1205-06-7

Basic information

• Product Name: 4-ETHOXYCARBONYLPHENYL ISOTHIOCYANATE
• Synonyms: ETHYL P-ISOTHIOCYANATOBENZOATE;4-ETHOXYCARBONYLPHENYL ISOTHIOCYANATE;Ethyl 4-isothiocyanatobenzoate;Phenylisothiocyanate, 4-ethoxycarbonyl;4-Ethoxycarbonylphenyl isothiocyanate 98%;Ethyl 4-isothiocyanatobenzoate 98%;4-Carbethoxyphenyl isothiocyanate;NSC 294821
• CAS NO: 1205-06-7
• Molecular Formula: C10H9NO2S
• Molecular Weight: 207.25
• EINECS: 214-880-0
• Product Categories: Phenyls & Phenyl-Het;Phenyls & Phenyl-Het
• Mol File: 1205-06-7.mol

Chemical Properties

• Melting Point: 57 °C
• Boiling Point: 123-127°C 1mm
• Flash Point: 123-127°C/1mm
• Appearance: /
• Density: 1.2784 (rough estimate)
• Vapor Pressure: 0.000201mmHg at 25°C
• Refractive Index: 1.5250 (estimate)
• Water Solubility: 18.65mg/L(25 oC)
• Sensitive: Moisture Sensitive/Lachrymatory
• BRN: 2213400
• CAS DataBase Reference: 4-ETHOXYCARBONYLPHENYL ISOTHIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-ETHOXYCARBONYLPHENYL ISOTHIOCYANATE(1205-06-7)
• EPA Substance Registry System: 4-ETHOXYCARBONYLPHENYL ISOTHIOCYANATE(1205-06-7)

Safety Data

• Hazard Codes: C,T,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 2811
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 1205-06-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
4-Ethoxycarbonylphenyl isothiocyanate is used as a reagent in pharmaceutical research for its ability to modify biomolecules, contributing to the development of new drugs. Its isothiocyanate functional group allows for the creation of novel chemical entities with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, 4-Ethoxycarbonylphenyl isothiocyanate is used as a key intermediate. Its unique reactivity makes it suitable for the synthesis of complex organic compounds, facilitating the production of a wide range of chemical products.
Used in Agrochemical Development:
4-Ethoxycarbonylphenyl isothiocyanate is also utilized in the development of agrochemicals. Its properties allow for the creation of new compounds that can be used in agriculture for pest control and crop protection, enhancing agricultural productivity and sustainability.
Used in Material Science:
In material science, 4-Ethoxycarbonylphenyl isothiocyanate is employed in the development of new materials. Its versatility contributes to the creation of innovative materials with unique properties, potentially useful in various industries such as electronics, textiles, and construction.

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

Upstream product

• 2926-29-6 Langlois reagent 
• 94-09-7 p-aminoethylbenzoate 
• 75-15-0 carbon disulfide 
• 96989-50-3 di-2-pyridyl thionocarbonate 
• 150-13-0 4-amino-benzoic acid 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 4314-19-6 bis(1H-benzo[d][1,2,3]triazol-1-yl)methanethione 
• 463-71-8 thiophosgene 

Downstream Products

• 89306-05-8 4-[N'-(4-chloro-phenyl)-thioureido]-benzoic acid ethyl ester 
• 1158-23-2 4-(N'-phenyl-thioureido)-benzoic acid ethyl ester 
• 1429-24-9 diethyl 4,4'-(thiocarbonylbis(azanediyl))dibenzoate 
• 89305-02-2 4-[N'(4-bromo-phenyl)-thioureido]-benzoic acid ethyl ester 
• 59995-07-2 4-[1,2,3]thiadiazol-5-ylamino-benzoic acid ethyl ester 
• 39931-28-7 4-(5,5-dimethyl-2-thioxo-tetrahydro-pyrrolo[1,2-b][1,2,4]oxadiazol-1-yl)-benzoic acid ethyl ester 
• 50455-85-1 4-(5,5-dimethyl-2-oxo-tetrahydro-pyrrolo[1,2-b][1,2,4]oxadiazol-1-yl)-benzoic acid ethyl ester 
• 39931-32-3 4-(5,5,7,7-tetramethyl-2-oxo-tetrahydro-pyrrolo[1,2-b][1,2,4]oxadiazol-1-yl)-benzoic acid ethyl ester 
• 79865-64-8 4-[2-(2,4-Dinitro-phenyl)-3-oxo-thiobutyrylamino]-benzoic acid ethyl ester 
• 78157-93-4 4-(3-Carbamoyl-4,5-dioxo-2-thioxo-pyrrolidin-1-yl)-benzoic acid ethyl ester 
• 78157-88-7 4-(3-Carboxy-2-cyano-3-oxo-thiopropionylamino)-benzoic acid ethyl ester 
• 150099-20-0 C₄₃H₃₈N₅O₄P 
• 474928-76-2 ethyl 4-(3-(4-(N-(5-methylisoxazol-3-yl)sulfamoyl)phenyl)thioureido)benzoate 
• 516459-86-2 C₂₈H₃₀N₂O₃S 

Relevant articles and documents

Na2S2O8-mediated efficient synthesis of isothiocyanates from primary amines in water

We have developed two green, practical, and efficient procedures, including a one-pot one, to synthesize isothiocyanates from amines and carbon disulfide via desulfurization with sodium persulfate. Water is used as the solvent. Basic conditions are necessary for good chemoselectivity for isothiocyanates. Structurally diverse linear and branched alkyl amines and aryl amines are readily converted to isothiocyanates by the two procedures in satisfactory yields. Halogens, benzylic C-H bonds, methylthio, nitro, ester, alkenyl, electron-rich or -deficient (hetero)aryls, acetylenyl, and even phenolic and alcoholic hydroxyls are well tolerated. The one-pot procedure in water can also be used to realize the preparation of chiral isothiocyanates from chiral amines, and the modification of bioactive structures with free amino groups. In large-scale preparation, simple and practical purification procedures independent of column chromatography are developed.

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.

Facile and versatile synthesis of alkyl and aryl isothiocyanates by using triphosgene and cosolvent

A mild and efficient method for the conversion of alkyl and aryl amines to isothiocyanates via dithiocarbamates has been developed using (CH 3)2CO-CS2 as co-solvent and triphosgene as dehydrosulfurization reagent. High yields, mild reaction conditions and excellent functional group compatibility make it become a versatile synthetic method for the preparation of isothiocyanates compared with reported methods. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]

Synthesis and SAR of selective small molecule neuropeptide y Y2 receptor antagonists

Highly potent and selective small molecule neuropeptide Y Y2 receptor antagonists are reported. The systematic SAR exploration of a hit molecule N-(4-ethoxyphenyl)-4-[hydroxy(diphenyl)methyl]piperidine-1-carbothioamide, identified from HTS, led to the discovery of highly potent NPY Y2 antagonists 16 (CYM 9484) and 54 (CYM 9552) with IC50 values of 19 nM and 12 nM respectively.

Structure-activity relationships (SAR) research of thiourea derivatives as dual inhibitors targeting both HIV-1 capsid and human cyclophilin A

HIV-1 capsid (CA) and human cyclophilin A (CypA) play important roles in HIV-1 assembly and disassembly processes, which are critical in HIV-1 replication. Based on the discovery of thiourea derivatives targeting both of the two proteins and indicating effective inhibitory activities in our group, we designed and synthesized a new class of thiourea derivatives. Their abilities to bind to capsid and cyclophilin A were determined by ultraviolet spectroscopic analysis, fluorescence binding affinity, and PPIase inhibition assay. Furthermore, the newly synthesized compounds were tested for their antiviral activities and cytotoxicities using CEM cells. According to the biological evaluation and subsequent molecular docking analyses, we studied the structure-activity relationships of thiourea derivatives. Three optimal compounds (K17, K24, K25) based on the achieved structure-activity relationships would be the basis for future optimization.

Selectively targeting T- and B-cell lymphomas: A benzothiazole antagonist of α4β1integrin

Current cancer chemotherapeutic agents clinically deployed today are designed to be indiscriminately cytotoxic, however, achieving selective targeting of cancer malignancies would allow for improved diagnostic and chemotherapeutic tools. Integrin α4β1, a heterodimeric cell surface receptor, is believed to have a low- affinity conformation in resting normal lymphocytes and an activated high-affinity conformation in cancerous cells, specifically T- and B-cell lymphomas. This highly attractive yet poorly understood receptor has been selectively targeted with the bisaryl urea peptidomimetic antagonist i. However, concerns regarding its preliminary pharmacokinetic (PK) profile provided an impetus to change the pharmacophore from a bisaryl urea to a 2-arylaminobenzothiazole moiety, resulting in an analogue with improved physicochemical properties, solubility, and kidney:tumor ratio while maintaining potency (6;IC50 = 53 pM). The results presented herein utilized heterocyclic and solid-phase chemistry, cell adhesion assay, and in vivo optical imaging using the cyanine dye Cy5.5 conjugate.

HETEROCYCLIC LIGANDS FOR INTEGRIN IMAGING AND THERAPY

The present invention provides α 4?1 integrin ligands that display high binding affinity, specificity, and stability. The ligands comprise a peptide having n independently selected amino acids, wherein at least one amino acid is an unnatural amino acid or a D-amino acid, and wherein n is an integer of from 3 to 20. Methods are provided for administering the ligands for treating cancer, inflammatory diseases, and autoimmune diseases. Also provided are methods for administering the ligands for imaging a tumor, organ, or tissue in a subject.

Highly potent, water soluble benzimidazole antagonist for activated α4β1 integrin

The cell surface receptor α4β1 integrin, activated constitutively in lymphoma, can be targeted with the bisaryl urea peptidomimetic antagonist 1 (LLP2A). However, concerns on its preliminary pharmacokinetic (PK) profile provided an impetus to change the pharmacophore from a bisaryl urea to a 2-arylaminobenzimidazole moiety, resulting in improved solubility while maintaining picomolar potency [5 (KLCA4); IC50 = 305 pM]. With exceptional solubility, this finding has the potential for improving PK to help diagnose and treat lymphomas.

Benzotriazole-assisted thioacylation

Benzotriazole reagents for thioacylation (RCSBt), thiocarbamoylation (RR'NCSBt), aryl/alkoxy-thioacylation (ROCSBt), and aryl/alkylthiothioacylation (RSCSBt) are synthesized, and their utility is assessed by syntheses of representative heteroaryl thioureas 3a-g, thioamides 15a-s, thionoesters 16a-h, thiocarbamates 17a-e, dithiocarbamates 18a-d, thiocarbonates 19a-c, and dithiocarbonates 20a-c.