89968-81-0

Basic information

• Product Name: 1-Phenylpentane-1,4-diol
• CAS NO: 89968-81-0
• Molecular Weight: 180.247
• Mol File: 89968-81-0.mol

Chemical Properties

• CAS DataBase Reference: 1-Phenylpentane-1,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Phenylpentane-1,4-diol(89968-81-0)
• EPA Substance Registry System: 1-Phenylpentane-1,4-diol(89968-81-0)

Safety Data

• Hazardous Substances Data: 89968-81-0(Hazardous Substances Data)

Upstream product

• 127811-25-0 2-Nitro-1-phenyl-pentane-1,4-diol 
• 27998-52-3 (+/-)-4-(phenylthio)-2-butanol 
• 100-52-7 benzaldehyde 
• 861399-10-2 (RS)-1-(n-butyltellanyl)-3-butanol 
• 135468-12-1 1-phenylpent-2-yne-1,4-diol 
• 109-72-8 n-butyllithium 
• 6089-15-2 4-iodo-butan-2-ol 
• 132205-09-5 (1R*,2Z,4S*)/(1R*,2Z,4R*)-1-Phenyl-2-pentene-1,4-diol 
• 1228681-29-5 1-phenyl-2-pentene-1,4-diol 
• 622-42-4 1-nitro-1-phenylmethane 
• 78-94-4 methyl vinyl ketone 
• 583-05-1 1-phenylpentane-1,4-dione 
• 36866-66-7 5-phenyloxolan-2-ol 
• 917-54-4 methyllithium 

Downstream Products

• 4457-59-4 tetrahydro-2-methyl-5-phenylfuran 
• 1009-14-9 phenyl butyl ketone 
• 27927-59-9 4-hydroxy-1-phenylpentan-1-one 
• 583-05-1 1-phenylpentane-1,4-dione 
• 3042-21-5 2-methyl-5-phenyl-1H-pyrrole 
• 533883-16-8 1-hexyl-2-phenyl-5-methylpyrrole 
• 154592-40-2 3,4-dihydro-2-methyl-5-phenyl-2H-pyrrole 

Relevant articles and documents

Nonclassical Mechanism in the Cyclodehydration of Diols Catalyzed by a Bifunctional Iridium Complex

1,4- and 1,5-diols undergo cyclodehydration upon treatment with cationic N-heterocyclic carbene (NHC)–IrIII complexes to give tetrahydrofurans and tetrahydropyrans, respectively. The mechanism was investigated, and a metal-hydride-driven pathway was proposed for all substrates, except for very electron-rich ones. This contrasts with the well-established classical pathways that involve nucleophilic substitution.

Palladium-catalyzed hydrogenation with use of ionic liquid bis(2-hydroxyethyl)ammonium formate [BHEA][HCO2] as a solvent and hydrogen source

We designed ionic liquid bis(2-hydroxyethyl)ammonium formate [BHEA][HCO2] for use as a solvent and hydrogen donor for hydrogenation. Catalytic hydrogenation of aromatic ketones, nitro groups, and olefins with PdCl2 in [BHEA][HCO2] generated the corresponding reduction products. Selective reduction of aromatic ketones over aliphatic ketones was observed. Hydrogenolysis of benzyl ethers and benzyl amines also proceeded. All these reactions were successfully carried out in good to excellent yields under mild and nonflammable conditions. In addition, the ionic liquid and Pd source can be reused several times.

Non-flammable and reusable hydrogenation of aromatic ketones in ionic liquid

A novel method of hydrogenation of aromatic ketones in the ionic liquid [BHEA][HCO2] was developed; this method is more enhanced in terms of flammability and reusability as compared to the conventional method (H 2 and Pd/C). The redu

Grignard reagents: Alkoxide-directed iodine-magnesium exchange at sp 3 centers

(Chemical Equation Presented) Sequential addition of i-PrMgCl and BuLi to sp3 hybridized iodoalcohols triggers a facile iodine-metal exchange. Intercepting the resulting cyclic Grignard reagents with a slight excess of an electrophile leads to a diverse range of substituted alcohols. The iodine-magnesium exchange strategy is effective with 3-carbon iodoalcohols bearing alkyl substitutents on the carbinol or adjacent carbons and with the chain-extended homolog 4-iodobutan-1-ol.

γ-Butyltelluro-2-butanol: A route to reactive 1,4-dianion intermediates

γ-Butyltelluro-2-butanol was reacted with 2 equiv of n-butyllithium. Both tellurium/lithium exchange and the proton abstraction reactions took place in a single step and the lithium dianion intermediate efficiently reacted with aldehydes and ketones, producing the corresponding diols.

Ruthenium- and enzyme-catalyzed dynamic kinetic asymmetric transformation of 1,4-diols: Synthesis of γ-hydroxy ketones

Enzymatic kinetic resolution of unsymmetrical 1,4-diols in combination with a ruthenium-catalyzed hydrogen transfer process led to a dynamic kinetic asymmetric transformation (DYKAT) of the least hindered alcohol. Oxidation of the second hydroxy group tak

Nitroalkanes in Aqueous Medium as an Efficient and Eco-Friendly Source for the One-Pot Synthesis of 1,4-Diketones, 1,4-Diols, δ-Nitroalkanols, and Hydroxytetrahydrofurans

The Michael addition of primary aliphatic nitro compounds to α,β-unsaturated enones, performed in aqueous media, provides the one-pot synthesis of 1,4-diketones, 1,4-diols, δ-nitroalkanols, and hydroxytetrahydrofurans, respectively, by the appropriate cho

Facile reduction of aromatic aldehydes, ketones, diketones and oxo aldehydes to alcohols by an aqueous TiCl3/NH3 system: Selectivity and scope

A simple and rapid procedure for the almost quantitative reduction of aromatic aldehydes, ketones, diketones and oxo aldehydes to alcohols by use of TiCl3/NH3 in aqueous methanol solution is reported. The reducing system distinguishes between different classes of aldehydes and/or ketones, and many functionalities that usually do not survive under reducing conditions are tolerated well. The concept of reversal of chemoselectivity has also been developed. A mechanism based on two sequential one-electron transfers from TiIII to the carbonyl carbon atom is proposed, the second SET becoming operative only in the presence of ammonium ion (either added or formed in situ). Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Functionalized organolithium compounds of DTBB-catalyzed sulfur-lithium exchange

The successive reaction of β- or γ-hydroxy or amino phenyl thioethers (1,4) with butyllithium and an excess of lithium powder in the presence of a catalytic amount of DTBB in THF at - 78°C leads to the formation of the corresponding β- or γ-functionalized organolithium compounds 2 or 5, respectively, which by treatment with different electrophiles [D2O, t- BuCHO, PhCHO, Me2CO, (CH2)4CO, (CH2)5CO] at temperatures ranging between - 78°C and room temperature yields, after hydrolysis with water, the expected functionalized alcohols or amines 3 or 6, respectively, in a completely regioselective manner.

Stereoselective Substitution at Phenyl-Substituted γ-Lactols with Organometallic Compounds

A variety of monosubstituted γ-lactols 4-6 were prepared in good yields by DIBAL reduction of the corresponding γ-lactones 1-3.The monophenyl-substituted lactols 4b-6b were transformed into disubstituted tetrahydrofuran derivatives by replacement of the hydroxyl group by the alkyl residue of organometallic compounds used as nucleophiles.The diastereoselectivity of the substitution was found to depend strongly on the substitution pattern of the γ-lactols.For the reaction of the 3- and 4-substituted derivatives 4b and 5b, respectively, good to excellent trans selectivity was observed, while the 5-substituted derivative reacted without any diastereoselectivity.These results were interpreted by means of the Felkin-Anh model. - Keywords: γ-Lactone / Reduction / γ-Lactol / Lewis acid / Tetrahydrofurans