19213-72-0

Basic information

• Product Name: 1-CARBETHOXYIMIDAZOLE
• Synonyms: 1H-Imidazole-1-carboxylic acid, ethyl ester;Ethyl 1-imidazolecarboxylate;1-CARBETHOXYIMIDAZOLE;ethyl 1H-imidazole-1-carboxylate;Einecs 242-883-7;Ethyl imidazolecarbamate;EtImC;N-Carboethoxyimidazole
• CAS NO: 19213-72-0
• Molecular Formula: C₆H₈N₂O₂
• Molecular Weight: 140.14
• EINECS: 242-883-7
• Mol File: 19213-72-0.mol

Chemical Properties

• Boiling Point: 231.7°Cat760mmHg
• Flash Point: 104℃
• Appearance: /
• Density: 1.162 g/mL at 25 °C
• Vapor Pressure: 9.61E-08mmHg at 25°C
• Refractive Index: n20/D1.472
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• PKA: 3.73±0.10(Predicted)
• Stability: Volatile
• CAS DataBase Reference: 1-CARBETHOXYIMIDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-CARBETHOXYIMIDAZOLE(19213-72-0)
• EPA Substance Registry System: 1-CARBETHOXYIMIDAZOLE(19213-72-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 19213-72-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
1-Carbethoxyimidazole is used as a precursor or intermediate for the synthesis of more complex chemical compounds. Its role in organic chemistry is significant due to its potential to contribute to the formation of various molecules with diverse applications.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, given its role in organic chemistry, 1-Carbethoxyimidazole may also be used in the pharmaceutical industry as a building block for the development of new drugs or drug candidates. Its reactivity and properties could be harnessed to create molecules with therapeutic potential, although further research and development would be necessary to explore these possibilities.
Used in Research and Development:
1-Carbethoxyimidazole is used as a research compound for studying its reactivity, toxicity, and potential applications in various fields. The need for careful handling and further research indicates that it is an active area of study, with scientists seeking to understand its full potential and limitations.

InChI:InChI=1/C13H9NOS/c14-9-16-8-13(15)12-6-5-10-3-1-2-4-11(10)7-12/h1-7H,8H2

Upstream product

• 288-32-4 1H-imidazole 
• 541-41-3 chloroformic acid ethyl ester 
• 63436-79-3 carbonic acid ethyl ester-isopropenyl ester 
• 74877-64-8 ethyl α-methoxyvinyl carbonate 
• 64-17-5 ethanol 
• 530-62-1 1,1'-carbonyldiimidazole 

Downstream Products

• 7098-07-9 N-Ethylimidazole 
• 19673-86-0 1,3-dibenzyl-1H-imidazol-3-ium bromide 
• 86911-07-1 1-ethoxycarbonyl-3-<4-(2-methoxycarbonylvinyl)benzyl>imidazolium bromide 
• 58704-04-4 N,N'-dicarbethoxy-1,2-diaminoethene 
• 75144-32-0 N,N'-dicarbethoxy-N-formyl-1,2-diaminoethene 
• 288-32-4 1H-imidazole 
• 34861-81-9 diethyl phenylsuccinate 
• 16042-25-4 1H-imidazole-2-carboxylic acid 
• 85938-30-3 1-ethoxycarbonyl-3-(4-ethoxycarbonylmethoxybenzyl)imidazolium iodide 
• 56739-27-6 3-cyclopropylmethyl-1-(3-nitro-phenyl)-1H-quinazoline-2,4-dione 
• 22719-81-9 4-methylphenyl ethyl carbonate 
• 5798-75-4 Ethyl 4-bromobenzoate 
• 1145-81-9 ethyl 2-(benzyloxycarbonylamino)ethanoate 
• 14062-25-0 Ethyl 4-bromophenylacetate 

Relevant articles and documents

A simple method for the functionalization of naked amino hydroxymethylenebisphosphonic acids via a carbamate bond

A simple and efficient procedure for the synthesis of alkylcarbamate hydroxymethylenebisphosphonic acids is described. Hydroxylated compounds are activated with carbonyldiimidazole and coupled to naked amino hydroxymethylenebisphosphonic acids.

Synthesis and properties of polymeric materials prepared by polymerization of epoxy oligomers with N,N′-carbonyldiimidazole transformation products

The reaction of N,N′-carbonyldiimidazole with ethanol and epoxy oligomers of diphenylolpropane diglycidyl ether and 4,4′- bis(glycidylamino)-3,3′-dichlorodiphenylmethane was studied by gas chromatography-mass spectrometry and differential scanning calorimetry. From these oligomers and N,N′-carbonyldiimidazole transformation products, epoxy polymers were synthesized, and their physicomechanical and adhesion properties were determined. Pleiades Publishing, Ltd., 2012.

Palladium-Catalyzed Oxidative C–H Alkoxycarbonylation of Arenes with Alkylcarbazates Directed by N-Heterocyclic Substituents

With alkyl carbazates as the green ester source, a novel palladium-catalyzed oxidative free radical carbonylative transformation of the C–H bond on aromatic rings to produce esters has been developed. Good yields of the corresponding products have been obtained with wide functional group tolerance and excellent regioselectivity. A variety of alkyl carbazates are found to be suitable reactants for the ortho-alkoxycarbonylation on the aromatic ring.

Method for preparing spiro2-diazido-indoline

The invention provides a method for preparing a compound shown in the formula II (please see the formula in the description). The method includes the following step of making indole shown in the formula I (please see the formula in the description) react with a precursor and ceric ammonium nitrate in the inert atmosphere so that spiro2-diazido-indoline can be obtained, wherein the precursor can provide azide groups. In the formula I and the formula II, R1 is selected from at least one of hydrogen, an alkyl group of C1-C5, alkoxy of C1-C5, F, Br and Cl; R2 is an alkyl group of C1-C5; Boc represents t-butyloxycarboryl. The precursor is sodium azide or trimethylsilyl azide. The mole ratio of indole shown in the formula I to the precursor to ceric ammonium nitrate is 1:(2-4):(4-8). According to the simple method, the two azide groups are introduced to the organic molecule, and in other words, spiro2-diazido-indoline is effectively prepared under the effects of the precursor capable of providing the azide groups and ceric ammonium nitrate with indole of different structures as the raw material. The raw material is easy to prepare, the reaction condition is gentle, operation is easy and convenient, and yield can reach 45% at most.

Preparation method of spiro-2-azidoindoline

The invention provides a preparation method of a compound represented by the formula (III) or formula (IV). According to the preparation method, in an inert atmosphere, indoles represented by the formula (I) or (II), a precursor that can provide azido groups, and ceric ammonium nitrate carry out reactions to obtain the spiro-2-azidoindoline. In the formula (I), (II), (III), and (IV), the R1 represents at least one of hydrogen, a C1-C5 alkyl group, a C1-C5 alkyloxy group, F, Br and Cl; the X represents O or TsN, TsN represents p-toluenesulfonyl; and the R2 represents a C1-C5 alkyl group. The precursor is sodium azide or trimethylsilyl azide. The mole ratio of indoles represented by the formula (I) or (II) to precursor to ceric ammonium nitrate is 1:(1-3):(2-6). According to the preparation method, azide is introduced into an organic molecule through a simple method, namely, indoles with different structures are tank as the raw materials, and under the effects of a precursor that can provide azido groups and ceric ammonium nitrate, spiro-2-azidoindoline is successfully prepared. The provided method has the advantages of easily prepared raw materials, mild reaction conditions, and convenient operation, and the yield can reach 94%.

CDI-mediated monoacylation of symmetrical diamines and selective acylation of primary amines of unsymmetrical diamines

A highly efficient and green protocol for monoacylation of symmetrical diamines and chemoselective acylation of primary amines of unsymmetrical diamines has been developed.

Solvent free, N,N'-carbonyldiimidazole (CDI) mediated amidation

The method involves CDI mediated amidation under solvent-free conditions. The protocol is green, simple, and scalable and has broad structural applicability. The protocol has also been used for BOC protection of amine. The protocol has reduced the time for CDI mediated amidation from 2-4 h to 5-10 min without the use of any dry organic solvent and nitrogen atmosphere.

Chemoselective N-acylation of indoles and oxazolidinones with carbonylazoles

Unique reactivity: In the presence of more reactive amine and alcohol functional groups and of carboxylic acids, the chemoselective N-acylation of indoles (see scheme) and oxazolidinones is achieved by taking advantage of the unique reactivity of carbonylazole acylating agents with catalytic amounts of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). Copyright

An efficient method for the preparation of mono α-aryl derivatives of diethyl malonate and ethyl cyanoacetate using ethyl-1-imidazole carbamate (EImC)

An efficient method for the synthesis of mono α-aryl derivatives of diethyl malonate and ethyl cyanoacetate using ethyl-1-imidazole carbamate (EImC) has been described. Using this method many sterically hindered and highly substituted mono α-aryl derivatives of diethyl malonate and ethyl cyanoacetate were synthesized in high yield.

On the reactivity of imidazole carbamates and ureas and their use as esterification and amidation reagents

The optimization, substrate scope, and mechanism of esterification and amidation of carboxylic acids mediated by imidazole-based reagents are discussed. The innate reactivity of carbonylimidazole reagents with a range of nucleophiles is also explored. New reagents developed for the synthesis of α,β-unsaturated esters are described, as are reagents for the preparation of tertiary amides directly from carboxylic acids.