26526-71-6

Basic information

• Product Name: ethyl 2-cyano-5-methylhexanoate
• CAS NO: 26526-71-6
• Molecular Formula: C₁₀H₁₇NO₂
• Molecular Weight: 183.2475
• Mol File: 26526-71-6.mol

Chemical Properties

• Boiling Point: 223.1°C at 760 mmHg
• Flash Point: 95.1°C
• Density: 0.958g/cm³
• Vapor Pressure: 0.098mmHg at 25°C
• Refractive Index: 1.435
• CAS DataBase Reference: ethyl 2-cyano-5-methylhexanoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-cyano-5-methylhexanoate(26526-71-6)
• EPA Substance Registry System: ethyl 2-cyano-5-methylhexanoate(26526-71-6)

Safety Data

• Hazardous Substances Data: 26526-71-6(Hazardous Substances Data)

Upstream product

• 105-56-6 ethyl 2-cyanoacetate 
• 590-86-3 isovaleraldehyde 
• 75-03-6 ethyl iodide 
• 107-82-4 i-pentyl bromide 
• 18852-51-2 sodium cyanoacetic acid ethyl ester 

Downstream Products

• 19424-34-1 5-methylhexanenitrile 
• 399556-78-6 2-ethyl-2-cyano-5-methyl-hexanoic acid ethyl ester 

Relevant articles and documents

Room Temperature, Reductive Alkylation of Activated Methylene Compounds: Carbon-Carbon Bond Formation Driven by the Rhodium-Catalyzed Water-Gas Shift Reaction

The rhodium-catalyzed water-gas shift reaction has been demonstrated to drive the reductive alkylation of several classes of activated methylene compounds at room temperature. Under catalysis by rhodium trichloride (2-3 mol %), carbon monoxide (10 bar), water (2-50 equiv), and triethylamine (2.5-7 equiv), the scope has been successfully expanded to cover a wide range of alkylating agents, including aliphatic and aromatic aldehydes, as well as cyclic ketones, in moderate to high yields. This method is comparable to, and for certain aspects, surpasses the established reductive alkylation protocols.

Towards organo-click reactions: Development of pharmaceutical ingredients by using direct organocatalytic bio-mimetic reductions

Economic and environmentally friendly bio-mimetic one-pot three and four-component Knoevenagel-hydrogenation (K-H), five-component Knoevenagel-hydrogenation-alkylation (K-H-A) and six-component Knoevenagel-hydrogenation-alkylation-Huisgen cycloaddition (K-H-A-HC) reactions of aldehydes, CH-acids, o-phenylenediamine, alkyl halides and azides using proline, proline-metal carbonate and proline-metal carbonate-Cu I-catalysis, respectively have been developed. Many of K-H and K-H-A compounds have direct application in pharmaceutical chemistry. The Royal Society of Chemistry.

Chemoenzymatic synthesis of a series of 4-substituted glutamate analogues and pharmacological characterization at human glutamate transporters subtypes 1-3

A series of nine L-2,4-s;yrc-4-alkylglutamic acid analogues (1a-i) were synthesized in high yield and high enantiomeric excess (>99% ee) from their corresponding 4-substituted ketoglutaric acids (2a-i), using the enzyme aspartate aminotransferase (AAT) from pig heart or E. coli. The synthesized compounds were evaluated as potential ligands for the glutamate transporters EAAT1, EAAT2, and EAAT3 (excitatory amino acid transporter, subtypes 1-3) in the FLIPR membrane potential (FMP) assay. We found a distinct change in the pharmacological profile when the 4-methyl group (compound 1a, an EAAT1 substrate and EAAT2,3 inhibitor) was extended to a 4-ethyl group, compound 1b, as this analogue is an inhibitor at all three subtypes, EAAT1-3. Furthermore, we conclude that both large and bulky hydrophobic substituents in the 4-position of L-2,4-syn Glu are allowed by all three glutamate transporter subtypes EAAT1-3 while maintaining inhibitory activity.

Synthesis of derivatives of prenylacetic acids by reactions of alkyl malonate, cyanoacetate, and acetoacetate with alkylating reagents in ionic liquids

A method for the synthesis of carboxylic acid derivatives containing one or two - CH2CHn(Me)CHn+1CH2 - fragments (n = 0, 1) was developed. The method is based on the alkylation of (di)alkyl malonates, cyanoacetates, and acetoacetates with acyclic prenyl halides in ionic liquids, 1-butyl-3-methylimidazolium hexafluorophosphate and tetrafluoroborate. For the ambident ethyl acetoacetate anion, the reactions with prenyl halides devoid of a double bond in the allylic position relative to the halogen atom carried out in the ionic liquids give mixtures of C- and O-alkylation products, while in the case of allylic prenyl halides, only C-alkylation products are formed. The reactions of ethyl 2-geranylmalonate and 2-geranylacetoacetate with bromocyclohexane and 1-chloro-3-dimethylaminopropane in ionic liquids provided derivatives of pharmacologically active geranylacetic acids. The product yields are higher than those in molecular organic solvents. The ionic liquids were recovered and reused in the alkylation.