1119-60-4

Basic information

• Product Name: 6-HEPTENOIC ACID
• Synonyms: RARECHEM AL BO 1361;6-HEPTENOIC ACID;hept-6-enoic acid;6-Heptenoic acid 99%
• CAS NO: 1119-60-4
• Molecular Formula: C₇H₁₂O₂
• Molecular Weight: 128.17
• EINECS: 214-283-5
• Product Categories: C7;Carbonyl Compounds;Carboxylic Acids;Building Blocks;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks
• Mol File: 1119-60-4.mol
• Article Data: 36

Chemical Properties

• Melting Point: −6.5 °C(lit.)
• Boiling Point: 222-224 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.946 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0305mmHg at 25°C
• Refractive Index: n20/D 1.439(lit.)
• Storage Temp.: 2-8°C
• PKA: 4.75±0.10(Predicted)
• Water Solubility: Miscible with water.
• BRN: 1747265
• CAS DataBase Reference: 6-HEPTENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 6-HEPTENOIC ACID(1119-60-4)
• EPA Substance Registry System: 6-HEPTENOIC ACID(1119-60-4)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 3
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 1119-60-4(Hazardous Substances Data)

Usage

Description

6-Heptenoic acid, a straight-chain terminal alkenoic acid, is characterized by the presence of a double bond at the 6th position. It has been studied for its electrochemical oxidation properties when adsorbed on a Pt(111) electrode surface. The preparation of 6-heptenoic acid has been reported in the literature.

Uses

Used in Chemical Synthesis:
6-Heptenoic acid is used as a key intermediate in the synthesis of various organic compounds. Its unique structure with a double bond at the 6th position allows for specific chemical reactions that can lead to the formation of different molecules.
Used in Pharmaceutical Industry:
6-Heptenoic acid is used as a building block for the preparation of pharmaceutical compounds. One such application is in the synthesis of 6-(iodomethyl)-hexanolide through iodo-lactonization, which can be further utilized in the development of drugs targeting specific medical conditions.
Used in Electrochemistry Research:
Due to its electrochemical properties, 6-Heptenoic acid is used in the study of electrode surfaces and the development of new electrochemical techniques. The understanding of its oxidation behavior on Pt(111) electrode surfaces can contribute to advancements in the field of electrochemistry and energy storage systems.

Synthesis Reference(s)

Journal of the American Chemical Society, 107, p. 4230, 1985 DOI: 10.1021/ja00300a025Tetrahedron, 51, p. 4991, 1995 DOI: 10.1016/0040-4020(95)98696-FTetrahedron Letters, 24, p. 4439, 1983

Synthesis

synthesis of 6-Heptenoic acid and higher homologs of this ω-unsaturated acid, a study of the pyrolysis of wheptano lactone was undertaken. The lactone was prepared by the oxidation of cycloheptanone under Baeyer-Villiger conditions. The pyrolysis of ω-unsaturated acid was effected by dropping the substance under a nitrogen atmosphere into a heated column packed with glass beads.Synthesis of 6-Heptenoic Acid

Precautions

Incompatible with strong oxidizing agents, strong acids and bases.

InChI:InChI=1/C7H12O2/c1-2-3-4-5-6-7(8)9/h2H,1,3-6H2,(H,8,9)

Upstream product

• 1119-51-3 bromopentene 
• 7782-77-6 cis-nitrous acid 
• 929-17-9 7-aminoheptanoic acid 
• 3710-30-3 1,7-Octadiene 
• 502-41-0 cycloheptanol 
• 2695-47-8 6-Bromo-1-hexene 
• 821-41-0 5-Hexen-1-ol 
• 151-50-8 potassium cyanide 
• 30964-00-2 hept-6-ynoic acid 
• 2549-59-9 7-methyl-2-oxepanone 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 108-94-1 cyclohexanone 
• 928-89-2 6-chlorohexene 
• 124-38-9 carbon dioxide 

Downstream Products

• 1121-18-2 2-methyl-2-cyclohexen-1-one 
• 2931-10-4 2-ethylcyclopent-2-en-1-one 
• 71404-76-7 7-phenylselenomethyl-2-oxepanone 
• 135520-27-3 N-(2-iodophenyl)-6-heptenamide 
• 141850-56-8 N-Boc-3(S)-(6-heptenoyloxy)-5(S)-<(tosyloxy)methyl>pyrrolidine 
• 141850-21-7 Hept-6-enoic acid (3R,5S)-1-(toluene-4-sulfonyl)-5-(toluene-4-sulfonyloxymethyl)-pyrrolidin-3-yl ester 
• 373-15-9 hex-5-enyl fluoride 
• 145866-23-5 cyclopentylmethyl fluoride 
• 1035797-71-7 2,3-di-4'-pentenylsuccinic acid 
• 115420-25-2 2-iodo-6-heptenoic acid 
• 41301-63-7 7-(cyclohexan-1-on-2-yl)heptanoic acid 
• 5288-67-5 2-(6-carboxyhexyl)cyclopentanone 
• 186807-26-1 (S)-2-(4-Hept-6-enoylamino-benzoylamino)-pentanedioic acid di-tert-butyl ester 
• 321983-75-9 hept-6-en-1-oyl-L-valine-L-phenylalanine-piperidine-3R-carboxylic acid ethyl ester 

Relevant articles and documents

INTRAMOLECULAR CYCLOADDITION AND SEQUENTIAL RING EXPANSION

Free radical expansion of fused-cyclobutanones gives bicyclic ketones expanded by three and four carbons, with the carbonyl group β to the ring junction.Four-carbon ring expansion shows stereoselectivity favoring the trans-fused product 6-trans.The radical precursor cyclobutanones are readily prepared by intramolecular cycloaddition of ketenes or keteniminium salts to olefins.

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A short synthesis of (±)-alloyohimbane via a thioisomunchnone based intramolecular dipolar-cycloaddition reaction

Thioisomunchnone dipoles were generated by the reaction of bromoalkenoyl chlorides with thioamides. The intramolecular dipolar-cycloaddition reaction was used for a short synthesis of the yohimbanoid alkaloid (±)- alloyohimbane.

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Experimental determination of the activation parameters and stereoselectivities of the intramolecular Diels-Alder reactions of 1,3,8-nonatriene, 1,3,9-decatriene, and 1,3,10-undecatriene and transition state modeling with the Monte Carlo-Jumping between Wells/molecular dynamics method

Experimental activation parameters for the intramolecular Diels-Alder reactions of 1,3,8-nonatriene, 1,3,9-decatriene, and 1,3,10-undecatriene have been measured, and the Monte Carlo-Jumping between Wells/Stochastic Dynamics [MC(JBW)/SD] method, which gives relative free energies of activation, was tested as a means to predict stereoselectivities. The predictions are compared to experimental results, and to predictions from quantum and molecular mechanics methods.

A Highly Catalytic and Selective Conversion of Carboxylic Acids to 1-Alkenes of One Less Carbon Atom

An equimolar mixture of a carboxylic acid and acetic anhydride produces a reagent combination that undergoes a highly efficient decarbonylation/dehydration at 250 deg C using either Pd- or Rh-based catalyst systems, affording excellent yields of the corresponding 1-alkenes of one less carbon atom.

New alkaloidal metabolites from cultures of entomopathogenic fungus Cordyceps takaomontana NBRC 101754

Two new alkaloidal metabolites, cordytakaoamides A (1) and B (2), as well as, 2-[(2-hydroxyethyl) amino] benzoic acid (3) and 2E-decenamide (4), and three known compounds (5–7) were isolated from ethyl acetate and n-butanol soluble portions of the entomopathogenic fungus, Cordyceps takaomontana NBRC 101754. Compounds 3 and 4 were isolated here for first time from natural resources. The chemical structures were established depending upon spectroscopic techniques such as 1D, 2D NMR, and HRMS. The absolute configuration of 1 and 2 was elucidated via the total synthesis of 1 as well as the experimental circular dichroism. Compound 3 was confirmed by a signal crystal X-ray analysis.

Ni-Catalyzed β-Alkylation of Cyclopropanol-Derived Homoenolates

Metal homoenolates are valuable synthetic intermediates which provide access to β-functionalized ketones. In this report, we disclose a Ni-catalyzed β-alkylation reaction of cyclopropanol-derived homoenolates using redox-active N-hydroxyphthalimide (NHPI) esters as the alkylating reagents. The reaction is compatible with 1°, 2°, and 3° NHPI esters. Mechanistic studies imply radical activation of the NHPI ester and 2e β-carbon elimination occurring on the cyclopropanol.

MACROCYCLIC COMPOUNDS AND RELATED COMPOSITONS AND METHODS OF USE

Compounds and compositions, which can be use for example, for treating cancer, are described herein.