5-Hydroxy-4-octanone

Base Information

• Chemical Name: 5-Hydroxy-4-octanone
• CAS No.: 496-77-5
• Molecular Formula: C8H16O2
• Molecular Weight: 144.214
• Hs Code.: 2914400090
• European Community (EC) Number: 207-830-4
• NSC Number: 1479
• UNII: WG070EDJ4X
• DSSTox Substance ID: DTXSID60862040
• Nikkaji Number: J6.098D
• Wikidata: Q27292617
• Metabolomics Workbench ID: 46950
• Mol file: 496-77-5.mol

Synonyms:5-Hydroxyoctan-4-one;5-Hydroxy-4-octanone;Butyroin;496-77-5;4-Octanone, 5-hydroxy-;5-Octanol-4-one;Octan-4-ol-5-one;FEMA No. 2587;UNII-WG070EDJ4X;WG070EDJ4X;NSC 1479;NSC-1479;EINECS 207-830-4;AI3-05612;5-hydroxy-octan-4-one;4-hydroxy-5-octanone;BUTYROIN [MI];SCHEMBL26945;(+/-)-BUTYROIN;(+/-)-5-Hydroxy-4-octanone;DTXSID60862040;NSC1479;CHEBI:179933;MFCD00021928;5-HYDROXY-4-OCTANONE [FHFI];AKOS006227777;DS-16801;B0971;FT-0623349;D88723;A827795;Q27292617

Chemical Property of 5-Hydroxy-4-octanone

Chemical Property:

• Appearance/Colour: yellowish liquid
• Vapor Pressure: 0.172mmHg at 25°C
• Melting Point: -10°C
• Refractive Index: n20/D 1.4315(lit.)
• Boiling Point: 187.7 °C at 760 mmHg
• PKA: 13.13±0.20(Predicted)
• Flash Point: 72 °C
• PSA: 37.30000
• Density: 0.927 g/cm³
• LogP: 1.51660
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 144.115029749
• Heavy Atom Count: 10
• Complexity: 99.4

Purity/Quality:

99% ^*data from raw suppliers

5-Hydroxyoctan-4-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC(C(=O)CCC)O
• Description: 5-Hydroxy-4-octanone has a sweet, slightly pungent, buttery, nutlike odor and a sweet, buttery, oily taste. May be prepared by reacting sodium metal with ethyl butyrate in boiling ether or in the same fashion starting from methyl butyrate.

Technology Process of 5-Hydroxy-4-octanone

There total 39 articles about 5-Hydroxy-4-octanone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.52%

butyraldehyde (123-72-8) → butyroin (496-77-5)

Guidance literature:

With 1-butyl-1H-1,3-benzodiazole hydrochloride; at 110 ℃; for 2h; under 4500.45 Torr;

Reference yield: 68.0%

carbon monoxide (201230-82-2) + n-propylmagnesium bromide (927-77-5) → butyroin (496-77-5)

Guidance literature:

With tributylphosphine; copper(l) cyanide; In tetrahydrofuran; 1.) -78 deg C; 2.) -78 deg C, 1.5 h; RT, 2 h;

DOI:10.1016/S0040-4039(97)00338-9

Reference yield: 63.0%

butanoic acid ethyl ester (105-54-4) → butyroin (496-77-5)

Guidance literature:

With Na on NaCl support; In diethyl ether; for 1.5h; Product distribution; Heating; other solvent;

DOI:10.1055/s-1997-763

upstream raw materials:

butanoic acid methyl ester

butanoic acid ethyl ester

butyryl chloride

2-oxopentanoic acid

Downstream raw materials:

5-benzylamino-octan-4-one

2-(4-methoxyphenyl)-5-propyl-4-propylidene-1,3,2-oxathiaphosphole 2-sulfide

2,3-dimethyl-2,3-butane diol

octan-4-ol

Refernces

• 1、 -. "Preparation method of acyloin compounds". Paragraph 0018; 0019; 0023; 0024. . Retrieved 2017/08/27.
• 2、 Dong, Kaiwu,Sang, Rui,Soule, Jean-Francois,Bruneau, Christian,Franke, Robert,Jackstell, Ralf,Beller, Matthias. "Efficient Domino Hydroformylation/Benzoin Condensation: Highly Selective Synthesis of α-Hydroxy Ketones". supporting information. p. 18033 - 18037. Retrieved 2015/12/24.