2-Chloro-5,7-dimethylquinoline-3-carboxaldehyde

Base Information

• Chemical Name: 2-Chloro-5,7-dimethylquinoline-3-carboxaldehyde
• CAS No.: 482639-32-7
• Molecular Formula: C12H10ClNO
• Molecular Weight: 219.671
• Hs Code.: 2933499090
• European Community (EC) Number: 809-408-0
• DSSTox Substance ID: DTXSID50355971
• Wikidata: Q82135076
• ChEMBL ID: CHEMBL1546522
• Mol file: 482639-32-7.mol

Synonyms:482639-32-7;2-Chloro-5,7-dimethylquinoline-3-carboxaldehyde;2-chloro-5,7-dimethylquinoline-3-carbaldehyde;MLS000709258;2-chloro-5,7-dimethyl-3-quinolinecarboxaldehyde;SMR000289925;2-chloro-5,7-dimethyl-3-quinolinecarbaldehyde;2-Chloro-5,7-dimethyl-quinoline-3-carbaldehyde;cid_818677;CHEMBL1546522;REGID_for_CID_818677;SCHEMBL14125963;BDBM34907;DTXSID50355971;HMS2592C22;MFCD02227047;AKOS000674003;AB11592;CS-0280392;2-chloro-5,7-dimethylquinolin-3-carbaldehyde;EN300-250826;2-chloranyl-5,7-dimethyl-quinoline-3-carbaldehyde;2-Chloro-5,7-dimethylquinoline-3-carboxaldehyde, AldrichCPR

Chemical Property of 2-Chloro-5,7-dimethylquinoline-3-carboxaldehyde

Chemical Property:

• Vapor Pressure: 1.57E-05mmHg at 25°C
• Refractive Index: 1.655
• Boiling Point: 365.4 °C at 760 mmHg
• Flash Point: 174.8 °C
• PSA: 29.96000
• Density: 1.27 g/cm³
• LogP: 3.31750
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 219.0450916
• Heavy Atom Count: 15
• Complexity: 246

Purity/Quality:

98%min ^*data from raw suppliers

2-Chloro-5,7-dimethylquinoline-3-carboxaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C2C=C(C(=NC2=C1)Cl)C=O)C
• Uses: 2-Chloro-5,7-dimethylquinoline-3-carboxaldehyde is a useful reactant in the synthesis of various organic compounds such as isoxazolo[5,?4-?b]?quinoline derivatives, and 2-?chloroquinolinyl-?4-?quinolinones.

Technology Process of 2-Chloro-5,7-dimethylquinoline-3-carboxaldehyde

There total 3 articles about 2-Chloro-5,7-dimethylquinoline-3-carboxaldehyde 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%

N-acetyl-3,5-dimethylaniline (2050-45-5) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → 2-chloro-5,7-dimethylquinoline-3-carbaldehyde (482639-32-7)

Guidance literature:

N,N-dimethyl-formamide; With trichlorophosphate; for 2h; Inert atmosphere; Reflux;

N-acetyl-3,5-dimethylaniline; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1021/jm201372q

Reference yield: 95.0%

N-acetyl-3,5-dimethylaniline (2050-45-5) → 2-chloro-5,7-dimethylquinoline-3-carbaldehyde (482639-32-7)

Guidance literature:

With trichlorophosphate; In N,N-dimethyl-formamide; at 80 ℃; for 8h; Schlenk technique; Inert atmosphere;

DOI:10.1002/ejoc.201901413

Reference yield:

3,5-dimethylaminoaniline (108-69-0) → 2-chloro-5,7-dimethylquinoline-3-carbaldehyde (482639-32-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

1.2: pH 12 - 14 / Cooling with ice

2.1: trichlorophosphate / 2 h / Inert atmosphere; Reflux

2.2: 3 h / 20 °C

2.3: Cooling with ice

With trichlorophosphate; In tetrahydrofuran;

upstream raw materials:

N-acetyl-3,5-dimethylaniline

N,N-dimethyl-formamide

3,5-dimethylaminoaniline

Downstream raw materials:

C₃₅H₃₀N₂O₄

C₃₆H₃₀N₂O₄

C₃₅H₂₉ClFN₃O₃

Refernces

• 1、 Bokosi, Fostino R.B.,Beteck, Richard M.,Mbaba, Mziyanda,Mtshare, Thanduxolo E.,Laming, Dustin,Hoppe, Heinrich C.,Khanye, Setshaba D.. "Design, synthesis and biological evaluation of mono- and bisquinoline methanamine derivatives as potential antiplasmodial agents". supporting information. . Retrieved 2021/03/01.
• 2、 Ghazvini, Helya Janatian,Armaghan, Mahsa,Janiak, Christoph,Balalaie, Saeed,Müller, Thomas J. J.. "Coupling-Isomerization-Cycloisomerization Reaction (CICIR) – An Unexpected and Efficient Domino Approach to Luminescent 2-(Hydroxymethylene)indenones". supporting information. p. 7058 - 7062. Retrieved 2019/11/11.