5497-67-6

Basic information

• Product Name: 2,2-Dimethyl-4-pentenal
• Synonyms: 2,2-DIMETHYL-4-PENTENAL;2，2-Dimethyl-4-penteneal;2,2-dimethylpent-4-enal;2,2-DIMETHYL-4-PENTENAL, TECH., 90%;2,2-Dimethyl-4-pentenal, stabilized, 97%;2,2-Dimethyl-4-pentenal,97%,stabilized;2,2-DiMethyl-4-pentenal, stabilized, 97% 5ML;2,2-Dimethyl-4-pentenal technical grade, 90%, contains 1000 ppm hydroquinone as stabilizer
• CAS NO: 5497-67-6
• Molecular Formula: C₇H₁₂O
• Molecular Weight: 112.17
• EINECS: 226-834-7
• Product Categories: Aldehydes;C7;Carbonyl Compounds
• Mol File: 5497-67-6.mol
• Article Data: 35

Chemical Properties

• Melting Point: -53.35°C (estimate)
• Boiling Point: 124-125 °C(lit.)
• Flash Point: 65 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 0.825 g/mL at 25 °C(lit.)
• Vapor Pressure: 8.18mmHg at 25°C
• Refractive Index: n20/D 1.4203(lit.)
• Storage Temp.: Refrigerator (+4°C) + Flammables area
• CAS DataBase Reference: 2,2-Dimethyl-4-pentenal(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-Dimethyl-4-pentenal(5497-67-6)
• EPA Substance Registry System: 2,2-Dimethyl-4-pentenal(5497-67-6)

Safety Data

• Hazard Codes: F,Xi,Xn
• Statements: 11-36/37/38-22
• Safety Statements: 16-26-33-36
• RIDADR: UN 1989 3/PG 3
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 5497-67-6(Hazardous Substances Data)

Usage

Description

2,2-Dimethyl-4-pentenal is a clear colorless to light yellow liquid that serves as a versatile electrophile in various chemical reactions and synthesis processes. It is characterized by its unique chemical structure, which allows it to participate in a range of applications across different industries.

Uses

Used in Pharmaceutical Industry:
2,2-Dimethyl-4-pentenal is used as an electrophile for the synthesis of rearranged bicyclo[6.3.0]undecane isoprenoid skeleton of cyclooctenoid sesquiterpene dactylol and 3a-epi-dactylolin. These compounds are essential in the development of novel pharmaceuticals and therapeutic agents.
Used in Chemical Synthesis:
2,2-Dimethyl-4-pentenal is used as an electrophile in the preparation of imine ligands via condensation with primary amines. This application is crucial in the synthesis of various organic compounds and materials, contributing to the advancement of chemical research and development.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 7, p. 177, 1990Synthetic Communications, 10, p. 273, 1980 DOI: 10.1080/00397918008062750Tetrahedron Letters, 14, p. 3, 1973

InChI:InChI=1/C7H12O/c1-4-5-7(2,3)6-8/h4,6H,1,5H2,2-3H3

Upstream product

• 37406-14-7 isobutyraldehyde diallyl acetal 
• 88304-20-5 N-(2-methylpropylidene)cyclohexanamine 
• 106-95-6 allyl bromide 
• 76352-72-2 methyl 2,2-dimethyl-4-pentenoate 
• 24401-26-1 [NMe₂(allyl)(CH=C(CH₃)2)]Br 
• 3420-42-6 2,2-dimethylpent-4-en-1-ol 
• 2978-30-5 2,2-dimethylpent-4-enenitrile 
• 2403-55-6 4-(2-methyl-1-propenyl)morpholine 
• 150675-15-3 tert-Butyl-[2,2-dimethyl-pent-4-en-(E)-ylidene]-amine 
• 78-84-2 isobutyraldehyde 
• 99097-34-4 (E)-2,2-dimethylpent-4-ene-1-thial S-oxide 
• 16487-57-3 N,N,2,2-tetramethylpent-4-enamide 
• 673-33-6 1-piperidino-1-isobutene 
• 107-05-1 3-chloroprop-1-ene 

Downstream Products

• 136861-52-4 2,2-dimethylpent-4-enal 
• 340027-44-3 4,4-dimethyl-1-phenyl-6-hepten-1-yn-3-ol 
• 882512-67-6 1-(2,3-dimethoxy-5-methylphenyl)-2,2-dimethylpent-4-en-1-ol 
• 356758-82-2 Cyclohexyl-[2,2-dimethyl-pent-4-en-(E)-ylidene]-amine 
• 4541-32-6 2,2-dimethylcyclopentanone 
• 61031-76-3 2,2-dimethyl-4-oxopentenal 
• 107-46-0 Hexamethyldisiloxane 
• 108207-98-3 8-Trimethylsilanyl-oct-6-yn-1-ol 
• 108207-91-6 2-(1,1-Dimethyl-but-3-enyl)-3-vinylidene-oxocane 
• 108207-90-5 2-(1,1-Dimethyl-but-3-enyl)-3-vinylidene-oxepane 
• 76711-41-6 1-(Trimethylsilyl)-2-hexyn-6-ol 
• 108207-89-2 2-(1,1-Dimethyl-but-3-enyl)-3-vinylidene-tetrahydro-pyran 
• 86486-02-4 1-(Trimethylsilyl)-2-pentyn-5-ol 
• 108207-88-1 2-(1,1-Dimethyl-but-3-enyl)-3-vinylidene-tetrahydro-furan 

Relevant articles and documents

Synthesis of 2,5-difunctionalised-3,3-dimethylpiperidines via ω-halogenated imines

2,5-Difunctionalised-3,3-dimethylpiperidines were prepared by addition of nucleophiles to piperideinium salts, formed by electrophile-induced cyclisation of γ,δ-unsaturated imines with N-bromosuccinimide in alcoholic medium.

Consecutive borylcupration/C-C coupling of ?-alkenyl aldehydes towards diastereoselective 2-(borylmethyl)cycloalkanols

Copper(i) catalyzes the borylative cyclization of ?-alkenyl aldehydes through chemo- and regioselective addition of Cu-B to C?C and concomitant intramolecular 1,2-addition of Cu-C on C?O. The products are formed in an exclusive diastereoselective manner and computational analysis identifies the key points for the observed chemo- and diastereoselectivity.

A One-Pot Intramolecular Tandem Michael-Aldol Annulation Reaction for the Synthesis of Chiral Pentacyclic Terpenes

A chiral tricyclic terpene possessing a 6,6,6-tricyclic framework and a 3,3-dimethyl-7-oxooctylidenyl side chain undergoes a double ring-closing reaction to give two chiral pentacyclic terpenes in a ratio of 4:3 via an intramolecular Michael addition followed by aldol condensation under basic conditions. Three new stereogenic centers are introduced in the initial Michael annulation reaction. Stereoselective installation of an ethoxycarbonyl group at C17 of the two pentacyclic terpenes separately gives the corresponding highly functionalized pentacyclic terpenoids with seven stereogenic centers. The structures and stereochemistry of key intermediates and products are established through X-ray crystallographic analysis. A mechanism is proposed for explaining the stereochemistry in the Michael annulation reaction.

Synthesis of a biofuel target through conventional organic chemistry

In this work, the biofuel target compound 2-ethyl-5,5-dimethylcyclopenta-1,3-diene (1) and its exo isomers (9a and 9b), were successfully synthesized via two different pathways from the common intermediate 4,4-dimethylcyclopent-2-ene-1-one (2). The first pathway produced the endocyclic product as a pure isomer via a triflate intermediate obtained from ketone 2 in 60% yield, followed by copper-catalyzed coupling with ethyl magnesium bromide in 63% yield. The second pathway employed a Grignard reaction with ketone 2, which generated an alcohol that was immediately subjected to mild acid-catalyzed elimination to yield primarily a mixture of exo isomers 9a and 9b in 46% yield. The preparation method developed by this work allowed for the production of a sufficient quantity of these targets to evaluate their fuel properties, which will be reported in a separate study.