1,9-Nonanediol

Base Information

• Chemical Name: 1,9-Nonanediol
• CAS No.: 3937-56-2
• Molecular Formula: C9H20O2
• Molecular Weight: 160.257
• Hs Code.: 2905.39
• European Community (EC) Number: 223-517-5
• NSC Number: 5416
• UNII: N4385C65C6
• DSSTox Substance ID: DTXSID5063237
• Nikkaji Number: J190B
• Wikidata: Q20054536
• NCI Thesaurus Code: C28777
• Mol file: 3937-56-2.mol

Synonyms:1,9-nonanediol

Chemical Property of 1,9-Nonanediol

Chemical Property:

• Appearance/Colour: white fused crystalline solid
• Vapor Pressure: 0.000196mmHg at 25°C
• Melting Point: 45-47 °C
• Refractive Index: 1.456
• Boiling Point: 292.4 °C at 760 mmHg
• PKA: 14.89±0.10(Predicted)
• Flash Point: 137 °C
• PSA: 40.46000
• Density: 0.931 g/cm³
• LogP: 1.70170
• Storage Temp.: Store below +30°C.
• Solubility.: Soluble in methanol.
• Water Solubility.: 5.7g/L at 20℃
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 8
• Exact Mass: 160.146329876
• Heavy Atom Count: 11
• Complexity: 56.6

Purity/Quality:

99%, ^*data from raw suppliers

1,9-Nonanediol ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(CCCCO)CCCCO
• General Description: 1,9-Nonanediol, also known as a,w-Nonanediol, NSC 5416, or 1,9-Dihydroxynonane, serves as a key intermediate in the chemoenzymatic synthesis of pinellic acids, which exhibit adjuvant activity for influenza vaccines. In this process, it is monoprotected with para-methoxybenzyl chloride (PMBCl) to facilitate subsequent oxidation and enantioselective transformations, contributing to the efficient asymmetric synthesis of biologically active compounds. 1,9-Nonanediol's role underscores its utility in multi-step synthetic pathways involving biocatalysis and chiral modifications.

Technology Process of 1,9-Nonanediol

There total 41 articles about 1,9-Nonanediol 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: 99.0%

9-hydroxynonyl-1-triphenylmethylether (82777-72-8) → 1,9-Nonanediol (3937-56-2)

Guidance literature:

9-hydroxynonyl-1-triphenylmethylether; With n-butyllithium; In hexane; at 0 ℃;

With naphthalene; lithium; In tetrahydrofuran; hexane; at 0 - 20 ℃; for 20h;

DOI:10.1055/s-2003-41057

Reference yield: 99.0%

1,9-di(trityloxy)nonane (634902-05-9) → 1,9-Nonanediol (3937-56-2)

Guidance literature:

With naphthalene; lithium; In tetrahydrofuran; at -30 ℃; for 3.5h;

DOI:10.1055/s-2003-41057

Reference yield: 98.0%

9-(triphenylsilyloxy)-1-nonanol (109027-55-6) → 1,9-Nonanediol (3937-56-2)

Guidance literature:

With naphthalene; lithium; In tetrahydrofuran; methanol; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2005.03.145

upstream raw materials:

Dimethyl azelate

diethyl azelate

azelaic acid

oleoyl alcohol

Downstream raw materials:

9-morpholino-nonan-1-ol

1,9-dimorpholino-nonane

1,9-dichlorononane

9-chloro-1-nonanol

Refernces

A chemoenzymatic asymmetric synthesis of (9S,12S,13S)- and (9S,12RS,13S)-pinellic acids

10.1016/j.tetlet.2009.06.069

The study presents a chemoenzymatic asymmetric synthesis of (9S,12S,13S)- and (9S,12RS,13S)-pinellic acids, which are significant due to their adjuvant activity for influenza vaccines. The synthesis involves several key steps and chemicals. Initially, 1,9-nonanediol is monoprotected with para-methoxybenzyl chloride (PMBCl) to form compound 3, which is then oxidized with pyridinium chlorochromate (PCC) to yield aldehyde 4. The reaction of 4 with vinylmagnesium bromide produces allylic alcohol 5. A crucial step involves Novozyme 435-catalyzed acetylation of 5 with vinyl acetate, yielding (S)-acetate 6 and (R)-alcohol 5 with high enantiomeric excesses. Another significant component, (R)-cyclohexylideneglyceraldehyde 7, is reacted with CH3(CH2)4Li to form the anti-triol derivative 8, which is then protected with tert-butyldiphenylsilyl chloride (TPSCl) to form silyl derivative 9. The acetal function of 9 is removed to yield diol 10, which is cleaved with NaIO4 to form aldehyde 11. The reaction of 11 with vinylmagnesium bromide produces allylic alcohol 12. A cross-metathesis reaction between (S)-5 and 12, catalyzed by Grubbs 2nd generation catalyst, yields diol 13. Further steps involve silylation, oxidative removal of PMB protection, oxidation to form acid 16, and final desilylation to obtain the target pinellic acids. This method highlights the use of biocatalysis and chiral templates for efficient asymmetric synthesis, offering a simpler and more efficient route to these biologically active compounds.

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