590-42-1

Usage

Uses

Used in the Synthesis of Organic Compounds:
TERT-BUTYL ISOTHIOCYANATE is used as a reagent for the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its isothiocyanate functional group allows for the formation of thioureas, thioamides, and other sulfur-containing compounds through reactions with amines and other nucleophiles.
Used in the Modification of Metal-Organic Frameworks:
TERT-BUTYL ISOTHIOCYANATE is used as a tool for the modification of the pore sizes on the top layer of heterostructured surface-mounted metal-organic frameworks. This modification can enhance the selectivity and performance of these materials in various applications, such as gas separation, catalysis, and sensing.
Used in Pharmaceutical Industry:
TERT-BUTYL ISOTHIOCYANATE is used as a building block for the synthesis of pharmaceutical compounds, including drugs with anti-inflammatory, analgesic, and antipyretic properties. Its isothiocyanate functional group can be used to form bioactive molecules with potential therapeutic applications.
Used in Agrochemical Industry:
TERT-BUTYL ISOTHIOCYANATE is used as a precursor for the synthesis of agrochemicals, such as herbicides, insecticides, and fungicides. Its reactivity and ability to form a variety of sulfur-containing compounds make it a valuable component in the development of new and effective agrochemical products.

Synthesis Reference(s)

Tetrahedron Letters, 34, p. 8283, 1993 DOI: 10.1016/S0040-4039(00)61411-9

InChI:InChI=1/C5H9NS/c1-5(2,3)6-4-7/h1-3H3

Upstream product

• 4041-95-6 N,N-di-tert-butylthiourea 
• 507-19-7 t-butyl bromide 
• 592-85-8 mercury(II) thiocyanate 
• 119072-55-8 tert-butylisonitrile 
• 66661-88-9 3-tert-Butyl-1,1,2-trimethyl-isothiourea 
• 13831-47-5 (C₆H₄O₂)BNH-t-C₄H₉ 
• 103-72-0 phenyl isothiocyanate 
• 507-20-0 tertiary butyl chloride 
• 333-20-0 potassium thioacyanate 
• 2092-17-3 barium thiocyanate 
• 77802-76-7 tert-Butyl-dithiocarbamic acid ethyl ester 
• 36791-67-0 2-(tert-butylimino)-3-methyl-4-tosylimino-1,3-thiazetidine 
• 105-53-3 diethyl malonate 
• 1858-25-9 phosphoryl-isothiocyanate 

Downstream Products

• 7204-48-0 N-(t-butyl)thiourea 
• 13431-39-5 4-tert-butyl-3-thiosemicarbazide 
• 75-64-9 tert-butylamine 
• 34780-32-0 N-cyclohexyl-N'-(t-butyl)thiourea 
• 4041-95-6 N,N-di-tert-butylthiourea 
• 14327-04-9 N-tert-butyl-N'-phenylthiourea 
• 69909-80-4 N-(2-tert-butyl-4-phenyl-3-thioxo-[1,2,4]thiadiazolidin-5-ylidene)-N'-phenyl-benzamidine 
• 3098-03-1 1-heptyl-2-thiourea 
• 16412-72-9 N-(N,N'-Diphenyl-carbamidoyl)-N'-(tert.-butyl)-thioharnstoff 
• 69818-66-2 N'-(tert-butyl-thiocarbamoyl)-N,N-diethyl-benzamidine 
• 32497-68-0 4-(N'-tert-Butyl-guanidino)-N-(4-chloro-phenyl)-benzamidine 
• 21076-42-6 4-tert.Butyl-2-cyclohexyl-thiosemicarbazid 
• 16412-73-0 N-(N_.N'-Di-o-tolyl-carbamimidoyl)-N'-(tert-butyl)-thioharnstoff 
• 14294-06-5 N-<(4-Chlor-phenyl)-carbamimidoyl>-N'-(tert.-butyl)-thioharnstoff 

Relevant academic research and scientific papers

A more sustainable isothiocyanate synthesis by amine catalyzed sulfurization of isocyanides with elemental sulfur

Isothiocyanates (ITCs) are typically prepared using amines and highly toxic reagents such as thiophosgene, its derivatives, or CS2. In this work, an investigation of a multicomponent reaction (MCR) using isocyanides, elemental sulfur and amines revealed that isocyanides can be converted to isothiocyanates using sulfur and catalytic amounts of amine bases, especially DBU (down to 2 mol%). This new catalytic reaction was optimized in terms of sustainability, especially considering benign solvents such as Cyrene or γ-butyrolactone (GBL) under moderate heating (40 °C). Purification by column chromatography was further optimized to generate less waste by maintaining high purity of the product. Thus, E-factors as low as 0.989 were achieved and the versatility of this straightforward procedure was shown by converting 20 different isocyanides under catalytic conditions, while obtaining moderate to high yields (34-95%). This journal is

2-(aryl (azacycloalkane-1-yl) methyl) phenol derivatives and uses thereof

The invention discloses 2-(aryl (azacycloalkane-1-yl) methyl) phenol derivatives and application thereof, and belongs to the technical field of medicines. The invention provides a compound shown in a formula I or pharmaceutically acceptable salt thereof. The series of compounds have good inhibitory activity on the histone demethylase KDM4 family in vitro, the median inhibitory concentration (IC50) of most molecules on KDM4D is less than 500 nM, and the compounds have good inhibitory effect on proliferation of various human tumor cell strains in vitro, so that the series of compounds provide a new effective choice for developing targeted histone demethylase KDM4D drugs and preparing drugs for treating and/or preventing cancers and reproductive system diseases, and have good application prospects.

Preparation method of isothiocyano compound

The invention discloses a preparation method of an isothiocyano compound. An ammonium thiocyanate, sodium thiocyanate or potassium thiocyanate water solution and a halide are used as raw materials, and an isothiocyano compound is synthesized under the action of a phase transfer catalyst. The requirements that the thiocyanate radical in each batch of reaction is excessive by 10% and the yield is high are met, the purpose that the concentration of thiocyanic acid in wastewater is very low is realized, complex wastewater treatment equipment and treatment operation are avoided, and environmental protection pressure is reduced. The preparation method is a green preparation method, and solves the problems of extremely difficult degradation and high biotoxicity of thiocyanate-containing wastewater in conventional isothiocyano compound production. The method is simple to operate and is suitable for industrial production.

Preparation method of buprofezin

The invention provides a preparation method of buprofezin, comprising the steps of 1), adding sodium thiocyanate and water into an esterification kettle until dissolution; adding tertiary butanol andhydrochloric acid to obtain a mixed ester; allowing transposition and catalytic reaction to obtain t-butyl isothiocyanate; 2), adding the t-butyl isothiocyanate into chlorobenzene, stirring, dropwiseadding isopropyl amine to obtain 1-isopropyl-3-tert-butylthiourea solution; 3), adding N-methylaniline into chlorobenzene; introducing carbonyl chloride and chlorine gas in sequence to obtain N-chloromethyl-N-benzenecarbamoylchloride solution; 4), adding sodium bicarbonate into water, and adding the resultant into chlorobenzene; adding the 1-isopropyl-3-tert-butylthiourea solution; dropwise addingthe N-chloromethyl-N-benzenecarbamoylchloride solution, filtering, allowing layering, performing high-vacuum steaming to remove the chlorobenzene, crystallizing, centrifuging, and drying to obtain buprofezin. The substitutive average yield of the preparation process of buprofezin reaches 90% and above; the content of finished buprofezin reaches 98.0% and above; the preparation process is free ofammonia nitrogen wastewater.

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.

4,5-Disubstituted N-Methylimidazoles as Versatile Building Blocks for Defined Side-Chain Introduction

Fungerin is a 1,4,5-trisubstituted imidazole natural product characterised by a broad spectrum of antifungal activities. We planned to develop flexible strategies to access to such compounds. Imidazoles bearing suitable anchor groups at C-4 and C-5 allow the introduction of various substituted side-chains, generating libraries of fungerin derivatives for biological tests. Starting from commercially available reactants, two N-methyl 4,5-substituted imidazole core units were synthesised. Derivatives of type 1 contained two orthogonally protected C-1 anchors. Selective side-chain introduction was achieved through a sequence of Grignard coupling at C-5 to replace a tosylate and a Horner olefination through an aldehyde attached to C-4. Two target fungerin derivatives were synthesised. Since the organometallic substitution of the C-5-CH2-positioned leaving group proved to suffer from limitations concerning potential competing side-reactions, a type 2 imidazole core was built up. These structures had a halogen centre at C-4 and a hydroxyethyl anchor at C-5. Now, selective side-chain introduction allowed us to use Julia olefination to form the allyl side-chain at C-5 and Heck reactions to introduce the C-4 acryl substituents. Eight derivatives, including fungerin, were synthesised by this latter strategy, without producing any regioisomers. The second approach had the advantage that various side-chains could be coupled at C-4 and C-5 in two final steps. Thus, this strategy represents a versatile way to build up libraries of fungerin derivatives for biological testing.

Synthesis of Isothiocyanates and Unsymmetrical Thioureas with the Bench-Stable Solid Reagent (Me4N)SCF3

A highly efficient, selective, and rapid transformation of primary amines and diamines to isothiocyanates and cyclic thioureas is disclosed. As opposed to established approaches that employ toxic or volatile electrophilic liquids and require reaction control (i.e., slow addition, cooling), this protocol utilizes the bench-stable, solid reagent (Me4N)SCF3 at room temperature. The method is characterized by operational simplicity, high speed, efficiency, high functional group tolerance, and late-stage applicability. The byproducts are solids, allowing isolation of the target compounds by filtration.

Catalytic Production of Isothiocyanates via a Mo(II)/Mo(IV) Cycle for the "soft" Sulfur Oxidation of Isonitriles

In the presence of excess amounts of elemental sulfur, the dimolybdenum dinitrogen complex {CpMo[N(iPr)C(Ph)N(iPr)]}2(μ-N2) (4; Cp? = η5-C5Me5) serves as a precatalyst for the production of isothiocyanates from isonitriles via highly efficient and atom-economical metal-mediated sulfur atom transfer (SAT) under mild conditions. Mechanistic and structural studies support a catalytic cycle for SAT involving initial formation of a Mo(II) bis(isonitrile) complex that then undergoes sulfination to generate a formal "side-bound" Mo(IV) κ 2-(C,S)-isothiocyanate as the key intermediate. This metal-catalyzed SAT process has further been employed for the "on-demand" production of isothiocyanates that are trapped in situ by benzhydrazides to provide thiosemicarbazides, which are useful precursors to biologically active thiadiazoles.

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.