(1R)-1-(3,4-dimethoxyphenyl)-2-iodoethanol

Base Information

• Chemical Name: (1R)-1-(3,4-dimethoxyphenyl)-2-iodoethanol
• CAS No.: 833353-17-6
• Molecular Formula: C10H13IO3
• Molecular Weight: 308.11289
• DSSTox Substance ID: DTXSID30458499
• Wikidata: Q82281829
• Mol file: 833353-17-6.mol

Synonyms:833353-17-6;(1R)-1-(3,4-dimethoxyphenyl)-2-iodoethanol;(alphaR)-alpha-(Iodomethyl)-3,4-dimethoxybenzenemethanol;FT-0670375;(|AR)-|A-(Iodomethyl)-3,4-dimethoxybenzenemethanol;DTXSID30458499

Chemical Property of (1R)-1-(3,4-dimethoxyphenyl)-2-iodoethanol

Chemical Property:

• PSA: 38.69000
• LogP: 2.17220
• Solubility.: Dichloromethane, Ethyl Acetate
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 307.99094
• Heavy Atom Count: 14
• Complexity: 165

Purity/Quality:

97% ^*data from raw suppliers

(αR)-α-(Iodomethyl)-3,4-dimethoxybenzenemethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C(CI)O)OC
• Isomeric SMILES: COC1=C(C=C(C=C1)[C@H](CI)O)OC
• Uses: (αR)-α-(Iodomethyl)-3,4-dimethoxy-benzenemethanol is used in the preparation of (R)-Isoprenaline, (R)-Norfluoxetine and (R)-Fluoxetine using stereoselective dihydroxylation method as key synthetic step.

Technology Process of (1R)-1-(3,4-dimethoxyphenyl)-2-iodoethanol

There total 3 articles about (1R)-1-(3,4-dimethoxyphenyl)-2-iodoethanol 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: 95.0%

(R)-toluene-4-sulfonic acid 2-(3,4-dimethoxyphenyl)-2-hydroxyethyl ester (833353-09-6) → (R)-1-(3,4-dimethoxyphenyl)-2-iodo-ethanol (833353-17-6)

Guidance literature:

With sodium iodide; In acetone; for 6h; Heating;

DOI:10.1016/j.tetasy.2004.11.005

Reference yield:

3,4-dimethoxystyrene (6380-23-0) → (R)-1-(3,4-dimethoxyphenyl)-2-iodo-ethanol (833353-17-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / potassium ferricyanide; potassium carbonate; osmium tetroxide / (DHQD)2PHAL / H₂O; 2-methyl-propan-2-ol; toluene / 24 h / 0 °C

2: 95 percent / dibutyltin oxide; triethylamine / CH₂Cl₂ / 0.75 h / 20 °C

3: 95 percent / sodium iodide / acetone / 6 h / Heating

With osmium(VIII) oxide; di(n-butyl)tin oxide; potassium carbonate; triethylamine; sodium iodide; potassium hexacyanoferrate(III); 1,4-bis(9-O-dihydroquinidine)phthalazine; In dichloromethane; water; acetone; toluene; tert-butyl alcohol; 1: Sharpless asymmetric dihydroxylation;

DOI:10.1016/j.tetasy.2004.11.005

Reference yield:

(R)-2-hydroxy-1-(3,4-dimethoxyphenyl)ethanol (326491-79-6) → (R)-1-(3,4-dimethoxyphenyl)-2-iodo-ethanol (833353-17-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / dibutyltin oxide; triethylamine / CH₂Cl₂ / 0.75 h / 20 °C

2: 95 percent / sodium iodide / acetone / 6 h / Heating

With di(n-butyl)tin oxide; triethylamine; sodium iodide; In dichloromethane; acetone;

DOI:10.1016/j.tetasy.2004.11.005

upstream raw materials:

(R)-toluene-4-sulfonic acid 2-(3,4-dimethoxyphenyl)-2-hydroxyethyl ester

3,4-dimethoxystyrene

(R)-2-hydroxy-1-(3,4-dimethoxyphenyl)ethanol

Downstream raw materials:

isoprenaline

(R)-(-)-1-(3,4-dimethoxyphenyl)-2-(isopropylamino)ethanol

Refernces