33432-52-9

Basic information

• Product Name: 2-methyl-4-(3-nitrophenyl)-3-butyn-2-ol
• Synonyms: 3-Butyn-2-ol, 2-methyl-4-(3-nitrophenyl)-; 2-Methyl-4-(3-nitrophenyl)-3-butyn-2-ol; 2-methyl-4-(3-nitrophenyl)but-3-yn-2-ol
• CAS NO: 33432-52-9
• Molecular Formula: C₁₁H₁₁NO₃
• Molecular Weight: 205.2099
• EINECS: 251-520-1
• Mol File: 33432-52-9.mol

Chemical Properties

• Boiling Point: 338.4°C at 760 mmHg
• Flash Point: 144.8°C
• Density: 1.24g/cm³
• Vapor Pressure: 3.83E-05mmHg at 25°C
• Refractive Index: 1.585
• CAS DataBase Reference: 2-methyl-4-(3-nitrophenyl)-3-butyn-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methyl-4-(3-nitrophenyl)-3-butyn-2-ol(33432-52-9)
• EPA Substance Registry System: 2-methyl-4-(3-nitrophenyl)-3-butyn-2-ol(33432-52-9)

Safety Data

• Hazardous Substances Data: 33432-52-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Methyl-4-(3-nitrophenyl)-3-butyn-2-ol is used as an intermediate in the synthesis of pharmaceuticals for its potential medicinal properties.
Used in Agrochemical Industry:
2-Methyl-4-(3-nitrophenyl)-3-butyn-2-ol is used as a building block in the synthesis of agrochemicals for its potential applications in crop protection and enhancement.
Used in Organic Synthesis:
2-Methyl-4-(3-nitrophenyl)-3-butyn-2-ol is used as a reagent in various organic synthesis processes for its ability to form new compounds and contribute to the development of novel organic molecules.

Upstream product

• 33432-46-1 Aethyl(4-mnitrophenyl-2-methyl-3-butyn-2-yl)acetal (IIb) 
• 585-79-5 m-nitrobromobenzene 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 645-00-1 m-iodonitrobenzene 
• 50624-25-4 4-hydroxy-4-methyl-2-pentynoic acid 

Downstream Products

• 3034-94-4 3-nitrophenylacetylene 
• 69088-96-6 2-methyl-4-(3-aminophenyl)-3-butyn-2-ol 
• 125600-44-4 C₁₃H₁₁NO₃ 
• 125600-39-7 C₁₀H₅NO₂ 
• 183319-69-9 erlotinib hydrochloride 
• 54060-30-9 3-acetylenephenylamine 
• 299912-59-7 3-butyn-2-ol, 4-[3-[[6,7-bis(2-methoxyethoxy)-4-quinazolinyl]amine]phenyl]-2-methyl, hydrochloride 
• 1621104-69-5 3-hydroxy-3-methyl-1-(3-nitrophenyl)butan-2-one 

Relevant articles and documents

Topochemical polymerization of unsymmetrical aryldiacetylene supramolecules with nitrophenyl substituents utilizing C-H...π interactions

Diacetylenes are versatile building blocks, in which many functional groups can be incorporated for the construction of new materials with desirable properties. In this study, 6-(p or m-nitrophenyl)-3,5-hexadiyne-1-ol (4a or 4b) containing nitrophenyl groups (host) and 2-hydroxyethyl groups (guest) in different diacetylene terminals were designed to establish an ordered supramolecular assembly that is complied with the strict requirements for the topochemical polymerization of diacetylenes. Crystal film and bulk crystals of compound 4b were obtained successfully by cast film and re-precipitation methods. Both of these could photopolymerize to the corresponding regular poly(diacetylene) polymer, as evidenced by UV-vis, IR, FL and Raman spectroscopy. The electrochemical properties and behaviors of 4a and 4b were also investigated, and the results show that the differences between the para and meta positions of the mono-phenylacetylene substituents probably result from the topochemical polymerization. Thus, m-nitrophenylbutadiyne derivatives with sizeable C-H...π interactions seemed to be effective for the formation of a polymerizable packing, which is appropriate for topochemical polymerization.

Practical synthesis of aryl-2-methyl-3-butyn-2-ols from aryl bromides via conventional and decarboxylative copper-free Sonogashira coupling reactions

Two efficient protocols for the palladium-catalyzed synthesis of aryl-2-methyl-3-butyn-2-ols from aryl bromides in the absence of copper were developed. A simple catalytic system consisting of Pd(OAc)2 and P(p-tol)3 using DBU as the base and THF as the solvent was found to be highly effective for the coupling reaction of 2-methyl-3-butyn-2-ol (4) with a wide range of aryl bromides in good to excellent yields. Analogously, the synthesis of aryl-2-methyl-3-butyn-2-ols was performed also through the decarboxylative coupling reaction of 4-hydroxy-4-methyl-2-pentynoic acid with aryl bromides, using a catalyst containing Pd(OAc)2 in combination with SPhos or XPhos in the presence of tetra-n-butylammonium fluoride (TBAF) as the base and THF as the solvent. Therefore, new efficient approaches to the synthesis of terminal acetylenes from widely available aryl bromides rather than expensive iodides and using 4 or propiolic acid rather than TMS-acetylene as inexpensive alkyne sources are described.

New method for the preparation of erlotinib

The present invention refers to an alternative method for the preparation of Erlotinib through a new chemical reaction for the preparation of the 4-(3-aminophenyl)-2-methyl-3-butyn-2-ol key intermediate of formula (IV) according to the following scheme.

METHOD FOR THE PREPARATION OF ERLOTINIB

An alternative method for the preparation of Erlotinib through a new chemical reaction for the preparation of the 4-(3-aminophenyl)-2-methyl-3-butyn-2-ol key intermediate of formula (IV) according to the following scheme.

A rapid and efficient synthetic route to terminal arylacetylenes by tetrabutylammonium hydroxide- and methanol-catalyzed cleavage of 4-aryl-2-methyl-3-butyn-2-ols

Tetrabutylammonium hydroxide with methanol as an additive was found to be a highly active catalyst for the cleavage of 4-aryl-2-methyl-3-butyn-2-ols. The reaction was performed at 55-75 °C and gave terminal arylacetylenes in good to excellent yields within several minutes. Compared with the usual reaction conditions (normally >110 °C, several hours), this novel catalyst system can dramatically decrease the reaction time under much milder conditions.

Solid-state polymerization of monophenylbutadiyne derivatives

Solid-state polymerization of phenylbutadiyne derivatives with o-nitro, m-nitro or p-nitro group was investigated. All monomers in bulk crystals could be thermally polymerized to become black suggesting formation of extended pi-conjugation system. However, no regular polydiacetylene structures were confirmed by the structural analysis. Nanocrystals of the m-nitro derivative were prepared, and the different polymerization behavior compared with in the bulk crystals was observed. Copyright Taylor & Francis Group, LLC.

A convenient high activity catalyst for the Sonogashira coupling of aryl bromides

A mixture of Na2PdCl4, CuI and (t-Bu) 3PH+BF4- (molar ratio 4:3:8) dispersed in H2N(i-Pr)2 Br can be used as a "single source" precatalyst for the Sonogashira coupling of aryl bromides with various aryl- and alkylacetylenes in HN(i-Pr)2 solvent. Arylacetylenes require just 0.005 mol % of Pd catalyst at 80°C, with TOFs ranging between 3,200 and 10,000 h-1.