2-Chloro-6-methoxyquinoline-3-methanol

Base Information

• Chemical Name: 2-Chloro-6-methoxyquinoline-3-methanol
• CAS No.: 92172-83-3
• Molecular Formula: C11H10ClNO2
• Molecular Weight: 223.659
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID50357713
• Wikidata: Q82137749
• Mol file: 92172-83-3.mol

Synonyms:2-Chloro-6-methoxyquinoline-3-methanol;92172-83-3;(2-chloro-6-methoxyquinolin-3-yl)methanol;2-chloro-3-hydroxymethyl-6-methoxyquinoline;3-Quinolinemethanol,2-chloro-6-methoxy-;(2-Chloro-6-methoxy-quinolin-3-yl)-methanol;Oprea1_656524;Oprea1_842324;SCHEMBL1886013;DTXSID50357713;AKKPSGFLKITYGV-UHFFFAOYSA-N;MFCD02232332;AKOS000589298;SB69825;(2-chloro-6-methoxy-3-quinolyl)methanol;TS-01519;CS-0314431;FT-0642223;A844163

Chemical Property of 2-Chloro-6-methoxyquinoline-3-methanol

Chemical Property:

• Vapor Pressure: 7.89E-07mmHg at 25°C
• Melting Point: 133 °C
• Refractive Index: 1.642
• Boiling Point: 391.4 °C at 760 mmHg
• Flash Point: 190.5 °C
• PSA: 42.35000
• Density: 1.342 g/cm³
• LogP: 2.38910
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 223.0400063
• Heavy Atom Count: 15
• Complexity: 215

Purity/Quality:

98%min ^*data from raw suppliers

2-Chloro-6-methoxyquinoline-3-methanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=CC(=C(N=C2C=C1)Cl)CO
• Uses: 2-Chloro-6-methoxyquinoline-3-methanol is a useful reactant for the synthesis tetrazolylmethyl quinolines.

Technology Process of 2-Chloro-6-methoxyquinoline-3-methanol

There total 4 articles about 2-Chloro-6-methoxyquinoline-3-methanol 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: 98.0%

2-chloro-6-methoxyquinolin-3-carboxaldehyde (73568-29-3) → 3-(hydroxymethyl)-2-chloro-6-methoxyquinoline (92172-83-3)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.5h;

Reference yield:

4-methoxyacetanilide (51-66-1) → 3-(hydroxymethyl)-2-chloro-6-methoxyquinoline (92172-83-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 - 90 °C

2: sodium tetrahydroborate; water / 0.02 h / 20 °C

With sodium tetrahydroborate; water;

DOI:10.2478/s11696-010-0058-y

Reference yield:

C12H11ClN2O2 → 3-(hydroxymethyl)-2-chloro-6-methoxyquinoline (92172-83-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trichlorophosphate / Cooling

1.2: Reflux

2.1: sodium tetrahydroborate / methanol / 20 °C

With sodium tetrahydroborate; trichlorophosphate; In methanol; 1.1: |Vilsmeier-Haack Formylation / 1.2: |Vilsmeier-Haack Formylation;

DOI:10.1016/j.ejmech.2017.01.043

upstream raw materials:

2-chloro-6-methoxyquinolin-3-carboxaldehyde

4-methoxyacetanilide

4-methoxy-aniline

Downstream raw materials:

2-chloro-3-(chloromethyl)-6-methoxyquinoline

2-chloro-6-methoxyquinolin-3-carboxaldehyde

(2-chloro-6-methoxyquinolin-3-yl)methyl 2,4-dichlorobenzoate

C₂₂H₂₀ClN₅O₃

Refernces

• 1、 Marganakop,Kamble,Nesaragi,Bayannavar,Joshi,Kattimani,Sudha. "Microwave assisted synthesis of quinoline fused benzodiazepines as anxiolytic and antimicrobial agents". . p. 1107 - 1114. Retrieved 2021/05/10.
• 2、 Mahesh, Kukkamudi,Ravi, Kanakaraju,Rathod, Praveen Kumar,Leelavathi, Panaganti. "Convenient synthesis of quinoline-fused triazolo-azepine/oxepine derivatives through Pd-catalyzed C-H functionalisation of triazoles". . p. 2367 - 2373. Retrieved 2020/02/20.