4-Chloro-5,6,7,8-tetrahydroquinoline

Base Information

• Chemical Name: 4-Chloro-5,6,7,8-tetrahydroquinoline
• CAS No.: 133092-34-9
• Molecular Formula: C9H10ClN
• Molecular Weight: 167.64
• Hs Code.: 2933499090
• European Community (EC) Number: 822-645-4
• DSSTox Substance ID: DTXSID80449155
• Wikidata: Q82268535
• Mol file: 133092-34-9.mol

Synonyms:4-chloro-5,6,7,8-tetrahydroquinoline;133092-34-9;Quinoline, 4-chloro-5,6,7,8-tetrahydro-;4-chloro-5,6,7,8-tetrahydro-quinoline;SCHEMBL2087344;DTXSID80449155;PAEQYSUYGGYPRU-UHFFFAOYSA-N;MFCD18803310;SB68507;AS-50177;CS-0102375;EN300-204076;O11216;A888186

Chemical Property of 4-Chloro-5,6,7,8-tetrahydroquinoline

Chemical Property:

• Boiling Point: 150 °C(Press: 5 Torr)
• PKA: 4.46±0.20(Predicted)
• PSA: 12.89000
• Density: 1.185±0.06 g/cm3(Predicted)
• LogP: 2.61380
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 167.0501770
• Heavy Atom Count: 11
• Complexity: 138

Purity/Quality:

NLT 98% ^*data from raw suppliers

4-Chloro-5,6,7,8-tetrahydroquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC2=NC=CC(=C2C1)Cl

Technology Process of 4-Chloro-5,6,7,8-tetrahydroquinoline

There total 8 articles about 4-Chloro-5,6,7,8-tetrahydroquinoline 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: 53.0%

5,6,7,8-tetrahydroquinolin-4-amine (14807-39-7) → 4-chloro-5,6,7,8-tetrahydroquinoline (133092-34-9)

Guidance literature:

5,6,7,8-tetrahydroquinolin-4-amine; With hydrogenchloride; sodium nitrite; In water; acetic acid; at 0 ℃; for 0.166667h;

With hydrogenchloride; copper(l) chloride; In water; acetic acid; at 0 - 20 ℃; for 17h;

DOI:10.1021/acsmedchemlett.8b00053

Reference yield:

4,7-dichloroquinoline (86-98-6,1138471-54-1) → 4-chloro-5,6,7,8-tetrahydroquinoline (133092-34-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: phenol; ammonium carbonate / 110 - 165 °C

2.1: 2 h / Reflux

3.1: platinum(IV) oxide; hydrogen; perchloric acid / acetic acid / 64 h / 20 °C / 2585.81 Torr

4.1: hydrogenchloride / water / 3 h / 70 °C

5.1: hydrogenchloride; sodium nitrite / acetic acid; water / 0.17 h / 0 °C

5.2: 17 h / 0 - 20 °C

With hydrogenchloride; platinum(IV) oxide; perchloric acid; hydrogen; ammonium carbonate; sodium nitrite; phenol; In water; acetic acid; 5.1: |Sandmeyer Reaction / 5.2: |Sandmeyer Reaction;

DOI:10.1021/acsmedchemlett.8b00053

Reference yield:

N-(7-chloroquinolin-4-yl)-acetamide → 4-chloro-5,6,7,8-tetrahydroquinoline (133092-34-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: platinum(IV) oxide; hydrogen; perchloric acid / acetic acid / 64 h / 20 °C / 2585.81 Torr

2.1: hydrogenchloride / water / 3 h / 70 °C

3.1: hydrogenchloride; sodium nitrite / acetic acid; water / 0.17 h / 0 °C

3.2: 17 h / 0 - 20 °C

With hydrogenchloride; platinum(IV) oxide; perchloric acid; hydrogen; sodium nitrite; In water; acetic acid; 3.1: |Sandmeyer Reaction / 3.2: |Sandmeyer Reaction;

DOI:10.1021/acsmedchemlett.8b00053

upstream raw materials:

5,6,7,8-tetrahydro-quinolin-4-ol

5,6,7,8-tetrahydroquinolin-4-amine

4-nitroquinoline-N-oxide

4-quinolinol 1-oxide

Downstream raw materials:

1-methyl-4-veratryl-1,2,3,4,5,6,7,8-octahydro-quinoline

4-veratryl-5,6,7,8-tetrahydro-quinoline

(4-methoxy-phenyl)-(5,6,7,8-tetrahydro-[4]quinolyl)-acetonitrile

Refernces