52089-55-1

Basic information

• Product Name: ETHYL 2-HYDROXYCAPROATE
• Synonyms: ETHYL DL-2-HYDROXYCAPROATE;ETHYL (+/-)-2-HYDROXYCAPROATE;ETHYL 2-HYDROXYCAPROATE;Ethyl 2-hydroxyhexanoate;ETHYL (+/-)-2-HYDROXYCAPROATE >=97%;Hexanoic acid, 2-hydroxy-, ethyl ester;2-Hydroxycaproic acid ethyl ester;2-Hydroxyhexanoic acid ethyl ester
• CAS NO: 52089-55-1
• Molecular Formula: C₈H₁₆O₃
• Molecular Weight: 160.21
• EINECS: 257-655-2
• Product Categories: Alphabetical Listings;E-F;Flavors and Fragrances;Building Blocks;C8 to C9;Carbonyl Compounds;Chemical Synthesis;Esters;Organic Building Blocks
• Mol File: 52089-55-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 80-83 °C11 mm Hg(lit.)
• Flash Point: 210 °F
• Appearance: /
• Density: 0.967 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.112mmHg at 25°C
• Refractive Index: n20/D 1.425(lit.)
• BRN: 1704446
• CAS DataBase Reference: ETHYL 2-HYDROXYCAPROATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2-HYDROXYCAPROATE(52089-55-1)
• EPA Substance Registry System: ETHYL 2-HYDROXYCAPROATE(52089-55-1)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 52089-55-1(Hazardous Substances Data)

Usage

Description

ETHYL 2-HYDROXYCAPROATE, also known as Ethyl 2-hydroxyhexanoate, is a clear colorless liquid that serves as a crucial starting material in the stereospecific synthesis of 2-fluorohexanoic acid. It is also involved in enantioselective transesterification reactions, which are catalyzed by lipase.

Uses

Used in Pharmaceutical Industry:
ETHYL 2-HYDROXYCAPROATE is used as a starting material for the stereospecific synthesis of 2-fluorohexanoic acid, which is an essential component in the development of various pharmaceutical products. Its role in the synthesis process is crucial for creating specific drug molecules with desired properties and effects.
Used in Chemical Synthesis:
ETHYL 2-HYDROXYCAPROATE is used as a reactant in enantioselective transesterification reactions, which are catalyzed by lipase. These reactions are vital for producing specific enantiomers, which are essential in the development of chiral compounds with unique properties and applications in various industries, including pharmaceuticals, agrochemicals, and fragrances.
Used in Research and Development:
ETHYL 2-HYDROXYCAPROATE is utilized in research and development for studying its chemical properties and potential applications in various fields. Its involvement in enantioselective transesterification reactions makes it an interesting subject for scientists to explore its potential in creating novel compounds and materials with specific characteristics.

InChI:InChI=1/C8H16O3/c1-3-5-6-7(9)8(10)11-4-2/h7,9H,3-6H2,1-2H3/t7-/m0/s1

Upstream product

• 64-17-5 ethanol 
• 636-36-2 rac-2-hydroxyhexanoic acid 
• 64350-07-8 2-hydroxyhexanenitrile 
• 5753-96-8 ethyl 2-oxohexanoate 
• 693-03-8 n-butyl magnesium bromide 
• 95-92-1 oxalic acid diethyl ester 
• 615-96-3 Ethyl 2-bromohexanoate 

Downstream Products

• 5753-96-8 ethyl 2-oxohexanoate 
• 123-66-0 Ethyl hexanoate 
• 6920-22-5 Hexane-1,2-diol 
• 113747-69-6 ethyl (R)-α-hydroxyhexanoate 
• 43201-07-6 (R)-2-hydroxyhexanoic acid 
• 70267-26-4 (S)-2-hydroxyhexanoic acid 
• 93097-40-6 (S)-2-hydroxyhexanoic acid ethyl ester 
• 139698-29-6 ethyl dl-2-hydroxycaproate benzoxyl ester 
• 488863-87-2 4-methoxy-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-octanenitrile 
• 14021-48-8 2-Amino-5-butyl-oxazol-4-one 
• 1265173-66-7 2-{4-[1-(4-trifluoromethoxyphenyl)-1H-[1,2,4]triazol-3-yl]phenylcarbamoyloxy}hexanoic acid ethyl ester 
• 1019196-89-4 5-butyl-4-hydroxy-3-(4-methoxyphenyl)furan-2(5H)-one 
• 149311-29-5 2-((1S,2S,5R)-1-Hydroxy-2-isopropyl-5-methyl-cyclohexyl)-hexanoic acid ethyl ester 

Relevant articles and documents

Asymmetric Transfer Hydrogenation of α-Keto Amides; Highly Enantioselective Formation of Malic Acid Diamides and α-Hydroxyamides

The asymmetric transfer hydrogenation (ATH) of α-keto-1,4-diamides using a tethered Ru/TsDPEN catalyst was achieved in high ee. Studies on derivatives identified the structural elements which lead to the highest enantioselectivities in the products. The α-keto-amide reduction products have been converted to a range of synthetically valuable derivatives.

Iron-catalyzed hydrogenation for the in situ regeneration of an NAD(P)H model: Biomimetic reduction of α-Keto-/α-iminoesters

Two irons for a smoother finish: An NAD(P)H model was regenerated readily in situ by iron-catalyzed reduction with molecular hydrogen. The subsequent biomimetic reduction of α-keto-/ α-iminoesters proceeded smoothly in the presence of an iron-based Lewis acid (LA) to provide α-hydroxyesters and amino acid esters in good to excellent yields (see scheme; NAD(P) +=nicotinamide adenine dinucleotide (phosphate), TM=transition metal). Copyright

HYDROBORATION OF 1-(5-HEXENYL)PIPERIDINE AND trans-1-(3-HEXENYL)PIPERIDINE

1-(5-Hexenyl)piperidine (Ia) and trans-1-(3-hexenyl)piperidine (Ib) were hydroborated with tetrahydrofuran-borane, diborane in situ, 9-borabicyclononane and triethylamine-borane.The hydroboration products were converted to 1-piperidinylhexanols IIa-IIe by hydrolysis with hydrochloric acid and subsequent oxidation with hydrogen peroxide in an alkaline medium.In addition to the alcohols IIa-IIe, the reaction also gave 1-hexylpiperidine (Ic).In the reactions with diborane in situ and triethylamine-borane, thermal isomerisation of the hydroboration products was also studied.Hydroboration of Ia with triethylamine-borane afforded a mixture of spirocyclic amine-boranes IIIa-IIIc from which 6-(1-piperidinyl)-3-hexylboronic acid hydrochloride (IV) was obtained by hydrolysis with hydrochloric acid.Compounds IIIa-IIIc were slowly decomposed with ethanol to give esters of boronic acids Id-If.The synthesis of compounds Ia and Ib is described.