2-Chloroquinoline-3-carbaldehyde

Base Information

• Chemical Name: 2-Chloroquinoline-3-carbaldehyde
• CAS No.: 73568-25-9
• Molecular Formula: C10H6 Cl N O
• Molecular Weight: 191.617
• Hs Code.: 29334900
• European Community (EC) Number: 628-254-3
• DSSTox Substance ID: DTXSID80351108
• Nikkaji Number: J277.188H
• Wikidata: Q72459294
• ChEMBL ID: CHEMBL4528828
• Mol file: 73568-25-9.mol

Synonyms:2-chloroquinoline-3-carbaldehyde;73568-25-9;2-Chloro-3-quinolinecarboxaldehyde;2-Chloroquinoline-3-carboxaldehyde;2-chloro-3-quinoline carboxaldehyde;3-Quinolinecarboxaldehyde, 2-chloro-;2-chloro-3-quinolinecarbaldehyde;2-chloro-3-formylquinoline;2-chloroquinolin-3-carbaldehyde;2-chloro-quinoline-3-carbaldehyde;SCHEMBL372264;CHEMBL4528828;DTXSID80351108;SDKQWXCBSNMYBN-UHFFFAOYSA-N;2-chloro-quinoline-3-carboxaldehyde;STK803332;AKOS000100788;CS-W015838;SB67455;2-Chloro-3-quinolinecarboxaldehyde, 98%;BP-12764;DS-13206;AM20070151;BB 0258201;C2289;FT-0611656;EN300-17224;A837856;Z56899135;F0010-0600;InChI=1/C10H6ClNO/c11-10-8(6-13)5-7-3-1-2-4-9(7)12-10/h1-6

Chemical Property of 2-Chloroquinoline-3-carbaldehyde

Chemical Property:

• Appearance/Colour: YELLOW CRYSTALLINE POWDER.
• Melting Point: 148-150 °C(lit.)
• Boiling Point: 335.8 °C at 760 mmHg
• PKA: -1.31±0.50(Predicted)
• Flash Point: 156.9 °C
• PSA: 29.96000
• Density: 1.364 g/cm³
• LogP: 2.70070
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Air Sensitive
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 191.0137915
• Heavy Atom Count: 13
• Complexity: 197

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Chloroquinoline-3-carbaldehyde ^*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

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=C(C(=N2)Cl)C=O

Technology Process of 2-Chloroquinoline-3-carbaldehyde

There total 24 articles about 2-Chloroquinoline-3-carbaldehyde 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%

N,N-dimethyl-formamide (68-12-2,33513-42-7) + Acetanilid (103-84-4) → 2-chloro-3-quinoline carboxaldehyde (73568-25-9)

Guidance literature:

N,N-dimethyl-formamide; With trichlorophosphate; at 0 ℃;

Acetanilid; at 80 - 90 ℃; for 12h;

DOI:10.1002/jhet.4460

Reference yield: 96.0%

Acetanilid (103-84-4) → 2-chloro-3-quinoline carboxaldehyde (73568-25-9)

Guidance literature:

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

DOI:10.1002/ejoc.201901413

Reference yield: 92.0%

2-Chloroquinoline (612-62-4) → 2-chloro-3-quinoline carboxaldehyde (73568-25-9)

Guidance literature:

With n-butyllithium; diisopropylamine; In tetrahydrofuran; N-methyl-acetamide; acetic acid;

upstream raw materials:

2-chloro-3-(hydroxyiminomethyl)quinoline

acetophenone oxime

N,N-dimethyl-formamide

acetophenone oxime

Downstream raw materials:

3-(4-Chloro-phenyl)-2-piperidin-1-yl-benzo[b][1,8]naphthyridine

3-(4-Chloro-phenyl)-2-morpholin-4-yl-benzo[b][1,8]naphthyridine

3-(4-Chloro-phenylsulfanyl)-2-morpholin-4-yl-benzo[b][1,8]naphthyridine

3-(4-Chloro-phenyl)-2-(4-methyl-piperazin-1-yl)-benzo[b][1,8]naphthyridine

Refernces

• 1、 Baruah, Biswajita,Bhuyan, Pulak J.. "Synthesis of some complex pyrano[2,3-b]- and pyrido[2,3-b]quinolines from simple acetanilides via intramolecular domino hetero Diels-Alder reactions of 1-oxa-1,3-butadienes in aqueous medium". . p. 7099 - 7104. Retrieved 2009.
• 2、 Ramesh, Ekambaram,Sree Vidhya, Tarakkad Krishnaji,Raghunathan, Raghavachary. "Indium chloride/silica gel supported synthesis of pyrano/thiopyranoquinolines through intramolecular imino Diels-Alder reaction using microwave irradiation". . p. 2810 - 2814. Retrieved 2008.
• 3、 Alizadeh, Abdolali,Roosta, Atefeh,Amir Ashjaee Asalemi, Kaveh. "One-pot three-component synthesis of 2H-thiopyrano[2,3-b]quinoline-2,3-dicarboxylates from 2-mercaptoquinoline-3-carbaldehydes, dialkyl acetylenedicarboxylates and Ph3P". . p. 435 - 442. Retrieved 2018.
• 4、 Devi, Ipsita,Baruah, Biswajita,Bhuyan, Pulak J.. "α-cyclisation of tertiary amines: Synthesis of some novel annelated quinolines via a three-component reaction under solvent-free conditions". . p. 2593 - 2596. Retrieved 2006.
• 5、 Liu, Zeng-Chen,Wang, Bao-Dui,Li, Bo,Wang, Qin,Yang, Zheng-Yin,Li, Tian-Rong,Li, Yong. "Crystal structures, DNA-binding and cytotoxic activities studies of Cu(II) complexes with 2-oxo-quinoline-3-carbaldehyde Schiff-bases". . p. 5353 - 5361. Retrieved 2010.
• 6、 Rahimi, Shahnaz,Khoee, Sepideh,Ghandi, Mehdi. "Preparation and characterization of rod-like chitosan–quinoline nanoparticles as pH-responsive nanocarriers for quercetin delivery". . p. 279 - 289. Retrieved 2019.
• 7、 Kumar, Rajnish,Abdullah, Mohd Mustaqeem. "Synthesis, characterization and anticonvulsant potential of 2,5-disubstituted 1,3,4-oxadiazole analogues". . p. 1389 - 1397. Retrieved 2019.
• 8、 Tang, Zhiren,Peng, Yang,Liu, Fangming. "Design and synthesis of novel quinoline derivatives bearing oxadiazole, isoxazoline, triazolothiadiazole, triazolothiadiazine, and piperazine moieties". . p. 2330 - 2338. Retrieved 2020.
• 9、 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.
• 10、 Gaikwad, Nikhil B.,Bansode, Sapana,Biradar, Shankar,Ban, Mayuri,Srinivas, Nanduri,Godugu, Chandraiah,Yaddanapudi, Venkata M.. "New 3-(1H-benzo[d]imidazol-2-yl)quinolin-2(1H)-one-based triazole derivatives: Design, synthesis, and biological evaluation as antiproliferative and apoptosis-inducing agents". . . Retrieved 2021/08/07.