Product Name

  • Name

    1,3-Dichloroisoquinoline

  • EINECS 627-814-4
  • CAS No. 7742-73-6
  • Article Data21
  • CAS DataBase
  • Density 1.407 g/cm3
  • Solubility
  • Melting Point 121-122 °C(lit.)
  • Formula C9H5Cl2N
  • Boiling Point 328.7 °C at 760 mmHg
  • Molecular Weight 198.051
  • Flash Point 182.6 °C
  • Transport Information
  • Appearance white to brown crystalline powder
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 7742-73-6 (1,3-Dichloroisoquinoline)
  • Hazard Symbols IrritantXi
  • Synonyms NSC 170843;
  • PSA 12.89000
  • LogP 3.54160

Synthetic route

2-cyanomethylbenzoic acid
6627-91-4

2-cyanomethylbenzoic acid

1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

Conditions
ConditionsYield
With phosphorus pentachloride; trichlorophosphate In 2-cyanomethylbenzoic acid at 20 - 70℃; for 17.5h;84.5%
4H-isoquinolin-1,3-dione
4456-77-3

4H-isoquinolin-1,3-dione

1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

Conditions
ConditionsYield
With P,P-dichlorophenylphosphine oxide at 130℃; for 2h;79%
With P,P-dichlorophenylphosphine oxide In tetrahydrofuran; water at 20 - 160℃;74%
With P,P-dichlorophenylphosphine oxide at 160℃; for 3h; neat;6.75 g
With P,P-dichlorophenylphosphine oxide9.30 g
With P,P-dichlorophenylphosphine oxide at 160℃; for 4h;
Homophthalic acid
89-51-0

Homophthalic acid

1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

Conditions
ConditionsYield
Stage #1: Homophthalic acid With ammonium hydroxide Heating;
Stage #2: With P,P-dichlorophenylphosphine oxide at 160℃; for 3h;		75%
Multi-step reaction with 2 steps
1.1: aq. NH3 / Heating
1.2: 1,2-dichloro-benzene / 3 h / 200 °C
2.1: 6.75 g / dichlorophenylphosphine oxide / 3 h / 160 °C / neat
View Scheme
isoquinoline-1,3-diol
86-94-2

isoquinoline-1,3-diol

1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

Conditions
ConditionsYield
With P,P-dichlorophenylphosphine oxide at 160℃;
2-phenethyl-4H-isoquinoline-1,3-dione
53558-67-1

2-phenethyl-4H-isoquinoline-1,3-dione

trichlorophosphate
10025-87-3, 12599-09-6, 63736-95-8

trichlorophosphate

1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

Conditions
ConditionsYield
at 140 - 150℃;
1.3-dioxy-isoquinoline

1.3-dioxy-isoquinoline

A

1-chloroisoquinolin-3-ol
53093-78-0

1-chloroisoquinolin-3-ol

B

1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

Conditions
ConditionsYield
With trichlorophosphate at 150 - 170℃;
4H-isoquinolin-1,3-dione
4456-77-3

4H-isoquinolin-1,3-dione

A

1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

B

1-chloro-3-oxy-isoquinoline

1-chloro-3-oxy-isoquinoline

Conditions
ConditionsYield
With trichlorophosphate at 150 - 170℃; im Rohr;
isoquinoline-1,3-diol
86-94-2

isoquinoline-1,3-diol

trichlorophosphate
10025-87-3, 12599-09-6, 63736-95-8

trichlorophosphate

A

1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

B

1-chloro-3-oxy-isoquinoline

1-chloro-3-oxy-isoquinoline

Conditions
ConditionsYield
at 150 - 170℃;
...Expand
P,P-dichlorophenylphosphine oxide
824-72-6

P,P-dichlorophenylphosphine oxide

isoquinoline-13 (2H4H)-dione

isoquinoline-13 (2H4H)-dione

1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

Conditions
ConditionsYield
In tetrahydrofuran; water
P,P-dichlorophenylphosphine oxide
824-72-6

P,P-dichlorophenylphosphine oxide

4H-isoquinolin-1,3-dione
4456-77-3

4H-isoquinolin-1,3-dione

1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

Conditions
ConditionsYield
In tetrahydrofuran; water
In tetrahydrofuran; water
fur-2-ylboronic acid
13331-23-2

fur-2-ylboronic acid

1,3‐dichloro‐4‐iodoisoquinoline
1168136-15-9

1,3‐dichloro‐4‐iodoisoquinoline

A

1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

B

C13H7Cl2NO
1168136-22-8

C13H7Cl2NO

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,3-dioxane; water at 75℃; for 12h; Suzuki coupling;
...Expand
1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

(3-chloro-isoquinolin-1-yl)-acetic acid tert-butyl ester
1402816-06-1

(3-chloro-isoquinolin-1-yl)-acetic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: acetic acid tert-butyl ester With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; tris-(dibenzylideneacetone)dipalladium(0); DavePhos In toluene at -78 - 20℃; for 1.25h;
Stage #2: 1,3-dichloroisoquinoline In toluene at 20℃; for 0.5h;		100%
1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

C19H21ClN2O5
630425-54-6

C19H21ClN2O5

Conditions
ConditionsYield
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With sodium hydride In DMF (N,N-dimethyl-formamide) at 0℃; for 0.5h;
Stage #2: 1,3-dichloroisoquinoline In DMF (N,N-dimethyl-formamide) at 20℃; for 12h;		99.8%
1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

1-amino-3-(dimethylamino)propane
109-55-7

1-amino-3-(dimethylamino)propane

N1-(3-chloro-1-isoquinolinyl)-N3,N3-dimethyl-1,3-propanediamine dihydrochloride

N1-(3-chloro-1-isoquinolinyl)-N3,N3-dimethyl-1,3-propanediamine dihydrochloride

Conditions
ConditionsYield
Stage #1: 1,3-dichloroisoquinoline; 1-amino-3-(dimethylamino)propane for 0.5h; Heating / reflux;
Stage #2: With hydrogenchloride In methanol		99%
1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

N-tert-butyloxycarbonyl-L-4-hydroxyphenylglycine
69651-48-5

N-tert-butyloxycarbonyl-L-4-hydroxyphenylglycine

(S)-tert-butoxycarbonylamino[4-(3-chloroisoquinolin-1-yloxy)phenyl]acetic acid
928162-16-7

(S)-tert-butoxycarbonylamino[4-(3-chloroisoquinolin-1-yloxy)phenyl]acetic acid

Conditions
ConditionsYield
With potassium tert-butylate In dimethyl sulfoxide at 40℃; for 336h;99%
1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

2-methoxynaphthalene-1-boronic acid
104116-17-8

2-methoxynaphthalene-1-boronic acid

3-chloro-1-(2-methoxylnaphthalen-1-yl)isoquinoline
190188-44-4

3-chloro-1-(2-methoxylnaphthalen-1-yl)isoquinoline

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); cesium fluoride In 1,2-dimethoxyethane at 90℃; Suzuki-Miyaura Coupling; regioselective reaction;96%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; ethanol at 90℃; for 120h; Suzuki-Miyaura Coupling; regioselective reaction;86%
With cesium fluoride; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane for 6h; Heating;85%
With cesium fluoride; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane at 90℃; for 18h; Suzuki cross-coupling;79%
methanol
67-56-1

methanol

1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

1-Chloro-3-methoxyisoquinoline
24649-22-7

1-Chloro-3-methoxyisoquinoline

Conditions
ConditionsYield
With sodium In acetonitrile at 65℃; for 1.5h;94%
1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

3-chloroisoquinoline-1-d

3-chloroisoquinoline-1-d

Conditions
ConditionsYield
With C60H48BP3Pd; potassium deuteroformate; [2.2.2]cryptande In tetrahydrofuran at 60℃; for 72h; Schlenk technique; Inert atmosphere;94%
1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

sodium methylate
124-41-4

sodium methylate

1-Chloro-3-methoxyisoquinoline
24649-22-7

1-Chloro-3-methoxyisoquinoline

Conditions
ConditionsYield
In 1,4-dioxane at 65℃;92.2%
1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

1,3-dichloro-5-nitroisoquinoline
18203-64-0

1,3-dichloro-5-nitroisoquinoline

Conditions
ConditionsYield
With sulfuric acid; nitric acid at 0 - 25℃;91%
With sulfuric acid; nitric acid In water at 0 - 5℃; for 2h;91%
With sulfuric acid; nitric acid at 0 - 25℃; for 16.5h;81%
1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

methylmagnesium bromide
75-16-1

methylmagnesium bromide

3-chloro-1-methylisoquinoline
15787-12-9

3-chloro-1-methylisoquinoline

Conditions
ConditionsYield
With iron(III)-acetylacetonate In tetrahydrofuran; toluene at 0℃; for 2h; Inert atmosphere; chemoselective reaction;91%
1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

phenylboronic acid
98-80-6

phenylboronic acid

3-chloro-1-phenylisoquinoline
89721-07-3

3-chloro-1-phenylisoquinoline

Conditions
ConditionsYield
With cesium fluoride; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane for 6h; Heating;90%
With tetrakis(triphenylphosphine) palladium(0); cesium fluoride In Dimethyl ether at 85℃; for 36h; Inert atmosphere;60%
With tetrakis(triphenylphosphine) palladium(0); cesium fluoride In 1,2-dimethoxyethane for 48h; Suzuki-Miyaura Coupling; Inert atmosphere; Reflux;56%
1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

N-aminopyridin-1-ium iodide
6295-87-0

N-aminopyridin-1-ium iodide

N-(3-chloroisoquinolin-1-yl)pyridinium aminide
1051915-84-4

N-(3-chloroisoquinolin-1-yl)pyridinium aminide

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 6h; Heating;90%
1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

1,3‐dichloro‐4‐iodoisoquinoline
1168136-15-9

1,3‐dichloro‐4‐iodoisoquinoline

Conditions
ConditionsYield
Stage #1: 1,3-dichloroisoquinoline With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.25h;
Stage #2: With iodine In tetrahydrofuran at 20℃;		90%
With iodine; lithium diisopropyl amide In tetrahydrofuran at -78℃;
1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

adamantylmethylamine
17768-41-1

adamantylmethylamine

N-(1-adamantylmethyl)-3-chloroisoquinolin-1-amine

N-(1-adamantylmethyl)-3-chloroisoquinolin-1-amine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 140℃; for 24h; Inert atmosphere;90%
1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

potassium tert-butylate
865-47-4

potassium tert-butylate

1-tert-butoxy-3-chloroisoquinoline
1241384-74-6

1-tert-butoxy-3-chloroisoquinoline

Conditions
ConditionsYield
In toluene at 80℃; for 3h;89.1%
In toluene Reflux;89%
1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

2-(adamantan-1-yloxy)ethan-1-amine
25225-13-2

2-(adamantan-1-yloxy)ethan-1-amine

N-[2-(1-adamantyloxy)ethyl]-3-chloroisoquinolin-1-amine

N-[2-(1-adamantyloxy)ethyl]-3-chloroisoquinolin-1-amine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 140℃; for 24h; Inert atmosphere;89%
With potassium carbonate In N,N-dimethyl-formamide at 140℃; for 24h; Activation energy;89%
1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

C9H4(2)HCl2N
1168136-27-3

C9H4(2)HCl2N

Conditions
ConditionsYield
Stage #1: 1,3-dichloroisoquinoline With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 2h;
Stage #2: With water-d2; hydrogen chloride In tetrahydrofuran		88%
1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

4-methylphenylboronic acid
5720-05-8

4-methylphenylboronic acid

3-chloro-1-(4-tolyl)isoquinoline
190188-42-2

3-chloro-1-(4-tolyl)isoquinoline

Conditions
ConditionsYield
With cesium fluoride; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane for 6h; Heating;87%
1-iodo-2-methyl-2-propene
3756-30-7

1-iodo-2-methyl-2-propene

1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

C13H11Cl2N
1168136-13-7

C13H11Cl2N

Conditions
ConditionsYield
Stage #1: 1,3-dichloroisoquinoline With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.25h;
Stage #2: 1-iodo-2-methyl-2-propene In tetrahydrofuran at 20℃;		87%
1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

allyl iodid
556-56-9

allyl iodid

4-allyl-1,3-dichloroisoquinoline
1168136-12-6

4-allyl-1,3-dichloroisoquinoline

Conditions
ConditionsYield
Stage #1: 1,3-dichloroisoquinoline With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.25h;
Stage #2: allyl iodid In tetrahydrofuran at 20℃;		87%
1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

(S)-1-Pyrrolidin-2-yl-methanol
23356-96-9

(S)-1-Pyrrolidin-2-yl-methanol

(S)-(1-(3-chloroisoquinolin-1-yl)pyrrolidin-2-yl)methanol

(S)-(1-(3-chloroisoquinolin-1-yl)pyrrolidin-2-yl)methanol

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 115℃; for 1h; Microwave irradiation;87%
1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

2-methyl-1-naphthylboronic acid
103989-84-0

2-methyl-1-naphthylboronic acid

3-chloro-1-(2-methylnaphthalen-1-yl)isoquinoline
1394249-29-6

3-chloro-1-(2-methylnaphthalen-1-yl)isoquinoline

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); cesium fluoride In 1,2-dimethoxyethane at 90℃; Suzuki-Miyaura Coupling; regioselective reaction;83%
With tetrakis(triphenylphosphine) palladium(0); cesium fluoride In 1,2-dimethoxyethane Suzuki Coupling; Reflux;82%
With tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane at 90℃; for 48h; Suzuki-Miyaura Coupling; regioselective reaction;81%
1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

benzaldehyde, hydrazone
5281-18-5

benzaldehyde, hydrazone

C16H12ClN3
1258543-03-1

C16H12ClN3

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In toluene at 100 - 104℃; for 2.5h; Inert atmosphere;81%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In toluene at 100℃; Inert atmosphere;81%
1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

methyl trifluoromethanesulfonate
333-27-7

methyl trifluoromethanesulfonate

1,3-dichloro-4-methyl-isoquinoline
15787-23-2

1,3-dichloro-4-methyl-isoquinoline

Conditions
ConditionsYield
Stage #1: 1,3-dichloroisoquinoline With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.25h;
Stage #2: methyl trifluoromethanesulfonate In tetrahydrofuran at 20℃;		80%
1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

mesitylboronic acid
5980-97-2

mesitylboronic acid

3-chloro-1-mesitylisoquinoline

3-chloro-1-mesitylisoquinoline

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); cesium fluoride In 1,2-dimethoxyethane for 24h; Inert atmosphere; Reflux;78%
1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

4-(1-isoquinolyl)-1-piperazinecarboxylic acid tert-butyl ester
205264-33-1

4-(1-isoquinolyl)-1-piperazinecarboxylic acid tert-butyl ester

Conditions
ConditionsYield
77%
1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

(S)-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester
101469-92-5

(S)-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

(S)-tert-butyl 3-((3-chloroisoquinolin-1-yl)oxy)pyrrolidine-1-carboxylate

(S)-tert-butyl 3-((3-chloroisoquinolin-1-yl)oxy)pyrrolidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: (S)-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester With sodium hydride In 1-methyl-pyrrolidin-2-one at 0℃; for 0.0833333h;
Stage #2: 1,3-dichloroisoquinoline In 1-methyl-pyrrolidin-2-one at 20 - 135℃; for 0.583333h; Microwave irradiation;		75%

1,3-Dichloroisoquinoline Specification

The Isoquinoline,1,3-dichloro- is an organic compound with the formula C9H5Cl2N. The IUPAC name of this chemical is 1,3-dichloroisoquinoline and the CAS registry number is 7742-73-6. In addition, the product's categories are Heterocyclic Series; Quinoline & Isoquinoline; Heterocycle Intermediates; Halogenated Heterocycles; Heterocyclic Building Blocks; Isoquinolines; Isoquinolines Building Blocks. Besides, this chemical is white to brown crystalline powder.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.50; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.499; (4)ACD/LogD (pH 7.4): 3.499; (5)ACD/BCF (pH 5.5): 268.453; (6)ACD/BCF (pH 7.4): 268.453; (7)ACD/KOC (pH 5.5): 1906.294; (8)ACD/KOC (pH 7.4): 1906.294; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.661; (13)Molar Refractivity: 51.977 cm3; (14)Molar Volume: 140.674 cm3; (15)Polarizability: 20.605×10-24 cm3; (16)Surface Tension: 51.579 dyne/cm; (17)Enthalpy of Vaporization: 54.841 kJ/mol; (18)Vapour Pressure: 0 mmHg at 25°C; (19)Exact Mass: 196.979905; (20)MonoIsotopic Mass: 196.979905; (21)Topological Polar Surface Area: 12.9; (22)Heavy Atom Count: 12; (23)Complexity: 163.

Uses of Isoquinoline,1,3-dichloro-: It can react with p-tolyl-boronic acid to get 3-chloro-1-(4-tolyl)isoquinoline. This reaction needs reagent CsF, catalytic agent Pd(PPh3)4 and solvent 1,2-dimethoxy-ethane by heating. The reaction time is 6 hours. The yield is 87%.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.

People can use the following data to convert to the molecule structure.
1. SMILES:c1ccc2c(c1)cc(nc2Cl)Cl
2. InChI:InChI=1/C9H5Cl2N/c10-8-5-6-3-1-2-4-7(6)9(11)12-8/h1-5H 
3. InChIKey:BRGZEQXWZWBPJH-UHFFFAOYAU

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