38778-05-1

Basic information

• Product Name: 4-PHENOXYTHIOPHENOL
• Synonyms: 4-PHENOXYTHIOPHENOL;4-PHENOXY-BENZENETHIOL
• CAS NO: 38778-05-1
• Molecular Formula: C₁₂H₁₀OS
• Molecular Weight: 202.27
• Mol File: 38778-05-1.mol

Chemical Properties

• Boiling Point: 128°C/0.1mm
• Flash Point: 140.3 °C
• Appearance: /
• Density: 1.171g/cm³
• Vapor Pressure: 0.00124mmHg at 25°C
• Refractive Index: 1.622
• CAS DataBase Reference: 4-PHENOXYTHIOPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-PHENOXYTHIOPHENOL(38778-05-1)
• EPA Substance Registry System: 4-PHENOXYTHIOPHENOL(38778-05-1)

Safety Data

• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 38778-05-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
4-Phenoxythiophenol is used as a building block for the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and pesticides due to its chemical properties and reactivity.
Used in Organic Chemistry as a Reagent:
In the realm of organic chemistry, 4-Phenoxythiophenol serves as a reagent, particularly for facilitating the formation of carbon-sulfur bonds, which are crucial in the synthesis of a wide range of organic compounds.
Used in Antioxidant Product Development:
4-Phenoxythiophenol is used as a potential antioxidant in the development of products designed to prevent or slow damage caused by oxidative stress, capitalizing on its inherent antioxidant properties for applications in various industries, including cosmetics, food, and health supplements.

InChI:InChI=1/C12H10OS/c14-12-8-6-11(7-9-12)13-10-4-2-1-3-5-10/h1-9,14H

Upstream product

• 1623-92-3 4-phenoxyphenylsulfonyl chloride 
• 101-55-3 4-Bromodiphenyl ether 
• 101-84-8 diphenylether 
• 831-82-3 4-Phenoxyphenol 
• 139-59-3 4-phenoxyanilin 
• 51289-12-4 4-(4-bromophenoxy)thiophenol 
• 2974-94-9 4-phenoxyiodobenzene 
• 198062-96-3 O-(4-phenoxyphenyl)-N,N-dimethylthiocarbamate 
• 198062-93-0 S-(4-phenoxyphenyl)-N,N-dimethylthiocarbamate 

Downstream Products

• 113113-66-9 1,2-bis(4-phenoxyphenyl)disulfane 
• 88590-36-7 1-(4-nitro-phenylsulfanyl)-4-phenoxy-benzene 
• 88590-35-6 1-(2-nitro-phenylsulfanyl)-4-phenoxy-benzene 
• 54758-84-8 C₂₂H₁₈O₂S 
• 54758-88-2 C₂₀H₁₈OS 
• 95452-30-5 p-phenoxy-phenylthioglycolic acid 
• 93656-49-6 p-phenoxy-2',4'-dinitrophenyl-mercaptobenzene 
• 202666-42-0 3-(4-phenoxy-phenylsulfanyl)-propan-1-ol 
• 274902-54-4 2-[2-(4-phenoxy-phenylsulfanyl)-ethoxy]-tetrahydro-pyran 
• 292605-09-5 4-(4-phenoxyphenylsulfanyl)-1-butene 
• 292605-10-8 5-(4-phenoxyphenylsulfanyl)-1-pentene 
• 3159-49-7 3-(4-phenoxyphenylsulfanyl)-1-propene 
• 397330-24-4 1-(4-phenoxy-phenylsulfanyl)-propan-2-one 
• 213014-03-0 4-(4-phenoxy-phenylsulfanylmethyl)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester 

Relevant articles and documents

Discovery of 3,5-Dimethyl-4-Sulfonyl-1 H-Pyrrole-Based Myeloid Cell Leukemia 1 Inhibitors with High Affinity, Selectivity, and Oral Bioavailability

Myeloid cell leukemia 1 (Mcl-1) protein is a key negative regulator of apoptosis, and developing Mcl-1 inhibitors has been an attractive strategy for cancer therapy. Herein, we describe the rational design, synthesis, and structure-activity relationship study of 3,5-dimethyl-4-sulfonyl-1H-pyrrole-based compounds as Mcl-1 inhibitors. Stepwise optimizations of hit compound 11 with primary Mcl-1 inhibition (52%@30 μM) led to the discovery of the most potent compound 40 with high affinity (Kd = 0.23 nM) and superior selectivity over other Bcl-2 family proteins (>40,000 folds). Mechanistic studies revealed that 40 could activate the apoptosis signal pathway in an Mcl-1-dependent manner. 40 exhibited favorable physicochemical properties and pharmacokinetic profiles (F% = 41.3%). Furthermore, oral administration of 40 was well tolerated to effectively inhibit tumor growth (T/C = 37.3%) in MV4-11 xenograft models. Collectively, these findings implicate that compound 40 is a promising antitumor agent that deserves further preclinical evaluations.

Novel 2-arylthiopropanoyl-CoA inhibitors of α-methylacyl-CoA racemase 1A (AMACR; P504S) as potential anti-prostate cancer agents

α-Methylacyl-CoA racemase (AMACR; P504S) catalyses an essential step in the degradation of branched-chain fatty acids and the activation of ibuprofen and related drugs. AMACR has gained much attention as a drug target and biomarker, since it is found at elevated levels in prostate cancer and several other cancers. Herein, we report the synthesis of 2-(phenylthio)propanoyl-CoA derivatives which provided potent AMACR inhibitory activity (IC50 = 22–100 nM), as measured by the AMACR colorimetric activity assay. Inhibitor potency positively correlates with calculated logP, although 2-(3-benzyloxyphenylthio)propanoyl-CoA and 2-(4-(2-methylpropoxy)phenylthio)propanoyl-CoA were more potent than predicted by this parameter. Subsequently, carboxylic acid precursors were evaluated against androgen-dependent LnCaP prostate cancer cells and androgen-independent Du145 and PC3 prostate cancer cells using the MTS assay. All tested precursor acids showed inhibitory activity against LnCaP, Du145 and PC3 cells at 500 μM, but lacked activity at 100 μM. This is the first extensive structure-activity relationship study on the influence of side-chain interactions on the potency of novel rationally designed AMACR inhibitors.

ISOTHIOCYANATE COMPOUND AND APPLICATION THEREOF

The present invention provides an isothiocyanate compound and its application. The compound is an aryl-substituted isothiocyanate compound that has a structure of the general formula I. The isothiocyanate compound of the present invention has very good solubility in water, far better inhibitory activity for XPO1 protein than other non-aryl substituted congeneric compounds, little side effects, and good biological safety and bioavailability, and is quite suitable for clinical application. Therefore, the isothiocyanate compound would have tremendous potential market space and economic benefits.

INHIBITORS OF MATRIX METALLOPROTEINASES TO TREAT NEUROLOGICAL DISORDERS

The invention provides methods to treat neurological disorders, ophthalmological disorders, or a combination thereof by administering a compound that inhibits MMPs. A compound that inhibits MMPs is represented by the compound of formula (I) shown herein.

A Convenient Synthesis of a Selective Gelatinase Inhibitor as an Antimetastatic Agent

Compound 1, 2-(4-phenoxyphenylsulfonylmethyl)thiirane, is a potent and selective inhibitor for human gelatinases (J. Am. Chem. Soc. 2000, 122, 6799-6800), enzymes implicated in a number of diseases, including cancer. This compound is showing excellent pro

α-amino-β-sulfonyl hydroxamic acid compounds

A family of molecules is disclosed that inhibit matrix metalloprotease (MMP) activity, and particularly inhibit the activity of one or more of MMP-2, MMP-9, or MMP-13, while generally exhibiting little activity against MMP-1. A contemplated compound also

Facile introduction of SH group on aromatic substrates via electrophilic substitution reactions

Herein, we describe a mild and efficient two-step procedure to introduce a thiol group on aromatic substrates. First, reaction with an activated sulfoxide leads to an arylsulfonium salt intermediate. Then, two successive β-elimination-based dealkylation reactions afford the desired arylthiols in good to excellent yields.

Inhibitors of matrix metallaproteinases

The invention provides compounds that inhibit MMPs; methods for treating or preventing cancer, angiogenesis, arthritis, connective tissue disease, cardiovascular disease, inflammation or autoimmune disease in a mammal; a method for inhibiting a matrix met

Design and synthesis of aryloxyethyl thiocyanate derivatives as potent inhibitors of Trypanosoma cruzi proliferation

As a part of our project directed at the search of new chemotherapeutic agents against American trypanosomiasis (Chagas' disease), several drugs possessing the 4-phenoxyphenoxy skeleton and other closely related structures employing the thiocyanate moiety as polar end group were designed, synthesized, and evaluated as antiproliferative agents against Trypanosoma cruzi, the parasite responsible for this disease. These thiocyanate analogues were envisioned bearing in mind the potent activity shown by 4- phenoxyphenoxyethyl thiocyanate (compound 8) taken as lead drug. This compound had previously proved to be an extremely active growth inhibitor against T. cruzi with IC50 values ranging from the very low micromolar level in epimastigotes to the low nanomolar level in the intracellular form of the parasite. Of the designed compounds, the ethyl thiocyanate drugs connected to nonpolar skeletons, namely, arylthio, 2,4-dichlorophenoxy, ortho-substituted aryloxy, and 2-methyl-4-phenoxyphenoxy (compounds 15, 34, 47, 52, 72, respectively), were shown to be very potent antireplicative agents against T. cruzi. On the other hand, conformationally restricted analogues as well as branched derivatives at the aliphatic side chain were shown to be moderately active against T. cruzi growth. The biological activity of drugs bearing the thiocyanate group correlated quite well with the activity exhibited by their normal precursors, the tetrahydropyranyl ether derivatives, when bonded to the same nonpolar skeleton. Compounds having the tetrahydropyranyl moiety as polar end were proportionally much less active than sulfur-containing derivatives in all cases. Drugs 47 and 72 also resulted to be very active against the amastigote form of the parasite growing in myoblasts; however, they were slightly less active than the lead drug 8. On the other hand, compounds 34 and 52 were almost devoid of activity against myoblasts. Surprisingly, the dithio derivative 15 was toxic for myoblasts.