99960-09-5

Basic information

• Product Name: 2-ETHOXYCARBONYLPHENYL ISOTHIOCYANATE
• Synonyms: ETHYL 2-ISOTHIOCYANATOBENZOATE;2-ISOTHIOCYANATO-BENZOIC ACID ETHYL ESTER;2-ETHOXYCARBONYLPHENYL ISOTHIOCYANATE;2-(Ethoxycarbonyl)phenyl isothiocyanate, 98+%;2-(etoxycarbonyl)phenylisothiocyanate;2-Ethoxycarbonylphenyl isothiocyate, 99%
• CAS NO: 99960-09-5
• Molecular Formula: C₁₀H₉NO₂S
• Molecular Weight: 207.25
• Product Categories: Organic Building Blocks;Sulfur Compounds;Thiocyanates/Isothiocyanates
• Mol File: 99960-09-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 150 °C1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.201 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00014mmHg at 25°C
• Refractive Index: n20/D 1.614(lit.)
• Sensitive: Moisture Sensitive
• BRN: 3267738
• CAS DataBase Reference: 2-ETHOXYCARBONYLPHENYL ISOTHIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ETHOXYCARBONYLPHENYL ISOTHIOCYANATE(99960-09-5)
• EPA Substance Registry System: 2-ETHOXYCARBONYLPHENYL ISOTHIOCYANATE(99960-09-5)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 23-26-36/37/39-45
• RIDADR: 2810
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 99960-09-5(Hazardous Substances Data)

Usage

General Description

2-Ethoxycarbonylphenyl isothiocyanate is a chemical compound with the molecular formula C11H9NO2S. It is commonly used in organic synthesis as a building block for the preparation of various biologically active molecules. 2-ETHOXYCARBONYLPHENYL ISOTHIOCYANATE is known for its ability to react with amines and amino acids, forming thiourea derivatives, which have been studied for their potential antimicrobial and antifungal properties. 2-Ethoxycarbonylphenyl isothiocyanate is also used in the development of pharmaceuticals and agrochemicals, as well as in the creation of fluorescent dyes and polymers. It is important to handle this compound with care, as it is a skin and eye irritant, and proper safety precautions should be taken when working with it.

InChI:InChI=1/C10H9NO2S/c1-2-13-10(12)8-5-3-4-6-9(8)11-7-14/h3-6H,2H2,1H3

Upstream product

• 2926-29-6 Langlois reagent 
• 87-25-2 2-ethoxycarbonylaniline 
• 13037-60-0 1-bromo-2-isothiocyanatobenzene 
• 541-41-3 chloroformic acid ethyl ester 
• 463-71-8 thiophosgene 

Downstream Products

• 100142-86-7 2-(2-thioxo-2,3-dihydro-imidazol-1-yl)-benzoic acid ethyl ester 
• 72368-55-9 ethyl 2-(thiopropanoylamino)benzoate 
• 99072-70-5 2-imidazol-1-yl-benzoic acid hydrazide 
• 13915-57-6 N-(o-Carbethoxyphenyl)-methantricarbonsaeure-diethylester-thioamid 
• 23051-17-4 2-thioureido-benzoic acid ethyl ester 

Relevant articles and documents

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.

Discovery of a novel 5-HT3 antagonist/5-HT1A agonist 3-amino-5,6,7,8-tetrahydro-2-{4-[4-(quinolin-2-yl)piperazin-1-yl]butyl} quinazolin-4(3 H)-one (TZB-30878) as an orally bioavailable agent for irritable bowel syndrome

We have prepared a series of quinazolinone derivatives linked with piperazinylquinoline for the treatment of irritable bowel syndrome (IBS). Using pharmacophore analysis, we designed and synthesized compounds which bind to both serotonin receptor subtype 1A (5-HT1A) and subtype 3 (5-HT 3). Quinazolinone derivatives with a sulfur atom in the linker showed high affinity in in vitro assays, but low in vivo activity. Focusing on the linker to improve the pharmacokinetic profile, the sulfur atom in the linker was replaced with a methylene group. Further optimization led to the discovery of compound 17m (TZB-30878) (J. Pharmacol. Exp. Ther. 2007, 322, 1315 -1323, Patent WO2005082887 (A1), 2005), a novel 5-HT1A agonist/5-HT3 antagonist in the 3-aminoquinazolinone series. In in vivo functional assays, 17m dose dependently inhibited the Bezold-Jarisch reflex and induced 5-HT 1A-mediated behaviors, and in an IBS animal model, 17m significantly inhibited stress-induced defecation. Pretreatment by WAY-100635 (5-HT 1A antagonist) significantly attenuated but did not abolish the inhibitory effects of 17m. These results suggested that 17m exerted inhibitory effects via both 5-HT1A agonistic and 5-HT3 antagonistic activities and that 17m would be useful as a therapeutic agent for IBS.