[ CAS No. 1532-91-8 ] {[proInfo.proName]}

Name: 1532-91-8|4-Chloroisoquinoline|95%
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COA NMR CNMR HPLC LC-MS

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Product Details of [ 1532-91-8 ]

CAS No. :	1532-91-8	MDL No. :	MFCD00234490
Formula :	C₉H₆ClN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LBEQEEIDWHKVAR-UHFFFAOYSA-N
M.W :	163.60	Pubchem ID :	640974
Synonyms :

Calculated chemistry of [ 1532-91-8 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	46.75
TPSA :	12.89 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.36 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.97
Log Po/w (XLOGP3) :	2.73
Log Po/w (WLOGP) :	2.89
Log Po/w (MLOGP) :	2.15
Log Po/w (SILICOS-IT) :	3.13
Consensus Log Po/w :	2.57

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.25
Solubility :	0.0926 mg/ml ; 0.000566 mol/l
Class :	Soluble
Log S (Ali) :	-2.65
Solubility :	0.362 mg/ml ; 0.00221 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.31
Solubility :	0.00807 mg/ml ; 0.0000493 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.24

Safety of [ 1532-91-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1532-91-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 1532-91-8 ]
Downstream synthetic route of [ 1532-91-8 ]

[ 1532-91-8 ] Synthesis Path-Upstream 1~8

1
[ 1532-91-8 ]
[ 23687-25-4 ]

Reference： [1] Organic Letters, 2015, vol. 17, # 23, p. 5934 - 5937

2
[ 23687-25-4 ]
[ 1532-91-8 ]

Reference： [1] Patent: US2005/20623, 2005, A1, . Location in patent: Page 104

3
[ 3336-49-0 ]
[ 1532-91-8 ]

Reference： [1] Journal of the American Chemical Society, 1958, vol. 80, p. 3443,3448

4
[ 108231-23-8 ]
[ 1532-91-8 ]

Reference： [1] Bulletin of the Polish Academy of Sciences, Chemistry, 1988, vol. 36, # 9-12, p. 417 - 424

5
[ 120569-14-4 ]
[ 1532-91-8 ]
[ 119-61-9 ]
[ 67-72-1 ]
[ 983-79-9 ]

Reference： [1] Tetrahedron Letters, 1988, vol. 29, # 48, p. 6287 - 6290

6
[ 94169-93-4 ]
[ 1532-91-8 ]

Reference： [1] Bulletin of the Polish Academy of Sciences, Chemistry, 1988, vol. 36, # 9-12, p. 417 - 424

7
[ 1532-91-8 ]
[ 557-21-1 ]
[ 34846-65-6 ]

Reference： [1] Tetrahedron Letters, 2006, vol. 47, # 19, p. 3303 - 3305

8
[ 1532-91-8 ]
[ 925890-48-8 ]

Reference： [1] Organic Letters, 2013, vol. 15, # 4, p. 792 - 795

[ 1532-91-8 ] Synthesis Path-Downstream 1~43

1
[ 3336-49-0 ]
[ 1532-91-8 ]

Reference： [1]Journal of the American Chemical Society,1958,vol. 80,p. 3443,3448

2
[ 1532-91-8 ]
4-chloroisoquinoline N-oxide [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 792 - 795
[2]Journal of the American Chemical Society,1958,vol. 80,p. 3443,3448

3
[ 1532-91-8 ]
[ 930-69-8 ]
[ 106510-95-6 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 2805 - 2809

4
[ 120569-14-4 ]
[ 1532-91-8 ]
[ 119-61-9 ]
[ 67-72-1 ]
[ 983-79-9 ]

Reference： [1]Tetrahedron Letters,1988,vol. 29,p. 6287 - 6290

5
[ 108231-23-8 ]
[ 1532-91-8 ]

Reference： [1]Bulletin of the Polish Academy of Sciences: Chemistry,1988,vol. 36,p. 417 - 424

8
diazonium chloride from <4>isoquinolylamine [ No CAS ]
[ 1532-91-8 ]

Reference： [1]Gazzetta Chimica Italiana,1959,vol. 89,p. 2222,2226

9
[ 1532-91-8 ]
[ 557-21-1 ]
[ 34846-65-6 ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 3303 - 3305

10
[ 94169-93-4 ]
[ 1532-91-8 ]

Reference： [1]Bulletin of the Polish Academy of Sciences: Chemistry,1988,vol. 36,p. 417 - 424

11
[ 1532-91-8 ]
[ 53599-88-5 ]

Yield	Reaction Conditions	Operation in experiment
88%	With sulfuric acid; potassium nitrate; at -5 - 20℃; for 1.0h;	To a solution of <strong>[1532-91-8]4-chloroisoquinoline</strong> 16a (10.0 g, 61 mmol) in 55 mL concentrated sulfuric acid was added a solution of potassium nitrate (7.98 g, 79 mmol) in 69.0 mL concentrated sulfuric acid at -5 C. The resulting mixture was stirred at 0 C. for 1 h and then stirred at room temperature overnight. The reaction mixture was poured to 300 mL ice water, adjusted pH to 8 using solid Na2CO3, extracted with EtOAc (200 mL*2). The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated. The crude product was purified by silica gel column chromatography (0-100% EtOAc/PE) to give 4-chloro-5-nitroisoquinoline 16b (11.2 g, white solid, yield: 88%). MS-ESI calc'd. [M+H]+ 209, found 209.
	With sulfuric acid; potassium nitrate; at 0℃; for 2.0h;	Intermediate 88 (375 mg) was dissolved in concentrated sulfuric acid (2 ml), then added with potassium nitrate (260 mg) with ice cooling and stirred for 2 hours. The reaction mixture was added with 28% aqueous ammonia (10 ml) and extracted twice with ethyl acetate (15 ml for each time). The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to obtain the title compound (332 mg).

Reference： [1]Patent: US2017/37050,2017,A1 .Location in patent: Paragraph 0240-0242
[2]Patent: US2005/20623,2005,A1 .Location in patent: Page 104

12
[ 23687-25-4 ]
[ 1532-91-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; copper(l) chloride; sodium nitrite; In water; at 0 - 20℃; for 15.0h;	Intermediate 87 (1.27 g) was dissolved in 1 N aqueous hydrochloric acid (36 ml) and added dropwise with an aqueous solution (36 ml) of sodium nitrite (1.21 g, Wako Pure Chemical Industries) with ice cooling. The obtained suspension was added dropwise to a solution of copper(I) chloride (1.83 g, Wako Pure Chemical Industries) in 1 N aqueous hydrochloric acid (20 ml) with ice cooling, then warmed to room temperature and stirred for 15 hours. The reaction mixture was added with 28% aqueous ammonia (50 ml) and extracted twice with ethyl acetate (150 ml for each time). The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1) to obtain the title compound (433 mg).

Reference： [1]Patent: US2005/20623,2005,A1 .Location in patent: Page 104

13
[ 1532-91-8 ]
[ 194032-34-3 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 16 1-[(4-Chloro-5-isoquinolinyl)sulfonyl]-hexahydro-1H-1,4-diazepine dihydrochloride Using 2.08 g of <strong>[1532-91-8]4-chloroisoquinoline</strong> (synthesised in accordance with J. Org. Chem., 1961, 26, 468), 4-chloro-5-chlorosulfonylisoquinoline was synthesised as in Reference Example 1.

Reference： [1]Patent: US6153608,2000,A
[2]Patent: US2017/37050,2017,A1

14
[ 1532-91-8 ]
[ 925890-48-8 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 792 - 795

15
[ 1532-91-8 ]
[ 88-69-7 ]
4-(2-isopropylphenoxy)isoquinoline [ No CAS ]

Reference： [1]Asian Journal of Chemistry,2014,vol. 26,p. 4747 - 4751

16
[ 1532-91-8 ]
[ 23687-25-4 ]

Reference： [1]Organic Letters,2015,vol. 17,p. 5934 - 5937

17
[ 1532-91-8 ]
[ 3336-49-0 ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 13493 - 13496

18
[ 1532-91-8 ]
[ 651310-21-3 ]

Reference： [1]Patent: US2017/37050,2017,A1

19
[ 1532-91-8 ]
[ 75-20-7 ]
[ 762-42-5 ]
dimethyl 2-(4-chloro-1-ethynylisoquinolin-2(1H)-yl)maleate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With tetrabutyl ammonium fluoride; In N,N-dimethyl acetamide; water; at 55℃; for 6.0h;Glovebox; Inert atmosphere;	General procedure: The N-heterocycle (1.1 mmol), acetylenic ester (1.0 mmol),carbide (2 mmol, 0.13 g), and TBAF·3 H2O (0.1-0.2 mmol; seeTables 2 and 3) were added to 1% H2O-DMA (3 mL), and themixture was stirred at 55 C for 6 h. When the reaction wascomplete, the mixture was diluted with EtOAc (5 mL) and sat. aqNH4Cl (5 mL). The mixture was stirred for an additional 30 minand then the two layers were separated. The aqueous layer wasextracted with EtOAc (3 × 10 mL), and the combined organiclayers were dried (MgSO4), filtered, and concentrated in vacuo.The residue was purified by chromatography [silica gel,hexane-EtOAc (5:1)].

Reference： [1]Synlett,2017,vol. 28,p. 2126 - 2130

20
[ 1532-91-8 ]
[ 24424-99-5 ]
[ 58635-45-3 ]
tert-butyl (R)-4-chloro-1-(3-(2-((methoxycarbonyl)amino)ethyl)-1H-indol-1-yl)isoquinoline-2(1H)-carboxylate [ No CAS ]
tert-butyl 4-chloro-1-(3-(2-((methoxycarbonyl)amino)ethyl)-1H-indol-1-yl)isoquinoline-2(1H)-carboxylate [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 6146 - 6154

21
[ 119-65-3 ]
[ 1532-91-8 ]

Yield	Reaction Conditions	Operation in experiment
92%	With [bis(acetoxy)iodo]benzene; chloroformic acid ethyl ester; In 1,2-dichloro-ethane; at 50℃; for 3.0h;	General procedure: To an 8 mL dram vial was added iodobenzene diacetate (0.6 mmol, 1.5 equiv), and heteroarene(0.4 mmol, 1 eq.), anhydrous dichloroethane (1 mL), then chloride source (5 equiv). The solutionwas allowed to stir (1000 rpm) at 50 C for the indicated amount of time. After which the solutionwas washed with saturated sodium bicarbonate, followed by saturated sodium thiosulfate andconcentrated. The crude mixture was then purified by column chromatography.

Reference： [1]Chem,2019,vol. 5,p. 417 - 428

22
[ 1532-91-8 ]
cyclobutanone O-(4-(trifluoromethyl)benzoyl) oxime [ No CAS ]
4-(4-chloroisoquinolin-1-yl)butanenitrile [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2019

23
[ 1532-91-8 ]
[ 79-31-2 ]
4-chloro-1-isopropylisoquinoline [ No CAS ]

Reference： [1]Organic Letters,2019

24
[ 1532-91-8 ]
[ 110-82-7 ]
4-chloro-1-cyclohexylisoquinoline [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2019,vol. 84,p. 12904 - 12912

25
[ 273-53-0 ]
[ 1532-91-8 ]
2-(isoquinolin-4-yl)benzo[d]oxazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With copper(l) iodide; potassium phosphate tribasic heptahydrate; palladium diacetate; nixantphos; In N,N-dimethyl-formamide; at 120℃; for 12.0h;Inert atmosphere;	General procedure: 2 mol% Pd(OAc)2/3 mol% Nixantphos, anhydrous DMF (1.0 ml) were added to an oven-dried 10 ml reaction vial equipped with a stir bar, the mixture was stirred at 45 C under an argon atmosphere for 1h to be a dark brown solution. 1 mol% CuI/1.1 mol% Nixantphos, anhydrous DMF (1.0 ml) were added to an oven-dried 10 ml reaction vial equipped with a stir bar, the mixture was stirred at 60 C under an argon atmosphere for 2h to be a colorless transparent solution. The amount of catalyst and solvent should scaled up by the number of reactions. Benzoxazoles (0.25 mmol), aryl chlorides (0.3 mmol) and K3PO4*7H2O (42.3 mg, 0.125 mmol, 0.5 equiv) were added to an oven-dried 10 ml reaction vial equipped with a stir bar. A stock solution of Pd(OAc)2/Nixantphos and CuI/Nixantphos in 1 ml of dry DMF was taken up by syringe and added to the reaction vial. The reaction vial filled with argon was then sealed with a septum. The reaction mixture was stirred for12 h or 24 h at 120 C, quenched with two drops of H2O, diluted with 3 mL of ethyl acetate, and filtered over a pad of MgSO4 and silica. The pad was rinsed with additional ethyl acetate, and the solution was concentrated in vacuo. The crude material was loaded onto a silica gel column and purified by flash chromatography.

Reference： [1]Tetrahedron Letters,2019,vol. 60

26
[ 1532-91-8 ]
[ 119-65-3 ]

Yield	Reaction Conditions	Operation in experiment
91%	With potassium <i>tert</i>-butylate; N,N-dimethyl-formamide at 35℃; for 24h; Schlenk technique; Inert atmosphere; Irradiation;

Reference： [1]Ding, Ting-Hui; Qu, Jian-Ping; Kang, Yan-Biao [Organic Letters, 2020, vol. 22, # 8, p. 3084 - 3088]

27
[ 1532-91-8 ]
1-[(4-chloro-5-isoquinolyl)sulfonyl]indoline-6-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: sulfuric acid; potassium nitrate / Petroleum ether / 12 h / 0 - 15 °C / Inert atmosphere 2.1: zinc; ammonium chloride / water; tetrahydrofuran / 3 h / 0 - 15 °C 3.1: hydrogenchloride; sodium nitrite / water / 1 h / -5 °C / Inert atmosphere 3.2: 2.5 h 4.1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 15 °C / Inert atmosphere