29430-66-8

Basic information

• Product Name: Benzenemethanol, a-phenyl-a-2-propynyl-
• Synonyms: 1-Hydroxy-1.1-diphenyl-butin-(3);1,1-Diphenyl-but-3-in-1-ol;1,1-diphenylbut-3-yn-1-ol;1,1-diphenyl-3-butyn-1-ol;1,1-Diphenyl-but-3-yn-1-ol
• CAS NO: 29430-66-8
• Molecular Formula: C16H14O
• Molecular Weight: 222.287
• Mol File: 29430-66-8.mol

Chemical Properties

• Boiling Point: 132 °C (0.5 mmHg)
• CAS DataBase Reference: Benzenemethanol, a-phenyl-a-2-propynyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanol, a-phenyl-a-2-propynyl-(29430-66-8)
• EPA Substance Registry System: Benzenemethanol, a-phenyl-a-2-propynyl-(29430-66-8)

Safety Data

• Hazardous Substances Data: 29430-66-8(Hazardous Substances Data)

Upstream product

• 106-96-7 propargyl bromide 
• 119-61-9 benzophenone 
• 463-49-0 1,2-propanediene 
• 22665-30-1 allenylzinc bromide 
• 18295-60-8 allenylmagnesium bromide 
• 18295-60-8 propargyl magnesium bromide 

Downstream Products

• 121816-51-1 1,1-bis-(4-methoxy-phenyl)-5,5-diphenyl-pentane-1,4-dien-3-one 
• 115915-86-1 1-(4-bromo-phenyl)-1,5,5-triphenyl-pent-2-yne-1,5-diol 
• 115915-87-2 1-(4-nitro-phenyl)-1,5,5-triphenyl-pent-2-yne-1,5-diol 
• 103165-98-6 1,1-bis-(4-bromo-phenyl)-5,5-diphenyl-pent-2-yne-1,5-diol 
• 17213-92-2 10-hydroxy-10-(4-hydroxy-4,4-diphenyl-but-1-ynyl)-anthrone 
• 7746-94-3 5,5-diphenyldihydrofuran-2(3H)-one 

Relevant articles and documents

One-Pot γ-Lactonization of Homopropargyl Alcohols via Intramolecular Ketene Trapping

A one-pot γ-lactonization of homopropargyl alcohols via an alkyne deprotonation/boronation/oxidation sequence has been developed. Oxidation of the generated alkynyl boronate affords the corresponding ketene intermediate, which is trapped by the adjacent hydroxy group to furnish the γ-lactone. We have optimized the conditions as well as examined the substrate scope and synthetic applications of this efficient one-pot lactonization.

Synthesis of Cyclopropanes via 1,3-migration of acyloxy groups triggered by formation of α-Imino Rhodium Carbenes

A novel and highly efficient synthetic approach to cyclopropanes was realized via 1,3-migration of acyloxy groups triggered by α-imino rhodium carbenes. Excellent chemoselectivity ensured broad compatibility of common functional groups. Merits such as readily available substrates, mild reaction conditions, and time-saving processes qualified this transformation as an attractive alternative strategy to synthesize multifunctionalized cyclopropanes. Primary investigations and discussion on the mechanism are presented.

Palladium-Catalyzed One-Pot Conversion of Aldehydes and Ketones into 4-Substituted Homopropargyl Alcohols and 5-En-3-yn-1-ols ?

Sequential treatment of 2,3-dichloropropene with magnesium and n-BuLi generated the equivalent of 1,3-dilithiopropyne, which adds regiospecifically to aldehydes and ketones to produce homopropargyl alcohols. The lithium acetylide intermediate formed in this protocol can be further reacted with aromatic and vinyl halides, under palladium catalysis, to produce 4-substituted homopropargyl alcohols and 5-en-3-yn-1-ols, respectively, in one-pot with good overall yields.

TBAI/K2S2O8 Initiated Radical Cyclization to Synthesize β- Arylsulfonyl Naphthalenes from Homopropargylic Alcohols and Sulfonyl Hydrazides

A metal-free radical addition method for the synthesis of β-arylsulfonyl naphthalenes with homopropargylic alcohols and sulfonyl hydrazides has been developed. In this reaction, sulfonyl hydrazide is employed as the source of sulfonyl radical to produce the desired sulfone directly. There is the first example for homopropargylic alcohol through direct intramolecular addition of vinyl radical to arenes with sulfonyl radical, which is initiated by the TBAI/K2S2O8 reaction system and generates the desired products in moderate yields. (Figure presented.).

Electrophilic cyclization and intermolecular acetalation of 2-(4- hydroxybut-1-yn-1-yl)benzaldehydes: Synthesis of diiodinated diepoxydibenzo[c,k][1,9]dioxacyclohexadecines

An expedient strategy for the preparation of diiodinated diepoxydibenzo[c,k][1,9]dioxacyclohexadecines from readily available 2-(4-hydroxybut-1-yn-1-yl)- benzaldehydes through electrophile-triggered tandem cyclization/ intermolecular acetalation sequence

Re-engineering of PIP3-antagonist triazole PITENIN's chemical scaffold: Development of novel antifungal leads

A novel 4-(1-phenyl-1-hydroxyethyl)-1-(o-hydroxyphenyl)-1H-1,2,3-triazole was designed by integrating the structural features of triazole PITENIN anticancer agents and the azole class of antifungal drugs. A two-step protocol comprising the Barbier proparg

Boronic acid/Br?nsted acid co-catalyst systems for the synthesis of 2: H -chromenes from phenols and α,β-unsaturated carbonyls

Protocols for the synthesis of substituted 2H-chromenes from α,β-unsaturated carbonyls and phenols are described. Optimal combinations of arylboronic acids and Br?nsted acids have been identified, such that both can be employed in catalytic quantities to accelerate these condensations. The method has been used to synthesize a variety of substituted 2H-chromenes, as well as photochromic naphthopyrans. The use of pentafluorophenylboronic acid and diphenylphosphinic acid enabled an expansion of the electrophile scope to include α,β-unsaturated ketones. Hall's 'phase-switching' of boronic acids has been exploited to achieve the separation of the two co-catalysts from unpurified reaction mixtures by a simple liquid-liquid extraction.

Copper-catalyzed one-pot trifluoromethylation/aryl migration/carbonyl formation with homopropargylic alcohols

A novel copper-catalyzed one-pot functionalization of homopropargylic alcohols that involves trifluoromethylation, aryl migration, and formation of a carbonyl moiety has been developed. This reaction constitutes the first direct conversion of homopropargy

One-pot, solvent-free regioselective addition reactions of propargyl bromide to carbonyl compounds mediated by Zn-Cu couple

A Barbier-type propargylation of carbonyl compounds with propargyl bromide has been achieved with reactive zinc-copper couple under solvent-free conditions. The reaction of aldehydes with propargyl bromide produced the unique homopropargyl alcohols in excellent yields at room temperature without the formation of homoallenyl alcohols. The ketones reacted with propargyl bromide to give the corresponding homopropargyl alcohols in good to excellent yields at -14 to -16 °C. The advantages of this method are excellent yields, short reaction time, high regioselectivity, and avoidance of the use of organic solvents.

The intricate assembling of gem-diphenylpropargylic units

While optimized procedures for selective propargylic - versus allenic - attack (in particular by alkynylsilanes) have proven to be compatible with many substitution patterns at the propargylic center, the case of diarylpropargyl electrophiles has remained problematic. The intrinsic reactivity of 1,1-diphenylpropargylic alcohols [R-C≡C-C(Ph2)OH (R = TMS, H, Me)] in the presence of various acids (and in the absence of additional nucleophile) has thus been systematically investigated. Whereas the monophenyl analogues [R-C≡C-CH(Ph)OH] afford the expected bis(phenylpropargyl) ethers, the diphenyl versions undergo complex but quite selective processes to afford various structural types: depending on the acid used, a diallene, an allenyne, an indenylallene, an indanone or a condensed tetra- and pentacycles were obtained. When the reactions were conducted in the presence of an alkynylsilane capable of playing the role of a competing nucleophile, the expected propargylic substitution products - dialkynyldiphenylmethanes or their isomers - were never observed. The hitherto unknown simple hydrocarbons diethynyl- and dipropynyl-diphenylmethane could, however, be obtained in low yields through a four-step sequence involving allenylidene- and alkynylruthenium intermediates. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.