40888-14-0

Basic information

• Product Name: 2-Methyl-4-o-tolylbut-3-yn-2-ol
• Synonyms: 2-Methyl-4-o-tolylbut-3-yn-2-ol;2-Methyl-4-(2-methylphenyl)-3-butyn-2-ol
• CAS NO: 40888-14-0
• Molecular Formula: C₁₂H₁₄O
• Molecular Weight: 174.23896
• Mol File: 40888-14-0.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-Methyl-4-o-tolylbut-3-yn-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-4-o-tolylbut-3-yn-2-ol(40888-14-0)
• EPA Substance Registry System: 2-Methyl-4-o-tolylbut-3-yn-2-ol(40888-14-0)

Safety Data

• Hazardous Substances Data: 40888-14-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Methyl-4-o-tolylbut-3-yn-2-ol is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to form carbon-carbon triple bonds and its reactivity in organic chemistry reactions.
Used in Organic Chemistry Research:
2-Methyl-4-o-tolylbut-3-yn-2-ol is used as a reagent in organic chemistry reactions, particularly for the formation of carbon-carbon triple bonds, enabling the development of new organic compounds and materials.

Upstream product

• 766-47-2 1-ethynyl-2-methylbenzene 
• 67-64-1 acetone 
• 1232660-55-7 o-tolyl 1H-imidazole-1-sulfonate 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 615-37-2 ortho-methylphenyl iodide 
• 29552-15-6 4-chloro-2-methylbut-3-yn-2-ol 
• 95-46-5 2-methylphenyl bromide 
• 40888-06-0 1-[3-(1-Ethoxy-ethoxy)-3-methyl-but-1-ynyl]-2-methyl-benzene 

Downstream Products

• 59105-21-4 1-methoxy-4-(2-(2-tolyl)ethynyl)benzene 
• 51331-98-7 C₁₆H₁₄O 
• 917507-06-3 (3E)-2-methoxy-2-methyl-4-(2-methylphenyl)-3-butene 
• 349668-00-4 (3Z)-2-methoxy-2-methyl-4-(2-methylphenyl)-3-butene 
• 917507-05-2 (3E)-2-methyl-4-(2-methylphenyl)-3-buten-2-ol 

Relevant articles and documents

Bimetal Cooperatively Catalyzed Arylalkynylation of Alkynylsilanes

An unprecedented Pd/Rh cooperatively catalyzed arylalkynylation of alkynylsilanes was developed to merge an alkynylidene moiety with benzosilacycle. These silaarenes possess a particular aggregation-induced emission behavior. Mechanistic investigations demonstrate that the relay trimetallic transmetalation plays a pivotal role in governing this transformation.

Ru(ii)-catalyzed allenylation and sequential annulation of: N -tosylbenzamides with propargyl alcohols

We hereby report Ru(ii)-catalyzed C(sp2)-H allenylation of N-tosylbenzamides to access multi-substituted allenylamides. Furthermore, the allenylamides were converted to the corresponding isoquinolone derivatives via base mediated annulation. The current protocol features low catalyst loading, mild reaction conditions, high functional group compatibility and desired scalability. The unique functionality of the afforded allenes allowed further transformations to expand the practicality of the protocol. This journal is

Rhodium-Catalyzed Annulation of Phenacyl Ammonium Salts with Propargylic Alcohols via a Sequential Dual C-H and a C-C Bond Activation: Modular Entry to Diverse Isochromenones

Given their omnipresence in natural products and pharmaceuticals, isochromenone congeners are one of the most privileged scaffolds to synthetic chemists. Disclosed herein is a dual (ortho/meta) C-H and C-C activation of phenacyl ammonium salts (acylammonium as traceless directing group) toward annulation with propargylic alcohols to accomplish rapid access for novel isochromenones by means of rhodium catalysis from readily available starting materials. This operationally simple protocol features broad substrate scope and wide functional group tolerance. Importantly, the protocol circumvents the need of any stoichiometric metal oxidants and proceeds under aerobic conditions.

DBU-promoted carbonylative synthesis of 1,3-oxathiolan-2-ones from propargylic alcohols with TFBen as the CO source

A DBU-promoted carbonylative cyclization of propargylic alcohols with sulfur was developed. Various 1,3-oxathiolan-2-ones were produced in 61-98% yields under mild conditions in the absence of metal catalysts. TFBen (benzene-1,3,5-triyl triformate) as an efficient and solid CO surrogate and S8 as an ideal sulfur source were employed and incorporated.

Cleavage of C–C and C–O Bonds to Form C–C Bonds: Direct Cross-Coupling between Acetylenic Alcohols and Benzylic Carbonates

A palladium-catalyzed cross-coupling reaction between C(sp) and C(sp3) centers was achieved in excellent yields via C–C bond cleavage and C–O bond cleavage. This procedure uses relatively stable acetylenic alcohols as reactants instead of unsta

Synthesis of Polysubstituted 2-Iodoindenes via Iodonium-Induced Cyclization of Arylallenes

A new chemoselective iodocarbocyclization of allenyl arenes was developed leading to the formation of 2-iodoindenes. In acetonitrile or nitromethane, electrophilic sources of iodine cations react selectively with the C2-C3 double bond of 1-arylallenes to give, after anti nucleophilic attack of the aromatic ring, 2-iodoindene products in high yields. Variations of the allenic skeletons revealed the high 5-endo selectivity and some competitive pathways of cyclization. Postfunctionalization reactions of the carbon-iodine bond, via Pd- and Cu-cross-couplings, gave rise to substituted indenes in good to excellent yields. (Chemical Equation Presented).

Palladium-Catalyzed Nitration of Meyer-Schuster Intermediates with tBuONO as Nitrogen Source at Ambient Temperature

A novel domino palladium-catalyzed nitration of Meyer-Schuster intermediates which were generated in situ from propargylic alcohols was developed, by the use of t-BuONO, leading to α-nitro enones in good to excellent yields at room temperature with a broa

Synthesis of Oxazolidin-2-ones by Tandem Cyclization of Propargylic Alcohols and Phenyl Isocyanate Promoted by Silver Catalysts as π-Lewis Acids

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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.

Microwave-promoted copper-free Sonogashira-Hagihara couplings of aryl imidazolylsulfonates in water

Aryl imidazol-1-ylsulfonates have been efficiently cross-coupled with aryl-, alkyl-, and silylacetylenes in neat water under copper-free conditions at 110 °C assisted by microwave irradiation. Using 0.5mol% of an oxime palladacycle as precatalyst, 2-dicyclohexylphosphino-2′,6′- dimethoxybiphenyl (SPhos, 2mol%) as ligand, hexadecyltrimethylammonium bromide (CTAB) as additive, and triethylamine (TEA) as base, a wide array of disubstituted alkynes has been prepared in good to high yields in only 30min. Copyright