18999-28-5

Basic information

• Product Name: 2-HEPTENOIC ACID
• Synonyms: RARECHEM AL BK 0163;TRANS-2-HEPTENOIC ACID;(2E)-2-Heptenoic acid;HEPT-2-ENOIC ACID;2-HEPTENOIC ACID;2-HEPTENOIC ACID 97%;2-Heptenoic Acid (contains 3-Heptenoic Acid)
• CAS NO: 18999-28-5
• Molecular Formula: C₇H₁₂O₂
• Molecular Weight: 128.17
• EINECS: 242-738-8
• Mol File: 18999-28-5.mol

Chemical Properties

• Boiling Point: 122 °C / 11.5mmHg
• Flash Point: 133.4 °C
• Appearance: colorless to pale yellow clear liquid
• Density: 0.95
• Vapor Pressure: 0.0295mmHg at 25°C
• Refractive Index: 1.4540-1.4580
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 2-HEPTENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-HEPTENOIC ACID(18999-28-5)
• EPA Substance Registry System: 2-HEPTENOIC ACID(18999-28-5)

Safety Data

• RIDADR: 3265
• RTECS: MJ9650000
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 18999-28-5(Hazardous Substances Data)

Usage

Definition

ChEBI: A heptenoic acid with the double bond at position 2.

Synthesis Reference(s)

Journal of the American Chemical Society, 89, p. 2754, 1967 DOI: 10.1021/ja00987a055

InChI:InChI=1/C7H12O2/c1-2-3-4-5-6-7(8)9/h5-6H,2-4H2,1H3,(H,8,9)

Upstream product

• 22104-77-4 hept-2-en-1-ol 
• 2463-63-0 3-Butyl-acrolein 
• 110-62-3 pentanal 
• 141-82-2 malonic acid 
• 122093-60-1 1,3-dibromo-1,1-difluoroheptane 
• 123-72-8 butyraldehyde 
• 79-11-8 chloroacetic acid 
• 154820-94-7 2-(hex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 124-38-9 carbon dioxide 
• 693-02-7 hex-1-yne 
• 592-41-6 1-hexene 

Downstream Products

• 50884-99-6 2-Bromo-3-fluoro-heptanoic acid 
• 2351-88-4 ethyl 2-heptenoate 
• 109-52-4 valeric acid 
• 50885-02-4 2-Amino-3-fluoro-heptanoic acid 
• 477534-15-9 methyl 7-(2-benzoylaminothiazol-5-yl)ethoxy-2-(2-heptenoyl)-1,2,3,4-tetrahydroisoquinoline-(3S)-carboxylate 
• 865466-24-6 narlaprevir 
• 254438-52-3 C₂₆H₃₇NO₃ 
• 1185253-10-4 C₂₂H₂₉NO₃ 
• 1184928-27-5 C₂₅H₃₄N₂O₂ 
• 1256345-29-5 C₃₆H₆₃N₅O₇S 
• 105858-75-1 (ethylenebis(bicyclohexylphosphane))Ni(cis,cis-1,5-cyclooctadiene) 
• 592-41-6 1-hexene 

Relevant articles and documents

Water-initiated hydrocarboxylation of terminal alkynes with CO2and hydrosilane

This work discloses a Cu(ii)-Ni(ii) catalyzed tandem hydrocarboxylation of alkynes with polysilylformate formed from CO2and polymethylhydrosiloxane that affords α,β-unsaturated carboxylic acids with up to 93% yield. Mechanistic studies indicate that polysilylformate functions as a source of CO and polysilanol. Besides, a catalytic amount of water is found to be critical to the reaction, which hydrolyzes polysilylformate to formic acid that induces the formation of Ni-H active species, thereby initiating the catalytic cycle.

Method for preparing alpha, beta-unsaturated carboxylic acid compound

The invention discloses a method for preparing an alpha, beta-unsaturated carboxylic acid compound, which comprises the following steps: 1) in an atmosphere containing carbon dioxide, heating and reacting a mixture containing hydrosilane and a copper catalyst to obtain a system I; and 2) adding a raw material containing alkyne and a nickel catalyst into the system I in the step 1), and heating to react. The method has the advantages of simple, easily available, cheap and stable raw materials, common, easily available and stable catalyst, mild reaction conditions, simple post-treatment, high yield and the like.

Exploration of New Biomass-Derived Solvents: Application to Carboxylation Reactions

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Alpha, beta-unsaturated carbonyl compound production method

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ENANTIO- AND STEREO-SPECIFIC SYNTHESES OF β-AMINO-α- HYDROXY AMIDES

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Base-Catalyzed Reactions of α,β-Unsaturated Esters and Nitriles. 4. Dimerization of β-Alkyl-Substituted Acrylates

2-Butenoates 1-C4 alkyl, cyclohexyl, or 1-bornyl> and higher β-alkyl-substituted acrylates 2-C9 n-alkyl> undergo highly selective (>95percent) dimerization in the presence of promoted potassium or sodium catalysts to yield corresponding 2-alkylidene-3-alkylglutarates (3).The reaction involves metalation of the β-alkylacrylate at the C-2 position, followed by addition at C-3 of a second monomeric molecule.Changes in the relative extent of dimerization (Kr) as a function of structural and experimentalvariables were determined.Kr is strongly dependent upon the inductive and steric characteristics of the alcoholic (R) group and of the β-alkyl substituent (R').For an n-alkyl group as R' the Kr value increases with increase in chain length from C1 to C4 but then decreases for longer substituents (C5-C9).Among the two geometric isomers in the dimeric product 3, the isomer with an α-vinylic hydrogen cis to the carboalkoxy group is predominant in all cases, but its relative concetration decreases with an increase in the size of R'.Branched or cyclic β-substituents in 2 prevent dimerization due to steric hindrance in the rate-determining addition step.Promoted potassium or sodium catalysts show much higher dimerization activity compared to supported alkali metals or to alkoxides.For conversions of up to 60percent, Kr values in proton-exchanging alkylbenzene solvents and in nonexchanging alkylcyclohexanes are closely similar, indicating faster abstraction of an α-vinylic hydrogen from the monomer, rather than a benzylic hydrogen from the solvent, in the chain regeneration step of the reaction.