33904-03-9

Basic information

• Product Name: 2,4-DIMETHOXYPHENYL ISOTHIOCYANATE
• Synonyms: 2,4-DIMETHOXYPHENYL ISOTHIOCYANATE;AKOS B016340;2,4-Dimethoxyphenyl isothiocyanate, 95+%;2,4-Dimethoxyphenyl isothiocyanate 95%;2,4-Dimethoxyphenyl isothiocyate, 98%
• CAS NO: 33904-03-9
• Molecular Formula: C₉H₉NO₂S
• Molecular Weight: 195.24
• Mol File: 33904-03-9.mol

Chemical Properties

• Melting Point: 52-55 °C(lit.)
• Boiling Point: 167 °C6 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Pale yellow/Powder
• Density: 1.2721 (rough estimate)
• Vapor Pressure: 0.000308mmHg at 25°C
• Refractive Index: 1.5270 (estimate)
• Sensitive: Moisture Sensitive
• BRN: 2723226
• CAS DataBase Reference: 2,4-DIMETHOXYPHENYL ISOTHIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DIMETHOXYPHENYL ISOTHIOCYANATE(33904-03-9)
• EPA Substance Registry System: 2,4-DIMETHOXYPHENYL ISOTHIOCYANATE(33904-03-9)

Safety Data

• Hazard Codes: C,Xi
• Statements: 34
• Safety Statements: 26-27-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 33904-03-9(Hazardous Substances Data)

Usage

Uses

Used in Biochemical Research:
2,4-Dimethoxyphenyl Isothiocyanate is used as a research tool for studying its biological activities and potential applications in various fields. Its unique chemical structure and reactivity make it valuable for investigating its interactions with other molecules and its effects on biological systems.
Used in Biomedical Applications:
2,4-Dimethoxyphenyl Isothiocyanate is used as a bioactive compound for its potential therapeutic effects. Its anti-cancer, anti-inflammatory, and anti-fungal properties make it a promising candidate for the development of new drugs and treatments.
Used in Drug Development:
2,4-Dimethoxyphenyl Isothiocyanate is used as a lead compound in the development of new pharmaceuticals. Its unique chemical properties and biological activities can be harnessed to create novel drugs with improved efficacy and safety profiles.
Used in Chemical Synthesis:
2,4-Dimethoxyphenyl Isothiocyanate is used as a reactive intermediate in the synthesis of various organic compounds. Its isothiocyanate functional group allows for the formation of a wide range of chemical products, making it a valuable building block in organic chemistry.
Used in Analytical Chemistry:
2,4-Dimethoxyphenyl Isothiocyanate is used as a derivatization agent in analytical chemistry. Its reactivity with various functional groups enables the formation of stable derivatives, which can be analyzed using different analytical techniques, such as chromatography and mass spectrometry.
Used in Pesticide Development:
2,4-Dimethoxyphenyl Isothiocyanate is used as a potential active ingredient in the development of new pesticides. Its anti-fungal and anti-inflammatory properties can be utilized to create effective and environmentally friendly pest control solutions.
Used in Material Science:
2,4-Dimethoxyphenyl Isothiocyanate is used in the development of new materials with specific properties. Its reactivity and chemical structure can be exploited to create materials with unique characteristics, such as improved stability, reactivity, or selectivity.

InChI:InChI=1/C9H9NO2S/c1-11-7-3-4-8(10-6-13)9(5-7)12-2/h3-5H,1-2H3

Upstream product

• 75-15-0 carbon disulfide 
• 2735-04-8 2,4-Dimethoxyaniline 
• 16420-13-6 N,N-Dimethylthiocarbamoyl chloride 
• 2926-29-6 Langlois reagent 
• 463-71-8 thiophosgene 

Downstream Products

• 895394-07-7 2-[3-(2,4-dimethoxy-phenyl)-thioureido]-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester 
• 874196-16-4 (Z)-3-(2,4-Dimethoxy-phenylamino)-1-(4-fluoro-phenyl)-3-methylsulfanyl-propenone 
• 874195-49-0 1-(2,4-dimethoxy-phenyl)-5-(4-fluoro-benzoyl)-6-methylsulfanyl-1H-pyridin-2-one 
• 874195-88-7 1-(2,4-dimethoxy-phenyl)-5-(4-fluoro-benzoyl)-6-methanesulfinyl-1H-pyridin-2-one 
• 893335-55-2 C₁₇H₁₈ClN₃O₃S 
• 891572-42-2 C₁₆H₁₇N₃O₄S 
• 122814-31-7 C₁₅H₁₉N₃O₄ 
• 1355959-89-5 C₁₃H₁₅N₃O₄ 
• 122813-69-8 4‐(2,4‐dimethoxyphenyl)thiosemicarbazide 
• 1358787-11-7 C₁₉H₁₉N₅O₂S 
• 116708-91-9 N-(2,4-dimethoxyphenyl)cyanothioformanilide 

Relevant articles and documents

An investigative study of antitumor properties of a novel thiazolo[4,5-d]pyrimidine small molecule revealing superior antitumor activity with CDK1 selectivity and potent pro-apoptotic properties

New thiazolo[4,5-d]pyrimidine analogues were synthesized and biologically assessed in-vitro for their antineoplastic activity. The growth inhibitory effects of these compounds were assessed through the National Cancer Institute-United States of America (NCI-USA) anticancer screening program. Compound 5 (7-Chloro-3-(2,4-dimethoxyphenyl)-5-methylthiazolo[4,5-d]pyrimidine-2(3H)-thione) was found to have a potent and broad-spectrum cytotoxic action against NCI panel with GI50 (50% growth inhibition concentration) mean graph midpoint (MG-MID) = 2.88 μM. MTT assay was used to determine IC50 values of the most potent agent against HCT-116 colorectal carcinoma and WI-38 human lung fibroblast cell lines; 5.33 μM ± 0.69 and 21.69 μM ± 1.04, respectively. Flow cytometric analysis revealed that compound 5 triggered apoptosis and G2/M cell cycle arrest. The ability of compound 5 to inhibit CDK1 (Cyclin-Dependent Kinase 1)/Cyclin B complex was evaluated, and its IC50 value was 97 nM ± 2.33. Moreover, according to the gene expression analysis, compound 5 up-regulated p53, BAX, cytochrome c, caspases-3,-8 and-9 besides down-regulated Bcl-2. In conclusion, compound 5 exerted a potent pro-apoptotic activity through the activation of the intrinsic apoptotic pathway and arrested the cell cycle at the G2/M phase.

Synthesis, in vitro biological investigation, and molecular dynamics simulations of thiazolopyrimidine based compounds as corticotrophin releasing factor receptor-1 antagonists

Corticotrophin releasing factor receptor-1 (CRFR1) is a potential target for treatment of depression and anxiety through modifying stress response. A series of new thiazolo[4,5-d]pyrimidine derivatives were designed, prepared and biologically evaluated as potential CRFR1 antagonists. Four compounds produced more than fifty percent inhibition in the [125I]-Tyr0-sauvagine specific binding assay. Assessment of binding affinities revealed that compound (3-(2,4-dimethoxyphenyl)-7-(dipropylamino)-5-methylthiazolo[4,5-d]pyrimidin-2(3H)-one) 8c was the best candidate with highest binding affinity (Ki = 32.1 nM). Further evaluation showed the ability of compound 8c to inhibit CRF induced cAMP accumulation in a dose response manner. Docking and molecular dynamics simulations were used to investigate potential binding modes of synthesized compounds as well as the stability of 8c-CRFR1 complex. These studies suggest similar allosteric binding of 8c compared to that of the co-crystalized ligand CP-376395 in 4K5Y pdb file.

A Selenourea-Thiourea Br?nsted Acid Catalyst Facilitates Asymmetric Conjugate Additions of Amines to α,β-Unsaturated Esters

β-Amino esters are obtained with high levels of enantioselectivity via the conjugate addition of cyclic amines to unactivated α,β-unsaturated esters. A related strategy enables the kinetic resolution of racemic cyclic 2-arylamines, using benzyl acrylate as the resolving agent. Reactions are facilitated by an unprecedented selenourea-thiourea organocatalyst. As elucidated by DFT calculations and 13C kinetic isotope effect studies, the rate-limiting and enantiodetermining step of the reaction is the protonation of a zwitterionic intermediate by the catalyst. This represents a rare case in which a thiourea compound functions as an asymmetric Br?nsted acid catalyst.

Synthesis and bioevaluation of N,4-diaryl-1,3-thiazole-2-amines as tubulin inhibitors with potent antiproliferative activity

A series of N,4-diaryl-1,3-thiazole-2-amines containing three aromatic rings with an amino linker were designed and synthesized as tubulin inhibitors and evaluated for their antiproliferative activity in three human cancer cell lines. Most of the target compounds displayed moderate antiproliferative activity, and N-(2,4-dimethoxyphenyl)-4-(4-methoxyphenyl)-1,3-thiazol-2-amine (10s) was determined to be the most potent compound. Tubulin polymerization and immunostaining experiments revealed that 10s potently inhibited tubulin polymerization and disrupted tubulin microtubule dynamics in a manner similar to CA-4. Moreover, 10s effectively induced SGC-7901 cell cycle arrest at the G2/M phase in both concentrationand time-dependent manners. The molecular docking results revealed that 10s could bind to the colchicine binding site of tubulin.

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.

Pyrazolopyrimidines: Potent Inhibitors Targeting the Capsid of Rhino- and Enteroviruses

There are currently no drugs available for the treatment of enterovirus (EV)-induced acute and chronic diseases such as the common cold, meningitis, encephalitis, pneumonia, and myocarditis with or without consecutive dilated cardiomyopathy. Here, we report the discovery and characterization of pyrazolopyrimidines, a well-tolerated and potent class of novel EV inhibitors. The compounds inhibit the replication of a broad spectrum of EV in vitro with IC50 values between 0.04 and 0.64 μM for viruses resistant to pleconaril, a known capsid-binding inhibitor, without affecting cytochrome P450 enzyme activity. Using virological and genetics methods, the viral capsid was identified as the target of the most promising, orally bioavailable compound 3-(4-trifluoromethylphenyl)amino-6-phenylpyrazolo[3,4-d]pyrimidine-4-amine (OBR-5-340). Its prophylactic as well as therapeutic application was proved for coxsackievirus B3-induced chronic myocarditis in mice. The favorable pharmacokinetic, toxicological, and pharmacodynamics profile in mice renders OBR-5-340 a highly promising drug candidate, and the regulatory nonclinical program is ongoing. Curing the common cold! A cluster of pyrazolopyrimidines with potent broad-spectrum activity against enteroviruses was discovered. Extensive structure-property relationship analyses led to the identification of 3-(4-trifluoromethyl-phenyl)amino-6-phenylpyrazolo[3,4-d]pyrimidine-4-amine, shown to be a blocker of the viral capsid protein, as a lead compound for drug development with favorable physicochemical, pharmacokinetic, and toxicological properties.

A diversified assembly of 1,2,4-oxadiazol-3-amines: Metallic thiophile catalyzed chemoselective one-pot reaction of aryl isothiocyanates, amidines/guanidines, and hydroxylamine

An efficient one-pot synthesis of 1,2,4-oxadiazol-3-amines from simple starting materials, isothiocyanates, amidines/guanidines, and hydroxylamine, is described. The reaction is facilitated by metallic-thiophile-assisted desulfurization of in situ formed amidino- or guanidinothiourea to give chemoselectively N-hydroxyguanidine intermediates that give exclusively various 1,2,4-oxadiazol-3-amines in good to excellent yields. The reaction mechanistic pathway may proceed through an intramolecular 5-exo-trig cyclization.