19241-24-8

Basic information

• Product Name: 4-TERT-BUTYLPHENYL ISOTHIOCYANATE
• Synonyms: 4-TERT-BUTYLPHENYL ISOTHIOCYANATE;RARECHEM AQ A4 0120;1-tert-Butyl-4-isothiocyanatobenzene;4-t-Butylphenyl Isothiocyanate;Isothiocyanic Acid 4-tert-Butylphenyl Ester;4-tert-Butylphenyl isothiocyate, 99%
• CAS NO: 19241-24-8
• Molecular Formula: C₁₁H₁₃NS
• Molecular Weight: 191.29
• Mol File: 19241-24-8.mol

Chemical Properties

• Melting Point: 42 °C
• Boiling Point: 92 °C
• Flash Point: 122.8 °C
• Appearance: /
• Density: 0.96 g/cm³
• Vapor Pressure: 0.0084mmHg at 25°C
• Refractive Index: 1.531
• Storage Temp.: Keep Cold
• CAS DataBase Reference: 4-TERT-BUTYLPHENYL ISOTHIOCYANATE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-TERT-BUTYLPHENYL ISOTHIOCYANATE(19241-24-8)
• EPA Substance Registry System: 4-TERT-BUTYLPHENYL ISOTHIOCYANATE(19241-24-8)

Safety Data

• Hazard Codes: T,Xi
• Statements: 20/21/22-36/37/38-43
• Safety Statements: 26-36/37/39-36/37
• RIDADR: 2811
• HazardClass: KEEP COLD, LACHRYMATOR, TOXIC
• PackingGroup: III
• Hazardous Substances Data: 19241-24-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-TERT-BUTYLPHENYL ISOTHIOCYANATE is used as a reagent in organic synthesis for its ability to form various chemical compounds and contribute to the development of new materials and pharmaceuticals.
Used in Chemical Reactions Study:
4-TERT-BUTYLPHENYL ISOTHIOCYANATE is utilized as a reactant in the study of chemical reactions to understand its behavior and interactions with other chemicals, which can lead to advancements in chemical research.
Used in Materials Science:
4-TERT-BUTYLPHENYL ISOTHIOCYANATE is used as a component in the development of new materials due to its potential as a ligand in metal complexes, which can enhance the properties of these materials.
Used in Pharmaceutical Research:
4-TERT-BUTYLPHENYL ISOTHIOCYANATE is employed as a research tool in pharmaceutical research for its potential applications in the development of new drugs and therapies, particularly in the areas of anticancer, antimicrobial, and pesticidal properties.
Used in Anticancer Applications:
4-TERT-BUTYLPHENYL ISOTHIOCYANATE is used as a potential anticancer agent, as its biological activities may contribute to the development of new cancer treatments.
Used in Antimicrobial Applications:
4-TERT-BUTYLPHENYL ISOTHIOCYANATE is used as a potential antimicrobial agent, which can be utilized in the development of new antibiotics or antimicrobial products.
Used in Pesticidal Applications:
4-TERT-BUTYLPHENYL ISOTHIOCYANATE is used as a potential pesticidal agent, which can be employed in the development of new pesticides for agricultural and other applications.

InChI:InChI=1/C11H13NS/c1-11(2,3)9-4-6-10(7-5-9)12-8-13/h4-7H,1-3H3

Upstream product

• 68714-39-6 N,N'-bis-(4-tert-butyl-phenyl)-thiourea 
• 479533-85-2 1-(4-tert-butylphenyl)-3-phenylthiourea 
• 112224-03-0 1,3-di(p-tert-butylphenyl)carbodiimide 
• 769-92-6 4-tert-Butylaniline 
• 102368-13-8 1,1'-Thiocarbonyldi-2(1H)-pyridone 
• 463-71-8 thiophosgene 
• 75-15-0 carbon disulfide 

Downstream Products

• 68714-39-6 N,N'-bis-(4-tert-butyl-phenyl)-thiourea 
• 4210-32-6 4-tert-butyl benzonitrile 
• 98-73-7 4-(1,1-dimethylethyl)benzoic acid 
• 479533-85-2 1-(4-tert-butylphenyl)-3-phenylthiourea 
• 53300-49-5 2-(4-tert-Butyl-phenylthiocarbamoyl)-malonic acid diethyl ester 
• 140835-39-8 C₁₉H₂₄N₆S₂ 
• 184003-53-0 1-(4-tert-Butyl-phenyl)-3-{4-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethoxy]-3-methoxy-benzyl}-thiourea 
• 927407-24-7 C₁₇H₂₁N₃S 
• 883556-90-9 (4-tert-butyl-phenyl)-[5-(3-methyl-pyridin-4-yl)-[1,3,4]oxadiazol-2-yl]-amine 
• 883556-93-2 (4-tert-butyl-phenyl)-[5-(4-methyl-pyridin-3-yl)-[1,3,4]oxadiazol-2-yl]-amine 
• 883556-87-4 (4-tert-butyl-phenyl)-[5-(2-methyl-pyridin-3-yl)-[1,3,4]oxadiazol-2-yl]-amine 
• 883556-94-3 (4-tert-butyl-phenyl)-[5-(2-methyl-quinolin-3-yl)-[1,3,4]oxadiazol-2-yl]-amine 
• 883557-52-6 (4-tert-butyl-phenyl)-{5-[2-(2-pyridin-4-yl-vinyl)-pyridin-3-yl]-[1,3,4]oxadiazol-2-yl}-amine 
• 883557-56-0 (4-tert-butyl-phenyl)-{5-[4-(2-pyridin-4-yl-vinyl)-pyridin-3-yl]-[1,3,4]oxadiazol-2-yl}-amine 

Relevant articles and documents

A catalyst-free method for the synthesis of 1,4,2-dithiazoles from isothiocyanates and hydroxylamine triflic acid salts

A catalyst-free method for the preparation of 1,4,2-dithiazoles is developed by reactions of isothiocyanates with hydroxylamine triflic acid salts. This reaction achieves C-S, C-N, and S-N bond formation, and a range of products are obtained in moderate to good yields. The obvious feature is using shelf-stable hydroxylamine triflic acid salts as a N source to synthesize heterocycles under mild conditions.

Synthesis of N-CF3Alkynamides and Derivatives Enabled by Ni-Catalyzed Alkynylation of N-CF3Carbamoyl Fluorides

The expansion of chemical space associated with ubiquitous motifs is key to unleash new properties and functions. In this context, alkynamides, prevalent in numerous drugs and materials, represent an untapped resource. We herein report the first synthetic access to N-trifluoromethyl alkynamides. Our strategy relies on a mild and operationally simple Ni-catalyzed coupling of N-CF3 carbamoyl fluorides with alkynyl silanes. The synthesized N-CF3 alkynamides proved to be highly robust and readily functioned as a platform to unlock access to valuable derivatives, such as N-CF3 decorated alkenyl amides, oxindoles, or quinolones, all of which were inaccessible to date.

N-Trifluoromethyl Hydrazines, Indoles and Their Derivatives

Reported herein is the first efficient strategy to synthesize a broad range of unsymmetrical N-CF3 hydrazines, which served as platform to unlock numerous currently inaccessible derivatives, such as tri- and tetra-substituted N-CF3 hydrazines, hydrazones, sulfonyl hydrazines, and valuable N-CF3 indoles. These compounds proved to be remarkably robust, being compatible with acids, bases, and a wide range of synthetic manipulations. The feasibility of RN(CF3)-NH2 to function as a directing group in C?H functionalization is also showcased.

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.

Isothiocyanate synthesized by three components and preparation method of isothiocyanate

The invention discloses isothiocyanate and a preparation method thereof. The method comprises the steps that primary amine, sodium difluorobromoacetate and elemental sulfur are taken as reactants forreaction; the reaction is carried out under the action of a copper catalyst, wherein the copper catalyst is any one of cuprous chloride, copper bromide, cuprous iodide, copper chloride and copper trifluoromethanesulfonate; an alkali is also added, wherein the alkali is any one of sodium bicarbonate, potassium carbonate, cesium carbonate, potassium phosphate, DABCO and sodium tert-butoxide; the whole reaction is carried out in a solvent, wherein the solvent is acetonitrile or dimethyl sulfoxide, the reaction temperature is 80-120 DEG C, and the reaction time is 10-14 hours. The method can directly synthesize the target product, does not need to separate intermediate products and only needs stirring and heating reaction under normal pressure to obtain the target product, and the yield can beup to 87%; a waste solution is fewer during the reaction, and the method protects the environment and ensures the health of an operator; in addition, a series of isothiocyanate derivatives can be prepared, and the method has a stronger substrate universality.

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.

Synthesis, structure-activity relationship and binding mode analysis of 4-thiazolidinone derivatives as novel inhibitors of human dihydroorotate dehydrogenase

A series of 4-thiazolidinone derivatives were synthesized and evaluated as novel human dihydroorotate dehydrogenase (hDHODH) inhibitors. Compounds 26 and 31 displayed IC50 values of 1.75 and 1.12 μM, respectively. The structure-activity relationship was summarized. Further binding mode analysis revealed that compound 31 could form a hydrogen bond with Tyr38 and a water-mediated hydrogen bond with Ala55, which may be necessary for maintaining the bioactivities of the compounds in this series. Further structural optimization of the para- or meta-position of the phenyl group at R will lead to the identification of more potent hDHODH inhibitors.

Double three bromo 1,3-di-pyridine salt-based propane and its preparation method, method of use, recovery method and application

The invention discloses a double tribromo 1,3-bipyridine onium salt dimethylmethane, and a preparation method, an application method, a recovery method and application thereof. The preparation method comprises the following steps: dissolving 1,3-bipyridine onium salt dimethylmethane by using water, and then adding potassium bromide; adding potassium peroxymonosulfate sulfate compound brine solution to prepare a clear solution after dissolving potassium bromide, and then stirring and reacting at -10 to 0 DEG C until solid is separated out; separating out solid, so as to obtain the double tribromo 1,3-bipyridine onium salt dimethylmethane. The product can be used for preparing isothiocyanate, aromatic thiourea or acetanilide. The preparation method disclosed by the invention is mild in condition, and simple to operate the reaction process, and raw materials are easily available. The double tribromo 1,3-bipyridine onium salt dimethylmethane not only can be used as a brominating reagent, but also can be used as organic synthesis intermediates, meanwhile, the reaction efficiency is improved, and the double tribromo 1,3-bipyridine onium salt dimethylmethane is convenient to recover and can be recycled.

Design, synthesis, X-ray crystallographic analysis, and biological evaluation of thiazole derivatives as potent and selective inhibitors of human dihydroorotate dehydrogenase

Human dihydroorotate dehydrogenase (HsDHODH) is a flavin-dependent mitochondrial enzyme that has been certified as a potential therapeutic target for the treatment of rheumatoid arthritis and other autoimmune diseases. On the basis of lead compound 4, which was previously identified as potential HsDHODH inhibitor, a novel series of thiazole derivatives were designed and synthesized. The X-ray complex structures of the promising analogues 12 and 33 confirmed that these inhibitors bind at the putative ubiquinone binding tunnel and guided us to explore more potent inhibitors, such as compounds 44, 46, and 47 which showed double digit nanomolar activities of 26, 18, and 29 nM, respectively. Moreover, 44 presented considerable anti-inflammation effect in vivo and significantly alleviated foot swelling in a dose-dependent manner, which disclosed that thiazole-scaffold analogues can be developed into the drug candidates for the treatment of rheumatoid arthritis by suppressing the bioactivity of HsDHODH.

Novel selective and potent inhibitors of malaria parasite dihydroorotate dehydrogenase: Discovery and optimization of dihydrothiophenone derivatives

Taking the emergence of drug resistance and lack of effective antimalarial vaccines into consideration, it is of significant importance to develop novel antimalarial agents for the treatment of malaria. Herein, we elucidated the discovery and structure-activity relationships of a series of dihydrothiophenone derivatives as novel specific inhibitors of Plasmodium falciparum dihydroorotate dehydrogenase (PfDHODH). The most promising compound, 50, selectively inhibited PfDHODH (IC50 = 6 nM, with >14 000-fold species-selectivity over hDHODH) and parasite growth in vitro (IC50 = 15 and 18 nM against 3D7 and Dd2 cells, respectively). Moreover, an oral bioavailability of 40% for compound 50 was determined from in vivo pharmacokinetic studies. These results further indicate that PfDHODH is an effective target for antimalarial chemotherapy, and the novel scaffolds reported in this work might lead to the discovery of new antimalarial agents.