Product Name

  • Name

    7-Chloro-2-methylquinoline

  • EINECS 440-600-3
  • CAS No. 4965-33-7
  • Article Data33
  • CAS DataBase
  • Density 1.225 g/cm3
  • Solubility
  • Melting Point 74-78 °C(lit.)
  • Formula C10H8ClN
  • Boiling Point 278.177 °C at 760 mmHg
  • Molecular Weight 177.633
  • Flash Point 148.736 °C
  • Transport Information
  • Appearance white to light yellow crystal powder
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 4965-33-7 (7-Chloro-2-methylquinoline)
  • Hazard Symbols HarmfulXn
  • Synonyms 7-Chloro-2-methylquinoline(7-Chloroquinaldine);Quinoline, 7-chloro-2-methyl-;7-chloro-2-methyl-quinoline;7-chlorquinaldine;7-Chloroquinaldine;
  • PSA 12.89000
  • LogP 3.19660

Synthetic route

4-Hydroxy-4-methyl-2-pentanone
123-42-2

4-Hydroxy-4-methyl-2-pentanone

2-amino-4-chlorobenzaldehyde
59236-37-2

2-amino-4-chlorobenzaldehyde

2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

Conditions
ConditionsYield
With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); sodium t-butanolate In toluene at 70℃; Inert atmosphere; Schlenk technique; chemoselective reaction;90%
trans-Crotonaldehyde
123-73-9

trans-Crotonaldehyde

3-chloro-aniline
108-42-9

3-chloro-aniline

2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

Conditions
ConditionsYield
With phospho-tungstic acid; phosphotungstic acid; silica gel for 0.2h; Doebner-Miller reaction; microwave irradiation;86%
With hydrogenchloride; chloranil In tetrahydrofuran; methanol; iso-butanol
7-chloro-2-methyl-1,2,3,4-tetrahydroquinoline

7-chloro-2-methyl-1,2,3,4-tetrahydroquinoline

2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

Conditions
ConditionsYield
With tetrasodium cobalt(II) 4,4',4'',4'''-tetrasulphophthalocyanine In water; ethyl acetate at 20℃; for 18h; Irradiation; Green chemistry;85%
With rose bengal; oxygen In N,N-dimethyl acetamide at 20℃; for 24h; Irradiation;73%
With rose bengal In N,N-dimethyl acetamide at 20℃; for 28h; Irradiation;73%
With tris(bipyridine)ruthenium(II) dichloride hexahydrate; Co(dmgH)2(4-MeCO2Py)Cl In water at 28℃; for 12h; Schlenk technique; Inert atmosphere; Irradiation;73%
With 1,10-Phenanthroline; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium tert-butylate; oxygen; nickel dibromide In tert-Amyl alcohol at 95℃; for 48h;42%
ethyl vinyl ether
109-92-2

ethyl vinyl ether

3-chloro-aniline
108-42-9

3-chloro-aniline

2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

Conditions
ConditionsYield
With magnetite-palladium-graphene nanocomposite In acetonitrile at 80℃; for 12h;72%
ethanol
64-17-5

ethanol

3-chloro-aniline
108-42-9

3-chloro-aniline

A

2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

B

2-methyl-5-chloroquinoline
4964-69-6

2-methyl-5-chloroquinoline

Conditions
ConditionsYield
With iron(III) chloride hexahydrate In tetrachloromethane at 140℃; for 4h; Autoclave; Inert atmosphere; Sealed tube;A 11%
B 67%
3-chloro-aniline
108-42-9

3-chloro-aniline

crotonaldehyde
123-73-9

crotonaldehyde

2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

Conditions
ConditionsYield
Stage #1: 3-chloro-aniline; crotonaldehyde With hydrogenchloride In water; toluene at 110℃; for 1.5h;
Stage #2: With zinc(II) chloride In tetrahydrofuran; water; acetone; toluene at 60℃; for 1h; Cooling with ice;
30%
With hydrogenchloride In water; toluene for 2h; Doebner-Miller Quinoline Synthesis; Reflux;
With hydrogenchloride; 1-methyl-2-nitrobenzene In water at 100℃; for 9h; Reagent/catalyst; Skraup Quinoline Synthesis; Reflux;
1,1,3-trimethoxybutane
10138-89-3

1,1,3-trimethoxybutane

3-chloroaniline hydrochloride
141-85-5

3-chloroaniline hydrochloride

2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

Conditions
ConditionsYield
With ethanol; iron(III) chloride; zinc(II) chloride
acetaldehyde
75-07-0

acetaldehyde

3-chloro-aniline
108-42-9

3-chloro-aniline

2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

Conditions
ConditionsYield
With hydrogenchloride
acetaldehyde
75-07-0

acetaldehyde

3-chloro-aniline
108-42-9

3-chloro-aniline

A

2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

B

2-methyl-5-chloroquinoline
4964-69-6

2-methyl-5-chloroquinoline

Conditions
ConditionsYield
With di-μ-chlorobis(norbornadiene)dirhodium(I); 3-Nitrochlorobenzene In ethanol at 180℃; for 4h; Yield given. Yields of byproduct given;
β-(m-chloroanilino)crotonaldehyde
106237-28-9

β-(m-chloroanilino)crotonaldehyde

A

2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

B

2-methyl-5-chloroquinoline
4964-69-6

2-methyl-5-chloroquinoline

Conditions
ConditionsYield
With sulfuric acid at 25℃; Rate constant;
formaldehyd
50-00-0

formaldehyd

3-chloro-aniline
108-42-9

3-chloro-aniline

A

2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

B

2-methyl-5-chloroquinoline
4964-69-6

2-methyl-5-chloroquinoline

Conditions
ConditionsYield
With sulfuric acid; sodium 3-nitrobenzenesulfonate at 120 - 130℃; for 1.83333h;A 8.64 g
B 0.28 g
With sulfuric acid; sodium 3-nitrobenzenesulfonate at 120 - 130℃; for 1.83333h;A 8.64 g
B 0.79 g
trans-Crotonaldehyde
123-73-9

trans-Crotonaldehyde

3-chloro-aniline
108-42-9

3-chloro-aniline

A

2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

B

2-methyl-5-chloroquinoline
4964-69-6

2-methyl-5-chloroquinoline

Conditions
ConditionsYield
With hydrogenchloride; chloranil In various solvent(s) for 0.333333h; Heating;
3-chloro-aniline
108-42-9

3-chloro-aniline

m-nitro-benzenesulfonate sodium

m-nitro-benzenesulfonate sodium

A

2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

B

5-chloro-quinaldine

5-chloro-quinaldine

Conditions
ConditionsYield
at 120 - 130℃; Behandeln mit Paraldehyd; Trennung der Isomeren ueber die Pikrate;
trans-Crotonaldehyde
123-73-9

trans-Crotonaldehyde

3-chloro-aniline
108-42-9

3-chloro-aniline

A

2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

B

2-methyl-5-chloroquinoline
4964-69-6

2-methyl-5-chloroquinoline

C

N-ethyl-3-chloroaniline
15258-44-3

N-ethyl-3-chloroaniline

D

Butyl-(3-chloro-phenyl)-amine
75813-68-2

Butyl-(3-chloro-phenyl)-amine

E

C10H12ClN

C10H12ClN

F

C10H12ClN

C10H12ClN

G

7-chlorotetrahydroquinaldine

7-chlorotetrahydroquinaldine

Conditions
ConditionsYield
With hydrogenchloride; chloranil In ethanol; water Product distribution; Heating; other substituted anilines; var. solvents, var. oxidants and acids, var. temperatures;
1-(m-chlorophenylamino)-3-(m-chlorophenylimino)-1-butene hydrochloride
106237-20-1

1-(m-chlorophenylamino)-3-(m-chlorophenylimino)-1-butene hydrochloride

2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 0.29 g / NaOH / H2O; ethanol / 2 h / 80 °C
2: 8.64 g / sodium m-nitrobenzenesulfonate, 72.2 percent H2SO4 / 1.83 h / 120 - 130 °C
View Scheme
aqueous crotonaldehyde

aqueous crotonaldehyde

diethyl ether
60-29-7

diethyl ether

3-chloro-aniline
108-42-9

3-chloro-aniline

2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

Conditions
ConditionsYield
zinc(II) chloride In hydrogenchloride; water
ethyl vinyl ether
109-92-2

ethyl vinyl ether

3-chloro-aniline
108-42-9

3-chloro-aniline

A

2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

B

N-ethyl-3-chloroaniline
15258-44-3

N-ethyl-3-chloroaniline

Conditions
ConditionsYield
With palladium on activated charcoal; palladium dichloride In acetonitrile at 80℃; for 24h;A 68 %Chromat.
B 23 %Chromat.
3,3'-dichloroazobenzene
15426-14-9, 106131-20-8, 106131-24-2

3,3'-dichloroazobenzene

A

2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

B

2-methyl-5-chloroquinoline
4964-69-6

2-methyl-5-chloroquinoline

Conditions
ConditionsYield
With copper(l) iodide In 1,2-dichloro-ethane at 120℃; for 12h; Inert atmosphere; Sealed tube; Overall yield = 44 %; Overall yield = 15.6 mg;
3-chloro-aniline
108-42-9

3-chloro-aniline

A

2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

B

2-methyl-5-chloroquinoline
4964-69-6

2-methyl-5-chloroquinoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: copper(I) bromide; pyridine / toluene / 20 h / 60 °C
2: copper(l) iodide / 1,2-dichloro-ethane / 12 h / 120 °C / Inert atmosphere; Sealed tube
View Scheme
ethylene glycol
107-21-1

ethylene glycol

3-chloro-aniline
108-42-9

3-chloro-aniline

A

2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

B

2-methyl-5-chloroquinoline
4964-69-6

2-methyl-5-chloroquinoline

Conditions
ConditionsYield
With tetrachloromethane; iron(III) chloride hexahydrate at 150℃; for 8h; Inert atmosphere; Sealed tube; Autoclave; Overall yield = 56 %;
1.3-butanediol
18826-95-4, 107-88-0

1.3-butanediol

3-chloro-aniline
108-42-9

3-chloro-aniline

A

2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

B

2-methyl-5-chloroquinoline
4964-69-6

2-methyl-5-chloroquinoline

C

7-chloro-4-methyl-quinoline
40941-53-5

7-chloro-4-methyl-quinoline

Conditions
ConditionsYield
With iron(III) chloride hexahydrate In tetrachloromethane at 150℃; for 8h; Inert atmosphere; Overall yield = 79 %;
(2-amino-4-chlorophenyl)methanol
37585-16-3

(2-amino-4-chlorophenyl)methanol

2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: manganese(IV) oxide / dichloromethane / Inert atmosphere
2: chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); sodium t-butanolate / toluene / 70 °C / Inert atmosphere; Schlenk technique
View Scheme
2-Amino-4-chlorobenzoic acid
89-77-0

2-Amino-4-chlorobenzoic acid

2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / Inert atmosphere
2: manganese(IV) oxide / dichloromethane / Inert atmosphere
3: chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); sodium t-butanolate / toluene / 70 °C / Inert atmosphere; Schlenk technique
View Scheme
7-chloro-2-methyl-1,2,3,4-tetrahydroquinoline

7-chloro-2-methyl-1,2,3,4-tetrahydroquinoline

A

2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

B

(R)-7-chloro-2-methyl-1,2,3,4-tetrahydroquinoline

(R)-7-chloro-2-methyl-1,2,3,4-tetrahydroquinoline

Conditions
ConditionsYield
With monoamine oxidase from Pseudomonas monteilii ZMU-T01 In aq. buffer at 37℃; pH=7.5; Resolution of racemate; enantioselective reaction;A n/a
B n/a
3-(3-chloroanilino)butyraldehyde

3-(3-chloroanilino)butyraldehyde

2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dichloromethane / 5 h / 40 °C / Acidic conditions
2: sulfuric acid / toluene; water / 100 °C
3: water / 70 °C
View Scheme
C10H10ClN

C10H10ClN

2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

Conditions
ConditionsYield
In water at 70℃; Temperature; Reagent/catalyst;
2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

7-chloro-2-methyl-1,2,3,4-tetrahydroquinoline

7-chloro-2-methyl-1,2,3,4-tetrahydroquinoline

Conditions
ConditionsYield
With (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate at -10℃; Green chemistry; enantioselective reaction;99%
1-bromocyclohexane
108-85-0

1-bromocyclohexane

2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

7-chloro-4-cyclohexyl-2-methylquinoline

7-chloro-4-cyclohexyl-2-methylquinoline

Conditions
ConditionsYield
With {Au(dppm)}2Cl2; trifluoroacetic acid In methanol Inert atmosphere; UV-irradiation;99%
2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

7-chloro-2-methyl-1,2,3,4-tetrahydroquinoline

7-chloro-2-methyl-1,2,3,4-tetrahydroquinoline

Conditions
ConditionsYield
With hydrogen In toluene at 100℃; under 37503.8 Torr; for 24h; chemoselective reaction;99%
With C46H49CoN3P4(2+)*2BF4(1-); hydrogen; potassium hydroxide In toluene; acetonitrile at 100℃; under 22801.5 Torr; for 48h; Autoclave; Glovebox; chemoselective reaction;87%
With sodium tetrahydroborate; hydrogen; cobalt(II) chloride In water at 150℃; under 30003 Torr; for 17h; Green chemistry; chemoselective reaction;67%
With sodium cyanoborohydride; acetic acid at 20℃; Sealed tube;
2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

(-)-7-chloro-2-methyl-1,2,3,4-tetrahydroquinoline
1260753-86-3

(-)-7-chloro-2-methyl-1,2,3,4-tetrahydroquinoline

Conditions
ConditionsYield
With bromopentacarbonylmanganese(I); potassium tert-butylate; hydrogen; E-1-(1H-benzo[d]imidazol-2-yl)-N-((SC,RFC)-1-(2-diphenylphosphino)ferrocenyl)methanimine In 1,4-dioxane at 80℃; under 45004.5 Torr; for 16h; Autoclave; enantioselective reaction;98%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; C73H100O2P2; hydrogen; iodine In toluene at 20℃; under 15201 Torr; for 24h; optical yield given as %ee; enantioselective reaction;
2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

phenol
108-95-2

phenol

C16H13NO

C16H13NO

Conditions
ConditionsYield
With potassium phosphate; copper(l) iodide; N1-benzyl-N2-(5-methyl-[1,1'-biphenyl]-2-yl)oxalamide In dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere;98%
2-aminopyridine
504-29-0

2-aminopyridine

2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

C15H13N3

C15H13N3

Conditions
ConditionsYield
With C51H57ClNiO2P2; sodium t-butanolate at 25℃;98%
2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

Isophthalaldehyde
626-19-7

Isophthalaldehyde

(E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde
120578-03-2

(E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde

Conditions
ConditionsYield
With lanthanum pentafluorobenzoate In toluene at 120℃; for 24h;97%
With tert-butylammonium hexafluorophosphate(V); calcium(II) trifluoromethanesulfonate In neat (no solvent) at 130℃; Green chemistry;93%
With acetic anhydride In toluene at 100 - 105℃; for 12 - 15h;75.15%
2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

N-Benzylaniline
758640-21-0

N-Benzylaniline

(E)-7-chloro-2-styrylquinoline
70382-84-2

(E)-7-chloro-2-styrylquinoline

Conditions
ConditionsYield
Stage #1: N-Benzylaniline With 2,3-dicyano-5,6-dichloro-p-benzoquinone In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Inert atmosphere;
Stage #2: 2-methyl-7-chloroquinoline In N,N-dimethyl-formamide at 70℃; for 24h; Inert atmosphere; diastereoselective reaction;
97%
2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

benzylamine
100-46-9

benzylamine

(E)-7-chloro-2-styrylquinoline
70382-84-2

(E)-7-chloro-2-styrylquinoline

Conditions
ConditionsYield
With lanthanum pentafluorobenzoate In toluene at 120℃; for 24h;97%
With tert.-butylhydroperoxide; N-Bromosuccinimide In water; acetonitrile at 100℃; for 48h; Schlenk technique; Darkness; Green chemistry;95%
With 1,10-phenanthroline-5,6-dione; trifluorormethanesulfonic acid; oxygen In chlorobenzene at 80℃; under 760.051 Torr; for 24h;86%
With tert.-butylhydroperoxide; water; sodium chloride at 100℃;75%
2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

7-chloro-2-(d3)methylquinoline

7-chloro-2-(d3)methylquinoline

Conditions
ConditionsYield
With water-d2; benzoic acid at 80℃; for 4h;97%
With water-d2; benzoic acid at 90℃; for 8h; Inert atmosphere; Schlenk technique;
2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

tert-butylamine
75-64-9

tert-butylamine

N-(tert-butyl)-2-methylquinolin-7-amine

N-(tert-butyl)-2-methylquinolin-7-amine

Conditions
ConditionsYield
With (PhPAd-DalPhos)NiCl(o-tol); sodium t-butanolate In toluene at 25℃; for 18h; Inert atmosphere; Glovebox; Sealed tube;97%
2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

isobutyric Acid
79-31-2

isobutyric Acid

7-chloro-4-isopropyl-2-methylquinoline

7-chloro-4-isopropyl-2-methylquinoline

Conditions
ConditionsYield
With 2-Picolinic acid; ferrous(II) sulfate heptahydrate; sodium bromate In water; dimethyl sulfoxide at 20℃; for 24h; Inert atmosphere; Irradiation;97%
2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

butan-1-ol
71-36-3

butan-1-ol

7-butoxy-2-methylquinoline

7-butoxy-2-methylquinoline

Conditions
ConditionsYield
With (4,4′-di-tert-butyl-2,2′-dipyridyl)Ni(o-tolyl)(Br); 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 80℃; for 12h; Inert atmosphere; Sealed tube; UV-irradiation;97%
2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

trifluoroethylamine
753-90-2

trifluoroethylamine

2-methyl-N-(2,2,2-trifluoroethyl)quinolin-7-amine

2-methyl-N-(2,2,2-trifluoroethyl)quinolin-7-amine

Conditions
ConditionsYield
With C33H43ClNiO6P2; sodium t-butanolate In toluene at 25℃; for 18h; Inert atmosphere; Sealed tube;97%
2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

benzaldehyde
100-52-7

benzaldehyde

(E)-7-chloro-2-styrylquinoline
70382-84-2

(E)-7-chloro-2-styrylquinoline

Conditions
ConditionsYield
With tert-butylammonium hexafluorophosphate(V); calcium(II) trifluoromethanesulfonate In neat (no solvent) at 130℃; Green chemistry;96%
With cobalt(II) chloride In water at 120℃; for 24h;93%
With 1,3-dimethylbarbituric acid; acetic acid In 1,4-dioxane; water at 60℃; for 24h;93%
2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

2-methylquinolin-7-amine
64334-96-9

2-methylquinolin-7-amine

Conditions
ConditionsYield
With ammonium hydroxide; potassium phosphate; copper(l) iodide; N1,N2-bis(5-methyl-[1,1'-biphenyl]-2-yl)oxalamide In water; dimethyl sulfoxide at 110℃; for 24h; Inert atmosphere;96%
With bis(1,5-cyclooctadiene)nickel (0); (R)-1-[(Sp)-2-(dicyclohexylphosphanyl)ferrocenyl]ethyldicyclohexylphosphane; ammonia; sodium t-butanolate In 1,4-dioxane; toluene at 105℃; under 5895.64 - 7757.43 Torr; for 18h; Sealed tube;92%
2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

bromo(2-ethoxy-2-oxoethyl)zinc
5764-82-9

bromo(2-ethoxy-2-oxoethyl)zinc

ethyl 2-(2-methyl-7-quinolyl)acetate

ethyl 2-(2-methyl-7-quinolyl)acetate

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); N,N,N,N,-tetramethylethylenediamine; C38H62P2 In tetrahydrofuran at 20℃; for 16h; Negishi Coupling; Inert atmosphere;96%
fur-2-ylboronic acid
13331-23-2

fur-2-ylboronic acid

2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

C14H11NO
1445086-33-8

C14H11NO

Conditions
ConditionsYield
With potassium phosphate; ((2-dicyclohexylphosphino-2',4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2‘-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate) In tetrahydrofuran at 20℃; for 0.5h; Suzuki-Miyaura Coupling;95%
With potassium phosphate; methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;95%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

C16H11ClN2

C16H11ClN2

Conditions
ConditionsYield
With tert-butylammonium hexafluorophosphate(V); calcium(II) trifluoromethanesulfonate In neat (no solvent) at 130℃; Green chemistry;95%
2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

formaldehyd
50-00-0

formaldehyd

7-chloro-2-ethenylquinoline
177748-00-4

7-chloro-2-ethenylquinoline

Conditions
ConditionsYield
With diethyl amine hydrochloride; triethylamine In 1,4-dioxane at 100℃; for 0.5h; Reagent/catalyst; Solvent; Temperature;95%
2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

2-(1H-benzo[d]imidazol-2-yl)-7-chloroquinoline

2-(1H-benzo[d]imidazol-2-yl)-7-chloroquinoline

Conditions
ConditionsYield
With iodine; oxygen In dimethyl sulfoxide at 110℃;95%
2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

tetramethylammonium trifluoromethylselenate(0)
75264-92-5

tetramethylammonium trifluoromethylselenate(0)

2-methyl-7-((trifluoromethyl)selanyl)quinoline

2-methyl-7-((trifluoromethyl)selanyl)quinoline

Conditions
ConditionsYield
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)nickel (0) In toluene at 50℃; for 12h; Inert atmosphere;95%
2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

C17H11ClN2O2

C17H11ClN2O2

Conditions
ConditionsYield
With tert-butylammonium hexafluorophosphate(V); calcium(II) trifluoromethanesulfonate In neat (no solvent) at 130℃; Green chemistry;94%
2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

C12H13OS(1-)*Na(1+)

C12H13OS(1-)*Na(1+)

7-(1-naphthyl)-2-methylquinoline

7-(1-naphthyl)-2-methylquinoline

Conditions
ConditionsYield
With η3-1-tert-butylindenyl palladium chloride dimer In toluene at 70℃; for 4h; Hiyama Coupling; Inert atmosphere; Glovebox; Sealed tube;94%
methanol
67-56-1

methanol

2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

7-chloro-4-(hydroxymethyl)-2-methylquinoline
19069-95-5

7-chloro-4-(hydroxymethyl)-2-methylquinoline

Conditions
ConditionsYield
With silver nitrate; Selectfluor In water at 80℃; for 4h; Sealed tube;94%
With sodium persulfate In water at 80℃; for 4h; Reagent/catalyst; Inert atmosphere;85%
With ferrous(II) sulfate heptahydrate; sulfuric acid; hydroxylamine-O-sulfonic acid In water for 3h;78%
2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

(R)-7-chloro-2-methyl-1,2,3,4-tetrahydroquinoline

(R)-7-chloro-2-methyl-1,2,3,4-tetrahydroquinoline

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; hydrogen; iodine; (((1R,3S,3'S)-3,3'-diethyl-3H,3'H-1,1'-spirobi[isobenzofuran]-7,7'-diyl)bis(oxy))bis(diphenylphosphane) In tetrahydrofuran at 20℃; under 18100.7 Torr; for 10h; Inert atmosphere; enantioselective reaction;94%
2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

methyl 2-(3-(3-formylphenyl)-3-oxopropyl)benzoate
949155-92-4

methyl 2-(3-(3-formylphenyl)-3-oxopropyl)benzoate

methyl 2-(3-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-oxopropyl)benzoate
149968-11-6

methyl 2-(3-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-oxopropyl)benzoate

Conditions
ConditionsYield
With acetic anhydride at 140℃; for 8h;93%
2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

C17H11Cl2N

C17H11Cl2N

Conditions
ConditionsYield
With tert-butylammonium hexafluorophosphate(V); calcium(II) trifluoromethanesulfonate In neat (no solvent) at 130℃; Green chemistry;93%
2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

7-chloro-2-((methylsulfonyl)methyl)quinoline

7-chloro-2-((methylsulfonyl)methyl)quinoline

Conditions
ConditionsYield
With benzophenone In acetone at 20℃; for 4h; Microwave irradiation;93%
2-methyl-7-chloroquinoline
4965-33-7

2-methyl-7-chloroquinoline

7-chloro-quinoline-2-carbaldehyde
59394-27-3

7-chloro-quinoline-2-carbaldehyde

Conditions
ConditionsYield
With selenium(IV) oxide In 1,4-dioxane at 60℃; Inert atmosphere;92%
With selenium(IV) oxide In 1,4-dioxane for 2.5h; Oxidation; Heating;84%
With selenium(IV) oxide; water In tetrahydrofuran at 25℃; for 6h;78%

7-Chloro-2-methylquinoline Chemical Properties

Molecular Structure:

Molecular Formula: C10H8ClN
Molecular Weight: 177.6302
IUPAC Name: 7-Chloro-2-methylquinoline
Synonyms of 7-Chloroquinaldine (CAS NO.4965-33-7): Quinoline, 7-chloro-2-methyl-
CAS NO: 4965-33-7
Product Categories: Quinolines, Quinazolines and derivatives ; Halides ; Quinolines, Isoquinolines & Quinoxalines ; Quinoline&Isoquinoline ; API ; Alkylquinolines ; Haloquinolines ; Quinolines ; Quinolines, Isoquinolines & Quinoxalines
Melting point: 74-78 °C 
Polar Surface Area: 12.89 Å2
Index of Refraction: 1.634
Molar Refractivity: 51.9 cm3
Molar Volume: 144.9 cm3
Surface Tension: 46.5 dyne/cm
Density: 1.225 g/cm3
Flash Point: 148.7 °C
Enthalpy of Vaporization: 49.6 kJ/mol
Boiling Point: 278.2 °C at 760 mmHg
Vapour Pressure: 0.00732 mmHg at 25°C

 

7-Chloro-2-methylquinoline Uses

 7-Chloroquinaldine (CAS NO.4965-33-7) is used as a  Pharmaceutical intermediates.

7-Chloro-2-methylquinoline Safety Profile

Safety Information of 7-Chloroquinaldine (CAS NO.4965-33-7):
Hazard Codes: Xi
Risk Statements: 36/37/38
36/37/38: Irritating to eyes, respiratory system and skin  
Safety Statements: 26-36
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing 
WGK Germany: 3

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