2-(3-Methylbenzo[b]thiophen-2-yl)acetic acid

Base Information

• Chemical Name: 2-(3-Methylbenzo[b]thiophen-2-yl)acetic acid
• CAS No.: 1505-52-8
• Molecular Formula: C11H10 O2 S
• Molecular Weight: 206.26
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID20381580
• Wikidata: Q82172478
• Mol file: 1505-52-8.mol

Synonyms:1505-52-8;2-(3-methylbenzo[b]thiophen-2-yl)acetic acid;2-(3-methyl-1-benzothiophen-2-yl)acetic acid;Benzo[b]thiophene-2-acetic acid, 3-methyl-;3-METHYLTHIANAPHTHENE-2-ACETIC ACID;3-Methylbenzo[b]thiophene-2-acetic acid;Maybridge1_005368;Oprea1_711047;SCHEMBL586189;HMS556L22;DTXSID20381580;MFVMWBIORCNCNB-UHFFFAOYSA-N;3-methyl thianaphthene-2acetic acid;MFCD00052299;AKOS002305970;3-methylbenzo[b]-thiophene-2-acetic acid;AS-65625;Benzo[b]thiophene-2-aceticacid,3-methyl-;FT-0608557;N-HYDROXY-2-NAPHTHALENECARBOXIMIDAMIDE;3-Methylthianaphthene-2-acetic acid, AldrichCPR;EN300-8675804;Z1269128994

Chemical Property of 2-(3-Methylbenzo[b]thiophen-2-yl)acetic acid

Chemical Property:

• Vapor Pressure: 7.65E-07mmHg at 25°C
• Melting Point: 148-150°C
• Boiling Point: 391.8°Cat760mmHg
• Flash Point: 190.8°C
• PSA: 65.54000
• Density: 1.315g/cm³
• LogP: 2.83680
• Storage Temp.: 2-8°C
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 206.04015073
• Heavy Atom Count: 14
• Complexity: 229

Purity/Quality:

98%min ^*data from raw suppliers

2-(3-Methylbenzo[b]thiophen-2-yl)aceticacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xn
• Statements: 36/37/38-36-22
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(SC2=CC=CC=C12)CC(=O)O

Technology Process of 2-(3-Methylbenzo[b]thiophen-2-yl)acetic acid

There total 7 articles about 2-(3-Methylbenzo[b]thiophen-2-yl)acetic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

2,3-dimethylbenzothiophene (4923-91-5) + carbon dioxide (124-38-9,18923-20-1) → 3-methylbenzo[b]-thiophene-2-acetic acid (1505-52-8)

Guidance literature:

With cesium fluoride; lithium tert-butoxide; at 150 ℃; for 13h; under 760.051 Torr; Sealed tube;

DOI:10.1021/acs.orglett.9b01386

Reference yield: 58.0%

carbon dioxide (124-38-9,18923-20-1) + (3-methylbenzo[b]thiophene-2-yl)-N,N,N-trimethylmethanammonium iodide → 3-methylbenzo[b]-thiophene-2-acetic acid (1505-52-8)

Guidance literature:

carbon dioxide; (3-methylbenzo[b]thiophene-2-yl)-N,N,N-trimethylmethanammonium iodide; With manganese; 2,9-dibutyl-4,7-dimethyl-1,10-phenanthroline; nickel(II) bromide diethylene glycol dimethyl ether; In N,N-dimethyl-formamide; at 90 ℃; for 72h; under 760.051 Torr; Schlenk technique;

With hydrogenchloride; In water; N,N-dimethyl-formamide; at 20 ℃; Schlenk technique;

DOI:10.1002/anie.201600697

Reference yield:

3-methylbenzothiophene (1455-18-1) → 3-methylbenzo[b]-thiophene-2-acetic acid (1505-52-8)

Guidance literature:

Multi-step reaction with 2 steps

1: boron fluoride ether adduct

2: morpholine; sulfur / Erwaermen des Reaktionsprodukts mit aethanol. Kalilauge

With morpholine; boron fluoride ether; sulfur;

DOI:10.1021/ja01129a011

upstream raw materials:

morpholine

2-acetyl-3-methyl-benzothiophene

2-chloromethyl-3-methylbenzothiophene

diethyl ether

Refernces

• 1、 Shigeno, Masanori,Sasaki, Keita,Nozawa-Kumada, Kanako,Kondo, Yoshinori. "Double-Carboxylation of Two C-H Bonds in 2-Alkylheteroarenes Using LiO- t-Bu/CsF". . p. 4515 - 4519. Retrieved 2019/06/27.