7597-68-4

Basic information

• Product Name: Ethyl 2-(1-benzothiophen-3-yl)acetate
• Synonyms: ethyl 2-(benzo[b]thiophen-3-yl)acetate;Ethyl 2-(1-benzothiophen-3-yl)acetate;Benzo[b]thiophene-3-acetic acid, ethyl ester
• CAS NO: 7597-68-4
• Molecular Formula: C₁₂H₁₂O₂S
• Molecular Weight: 220.29
• Mol File: 7597-68-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 331.8 °C at 760 mmHg
• Flash Point: 154.4 °C
• Appearance: /
• Density: 1.208 g/cm³
• Vapor Pressure: 0.000152mmHg at 25°C
• Refractive Index: 1.608
• CAS DataBase Reference: Ethyl 2-(1-benzothiophen-3-yl)acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 2-(1-benzothiophen-3-yl)acetate(7597-68-4)
• EPA Substance Registry System: Ethyl 2-(1-benzothiophen-3-yl)acetate(7597-68-4)

Safety Data

• Hazardous Substances Data: 7597-68-4(Hazardous Substances Data)

Usage

General Description

Ethyl 2-(1-benzothiophen-3-yl)acetate is a chemical compound with the molecular formula C13H12O2. It is a ester derivative of the 1-benzothiophene-3-ylacetic acid and is commonly used in the pharmaceutical and organic synthesis industries. Ethyl 2-(1-benzothiophen-3-yl)acetate is known for its aromatic properties and is often used as a building block in the synthesis of various pharmaceutical drugs and organic compounds. It has the potential to exhibit a range of biological activities, making it a valuable and versatile chemical in the field of medicinal chemistry and drug development. Additionally, it is important to handle this compound with appropriate safety precautions due to its potential hazards if mishandled.

InChI:InChI=1/C12H12O2S/c1-2-14-12(13)7-9-8-15-11-6-4-3-5-10(9)11/h3-6,8H,2,7H2,1H3

Upstream product

• 106-95-6 allyl bromide 
• 149682-18-8 diethyl 3-benzothiophenemalonate 
• 36748-88-6 3-iodobenzo[b]thiophene 
• 188610-79-9 ethyl 2,3-dihydrobenzo[b]thiene-3-acetate 
• 84-58-2 2,3-dicyano-5,6-dichloro-p-benzoquinone 

Downstream Products

• 87894-75-5 1-phenyl-3H-thiopyrano<3,4-b><1>benzothiophen-3-one 
• 87894-73-3 1-phenyl-3H-<1>benzothieno<2,3-c>pyran-3-one 
• 87894-74-4 1-phenyl-3H-<1>benzothieno<2,3-c>pyran-3-thione 
• 87894-77-7 1-phenyl-3H-<1>benzothieno<2,3-c>pyran-3-one 9,9-dioxide 
• 87894-79-9 1-phenyl-3H-<1>benzothieno<2,3-c>pyran-3-thione 9,9-dioxide 

Relevant articles and documents

Antidepressant 1-arylalkyl-4-(alkoxy pyridinyl)-and 4-(alkoxypyrimidinyl) piperazine derivatives

Novel compound of formula I and pharmaceutically acceptable salts thereof are useful CNS agents: STR1 wherein X is CH or N; X' is CH or a direct covalent link; Y is CH, CH2 or N; Y' is N, NH, O or S; R1 is H, Br, Cl, F, C1-4 alkyl, C1-4 alkoxy, C1-4 alkoxycarbonyl, CN, CONH2 or CH3 SO2 NH; n is 2 or 3; R2 is H or C1-4 alkyl; R3 is C1-4 alkoxy; R4 is H, Br, Cl, or F; and Z is CH or N.

Cope Rearrangements in the Benzothiophene Series

The inability to observe Cope rearrangement products at elevated temperatures for diethyl α-allyl-2-naphthalenemalonate (1) and diethyl α-allyl-9-phenanthrenemalonate (2) does not extend to the analogous systems resulting from replacement of the aromatic units by 2- and 3-benzothiophene nuclei.Thermal rearrangement of diethyl α-allyl-3-benzothiophenemalonate (5) at 215-255 deg C for 11 h produces the expected Cope rearrangement product diethyl 2-allyl-3-benzothiophenemalonate (10) (8percent) accompanied by trans- and cis-ethyl 2,3-dihydro-1-(ethoxycarbonyl)-1H-benzocyclopentathiophene-2-acetate (9a) (10percent) and (9b) (5percent), respectively.The structure elucidation of 10, 9a, and 9b was done by spectroscopy.The attempted structure verification of 10 by an independent route gave diethyl 2-(1-propenyl)-3-benzothiophenemalonate (12) which when heated at 230-240 deg C for 18 h gave 1-carbethoxy-2-hydroxy-3-methyldibenzothiophene (16) as a major product.Similar results were observed with 2-substituted analogues of 5, both diethyl 3-allyl-2-benzothiophenemalonate (24) and ethyl 1,2-dihydro-3-(ethoxycarbonyl)-3H-benzocyclopentathiophene-2-acetate (25) being formed.In this case the structure of 24 was verified by synthesis.An extension of this involved a study of thermal rearrangement of analogous compound ethyl α-allyl-α-cyano-3-benzothiopheneacetate (30).Thermal rearrangement of 30 at 235-245 deg C for 8 h gave the expected Cope rearrangement product ethyl α-cyano-2-allyl-3-benzothiopheneacetate (32) (6percent) along with an unexpected diastereomeric mixture of 1-cyano-1-(ethoxycarbonyl)-2-methyl-2,3-dihydro-1H-benzocyclopentathiophenes (33) (18percent).Speculative mechanistic considerations are offered regarding the mode of transformation of 12 to 16 and 32 to 33.