2131-57-9

Basic information

• Product Name: 4-ACETYLPHENYL ISOTHIOCYANATE
• Synonyms: Phenylisothiocyanate, 4-acetyl;1-(4-ISOTHIOCYANATO-PHENYL)-ETHANONE;AKOS B022538;4-ACETYLPHENYL ISOTHIOCYANATE;4-Acetylphenyl isothiocyanate, 1-(4-Isothiocyanatophenyl)ethan-1-one;ethanone, 1-(4-isothiocyanatophenyl)-;4-Acetylphenyl isothiocyate, 98%
• CAS NO: 2131-57-9
• Molecular Formula: C₉H₇NOS
• Molecular Weight: 177.22
• Mol File: 2131-57-9.mol
• Article Data: 11

Chemical Properties

• Melting Point: 82 °C
• Boiling Point: 112 °C
• Flash Point: 112°C/6mm
• Appearance: /
• Density: 1.2153 (rough estimate)
• Vapor Pressure: 0.000335mmHg at 25°C
• Refractive Index: 1.5364 (estimate)
• Water Solubility: 16.84mg/L(25 oC)
• Sensitive: Lachrymatory
• BRN: 2207978
• CAS DataBase Reference: 4-ACETYLPHENYL ISOTHIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-ACETYLPHENYL ISOTHIOCYANATE(2131-57-9)
• EPA Substance Registry System: 4-ACETYLPHENYL ISOTHIOCYANATE(2131-57-9)

Safety Data

• Hazard Codes: Xi,C
• Statements: 20/21/22-36/37/38-43-34
• Safety Statements: 26-36/37/39-45
• RIDADR: 2811
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 2131-57-9(Hazardous Substances Data)

Usage

General Description

4-ACETYLPHENYL ISOTHIOCYANATE, also known as 4-isothiocyanatoacetophenone, is a chemical compound with the molecular formula C10H7NOS. It is a yellowish liquid that is commonly used in the synthesis of various organic compounds, particularly in the pharmaceutical and agrochemical industries. 4-ACETYLPHENYL ISOTHIOCYANATE is known for its strong odor and is used as a reagent in organic chemistry reactions, specifically in the preparation of thioamides and isothiocyanates. 4-ACETYLPHENYL ISOTHIOCYANATE has also been studied for its potential use as an anticancer agent, with research suggesting its ability to induce apoptosis in cancer cells. However, its high reactivity and potential health hazards should be taken into consideration when handling this chemical.

InChI:InChI=1/C9H7NOS/c1-7(11)8-2-4-9(5-3-8)10-6-12/h2-5H,1H3

Upstream product

• 87551-33-5 C₉H₉NOS₂ 
• 99-92-3 p-aminobenzophenone 
• 2926-29-6 Langlois reagent 
• 14235-81-5 4-Ethynylaniline 
• 75-15-0 carbon disulfide 
• 1158178-31-4 C₆H₁₅N*C₉H₉NOS₂ 
• 41656-75-1 N-(4-acetylphenyl)formamide 
• 463-71-8 thiophosgene 

Downstream Products

• 42084-03-7 N,N'-Bis--thioharnstoff 
• 74661-40-8 1-{4-[(1.3-benzothiazol-2-yl)amino]phenyl}ethan-1-one 
• 891560-05-7 4-(4-acetylphenyl)-1-(3-chlorobenzoyl)thiosemicarbazide 
• 1623153-72-9 1-(4-acetylphenyl)-3-(1-(2-(7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)thiourea 
• 1623153-54-7 1-(4-acetylphenyl)-3-(1-(2-(7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)thiourea 
• 1383254-27-0 1-[4-(1-thia-3-aza-spiro[5.5]undec-2-en-2-ylamino)-phenyl]-ethanone 

Relevant articles and documents

Organophosphine-free copper-catalyzed isothiocyanation of amines with sodium bromodifluoroacetate and sulfur

A copper-catalyzed isothiocyanation of amines with sodium bromodifluoroacetate and sulfur in the absence of organophosphine has been established. This approach represents a simple and efficient one-pot synthesis of isothiocyanates, and features excellent functional group tolerance and the use of a cheap, safe and odorless sulfur source. Moreover, this process could directly provide isothiocyanate analogous bioactive molecules, thiocarbonyl-containing pesticides and facile construction of benzoxazole and benzimidazole frames.

Isothiocyanation of amines using the Langlois reagent

The Langlois reagent was found to be effective for the isothiocyanation of primary amines in the presence of copper iodide and diethyl phosphonate.

Synthesis and evaluation of frentizole-based indolyl thiourea analogues as MAO/ABAD inhibitors for Alzheimer's disease treatment

Alzheimer's disease (AD) is a neurodegenerative disorder associated with an excessive accumulation of amyloid-beta peptide (Aβ). Based on the multifactorial nature of AD, preparation of multi-target-directed ligands presents a viable option to address more pathological events at one time. A novel class of asymmetrical disubstituted indolyl thioureas have been designed and synthesized to interact with monoamine oxidase (MAO) and/or amyloid-binding alcohol dehydrogenase (ABAD). The design combines the features of known MAO inhibitors scaffolds (e.g. rasagiline or ladostigil) and a frentizole moiety with potential to interact with ABAD. Evaluation against MAO identified several compounds that inhibited in the low to moderate micromolar range. The most promising compound (19) inhibited human MAO-A and MAO-B with IC50values of 6.34 μM and 0.30 μM, respectively. ABAD activity evaluation did not show any highly potent compound, but the compound series allowed identification of structural features to assist the future development of ABAD inhibitors. Finally, several of the compounds were found to be potent inhibitors of horseradish peroxidase (HRP), preventing the use of the Amplex Red assay to detect hydrogen peroxide produced by MAO, highlighting the need for serious precautions when using an enzyme-coupled assay.