876353-81-0

Basic information

• Product Name: tert-butyl 2,6-dimethylphenylcarbamate
• Synonyms: tert-butyl 2,6-dimethylphenylcarbamate
• CAS NO: 876353-81-0
• Molecular Formula: C13H19NO2
• Molecular Weight: 221.29546
• Mol File: 876353-81-0.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: tert-butyl 2,6-dimethylphenylcarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 2,6-dimethylphenylcarbamate(876353-81-0)
• EPA Substance Registry System: tert-butyl 2,6-dimethylphenylcarbamate(876353-81-0)

Safety Data

• Hazardous Substances Data: 876353-81-0(Hazardous Substances Data)

Usage

Uses

Used in Agricultural Industry:
Tert-butyl 2,6-dimethylphenylcarbamate is utilized as a carbamate insecticide for the purpose of pest control. It is applied to protect crops from various pests, thereby ensuring the health and productivity of agricultural yields. The effectiveness of tert-butyl 2,6-dimethylphenylcarbamate in controlling pests is attributed to its ability to interfere with the nervous systems of insects, leading to their paralysis and eventual death.
Given its toxic nature when ingested, inhaled, or absorbed through the skin, the use of tert-butyl 2,6-dimethylphenylcarbamate is subject to stringent regulations and safety precautions. These measures are implemented to safeguard both human health and the environment from potential adverse effects. Handlers and applicators of tert-butyl 2,6-dimethylphenylcarbamate must exercise caution and adhere to the established guidelines to minimize exposure and mitigate risks.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 87-62-7 2,6-dimethylaniline 
• 4248-19-5 tert-butyl carbazate 
• 6781-98-2 2,6-dimethyl-1-chlorobenzene 
• 28556-81-2 2,6-dimethylphenylisocyanate 
• 75-65-0 tert-butyl alcohol 
• 81-20-9 2,6-dimethylnitrobenzene 

Relevant articles and documents

Integrating Hydrogen Production and Transfer Hydrogenation with Selenite Promoted Electrooxidation of α-Nitrotoluenes to E-Nitroethenes

Developing an electrochemical carbon-added reaction with accelerated kinetics to replace the low-value and sluggish oxygen evolution reaction (OER) is markedly significant to pure hydrogen production. Regulating the critical steps to precisely design electrode materials to selectively synthesize targeted compounds is highly desirable. Here, inspired by the surfaced adsorbed SeOx2? promoting OER, NiSe is demonstrated to be an efficient anode enabling α-nitrotoluene electrooxidation to E-nitroethene with up to 99 % E selectivity, 89 % Faradaic efficiency, and the reaction rate of 0.25 mmol cm?2 h?1 via inhibiting side reactions for energy-saving hydrogen generation. The high performance can be associated with its in situ formed NiOOH surface layer and absorbed SeOx2? via Se leaching-oxidation during electrooxidation, and the preferential adsorption of two -NO2 groups of intermediate on NiOOH. A self-coupling of α-carbon radicals and subsequent elimination of a nitrite molecule pathway is proposed. Wide substrate scope, scale-up synthesis of E-nitroethene, and paired productions of E-nitroethene and hydrogen or N-protected aminoarenes over a bifunctional NiSe electrode highlight the promising potential. Gold also displays a similar promoting effect for α-nitrotoluene transformation like SeOx2?, rationalizing the strategy of designing materials to suppress side reactions.

Sustainable and chemoselective N-Boc protection of amines in biodegradable deep eutectic solvent

Abstract: A green and practical approach for the chemoselective N-tert-butyloxycarbonylation of structurally diverse amines with di-tert-butyl dicarbonate (Boc2O) is described. Selective N-Boc protection was achieved in excellent yields in urea-choline chloride deep eutectic solvent (DES) as the most promising environmentally benign and cost-effective solvent under mild reaction condition. DES can protect various aromatic and aliphatic amines using Boc2O in good to excellent yields in short reaction times without any side products. Graphical abstract: [Figure not available: see fulltext.].

Direct Amidation of N-Boc- and N-Cbz-Protected Amines via Rhodium-Catalyzed Coupling of Arylboroxines and Carbamates

N-Boc- and N-Cbz-protected amines are directly converted into amides by a novel rhodium-catalyzed coupling of arylboroxines and carbamates, replacing the traditional two-step deprotection-condensation sequence. Both protected anilines and aliphatic amines are efficiently transformed into a wide variety of secondary benzamides, including sterically hindered and electron-deficient amides, as well as in the presence of acid-labile and reducible functional groups.

Pd-catalyzed amidation of aryl(Het) halides with tert-butyl carbamate

Pd-catalyzed cross-coupling reaction of tert-butyl carbamate with various aryl(Het) halides with Cs2CO3 as base in 1,4-dioxane as solvent was investigated, which resulted in the formation of the desired compounds in moderate to excellent yields.

Indium(III) halides as new and highly efficient catalysts for N-tert-butoxycarbonylation of amines

Indium(III) bromide and chloride efficiently catalysed the N-tert-butoxycarbonylation of amines with (Boc)2O at room temperature and under solvent-free conditions. Various aromatic, heteroaromatic and aliphatic amines were converted to N-tert-butylcarbamates in excellent yields in short times. Chiral amines, esters of α-amino acids and β-amino alcohols afforded optically pure N-t-Boc derivatives in high yields. The reactions were chemoselective and no competitive side reactions such as isocyanate, urea, and N,N-di-t-Boc formation were observed. Chemoselective conversion to N-tert-butylcarbamates took place with amino alcohols without any formation of oxazolidinones. Georg Thieme Verlag Stuttgart.

A rate enhancement of tert-butoxycarbonylation of aromatic amines with Boc2O in alcoholic solvents

A rate enhancement of tert-butoxycarbonylation of aromatic amines by Boc2O in alcohols compared to aprotic solvents was demonstrated. Kinetic analysis by NMR suggested that the reaction in CD3OD was faster than in CDCl3 by a factor of 70. Reactions between Boc2O and various aliphatic and aromatic amines in ethanol provided the N-Boc derivatives in good to excellent yields in short reaction times.

Copper(II) tetrafluoroborate as a novel and highly efficient catalyst for N-tert-butoxycarbonylation of amines under solvent-free conditions at room temperature

Commercially available copper(II) tetrafluoroborate hydrate was found to be a highly efficient catalyst for chemoselective N-tert-butoxycarbonylation of amines with di-tert-butyl dicarbonate under solvent-free conditions and at room temperature. Various aromatic amines were protected as their N-tert-butyl carbamates in high yields and in short times. No competitive side reactions such as isocyanate, urea, and N,N-di-t-Boc formation was observed. Chemoselective N-tert-butoxycarbonylation was achieved with substrates bearing OH and SH groups. Chiral α-amino acid esters afforded the corresponding N-t-Boc derivatives in excellent yields.

Palladium-catalyzed silane/siloxane reductions in the one-pot conversion of nitro compounds into their amines, hydroxylamines, amides, sulfonamides, and carbamates

A combination of palladium(II) acetate, aqueous potassium fluoride, and polymethylhydrosiloxane (PMHS) facilitates the room-temperature reduction of aromatic nitro compounds to anilines. These reactions tend to be quick (30 min), high-yielding, and tolerate a range of other functional groups. Replacement of PMHS/KF with triethylsilane allows for the reduction of aliphatic nitro compounds to their corresponding hydroxylamines. Depending on the substrate, both conditions can allow for the in situ conversion of the product amines into amides, sulfonamides, and carbamates. Georg Thieme Verlag Stuttgart.