7541-17-5

Basic information

• Product Name: tert-butyl dimethylcarbamate
• CAS NO: 7541-17-5
• Molecular Formula: C₇H₁₅NO₂
• Molecular Weight: 145.1995
• Mol File: 7541-17-5.mol

Chemical Properties

• Boiling Point: 162.2°C at 760 mmHg
• Flash Point: 51.9°C
• Density: 0.937g/cm³
• Vapor Pressure: 2.19mmHg at 25°C
• Refractive Index: 1.429
• CAS DataBase Reference: tert-butyl dimethylcarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl dimethylcarbamate(7541-17-5)
• EPA Substance Registry System: tert-butyl dimethylcarbamate(7541-17-5)

Safety Data

• Hazardous Substances Data: 7541-17-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Tert-butyl dimethylcarbamate is employed as a reagent in organic synthesis for its ability to facilitate various chemical reactions. Its properties make it a valuable component in the creation of complex organic molecules and contribute to the advancement of organic chemistry.
Used as a Protecting Group in Amines and Phenols:
In the chemical industry, tert-butyl dimethylcarbamate is used as a protecting group for amines and phenols. This application is crucial for preventing unwanted side reactions during the synthesis of complex organic compounds, ensuring the desired product is obtained without unwanted modifications to the amine or phenol functional groups.
Used in Laboratory Research:
Due to its stability and reactivity, tert-butyl dimethylcarbamate is also used in laboratory research for the study of organic reactions and the development of new synthetic methods. Its role in protecting sensitive functional groups makes it an essential tool for researchers working with amines and phenols.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 124-40-3 dimethyl amine 
• 60-34-4 methylhydrazine 
• 75-91-2 tert.-butylhydroperoxide 
• 68-12-2 N,N-dimethyl-formamide 
• 100-46-9 benzylamine 
• 34619-03-9 tert-butyldicarbonate 
• 506-59-2 N,N-dimethylammonium chloride 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 79-44-7 N,N-Dimethylcarbamoyl chloride 
• 6627-89-0 tert-butyl phenyl carbonate 
• 75-65-0 tert-butyl alcohol 

Downstream Products

• 81616-14-0 tert-butyl N-benzyl-N-methylcarbamate 
• 312728-28-2 carbamic acid, N-methyl-N-(3-butenyl), 1,1-dimethylethyl ester 
• 385765-91-3 carbamic acid N-methyl-N-[2-phenyl-5-methyl-2,3-hexadienyl] 1,1-dimethylethyl ester 
• 849728-30-9 carbamic acid N-methyl-N-[2-(3-phenylpropyl)-5-methyl-2,3-hexadienyl] 1,1-dimethylethyl ester 
• 849728-31-0 carbamic acid N-[2-(2-benzoyloxyethyl)-5-methyl-2,3-hexadienyl]-N-methyl 1,1-dimethylethyl ester 
• 849728-32-1 carbamic acid N-methyl-N-[2-(2-phenylethenylidene)hexyl] 1,1-dimethylethyl ester 
• 849728-33-2 carbamic acid N-[2,4-diphenyl-2,3-butadienyl]-N-methyl 1,1-dimethylethyl ester 
• 849728-34-3 N-[2-[(cyclohexylidene)methylene]hexyl]-N-methylcarbamic acid 1,1-dimethylethyl ester 
• 385765-91-3 methyl-[2-phenyl-5-methyl-2,3-hexadien-1-yl]-carbamic acid 1,1-dimethylethyl ester 
• 1462235-94-4 tert-butyl ethyl(4-methoxybenzyl)carbamate 
• 218900-28-8 N-(tert-butoxycarbonyl)-N-benzylethylamine 
• 1610605-33-8 tert-butyl (2-(3-methoxyphenyl)-2-oxoethyl)(methyl)carbamate 

Relevant articles and documents

Photochemical regioselective C(sp3)-H amination of amides using N-haloimides

A metal-free regioselective C(sp3)-H amination of amides using N-haloimides in the presence of lithium tert-butoxide and visible light is presented herein. This photoexcited approach is straightforward, and it aminates a wide variety of amides under mild conditions without the use of photocatalysts, external radical initiators, or oxidants. A halogen-bonded intermediate between the tert-butoxide base and the N-haloimide is proposed to be responsible for the increased photoreactivity. Calculations show that the formation of this electron donor-acceptor complex presents an exergonic energy profile.

Direct α-Monofluoroalkenylation of Heteroatomic Alkanes via a Combination of Photoredox Catalysis and Hydrogen-Atom-Transfer Catalysis

In this study, a new C(sp3)-H monofluoroalkenylation reaction involving cooperative visible-light photoredox catalysis and hydrogen-atom-transfer catalysis to afford products generated by selective hydrogen abstraction and radical-radical cross-coupling was described. This mild, efficient reaction shows high regioselectivity for the α-carbon atoms of amines, ethers, and thioethers and thus allows the preparation of monofluoroalkenes bearing various substituents. The reaction was applied to two bioactive molecules, indicating its utility for late-stage monofluoroalkenylation of compounds with inert C(sp3)-H bonds.

Design and synthesis of 3-aminophthalazine derivatives and structural analogues as PDE5 inhibitors: anti-allodynic effect against neuropathic pain in a mouse model

Neuropathic pain is a chronic pain caused by a lesion or disease affecting the somatosensory nervous system. To date, no specific treatment has been developed to cure this pain. Antidepressants and anticonvulsant drugs are used, but they do not demonstrate universal efficacy, and they often cause detrimental adverse effects. Some studies highlighted the efficacy of sildenafil, a well-known inhibitor of phosphodiesterase 5 (PDE5, (IC50 = 3.3 nM)), in models of pain. Based on these results, we focused our attention on MY 5445, another known PDE5 inhibitor. Homologues, isosteres and structural analogues of MY 5445 were designed and all synthesized compounds were evaluated for their inhibitory activity toward PDE5. Selectivity profiles towards other PDE1-4 isoenzymes, water solubility and stability in acidic medium of the most potent PDE5 inhibitors were determined and the aminophthalazine 16h and its mimetic 41n (3-aminoindazole)were evaluated in comparison to MY 5445 (4b)in vivo in a model of neuropathic pain induced by sciatic nerve cuffing in mice (3 and 0.5 mg/kg, ip twice a day). Both compounds showed the same efficacy on neuropathic allodynia as MY 5445, and thus produced a significant relief of mechanical hypersensitivity after 12 days of treatment.

Photoredox-Mediated Direct Cross-Dehydrogenative Coupling of Heteroarenes and Amines

A photoredox-mediated direct cross-dehydrogenative coupling reaction to accomplish α-aminoalkylation of N-heteroarenes is reported. This mild reaction has a broad substrate scope, offers the first general method for synthesis of aminoalkylated N-heteroarenes without the need for substrate prefunctionalization, and is scalable to the gram level. Furthermore, the reaction was found to be applicable to other hydrogen donors besides amines (i.e., ethers, an aldehyde, a formamide, p-xylene, and alkanes), thus enabling the preparation of N-heteroarenes bearing various types of substituents.

A Lewis Base Catalysis Approach for the Photoredox Activation of Boronic Acids and Esters

We report herein the use of a dual catalytic system comprising a Lewis base catalyst such as quinuclidin-3-ol or 4-dimethylaminopyridine and a photoredox catalyst to generate carbon radicals from either boronic acids or esters. This system enabled a wide range of alkyl boronic esters and aryl or alkyl boronic acids to react with electron-deficient olefins via radical addition to efficiently form C?C coupled products in a redox-neutral fashion. The Lewis base catalyst was shown to form a redox-active complex with either the boronic esters or the trimeric form of the boronic acids (boroxines) in solution.

Amide-ligand-controlled highly para-selective arylation of monosubstituted simple arenes with arylboronic acids

Pd-catalyzed highly para-selective arylations of monosubstituted simple arenes with arylboronic acids to widely existed biaryls have been developed. Inspired by requisite amide-directing groups in reported selective oxidative couplings, amide ligands, especially DMF, are designed and found to be critical for the selectivity control in current arylations.

CHEMICAL BLOWING AGENT AND THERMALLY EXPANDABLE THERMOPLASTIC COMPOSITION

The present invention relates to a chemical blowing agent comprising at least one tertiary alkyl carbamate. The chemical blowing agent can be activated thermally and is suitable for foaming thermoplastic materials and can for example be incorporated into thermally expandable baffle and/or reinforcement elements which are used in automotive manufacturing and building insulation.

Oxidative coupling of methylamine with an aminyl radical: Direct amidation catalyzed by I2/TBHP with HCl

Oxidative coupling of methylamines with an aminyl radical to construct amides was developed in the presence of an I2/TBHP catalyst under acidic conditions via the two cleavages of the sp3 C-N bond of aryl-methylamines and the sp2 C-N bond of N-substituted formamides respectively. This transition-metal-free protocol provides a novel synthetic tool for the construction of N-substituted amides and a series of arylamides can be easily obtained with good yields. This journal is the Partner Organisations 2014.

Ligand-controlled α- And β-arylation of acyclic N-boc amines

The palladium-catalyzed ligand-controlled arylation of α-zincated acyclic amines, obtained by directed α-lithiation and transmetalation, is described. Whereas PtBu3 gave rise to α-arylated Boc-protected amines, more flexible N-phenylazole-based phosphine ligands induced major β-arylation through migrative cross-coupling. All manner of control: The arylation of α-zincated acyclic Boc-protected amines was selectively performed at the α- or β-position in a ligand-controlled manner. α-Arylation occurs by direct reductive elimination of the α-palladated intermediate whereas β-arylation involves palladium migration along the alkyl chain. Boc=tert-butoxycarbonyl.

An efficient and chemoselective Br?nsted acidic ionic liquid-catalyzed N-Boc protection of amines

The first report of a Br?nsted acidic ionic liquid, 1-methylimidazolium tetrafluoroborate [(HMIm)BF4], catalyzed efficient and chemoselective N-Boc protection of various amines using (Boc)2O is presented. Optically pure amino alcohols and amino acid esters were converted efficiently to their corresponding optically pure N-Boc derivatives. The reported method is mild, solvent-free and has the advantages of both homogeneous and heterogeneous catalysis with high product yields, selectivity and ease of product separation.