6126-50-7

Basic information

• Product Name: E-4-Hexen-1-ol
• Synonyms: 4-Hexen-l-ol;Fema no. 3430
• CAS NO: 6126-50-7
• Molecular Formula: C₆H₁₂O
• Molecular Weight: 100.16
• EINECS: 213-188-6
• Mol File: 6126-50-7.mol
• Article Data: 18

Chemical Properties

• Melting Point: 22.55°C (estimate)
• Boiling Point: 152.63°C (estimate)
• Flash Point: 59.9 °C
• Appearance: /
• Density: 0.8513
• Vapor Pressure: 0.929mmHg at 25°C
• Refractive Index: 1.4402
• CAS DataBase Reference: E-4-Hexen-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: E-4-Hexen-1-ol(6126-50-7)
• EPA Substance Registry System: E-4-Hexen-1-ol(6126-50-7)

Safety Data

• Hazardous Substances Data: 6126-50-7(Hazardous Substances Data)

Usage

Description

E-4-Hexen-1-ol, also known as leaf alcohol, is an organic compound with a pungent oily odor. It is a colorless to pale yellow liquid and is one of the most abundant green leaf volatiles found in nature. It is synthesized by treating cisand trans-3-chloro-2-methyl-tetrahydropyrone with sodium in ether.

Uses

Used in Flavor and Fragrance Industry:
E-4-Hexen-1-ol is used as a flavor compound for its green, tomato, and fresh herbal vegetable taste characteristics at 20 ppm. It is commonly found in the cisand trans-forms in banana and the cis-form in passion fruit. It is also reported in beans, butter, and olive.
Used in Chemical Synthesis:
E-4-Hexen-1-ol is used as a starting material in the synthesis of various chemicals, such as other volatile organic compounds and fragrances.
Used in Research:
E-4-Hexen-1-ol is used in research to study the chemical properties and behavior of green leaf volatiles, as well as their role in the flavor and fragrance industry.
Used in Environmental Applications:
E-4-Hexen-1-ol can be used as a biomarker for the detection of plant stress and environmental changes, as it is released by plants in response to various stressors, such as herbivory or mechanical damage.
Used in Cosmetics and Personal Care Products:
E-4-Hexen-1-ol can be used as a fragrance ingredient in cosmetics and personal care products, providing a natural and fresh scent.

Preparation

By treating cis- and trans-3-chloro-2-methyl-tetrahydropyrone with sodium in ether.

InChI:InChI=1/C6H12O/c1-2-3-4-5-6-7/h2-3,7H,4-6H2,1H3/b3-2-

Upstream product

• 27925-22-0 6,8-dioxa-bicyclo[3.2.1]oct-2-ene 
• 51368-03-7 hex-4-enoic acid ethyl ester 
• 98096-52-7 C₈H₁₉NO₂ 
• 701-75-7 3-(phenylthio)but-1-ene 
• 540-51-2 2-bromoethanol 
• 111-28-4 2,4-hexadiene-1-ol 
• 17102-64-6 Sorbyl alcohol 
• 821-41-0 5-Hexen-1-ol 
• 142-83-6 trans,trans-2,4-Hexadienal 
• 629-11-8 1,6-hexanediol 
• 35194-36-6 hex-4-enoic acid 
• 928-95-0 (E)-2-Hexen-1-ol 
• 110-82-7 cyclohexane 
• 5371-52-8 2-hydroxytetrahydrofuran 

Downstream Products

• 129620-49-1 pentacarbonyl{(4-hexen-1-yloxy)(phenyl)carbene}chromium⁽⁰⁾ 
• 1003-30-1 2-ethyltetrahydrofuran 
• 629-30-1 1,7-heptandiol 
• 13175-27-4 heptane-1,6-diol 
• 36851-77-1 6-bromo-hex-2-ene 
• 35194-36-6 hex-4-enoic acid 
• 62614-72-6 cis-1-chlorohex-4-ene 
• 114524-26-4 2-methyl-3-(phenylselanyl)tetrahydro-2H-pyran 

Relevant articles and documents

Cobalt-Catalyzed Intermolecular Hydrofunctionalization of Alkenes: Evidence for a Bimetallic Pathway

A functional group tolerant cobalt-catalyzed method for the intermolecular hydrofunctionalization of alkenes with oxygen- and nitrogen-based nucleophiles is reported. This protocol features a strategic use of hypervalent iodine(III) reagents that enables a mechanistic shift from conventional cobalt-hydride catalysis. Key evidence was found supporting a unique bimetallic-mediated rate-limiting step involving two distinct cobalt(III) species, from which a new carbon-heteroatom bond is formed.

Pd(II)-Catalyzed [4 + 2] Heterocyclization Sequence for Polyheterocycle Generation

A new Pd(II)-catalyzed cascade sequence for the formation of polyheterocycles, from simple starting materials, is reported. The sequence is applicable to both indole and pyrrole substrates, and a range of substituents are tolerated. The reaction is thought to proceed by a Pd(II)-catalyzed C-H activated Heck reaction followed by a second Pd(II)-catalyzed aza-Wacker reaction with two Cu(II)-mediated Pd(0) turnovers per sequence. The sequence can be considered a formal [4 + 2] heterocyclization.

Reactions of 2-Methyltetrahydropyran on Silica-Supported Nickel Phosphide in Comparison with 2-Methyltetrahydrofuran

The reactions of 2-methyltetrahydropyran (2-MTHP, C6H12O) on Ni2P/SiO2 provide insights on the interactions between a cyclic ether, an abundant component of biomass feedstock, with a transition-metal phosphide, an effective hydrotreating catalyst. At atmospheric pressure and a low contact time, conditions similar to those of a fast pyrolysis process, 70% of products formed from the reaction of 2-MTHP on Ni2P/SiO2 were deoxygenated products, 2-hexene and 2-pentenes, indicating a good oxygen removal capacity. Deprotonation, hydrogenolysis, dehydration, and decarbonylation were the main reaction routes. The reaction sequence started with the adsorption of 2-MTHP, followed by ring-opening steps on either the methyl substituted side (Path I) or the unsubstituted side (Path II) to produce adsorbed alkoxide species. In Path I, a primary alkoxide was oxidized at the α-carbon to produce an aldehyde, which subsequently underwent decarbonylation to 2-pentenes. The primary alkoxide could also be protonated to give a primary alcohol which could desorb or form the final product 2-hexene. In Path II, a secondary alkoxide was oxidized to produce a ketone or was protonated to a secondary alcohol that was dehydrated to give 2-hexene. The active sites for the adsorption of 2-MTHP and O-intermediates were likely to be Ni sites.