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

Uses

Used in Organic Synthesis:
2-Ethoxycarbonylphenyl isothiocyanate is used as a building block in organic synthesis for the preparation of various biologically active molecules, contributing to the development of new compounds with potential applications in medicine and other fields.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 2-Ethoxycarbonylphenyl isothiocyanate is utilized as a key intermediate in the synthesis of drugs, leveraging its reactivity to form thiourea derivatives with potential therapeutic properties.
Used in Agrochemical Production:
2-Ethoxycarbonylphenyl isothiocyanate is employed in the creation of agrochemicals, where its ability to form active thiourea derivatives can be harnessed for applications in pest and disease control in agriculture.
Used in Fluorescent Dyes and Polymers:
2-ETHOXYCARBONYLPHENYL ISOTHIOCYANATE is also used as a precursor in the development of fluorescent dyes and polymers, where its chemical properties can be exploited to create materials with specific optical characteristics for use in research and industry.

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

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

Downstream Products

• 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 
• 100142-86-7 2-(2-thioxo-2,3-dihydro-imidazol-1-yl)-benzoic acid ethyl ester 
• 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.

Integrated one-flow synthesis of heterocyclic thioquinazolinones through serial microreactions with two organolithium intermediates

The synthesis of pharmaceutical compounds via short-lived intermediates in a microreactor is attractive, because of the fast flow and high throughput. Additionally, intermediates can be utilized sequentially to efficiently build up a library in a short time. Here we present an integrated microfluidic synthesis of biologically active thioquinazolinone libraries. Generation of o-lithiophenyl isothiocyanate and subsequent reaction with aryl isocyanate is optimized by controlling the residence time in the microreactor to 16 ms at room temperature. Various S-benzylic thioquinazolinone derivatives are synthesized within 10 s in high yields (75-98%) at room temperature. These three-step reactions involve two organolithium intermediates, an isothiocyanate-functionalized aryllithium intermediate, and a subsequent lithium thiolate intermediate. We also demonstrate the gram-scale synthesis of a multifunctionalized thioquinazolinone in the microfluidic device with a high yield (91%) and productivity (1.25 g in 5 min).

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.