6-Chloroisoquinoline supplier

Name
Isoquinoline, 6-chloro- (6CI,9CI)
EINECS -0
CAS No. 62882-02-4
Article Data7
CAS DataBase
Density 1.27 g/cm³
Solubility
Melting Point 39-40 °C
Formula C₉H₆ClN
Boiling Point 289.5 °C at 760 mmHg
Molecular Weight 163.606
Flash Point 156.4 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms isoquinoline, 6-chloro-;MFCD09991646;
PSA 12.89000
LogP 2.88820

Synthetic route

: 3970-52-3
6-chloro-1H-indene

: 62882-02-4
6-chloroisoquinoline

Conditions

Conditions	Yield
Stage #1: 6-chloro-1H-indene With ozone In methanol; dichloromethane at -78℃; ozonolysis; Stage #2: With dimethylsulfide; sodium hydrogencarbonate In methanol; dichloromethane for 6h; Reduction; Stage #3: With ammonium hydroxide In methanol; dichloromethane for 15h; Cyclization; Further stages.;	64%
Multi-step reaction with 2 steps 1.1: ozone; oxygen / methanol; dichloromethane / 0.5 h / -78 - -65 °C / Inert atmosphere 1.2: 16 h / 20 °C / Inert atmosphere 2.1: ammonium hydroxide / dichloromethane; methanol / 24 h / 20 °C View Scheme

: 267877-39-4
2-acetyl-3-(4-chlorophenyl)isoxazol-5(2H)-one

A: 623-03-0
4-Cyanochlorobenzene

B: 62882-02-4
6-chloroisoquinoline

C: 79965-68-7
4-(4-chlorophenyl)-2-methyloxazole

D: 140-53-4
p-chlorobenzyl cyanide

Conditions

Conditions	Yield
at 750℃; Rearrangement; Further byproducts given;	A 22% B 8% C 10% D 17%

...Expand

: 101263-60-9
(4-chloro-benzylidenamino)-acetaldehyde diethylacetal

: 62882-02-4
6-chloroisoquinoline

Conditions

Conditions	Yield
With sulfuric acid; phosphorus pentoxide at 150℃;

: 54879-73-1
[1-(4-Chloro-phenyl)-meth-(Z)-ylidene]-(2,2-dimethoxy-ethyl)-amine

: 62882-02-4
6-chloroisoquinoline

Conditions

Conditions	Yield
With sulfuric acid at 140 - 150℃; for 0.5h;

: 104-88-1
4-chlorobenzaldehyde

KOH-solution: KOH-solution

: 62882-02-4
6-chloroisoquinoline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / benzene / Heating 2: concd. H2SO4 / 0.5 h / 140 - 150 °C View Scheme

: 104-88-1
4-chlorobenzaldehyde

: 62882-02-4
6-chloroisoquinoline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: concentrated sulfuric acid; phosphorus (V)-oxide / 150 °C View Scheme

: 33781-38-3, 147592-14-1
5-chloro-2,3-dihydro-1H-inden-1-ol

: 62882-02-4
6-chloroisoquinoline

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: toluene-4-sulfonic acid / toluene / 1.5 h / 120 °C / Dean-Stark 2.1: ozone; oxygen / methanol; dichloromethane / 0.5 h / -78 - -65 °C / Inert atmosphere 2.2: 16 h / 20 °C / Inert atmosphere 3.1: ammonium hydroxide / dichloromethane; methanol / 24 h / 20 °C View Scheme

: C9H7ClO2

: 62882-02-4
6-chloroisoquinoline

Conditions

Conditions	Yield
With ammonium hydroxide In methanol; dichloromethane at 20℃; for 24h;	2.74 g

: 42348-86-7
5-chloro-1-indanone

: 62882-02-4
6-chloroisoquinoline

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium tetrahydroborate / methanol / 1.5 h / 20 °C / Inert atmosphere 2.1: toluene-4-sulfonic acid / toluene / 1.5 h / 120 °C / Dean-Stark 3.1: ozone; oxygen / methanol; dichloromethane / 0.5 h / -78 - -65 °C / Inert atmosphere 3.2: 16 h / 20 °C / Inert atmosphere 4.1: ammonium hydroxide / dichloromethane; methanol / 24 h / 20 °C View Scheme

: 62882-02-4
6-chloroisoquinoline

: 611-19-8
1-chloro-2-(chloromethyl)benzene

: 2-(2-chlorobenzyl)-isoquinolinium chloride

Conditions

Conditions	Yield
In acetonitrile at 20℃;	97%

: 62882-02-4
6-chloroisoquinoline

: 6-chloroisoquinoline 2-oxide

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 2h;	96%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 2h;	96%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 24h;
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 6h;	3.4 g

: 62882-02-4
6-chloroisoquinoline

: 110-82-7
cyclohexane

: 6-chloro-1-cyclohexylisoquinoline

Conditions

Conditions	Yield
With dipotassium peroxodisulfate; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; trifluoroacetic acid In acetonitrile at 20℃; for 16h; Irradiation; Inert atmosphere;	93%

: 623-73-4
diazoacetic acid ethyl ester

: 62882-02-4
6-chloroisoquinoline

: 1609-47-8
diethyl dicarbonate

: ethyl (R)-6-chloro-1-(1-diazo-2-ethoxy-2-oxoethyl)isoquinoline-2(1H)-carboxylate

Conditions

Conditions	Yield
With (R)-6,6’-bis((4-(tert-butyl)-2-methylphenyl))-1,1'-spirobiindane-7,7'-diyl phosphate In toluene at -20℃; for 88h; Inert atmosphere; Molecular sieve; enantioselective reaction;	92%

...Expand

: 109-99-9
tetrahydrofuran

: 62882-02-4
6-chloroisoquinoline

: 6-chloro-1-(tetrahydrofuran-2-yl)isoquinoline

Conditions

Conditions	Yield
With ammonium persulfate; 1-hydroxy-pyrrolidine-2,5-dione In water at 40℃; for 24h; Green chemistry;	90%
With ethanol; bis-[(trifluoroacetoxy)iodo]benzene In dimethyl sulfoxide; 1,2-dichloro-ethane at 20℃; for 12h; Schlenk technique; Inert atmosphere; Irradiation;	83%
With C24H42N3(1+)*ClO4(1-); lithium perchlorate; acetic acid; trifluoroacetic acid In acetonitrile at 20℃; for 36h; Irradiation; Electrochemical reaction; Inert atmosphere;	81%

: 62882-02-4
6-chloroisoquinoline

: 1402010-11-0, 1402085-44-2, 1402085-52-2
potassium (1-benzyloxy-3-phenylpropyl)trifluoroboranuide

: 1402010-77-8
6-(1-(benzyloxy)-3-phenylpropyl)isoquinoline

Conditions

Conditions	Yield
With cesiumhydroxide monohydrate; cyclopentyl methyl ether; [2′-(amino-κN)[1,1′-biphenyl]-2-yl-κC][butylbis(tricyclo-[3.3.1.13,7]dec-1-yl)phosphine]chloropalladium at 105℃; for 24h; Suzuki-Miyaura Coupling; Sealed tube;	88%

: 62882-02-4
6-chloroisoquinoline

: 6-chloro-5-nitroisoquinoline

Conditions

Conditions	Yield
With sodium nitrate; sulfuric acid at 0℃; for 2h;	88%

: 62882-02-4
6-chloroisoquinoline

: 368-47-8
phenyltrifluorosilane

: 70125-61-0
6-phenylisoquinoline

Conditions

Conditions	Yield
Stage #1: phenyltrifluorosilane With tetrabutyl ammonium fluoride; palladium diacetate; XPhos In tert-butyl alcohol at 20℃; for 0.0833333h; Hiyama cross-coupling reaction; Inert atmosphere; Sealed vial; Stage #2: 6-chloroisoquinoline In tert-butyl alcohol at 100℃; Hiyama cross-coupling reaction; Inert atmosphere; Sealed vial;	85%

: 62882-02-4
6-chloroisoquinoline

: 1609-47-8
diethyl dicarbonate

: 27491-70-9, 28447-24-7, 25411-73-8
dimethyl diazomethylphosphonate

: ethyl (R)-6-chloro-1-(diazo(dimethoxyphosphoryl)methyl)isoquinoline-2(1H)-carboxylate

Conditions

Conditions	Yield
With (R)-6,6’-bis(3',4',5'-trifluoro-2,6-dimethyl[1,1'-biphenyl]-4-yl)-1,1'-spirobiindane-7,7'-diyl phosphate In toluene at -30℃; for 90h; Inert atmosphere; Molecular sieve; enantioselective reaction;	83%

...Expand

: 62882-02-4
6-chloroisoquinoline

: 89343-06-6
tris-iso-propylsilyl acetylene

: 2937-50-0
Allyl chloroformate

: C24H32ClNO2Si

Conditions

Conditions	Yield
Stage #1: tris-iso-propylsilyl acetylene With isopropylmagnesium bromide In tetrahydrofuran; 2-methyltetrahydrofuran for 1h; Inert atmosphere; Stage #2: With zinc(II) chloride In tetrahydrofuran; 2-methyltetrahydrofuran at 20℃; for 2h; Inert atmosphere; Stage #3: 6-chloroisoquinoline; Allyl chloroformate Further stages;	82%

...Expand

: 62882-02-4
6-chloroisoquinoline

: 78-59-1
3,5,5-Trimethylcyclohex-2-en-1-one

: 2-(isoquinolin-6-yl)-3,5,5-trimethylcyclohex-2-en-1-one

Conditions

Conditions	Yield
With palladium diacetate; 2-(2-(di-tert-butylphosphanyl)phenyl)-1-methyl-1H-indole; lithium tert-butoxide In 1,4-dioxane at 100℃; for 18h; Schlenk technique; Inert atmosphere;	80%

: 62882-02-4
6-chloroisoquinoline

: 150-76-5
4-methoxy-phenol

: 6-(4-methoxyphenoxy)isoquinoline

Conditions

Conditions	Yield
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;	79%

: 62882-02-4
6-chloroisoquinoline

: 1,3-dioxoisoindolin-2-yl cyclohexanecarboxylate

: 6-chloro-1-cyclohexylisoquinoline

Conditions

Conditions	Yield
With tetrakis(acetonitrile)copper(I)tetrafluoroborate; 2.9-dimethyl-1,10-phenanthroline; zinc trifluoromethanesulfonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl acetamide for 24h; Inert atmosphere; Irradiation;	78%

: 590-28-3
potassium cyanate

: 62882-02-4
6-chloroisoquinoline

: 71-36-3
butan-1-ol

: butyl isoquinolin-6-ylcarbamate

Conditions

Conditions	Yield
With potassium phosphate; copper(l) iodide; 2-((2-methylnaphthalen-1-yl)amino)-2-oxoacetic acid at 120℃; for 48h; Schlenk technique; Inert atmosphere; Sealed tube;	75%

...Expand

: 62882-02-4
6-chloroisoquinoline

: 29526-96-3
1-phenylcyclopropan-1-ol

: 3-(6-chloroisoquinolin-1-yl)-1-phenylpropan-1-one

Conditions

Conditions	Yield
With dipotassium peroxodisulfate In water; dimethyl sulfoxide at 70℃; for 12h; Inert atmosphere;	74%

: 62882-02-4
6-chloroisoquinoline

: 74-88-4
methyl iodide

: 6-chloro-2-methylisoquinolin-2-ium iodide

Conditions

Conditions	Yield
In acetonitrile at 80℃; for 16h;	73%
In acetonitrile for 12h; Reflux;
In 1,4-dioxane Reflux;

: 62882-02-4
6-chloroisoquinoline

: 50625-29-1
3-methoxybenzenetrifluorosilane

: 1337563-02-6
6-(3-methoxybenzene)isoquinoline

Conditions

Conditions	Yield
Stage #1: 3-methoxybenzenetrifluorosilane With tetrabutyl ammonium fluoride; palladium diacetate; XPhos In tert-butyl alcohol at 20℃; for 0.0833333h; Hiyama cross-coupling reaction; Inert atmosphere; Sealed vial; Stage #2: 6-chloroisoquinoline In tert-butyl alcohol at 100℃; Hiyama cross-coupling reaction; Inert atmosphere; Sealed vial;	71%

: 62882-02-4
6-chloroisoquinoline

: 108-88-3
toluene

: 2-benzyl-6-chloroisoquinoline-1,3,4(2H)-trione

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; iodine In water at 110℃; for 24h; Sealed tube;	67%

: 62882-02-4
6-chloroisoquinoline

: 81290-20-2
(trifluoromethyl)trimethylsilane

: 6-chloro-1-(trifluoromethyl)isoquinoline

Conditions

Conditions	Yield
With potassium fluoride; bis-[(trifluoroacetoxy)iodo]benzene In 1-methyl-pyrrolidin-2-one at 0℃; for 24h; Glovebox; Inert atmosphere; Sealed tube; regioselective reaction;	64%

: 96-47-9
2-methyltetrahydrofuran

: 62882-02-4
6-chloroisoquinoline

: 6-chloro-1-(5-methyltetrahydrofuran-2-yl)isoquinoline

Conditions

Conditions	Yield
With C24H42N3(1+)*ClO4(1-); lithium perchlorate; acetic acid; trifluoroacetic acid In acetonitrile at 20℃; for 36h; Irradiation; Electrochemical reaction; Inert atmosphere; regioselective reaction;	62%

: 62882-02-4
6-chloroisoquinoline

: 29681-57-0
tert-butyldimethylsilane

: C15H20ClNSi

Conditions

Conditions	Yield
With sodium persulfate; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate In dimethyl sulfoxide; 1,2-dichloro-ethane at 30℃; for 24h; Irradiation; regioselective reaction;	61%

: 62882-02-4
6-chloroisoquinoline

: 75-88-7
1,1,1-trifluoro-2-chloroethane

: 6-(2,2,2-trifluoroethyl)isoquinoline

Conditions

Conditions	Yield
With 4,4'-di-tert-butyl-2,2'-bipyridine; magnesium chloride; nickel dibromide; zinc In N,N-dimethyl acetamide at 80℃; for 12h; Inert atmosphere; Schlenk technique;	55%

: 62882-02-4
6-chloroisoquinoline

: 626-62-0
1-iodocyclohexane

: 6-chloro-1-cyclohexylisoquinoline

Conditions

Conditions	Yield
With tert-butyl peroxyacetate; [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; trifluoroacetic acid In acetonitrile at 20℃; for 24h; Inert atmosphere; Sealed tube; Irradiation;	54%

: 62882-02-4
6-chloroisoquinoline

: tert-butyl (Z)-(1-(((chloro(phenyl)methylene)amino)oxy)-1-oxo-3-phenylpropan-2-yl)carbamate

: tert-butyl (1-(6-chloroisoquinolin-1-yl)-2-phenylethyl)carbamate

Conditions

Conditions	Yield
With [4,4’-bis(1,1-dimethylethyl)-2,2’-bipyridine-N1,N1‘]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate In acetonitrile at 20℃; for 12h; Minisci Aromatic Substitution; Inert atmosphere; Irradiation;	53%

: 62882-02-4
6-chloroisoquinoline

: 5526-13-6
1H-indol-7-yl acetate

: 13360-57-1
dimethylamino sulfonyl chloride

: C21H20ClN3O4S

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In toluene at 50℃; for 1h; Inert atmosphere;	48%

...Expand

: 62882-02-4
6-chloroisoquinoline

: 5526-13-6
1H-indol-7-yl acetate

: 209971-18-6
2-cyanoethyl(methyl)sulfamoyl chloride

: C23H21ClN4O4S

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In toluene at 45℃; for 1h; Inert atmosphere;	46%

...Expand

: 62882-02-4
6-chloroisoquinoline

: 1357927-37-7
[Ru(bda)(DMSO)2]

: C30H18Cl2N4O4Ru

Conditions

Conditions	Yield
In methanol at 80℃; for 8h; Inert atmosphere;	42%

: 62882-02-4
6-chloroisoquinoline

: 6790-58-5
(-)-ambroxide

: 6-chloro-1-((3aR,5aS,9aS,9bR)-3 a,6,6,9 a-tetramethyldodecahydronaphtho[2,1-b]furan-2-yl)isoquinoline

Conditions

Conditions	Yield
With ethanol; bis-[(trifluoroacetoxy)iodo]benzene In dimethyl sulfoxide; 1,2-dichloro-ethane at 20℃; for 12h; Schlenk technique; Inert atmosphere; Irradiation; diastereoselective reaction;	31%

: 62882-02-4
6-chloroisoquinoline

: 98-59-9
p-toluenesulfonyl chloride

: (6-chloroisoquinolin-2-ium-2-yl)(tosyl)amide

Conditions

Conditions	Yield
Stage #1: 6-chloroisoquinoline With O-(2,4-dinitrophenyl)hydroxylamine In acetonitrile at 20℃; for 24h; Inert atmosphere; Stage #2: p-toluenesulfonyl chloride With potassium carbonate In tetrahydrofuran; water at 20℃; for 12h; Inert atmosphere;	26%

6-Chloroisoquinoline Specification

The 6-Chloroisoquinoline, with the CAS registry number 62882-02-4, is also called isoquinoline, 6-chloro-. It belongs to the product category of isoquinoline. And the molecular formula of the chemical is C₉H₆ClN.

The characteristics of this chemical are as followings: (1)ACD/LogP: 2.55; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.47; (4)ACD/LogD (pH 7.4): 2.55; (5)#H bond acceptors: 1; (6)#H bond donors: 0; (7)#Freely Rotating Bonds: 0; (8)Polar Surface Area: 12.89 Å²; (9)Index of Refraction: 1.652; (10)Molar Refractivity: 47.08 cm³; (11)Molar Volume: 128.7 cm³; (12)Polarizability: 18.66×10^-24cm³; (13)Surface Tension: 49.3 dyne/cm; (14)Density: 1.27 g/cm³; (15)Flash Point: 156.4 °C; (16)Enthalpy of Vaporization: 50.76 kJ/mol; (17)Boiling Point: 289.5 °C at 760 mmHg; (18)Vapour Pressure: 0.00382 mmHg at 25°C.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: Clc1ccc2cnccc2c1
(2)InChI: InChI=1/C9H6ClN/c10-9-2-1-8-6-11-4-3-7(8)5-9/h1-6H
(3)InChIKey: NCJNOOHAQSFEJN-UHFFFAOYAS

Product Name

Isoquinoline, 6-chloro- (6CI,9CI)

Synthetic route

6-Chloroisoquinoline Specification

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