24165-63-7

Basic information

• Product Name: 1-(4-METHYLPHENYL)-3-BUTEN-1-OL 97
• Synonyms: 1-(4-METHYLPHENYL)-3-BUTEN-1-OL 97;1-(4-METHYLPHENYL)-3-BUTEN-1-OL 97%
• CAS NO: 24165-63-7
• Molecular Formula: C₁₁H₁₄O
• Molecular Weight: 162.23
• Product Categories: Acyclic;Alkenes;Organic Building Blocks;Building Blocks;Chemical Synthesis;Organic Building Blocks
• Mol File: 24165-63-7.mol
• Article Data: 196

Chemical Properties

• Boiling Point: 253 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.983 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00488mmHg at 25°C
• Refractive Index: n20/D 1.5270(lit.)
• PKA: 14.36±0.20(Predicted)
• CAS DataBase Reference: 1-(4-METHYLPHENYL)-3-BUTEN-1-OL 97(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-METHYLPHENYL)-3-BUTEN-1-OL 97(24165-63-7)
• EPA Substance Registry System: 1-(4-METHYLPHENYL)-3-BUTEN-1-OL 97(24165-63-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 24165-63-7(Hazardous Substances Data)

Usage

General Description

1-(4-Methylphenyl)-3-buten-1-ol (1-p-tolyl-but-3-en-1-ol) is a homoallylic alcohol derivative. It can be prepared by the allylation of 4-methylbenzaldehyde using potassium allyltrifluoroborate in the presence of 18-crown-6. It can undergo Prins cyclization with in the presence of cellulose-sulfonic acid to form the corresponding tetrahydropyran-4-ol.

InChI:InChI=1/C11H14O/c1-3-4-11(12)10-7-5-9(2)6-8-10/h3,5-8,11-12H,1,4H2,2H3

Upstream product

• 36971-15-0 3-isopropyl-2-methyl-hex-5-en-3-ol 
• 104-87-0 4-methyl-benzaldehyde 
• 107-37-9 allyltrichlorosilane 
• 72824-04-5 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 118722-54-6 allyldimethyl(2-pyridyl)silane 
• 18854-66-5 tris(allyl)aluminum 
• 591-87-7 Allyl acetate 
• 589-18-4 4-Methylbenzyl alcohol 
• 106-95-6 allyl bromide 
• 107-18-6 allyl alcohol 
• 7393-43-3 tetraallyl tin 
• 762-72-1 allyl-trimethyl-silane 
• 107-05-1 3-chloroprop-1-ene 
• 627-15-6 1,3-dibromopropene 

Downstream Products

• 4160-52-5 1-(4-methylphenyl)butan-1-one 
• 32271-53-7 (E)-4-(p-tolyl)but-3-en-2-ol 
• 362598-56-9 3-methyl-2-[4-(4-methylphenyl)-4-oxobutyl]cyclopent-2-en-1-one 
• 1027300-03-3 C₁₆H₂₄OSi 
• 1026779-14-5 (E)-1-(3-methoxybut-1-enyl)-4-methylbenzene 
• 1251857-73-4 (E)-1-methyl-4-((4-(p-tolyl)but-3-en-2-yl)sulfonyl)benzene 

Relevant articles and documents

2,3-Wittig rearrangement by partial reduction of diallyl acetals with SmI2 in acetonitrile

Diallyl acetals undergo reductive cleavage of an allyloxy group by SmI2 to generate α-allyloxy carbanions, which are transformed into homoallyl alcohols by 2,3-Wittig rearrangement.

Organocatalytic Asymmetric Synthesis of Cyclic Acetals with Spirooxindole Skeleton

An organocatalytic asymmetric synthesis of cyclic acetal with spirooxindole skeleton has been developed via a domino reaction between isatin and γ-hydroxy enones. Bifunctional squaramide catalyst with adamantyl motif was found to be the most effective for the cascade reaction. With 10 mol% of the catalyst, the desired products were obtained in 1.8:1 to 9:1 diastereo- and 86% to >99% enantioselectivities from a range of substituted isatins and γ-hydroxy enones. (Figure presented.).

Photocatalytic Umpolung Synthesis of Nucleophilic π-Allylcobalt Complexes for Allylation of Aldehydes

The concept of "umpolung"reactivity of π-allylmetal complexes has been developed as a powerful method for the allylation of aldehydes. This paper describes the photocatalytic umpolung strategy for the synthesis of nucleophilic allylcobalt complexes through a single-electron-transfer (SET) process. This strategy enables the metallaphotoredox allylation of carbonyls with allyl acetate using organic N,N-diisopropylethylamine as the terminal reductant bypassing the use of a stoichiometric amount of metals. Ultraviolet-visible spectroscopy was used to monitor the redox changes of cobalt in the reaction.