51721-22-3

Basic information

• Product Name: (4-tert-butyl-1H-iMidazol-5-yl)Methanol
• Synonyms: (4-tert-butyl-1H-iMidazol-5-yl)Methanol;5-(1,1-Dimethylethyl)-1H-imidazole-4-methanol;1H-Imidazole-5-methanol, 4-(1,1-dimethylethyl)-
• CAS NO: 51721-22-3
• Molecular Formula: C₈H₁₄N₂O
• Molecular Weight: 154.20956
• Mol File: 51721-22-3.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (4-tert-butyl-1H-iMidazol-5-yl)Methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (4-tert-butyl-1H-iMidazol-5-yl)Methanol(51721-22-3)
• EPA Substance Registry System: (4-tert-butyl-1H-iMidazol-5-yl)Methanol(51721-22-3)

Safety Data

• Hazardous Substances Data: 51721-22-3(Hazardous Substances Data)

Usage

General Description

(4-tert-butyl-1H-imidazol-5-yl)methanol is a chemical compound with the molecular formula C10H16N2O. It is a derivative of imidazole and is commonly used in medicinal chemistry as a building block for the synthesis of pharmaceutical compounds. The tert-butyl group is a common protecting group in organic chemistry, providing stability and control during chemical reactions. The presence of the methanol group makes this compound potentially useful in the synthesis of various drug candidates. Overall, (4-tert-butyl-1H-imidazol-5-yl)methanol is a versatile intermediate compound with potential applications in the pharmaceutical industry.

Upstream product

• 51721-21-2 ethyl 4-(tert-butyl)-1H-imidazole-5-carboxylate 
• 17094-34-7 ethyl pivaloylacetate 
• 29509-07-7 2-chloro-4,4-dimethyl-3-oxopentanoic acid ethyl ester 
• 714273-89-9 5-(tert-butyl)oxazole-4-carboxylic acid ethyl ester 
• 51721-21-2 5-(tert-butyl)-1H-imidazole-4-carboxylic acid ethyl ester 
• 1538-75-6 2,2-dimethylpropanoic anhydride 
• 50-00-0 formaldehyd 
• 21149-98-4 tert-butyl imidazole 
• 5469-26-1 1-Bromopinacolon 

Downstream Products

• 714273-83-3 4-tert-butyl-1H-imidazole-5-carbaldehyde 
• 714272-27-2 (3Z,6Z)-3-[[5-(1,1-dimethylethyl)-1H-imidazol-4-yl]methylene]-6-(phenylmethylene)piperazine-2,5-dione 
• 714272-83-0 3-{(Z)-1-[5-(tert-butyl)-1H-4-imidazolyl]methylidene}-6-[(Z)-1-(3-methylphenyl)methylidene]-2,5-piperazinedione trifluoroacetate 
• 714272-81-8 3-{(Z)-1-[5-(tert-butyl)-1H-4-imidazolyl]methylidene}-6-[(Z)-1-(2-fluorophenyl)methylidene]-2,5-piperazinedione trifluoroacetate 
• 714272-77-2 3-{(Z)-1-[5-(tert-butyl)-1H-4-imidazolyl]methylidene}-6-[(Z)-1-(3-fluorophenyl)methylidene]-2,5-piperazinedione trifluoroacetate 
• 714272-75-0 3-{(Z)-1-[5-(tert-butyl)-1H-4-imidazolyl]methylidene}-6-[(Z)-1-(4-fluorophenyl)methylidene]-2,5-piperazinedione trifluoroacetate 
• 714273-67-3 (3Z,6Z)-3-((5-tert-butyl-1H-imidazol-4-yl)methylene)-6-(2,5-difluorobenzylidene)piperazine-2,5-dione trifluoroacetate 
• 714272-43-2 3-{(Z)-1-[5-(tert-butyl)-1H-4-imidazolyl]methylidene}-6-[(Z)-1-(2-chlorophenyl)methylidene]-2,5-piperazinedione trifluoroacetate 
• 714272-45-4 3-{(Z)-1-[5-(tert-butyl)-1H-4-imidazolyl]methylidene}-6-[(Z)-1-(3-chlorophenyl)methylidene]-2,5-piperazinedione trifluoroacetate 
• 714273-43-5 3-{(Z)-1-[5-(tert-butyl)-1H-4-imidazolyl]methylidene}-6-[(Z)-1-(2,3-dichlorophenyl)methylidene]-2,5-piperazinedione trifluoroacetate 
• 714273-07-1 3-{(Z)-1-[5-(tert-butyl)-1H-4-imidazolyl]methylidene}-6-[(Z)-1-(2-bromophenyl)methylidene]-2,5-piperazinedione trifluoroacetate 
• 714272-89-6 3-{(Z)-1-[5-(tert-butyl)-1H-4-imidazolyl]methylidene}-6-[(Z)-1-(3-bromophenyl)methylidene]-2,5-piperazinedione trifluoroacetate 
• 714272-87-4 3-{(Z)-1-[5-(tert-butyl)-1H-4-imidazolyl]methylidene}-6-[(Z)-1-(4-bromophenyl)methylidene]-2,5-piperazinedione trifluoroacetate 
• 714272-99-8 3-{(Z)-1-[5-(tert-butyl)-1H-4-imidazolyl]methylidene}-6-[(Z)-1-(2-nitrophenyl)methylidene]-2,5-piperazinedione trifluoroacetate 

Relevant articles and documents

Preparation method of plinabulin intermediate imidazole formaldehyde compound

The invention discloses a preparation method of an imidazole formaldehyde compound. According to the preparation method, the operation danger level and the production cost are reduced by optimizing and improving a preparation route method, optimizing reaction conditions and improving a post-treatment and purification method; the requirement on the corrosion resistance grade of reaction container equipment is low, the operation safety is good, and the post-treatment is green and environment-friendly; and the preparation method has the advantages of simple operation of each step, safe and feasible solvent and process conditions, realization of environment-friendly production, and wide application prospect.

Development of MBRI-001, a deuterium-substituted plinabulin derivative as a potent anti-cancer agent

Plinabulin, a drug targeting microtubule of cancer cells, has been currently tried in its phase III clinical study. However, low efficacy caused by poor pharmacokinetic (PK) properties has been considered to be the main obstacle to approved by the Food and Drug Administration. Herein, we introduced a deuterium atom as an isostere in its structure to become a new compound named (MBRI-001, No. 9 in a series of deuterium-substituted compounds). The structure of MBRI-001 was characterized by HRMS, NMR, IR and a single crystal analysis. MBRI-001 exhibited better pharmacokinetic characteristics than that of plinabulin. Additionally, its antitumor activity is in a low nanomolar level for a variety of cancer cell lines and high activity against human NCI-H460 xenograted in mice intravenous administration. Importantly, continuous administration of MBRI-001 exhibited lower toxicity compared to docetaxel. We thus suggest that MBRI-001 could be developed as a promising anti-cancer agent in near future.

Preparation and purification method of high-purity Plinabulin compound

The invention provides a preparation and purification method of high-purity Plinabulin compound, which aims at mainly removing a trans-isomer. The preparation and purification method has the advantages that (3Z,6Z)-3-benzylidene-6-((5-tert-butyl-1H-imidazole-4-yl)methylene)piperazine-2,5-diketone monohydrate and (3Z,6Z)-3-benzylidene-6-((5-tert-butyl-1H-imidazole-4-yl)deuterated methylene)piperazine-2,5-diketone monohydrate are prepared; the purity of the prepared product is higher than 99.5%, and the content of the trans-isomer is smaller than 0.1%. The invention also relates to the preparation and purification of important intermediates, such as 5-(tert-butyl)-1H-imidazole-4-ethyl formate and 1,4-diacetylpiperazine-2,5-diketone. The preparation and purification method has the advantages that the production cost is reduced, the pos-treatment difficulty is decreased, and the technology more meets the requirements of industrialized production.