143090-18-0

Basic information

• Product Name: TERT-BUTYL 4-CYANOPHENYLCARBAMATE
• Synonyms: TERT-BUTYL 4-CYANOPHENYLCARBAMATE;Carbamic acid, (4-cyanophenyl)-, 1,1-dimethylethyl ester (9CI);N-Boc-4-aminobenzonitrile
• CAS NO: 143090-18-0
• Molecular Formula: C₁₂H₁₄N₂O₂
• Molecular Weight: 218.25176
• Product Categories: N-BOC
• Mol File: 143090-18-0.mol

Chemical Properties

• Melting Point: 118-123°C
• Boiling Point: 302 °C at 760 mmHg
• Flash Point: 136.4 °C
• Appearance: /
• Density: 1.12 g/cm³
• Storage Temp.: 2-8°C
• PKA: 12.83±0.70(Predicted)
• CAS DataBase Reference: TERT-BUTYL 4-CYANOPHENYLCARBAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL 4-CYANOPHENYLCARBAMATE(143090-18-0)
• EPA Substance Registry System: TERT-BUTYL 4-CYANOPHENYLCARBAMATE(143090-18-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 143090-18-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
TERT-BUTYL 4-CYANOPHENYLCARBAMATE is used as a reagent for the synthesis of various pharmaceutical compounds due to its ability to facilitate the formation of carbamates, which are important in the development of drugs with diverse therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, TERT-BUTYL 4-CYANOPHENYLCARBAMATE is used as an intermediate in the production of insecticides and herbicides, contributing to the development of effective crop protection agents.
Used in Specialty Chemicals Industry:
TERT-BUTYL 4-CYANOPHENYLCARBAMATE is utilized as a key intermediate in the synthesis of specialty chemicals, where its unique properties allow for the creation of compounds with specific applications in various industries.
Used in Chemical Reactions:
TERT-BUTYL 4-CYANOPHENYLCARBAMATE is used as a protecting agent for alcohols during chemical reactions, preventing unwanted side reactions and ensuring the desired product formation.
Used in Research and Development:
TERT-BUTYL 4-CYANOPHENYLCARBAMATE is employed in research for its potential anti-cancer and anti-inflammatory properties, with ongoing studies exploring its therapeutic potential in various disease conditions.

Upstream product

• 4248-19-5 tert-butyl carbazate 
• 623-00-7 4-bromobenzenecarbonitrile 
• 873-74-5 4-Aminobenzonitrile 
• 14618-59-8 N-(tert-butoxycarbonyl)-4-methylaniline 
• 317842-48-1 tert-butyl (4-ethynylphenyl)carbamate 
• 131818-17-2 tert-butyl (4-bromophenyl)carbamate 
• 623-03-0 4-Cyanochlorobenzene 
• 1239374-05-0 tert-butyl 4-cyanophenyl(3-perfluorooctylpropoxy)carbamate 
• 104741-75-5 1-(tert-butoxycarbonyloxy)-4-methylbenzene 
• 24424-99-5 di-tert-butyl dicarbonate 
• 2570-98-1 4-aminobenzonitrile hydrochloride 
• 404586-94-3 1-(tert-butoxy)-2-(tert-butoxy)carbonyl-1,2-dihydroisoquinoline 
• 226065-32-3 tert-butyl 1-(4-cyanophenyl)hydrazine-1-carboxylate 
• 1132941-66-2 4-((tert-butoxycarbonyl)amino)phenyl methanesulfonate 

Downstream Products

• 918967-52-9 tert-butyl (4-(N’-hydroxycarbamimidoyl)phenyl)carbamate 
• 40465-45-0 p-cyanophenyl isocyanate 
• 24722-24-5 N-(4-cyanophenyl)-3-phenylpropanamide 
• 356100-65-7 N-(4-cyanophenyl)butyramide 
• 10003-73-3 4-(aminomethyl)aniline dihydrochloride 
• 1021389-89-8 4-(1H-tetrazol-5-yl)benzenaminium chloride 
• 918967-52-9 tert-butyl [4-(N-hydroxycarbamimidoyl)phenyl]carbamate 

Relevant articles and documents

A Greener Approach for the Chemoselective Boc Protection of Amines Using Sulfonated Reduced Graphene Oxide as a Catalyst in Metal- And Solvent-Free Conditions

Sulfonated reduced graphene oxide (SrGO) has displayed great potential as a solid acid catalyst due to its efficiency, cost-effectiveness, and reliability. In this study, SrGO was synthesized by the introduction of sulfonic acid-containing aryl radicals onto chemically reduced graphene oxide using ultrasonication. The SrGO catalyst was characterized by Fourier Transform Infrared (FTIR) spectroscopy, Raman spectroscopy, powder X-ray diffraction (PXRD), thermogravimetric analysis (TGA), scanning electron microscopy (SEM), energy dispersive spectroscopy (EDS) and transmission electron microscopy (TEM). Further, SrGO was effectively utilized as a metal-free and reusable solid acid catalyst for the chemoselective N - t -Boc protection of various aromatic and aliphatic amines under solvent-free conditions. The N - t -Boc protection of amines was easily achieved under ambient conditions affording high yields (84-95percent) in very short reaction times (5 min-2 h). The authenticity of the approach was confirmed by a crystal structure. The catalyst could be easily recovered and was reused up to seven consecutive catalytic cycles without any substantial loss in its activity.

ARYL SULFONAMIDES AS SMALL MOLECULE STAT3 INHIBITORS

The present disclosure provides pharmaceutical compositions comprising aryl sulfonamide Stat3 small molecule inhibitors and certain pharmaceutically acceptable salts thereof, and methods of their use for treating cancer.

Development of Potent 3-Br-isoxazoline-Based Antimalarial and Antileishmanial Compounds

Starting from the structure of previously reported 3-Br-isoxazoline-based covalent inhibitors of P. falciparum glyceraldehyde 3-phosphate dehydrogenase, and with the intent to improve their metabolic stability and antimalarial activity, we designed and synthesized a series of simplified analogues that are characterized by the insertion of the oxadiazole ring as a bioisosteric replacement for the metabolically labile ester/amide function. We then further replaced the oxadiazole ring with a series of five-membered heterocycles and finally combined the most promising structural features. All the new derivatives were tested in vitro for antimalarial as well as antileishmanial activity. We identified two very promising new lead compounds, endowed with submicromolar antileishmanial activity and nanomolar antiplasmodial activity, respectively, and a very high selectivity index with respect to mammalian cells.

Tert-Butyl(3-cyano-4,6-dimethylpyridin-2-yl)carbonate as a green and chemoselective N-tert-butoxycarbonylation reagent

The use of tert-butyl(3-cyano-4,6-dimethylpyridin-2-yl)carbonate as a chemoselective tert-butoxycarbonylation reagent for aromatic and aliphatic amines has been demonstrated. To gain insight into this reaction, in situ React IR technology was used to confirm the effectivity and chemoselectivity of this novel Boc reagent. The reaction was carried out chemoselectively in high yield under mild, environment-friendly conditions and was completed quickly within 1 hour. Simultaneously, the Boc carrier was easily recyclable, and has great application prospects for industrial production.

HETEROCYCLIC COMPOUNDS AS FUNGICIDES

The present invention relates to novel heterocyclic compound of Formula (I), (I) wherein, Het, L1, A, L2 and R12 are as defined in the detailed description, for use as fungicides.

N-Arylation of Carbamates through Photosensitized Nickel Catalysis

A highly efficient method of visible light mediated Ni(II)-catalyzed photoredox N-arylation of Cbz-amines/Boc-amines with aryl electrophiles at room temperature is reported. The methodology provides a common access to a wide variety of N-aromatic and N-heteroaromatic carbamate products that find use in the synthesis of several biologically active molecules and provides a distinct advantage over traditional palladium-catalyzed Buchwald reaction.

Selective Oxidative Coupling Reaction of Isocyanides Using Peroxide as Switchable Alkylating and Alkoxylating Reagent

A switchable oxidative coupling reaction of isocyanide and peroxide has been disclosed. In the presence of iron catalyst, the coupling reaction affords N-arylacetamides in good yields. By simply replacing the iron with copper catalyst, another different coupling reaction takes place in which peroxide can serve as alkoxylating source. This protocol represents a new fundamental coupling of two basic chemicals involving C?C and C?O bond-forming process. The unusual reactivity of an isocyano group in a radical reaction acting formally as an amidoyl synthon has also been well established. The experiment outcome reveals that aromatic isocyanides are particularly compatible reaction partners in present coupling reaction, whereas no desired products are observed when aliphatic isocyanides are used. (Figure presented.).

2-ARYLSULFONAMIDO-N-ARYLACETAMIDE DERIVATIZED STAT3 INHIBITORS

The present disclosure provides pharmaceutical compositions comprising 2-arylsulfonamido-N-arylacetamide derivatized Stat3 inhibitors and certain pharmaceutically acceptable salts thereof, and methods of their use.

BIFUNCTIONAL COMPOUNDS AND USE FOR REDUCING URIC ACID LEVELS

Bifunctional compounds that increase uric acid excretion and reduce uric acid production, and monofunctional compounds that either increase uric acid excretion or reduce uric acid production. Methods of using these compounds for reducing uric acid levels

Highly ortho-Selective Chlorination of Anilines Using a Secondary Ammonium Salt Organocatalyst

An organocatalytic, highly facile, efficient, and regioselective ortho-chlorination of anilines is described. A secondary ammonium chloride salt has been employed as the catalyst and the reaction can be conducted at room temperature without protection from air and moisture. In addition, the reaction is readily scalable and the catalyst can be recycled and reused. This catalytic protocol has been applied to the efficient synthesis of a highly potent c-Met kinase inhibitor. Mechanistic studies revealed that unique structural features of the secondary ammonium chloride salt are important for both the catalysis and regioselectivity of the electrophilic ortho-chlorination.