3-Benzyloxy-1-propanol

Base Information

• Chemical Name: 3-Benzyloxy-1-propanol
• CAS No.: 4799-68-2
• Molecular Formula: C10H14O2
• Molecular Weight: 166.22
• Hs Code.: 2909499000
• NSC Number: 406922
• DSSTox Substance ID: DTXSID30324524
• Nikkaji Number: J100.239B
• Wikidata: Q72442532
• Mol file: 4799-68-2.mol

Synonyms:3-Benzyloxy-1-propanol;4799-68-2;3-(Benzyloxy)propan-1-ol;3-Benzyloxypropanol;1-Propanol, 3-(phenylmethoxy)-;3-phenylmethoxypropan-1-ol;3-Benzyloxypropan-1-ol;3-(Benzyloxy)-1-propanol;1-Propanol, 3-(benzyloxy)-;3-(BENZYLOXY)-PROPANE-1-OL;MFCD00029659;1,3-Propanediol monobenzyl ether;3-Benzyloxy-propan-1-ol;3-(Benzyl-Oxy)Propan-1-Ol;3-benzyloxy-propanol;NSC406922;C(OCCCO)c1ccccc1;3-(benzyloxy)propanol;3-benzyloxy-l-propanol;3-benzyloxypropane-1-ol;3-phenylmethoxy-1-propanol;1-(Benzyloxy)-3-propanol;SCHEMBL345616;3-(phenylmethoxy)-1-propanol;3-(Benzyloxy)-1-propanol #;3-Benzyloxy-1-propanol, 97%;DTXSID30324524;3-[(phenylmethyl)oxy]propan-1-ol;Trimethylene glycol monobenzyl ether;BBL102421;STL556223;AKOS009156986;CS-W004789;NSC 406922;NSC-406922;AC-25474;SY015683;B3277;FT-0635447;EN300-115110;A827418;W-202841;Z1080358454

Chemical Property of 3-Benzyloxy-1-propanol

Chemical Property:

• Appearance/Colour: Colorless viscous liquid
• Vapor Pressure: 0.00264mmHg at 25°C
• Melting Point: 38oC
• Refractive Index: n20/D 1.516
• Boiling Point: 274.3 °C at 760 mmHg
• PKA: 14.88±0.10(Predicted)
• Flash Point: 126.9 °C
• PSA: 29.46000
• Density: 1.044 g/cm³
• LogP: 1.58560
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 166.099379685
• Heavy Atom Count: 12
• Complexity: 98

Purity/Quality:

99% ^*data from raw suppliers

3-Benzyloxy-1-propanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COCCCO
• Uses: 3-Benzyloxy-1-propanol may be used for the synthesis of 1-benzyloxy-3-iodopropane.

Technology Process of 3-Benzyloxy-1-propanol

There total 37 articles about 3-Benzyloxy-1-propanol 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: 100.0%

benzyl bromide (100-39-0) + trimethyleneglycol (504-63-2) → 3-benzyloxypropan-1-ol (4799-68-2)

Guidance literature:

With sodium hydride; at 0 - 100 ℃; for 18h; Inert atmosphere;

DOI:10.1080/00498254.2021.1943566

Reference yield: 97.0%

3-tert-butyldimethylsilyloxy-1-propyl benzyl ether (203738-77-6) → 3-benzyloxypropan-1-ol (4799-68-2)

Guidance literature:

With diisobutylaluminium hydride; In hexane; dichloromethane; at -20 ℃; for 3.5h;

DOI:10.1016/j.tetlet.2010.09.126

Reference yield: 95.0%

[2-(3-benzyloxy-propoxymethoxy)-ethyl]-trimethyl-silane → 3-benzyloxypropan-1-ol (4799-68-2)

Guidance literature:

With magnesium bromide; In diethyl ether; nitromethane; at 20 ℃; for 5h;

DOI:10.1021/ol0057784

upstream raw materials:

2-phenyl-1,3-dioxane

benzyl chloride

trimethyleneglycol

benzyl alcohol

Downstream raw materials:

1-chloro-3-benzyloxypropane

1-[(3-bromopropoxy)methyl]-benzene

1-benzyloxy-3-tosyloxypropane

methyl β-benzyloxypropionate

Refernces

Nonracemic α-Fluoro Aldehydes: Asymmetric Synthesis of 4-Deoxy-4-fluoro-D-arabinopyranose

10.1021/jo9714829

The research focuses on the enantioselective synthesis of epimerizable R-fluoro aldehydes and their application in the synthesis of 4-deoxy-4-fluoro-D-arabinopyranose. Key chemicals involved in this research include 3-(benzyloxy)-1-propanol, which was oxidized to an acid and then converted to an acid chloride. The acid chloride reacted with the lithium salt of (4R,5S)-(+)-4-methyl-5-phenyl-2-oxazolidinone to form an intermediate. Electrophilic fluorination using N-fluorobenzenesulfonimide (NFSi) yielded a crucial R-fluoro carboximide. Reduction with LiBH4 produced a 2-fluorohydrin, which was subsequently oxidized using the Dess-Martin periodinane reagent to form the desired R-fluoro aldehydes. These aldehydes were then used in a Horner-Wadsworth-Emmons reaction and a Sharpless asymmetric dihydroxylation to ultimately synthesize the target 4-deoxy-4-fluoro-D-arabinopyranose. The study highlights the importance of fluorine in enhancing biological and pharmacological activity, and the challenges and successes in synthesizing and utilizing chiral R-fluoro aldehydes as building blocks.