49761-82-2

Basic information

• Product Name: N-BOC-IMIDAZOLE
• Synonyms: 1H-Imidazole-1-carboxylic acid, 1,1-dimethylethyl ester;tert-Butyl 1H-imidazole-1-carboxylate;BOC-IMIDAZOLE;1-(TERT-BUTOXYCARBONYL)IMIDAZOLE;N-BOC-IMIDAZOLE;N-T-BOC-IMIDAZOLE;N-TERT-BUTOXYCARBONYLIMIDAZOLE;N-Boc-imidazole,98%
• CAS NO: 49761-82-2
• Molecular Formula: C₈H₁₂N₂O₂
• Molecular Weight: 168.19
• EINECS: 256-475-1
• Product Categories: Protection & Derivatization Reagents (for Synthesis);Protective Reagents (Peptide Synthesis);Biochemistry;Peptide Synthesis;Synthetic Organic Chemistry;Building Blocks;Heterocyclic Building Blocks;Imidazoles;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 49761-82-2.mol

Chemical Properties

• Melting Point: 45-47 °C(lit.)
• Boiling Point: 147-150 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.1835 (rough estimate)
• Vapor Pressure: 0.0257mmHg at 25°C
• Refractive Index: 1.4200 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Soluble in hexane, acetone, and DMF.
• PKA: 3.49±0.10(Predicted)
• Sensitive: Moisture Sensitive
• BRN: 607792
• CAS DataBase Reference: N-BOC-IMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: N-BOC-IMIDAZOLE(49761-82-2)
• EPA Substance Registry System: N-BOC-IMIDAZOLE(49761-82-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 49761-82-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-BOC-IMIDAZOLE is used as a protecting group for amines and alcohols during organic synthesis. It serves as a temporary shield to prevent unwanted reactions at the amine or alcohol functional groups, allowing for selective reactions at other sites in the molecule. This selective protection is crucial in the synthesis of complex pharmaceutical compounds, ensuring the desired product is obtained with minimal side reactions.
Used in Chemical Synthesis:
N-BOC-IMIDAZOLE is used as a coupling agent in the formation of peptide bonds. It activates carboxylic acids towards nucleophilic substitution by amines, facilitating the formation of amide bonds that are essential in peptide and protein synthesis. This application is vital in the development of new drugs and the study of protein structure and function.
Used in Material Science:
N-BOC-IMIDAZOLE is used in the preparation of water-soluble polyrotaxane via the modification of α-cyclodextrin in the presence of KOH and N,N'-carbonyldiimidazole. Polyrotaxane is a type of supramolecular polymer with potential applications in drug delivery, sensors, and responsive materials. The use of N-BOC-IMIDAZOLE in this process enhances the solubility and functionality of the resulting polymer, broadening its potential applications in various industries.

InChI:InChI=1/C8H12N2O2/c1-8(2,3)12-7(11)10-5-4-9-6-10/h4-6H,1-3H3

Upstream product

• 530-62-1 1,1'-carbonyldiimidazole 
• 75-65-0 tert-butyl alcohol 
• 288-32-4 1H-imidazole 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1202657-31-5 methyl 1-tert-butoxycarbonyl-3-amino-1H-pyrazole-5-carboxylate 
• 98015-52-2 1,2,2,2-Tetrachloroethyl tert-Butyl Carbonate 
• 98015-51-1 tert-butyl (1-chloroethyl) carbonate 

Downstream Products

• 3236-56-4 dipercarbonate de O,O-t-butyle 
• 5488-13-1 percarbonate de O,O-t-butyle et O-t-butyle 
• 85293-46-5 1-tert-butyl 3-methyl 2,2-dimethylmalonate 
• 288-32-4 1H-imidazole 
• 240143-60-6 (2-acetylamino-vinyl)-carbamic acid tert-butyl ester 
• 145586-78-3 phenacyl tert-butyl carbonate 
• 117499-16-8 bis(2-tert-butyloxycarbonylaminoethyl)amine 
• 442514-22-9 N-(3-methylaminopropyl)carbamic acid tert-butyl ester 
• 848844-32-6 (Z)-3,7-anhydro-4,5,6,8-tetra-O-benzyl-1-O-tert-butoxycarbonyl-2,3-dideoxy-D-galacto-oct-2-enitol 
• 904674-30-2 (Z)-3,7-anhydro-4,5,6,8-tetra-O-benzyl-1-O-tert-butoxycarbonyl-2,3-dideoxy-D-gluco-oct-2-enitol 
• 931-40-8 4-hydroxymethyl-1,3-dioxolan-2-one 
• 108-32-7 1,2-propylene cyclic carbonate 
• 120397-52-6 dimethyl-4-tert-butoxycarbonyloxyphenylsulfonium hexafluoroarsenate 
• 135632-53-0 tert-butyl N-(4-piperidinylmethyl)carbamate 

Relevant articles and documents

Synthesis and characterisation of polyamide dendrimers with systematically varying surface functionality

Remarkable changes of properties result from systematically varying the surface functionality of polyamide dendrimers within a single generation. The Royal Society of Chemistry 2009.

Probing the mid-gorge of cholinesterases with spacer-modified bivalent quinazolinimines leads to highly potent and selective butyrylcholinesterase inhibitors

The spacer structure of homobivalent quinazolinimes acting as potent acetyl-(AChE)- and butyrylcholinesterase (BChE) inhibitors was chemically modified introducing tertiary amine and acyl-amide moieties, and the activities at both ChEs were evaluated. Molecular docking was applied to explain the data and probe the capacity of the mid-gorge site of both ChEs. The novel spacer structures considerably alter the biological profile of bivalent quinazolinimines with regard to both inhibitory activity and selectivity. Mutual interaction of binding to the various sites of the enzymes was further investigated by applying also different spacer lengths and ring sizes of the alicycle of the tricyclic quinazolinimines. In order to achieve selectivity toward BChE and to improve inhibitory activities, the spacer structure was optimized and identified a highly potent and selective BChE inhibitor.

Solvent-freeN-Boc deprotection byex situgeneration of hydrogen chloride gas

An efficient, scalable and sustainable method for the quantitative deprotection of thetert-butyl carbamate (N-Boc) protecting group is described, using down to near-stoichiometric amounts of hydrogen chloride gas in solvent-free conditions. We demonstrate theex situgeneration of hydrogen chloride gas from sodium chloride and sulfuric acid in a two-chamber reactor, introducing a straightforward method for controlled and stoichiometric release of HCl gas. The solvent-free conditions allow deprotection of a wide variety ofN-Boc derivatives to obtain the hydrochloride salts in quantitative yields. The procedure obviates the need for any work-up or purification steps providing an uncomplicated green alternative to standard methods. Due to the solvent-free, anhydrous conditions, this method shows high tolerance towards acid sensitive functional groups and furnishes expanded functional group orthogonality.

Enantioselective Syntheses of Strychnos and Chelidonium Alkaloids through Regio- and Stereocontrolled Cooperative Catalysis

We describe enantioselective syntheses of strychnos and chelidonium alkaloids. In the first case, indole acetic acid esters were established as excellent partner nucleophiles for enantioselective cooperative isothiourea/Pd catalyzed α-alkylation. This provides products containing indole-bearing stereocenters in high yield and with excellent levels of enantioinduction in a manner that is notably independent of the N-substituent. This led to concise syntheses of (?)-akuammicine and (?)-strychnine. In the second case, the poor performance of ortho-substituted cinnamyl electrophiles in the enantioselective cooperative isothiourea/Ir catalyzed α-alkylation was overcome by appropriate substituent choice, leading to enantioselective syntheses of (+)-chelidonine, (+)-norchelidonine, and (+)-chelamine.

Organic/inorganic Fe3O4@MCM-41@Zr-piperazine: An impressive magnetite nanocatalyst for N-Tert-Butoxycarbonylation of amines

Fe3O4@MCM-41@Zirconium magnetic nanoparticles modified with piperazine (Fe3O4@MCM-41@Zr-piperazine), as a newly reported catalyst, shows excellent catalytic activity in N-tertbutoxycarbonylation of amines under the mild and solvent-free conditions. Accordingly, different derivatives of N-tert-butylcarbamates owning diverse aliphatic, aromatic and heteroaromatic amines were prepared efficiently. Good performance of this method for the majority of used complex or acidsensitive substrates and facile separation of this nanocatalyst due to its superparamagnetic nature from the reaction mixture via an external magnetic field for several times are the most important striking features of this protocol.

Preparation method of (2-methylamine-ethyl)-tert-butyl carbamate

The invention discloses a preparation method of (2-methylamine-ethyl)-tert-butyl carbamate, and belongs to the technical field of organic chemical synthesis. The preparation method comprises followingsteps: 1, imidazole is dissolved in dichloromethane, and di-tert-butyl dicarbonate ester is added at room temperature, reaction is carried out for 2 to 3h at room temperature, and water washing drying are carried out so as to obtain an intermediate; and 2, the intermediate is dissolved in toluene, N-methylethylenediamine is added, an obtained mixture is heated to 60 to 70 DEG C, reaction is carried out for 2 to 4h, reduced pressure distillation is carried out to remove toluene, and purification is carried out so as to obtain (2-methylamine-ethyl)-tert-butyl carbamate. The operation steps arefew; by-product content is reduced with ensured (2-methylamine-ethyl)-tert-butyl carbamate synthesis yield; cost is relatively low; and batch production requirements are satisfied.

LIPID DELIVERY OF THERAPEUTIC AGENTS TO ADIPOSE TISSUE

A method of treating a disease mediated by protein expression in adipose tissue by intraperitoneally administering a composition comprising a lipid nanoparticle encapsulating or associated with a therapeutic agent (e.g., a nucleic acid), thereby delivering the therapeutic agent to adipose tissue of the subject and altering protein expression in the adipose tissue is provided herein. A method for delivering a therapeutic agent to adipose tissue of a subject in need thereof is also provided.

Copper nanoparticles catalyzed N-H functionalization: An efficient solvent-free N-tert-butyloxycarbonylation strategy

A chemoselective transformation of amines to their tert-butyloxycarbonyl (Boc) protected derivatives (NBoc) is described using Cu-NPs under solvent-free conditions. Simple method, rapid reaction rate, mild conditions, tolerance of a wide range of functional groups, excellent yield, ease recovery and high catalytic turnover are the salient features of this approach. tert-Butyloxycarbonylation of chiral amino acid esters and amino alcohols were performed without racemization.

Preparation, characterization and application of 1,4-disulfopiperazine-1,4-diium chloride ([Piper-(SO3H)2]·2Cl) as an efficient dicationic ionic catalyst for the N-Boc protection of amines

In this work, 1,4-disulfopiperazine-1,4-diium chloride ([Piper-(SO3H)2]·2Cl), as a novel Br?nsted acidic ionic catalyst is synthesized and characterized using a series of techniques including FT-IR, TGA, DTA, SEM, pH analysis and Hammett acidity function. This substance can significantly catalyze the N-Boc protection of amines without solvent interference at room temperature. The advantages of this manner are chemoselectivity, short reaction times, suitable yields, excellent yields of the products, without solvent interference and ease of preparation as well as reusability of the catalyst.

Chemoselective acylation of 2-amino-8-quinolinol in the generation of C2-amides or C8-esters

Two different ways to carry out the chemoselective acylation of 2-amino-8-quinolinol with unique features to generate C2-amides or C8-esters were developed. The coupling reaction with a variety of carboxylic acids using EDCI and DMAP provided C8-ester derivatives, whereas N-heteroaromatic acids were not introduced on the C8-hydroxy group, but rather on the C2-amino group under the same conditions. To obtain C2-amides selectively, the anionic nucleophile from 2-amino-8-quinolinol was treated with less reactive acyl imidazolides or esters.