2-(1H-pyrazol-4-yl)thieno[2,3-b]pyridin-4-yl]benzenesulfonamide 
• 1312593-39-7 3-chloro-N-[3,6-dimethyl-2-(3-pyridinyl)thieno[2,3-b]pyridin-4-yl]benzenesulfonamide 

Relevant articles and documents

Design, molecular modeling and synthesis of metal-free sensitizers of thieno pyridine dyes as light-harvesting materials with efficiency improvement using plasmonic nanoparticles

Considering the thiophene unit as an electron-rich heterocycle, it is investigated with the aim of elucidating its potential efficiency for solar cell application. With the introduction of active substituents such as COOEt, CONH2 and CN into the thiophene segment, three novel thieno pyridine sensitizers (6a–c), based on donor-acceptor D-π-A construction, are designed and synthesized. The effect of the anchoring groups is investigated based on their molecular orbital’s (MO’s) energy gap (Eg). The electrostatic interaction between the synthesized dyes and metal nanoparticles, namely gold, silver and ruthenium, is believed to improve their performance as organic sensitizers. The dye-sensitized solar cells (DSSCs) are manufactured using the novel diazenyl pyridothiophene dyes, along with their metal nanoparticles conjugates as sensitizers, and were examined for efficiency improvement. Accordingly, using this modification, the photovoltaic performance was significantly improved. The promising results of conjugate (6b/AgNPs), compared with reported organic and natural sensitizers (JSC (1.136 × 10–1 mA/cm2), VOC (0.436 V), FF (0.57) and η (2.82 × 10–2%)), are attributed to the good interaction between the amide, methyl, amino and cyano groups attached to the thiophene pyridyl scaffolds and the surface of TiO2 porous film. Implementation of a molecular modeling study is performed to predict the ability of the thiophene moiety to be used in solar cell applications.

A green chemical approach: a straightforward one-pot synthesis of 2-aminothiophene derivatives via Gewald reaction in deep eutectic solvents

Abstract: The synergic effect of choline chloride/urea as a deep eutectic solvent was investigated in the synthesis of 2-aminothiophene derivatives via a three-component cyclocondensation of a ketone or an aldehyde with activated nitriles and elemental sulfur catalyzed by NaOH as cheap and highly accessible base. The advantages of this catalytic protocol are eco-friendly, easy to set up, reusability, and a simple separation and purification of products without using chromatography in high yields at short times. Graphical abstract: [Figure not available: see fulltext.]

2,4-diamino-thieno [2,3-d] pyrimidine derivatives and process for their preparation and use

The invention discloses a 2, 4-diamino-thieno [2, 3-d] pyrimidine derivative represented as a general formula (I), wherein definitions of R and X are specified in the instruction. Besides, the invention further discloses a preparation method and medical composition of the compound. The compound represented as the general formula (I) has an inhibiting effect on human lung cancer (A549), human cervical carcinoma (HeLa) and human colorectal cancer (HCT-116) cell proliferation, and can be used as an antitumor medicine.

First Gewald reaction ignited by sodium polysulfide: Greener ultrasound-promoted synthesis of substituted 2-aminothiophenes in the absence of catalyst

In this paper, a modified and facile Gewald reaction triggered by sodium polysulfide in the absence of catalytic base was developed. This approach involves a one-pot ultrasound-irritated aqueous reaction between ketones or aldehydes, malononitrile, and sodium polysulfide, which are converted into the corresponding 2-aminothiophene derivatives in moderate to high yields. In comparison with conventional methods, the prominent features of this sonocatalyzed procedure are experimental simplicity, good functional group tolerance, atom efficiency, and the use of water as a green solvent.

Bovine serum albumin-catalyzed one-pot synthesis of 2-aminothiophenes via Gewald reaction

A novel bovine serum albumin (BSA)-catalyzed Gewald reaction in one-pot was developed in this work. The influence of reaction conditions including solvent, temperature and catalyst loading was investigated, and 12 multi-substituted 2-aminothiophene derivatives were prepared with moderate to excellent yields. Recycle experiments were designed to demonstrate the reusability of BSA. This novel activity of BSA to catalyze Gewald reaction is of practical significance in expanding the application of biocatalysts.

A facile and practical one-pot synthesis of multisubstituted 2-aminothiophenes via imidazole-catalyzed Gewald reaction

A simple and efficient procedure was developed for the synthesis of multisubstituted 2-aminothiophene derivatives. In the presence of catalytic amount of imidazole, ketones or aldehydes, dicyanomethane and elemental sulfur were converted into the corresponding 2-aminothiophene derivatives in moderate to high yields in DMF at 60 °C.

Thienopyrimidine derivatives

4-Substituted-thieno[2,3-d], [3,2-d], and [3,4-d]pyrimidines having fungicidal, insecticidal, and miticidal utility are disclosed. Related 3-substituted-thieno[2,3-d], [3,2-d], and [3,4-d]pyrimidin-4-(3H)-imines are useful as fungicides, insecticides, and