[ CAS No. 3951-95-9 ] {[proInfo.proName]}

Name: 3951-95-9|4-Bromoisoquinolin-1(2H)-one|97%
Brand: Ambeed
SKU: A148796
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Quality Control of [ 3951-95-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 3951-95-9 ]

SDS Specification

Alternatived Products of [ 3951-95-9 ]

Product Details of [ 3951-95-9 ]

CAS No. :	3951-95-9	MDL No. :	MFCD08437036
Formula :	C₉H₆BrNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZOPUFLIYIMVOGZ-UHFFFAOYSA-N
M.W :	224.05	Pubchem ID :	319772
Synonyms :

Calculated chemistry of [ 3951-95-9 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	52.27
TPSA :	32.86 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) :	-6.43 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.83
Log Po/w (XLOGP3) :	1.74
Log Po/w (WLOGP) :	2.29
Log Po/w (MLOGP) :	2.37
Log Po/w (SILICOS-IT) :	3.26
Consensus Log Po/w :	2.3

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.94
Solubility :	0.256 mg/ml ; 0.00114 mol/l
Class :	Soluble
Log S (Ali) :	-2.05
Solubility :	2.01 mg/ml ; 0.00898 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.47
Solubility :	0.00764 mg/ml ; 0.0000341 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.61

Safety of [ 3951-95-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 3951-95-9 ]

* 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 [ 3951-95-9 ]
Downstream synthetic route of [ 3951-95-9 ]

[ 3951-95-9 ] Synthesis Path-Upstream 1~7

1
[ 3951-95-9 ]
[ 66728-98-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	Reflux	A mixture of 4-bromoisoquinolin-1-ol (1.4 g, 5.80 mmol) and POCl3 (8.9 g, 58.09 mmol, 10 eq) was heated to reflux with stirring. The progress of the reaction was monitored by LCMS and was found to be complete after 4 h. The reaction mixture was cooled to RT, quenched with ice-cold water (100 mL) and extracted with EtOAc (3 × 25 mL). The combined organic layers were washed with water (3 × 20 mL) followed by saturated aqueous NaHCO3 solution (30 mL) and brine (20 mL). The organic layer was dried over anhydrous sodium sulfate. Removal of solvent under reduced pressure afforded 1.3 g (87percent) of 4-bromo-1-chloroisoquinoline as a white solid.

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 217 - 222

2
[ 3951-95-9 ]
[ 66728-98-1 ]

Reference： [1] Synthetic Communications, 2007, vol. 37, # 23, p. 4199 - 4208

3
[ 3951-95-9 ]
[ 74-88-4 ]
[ 33930-63-1 ]

Reference： [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 4462 - 4475
[2] Advanced Synthesis and Catalysis, 2018, vol. 360, # 2, p. 379 - 384
[3] Patent: US2018/44335, 2018, A1, . Location in patent: Paragraph 0720-0721

4
[ 491-30-5 ]
[ 3951-95-9 ]

Yield	Reaction Conditions	Operation in experiment
68%	With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 2 h;	Intermediate 6 4-bromoisoquinolin-1(2H)-one [0497] [0498] To a solution of isoquinolin-1(2H)-one (105 mg, 0.723 mmol) in DMF (2 mL), was added NBS (142 mg, 0.796 mmol). The mixture was stirred at rt for 2 h, then was concentrated. The crude product was purified via preparative HPLC to afford 110 mg (68percent) of Intermediate 6. [0499] MS (ESI) m/z: 223.9 (M+H)⁺; ¹H NMR (500 MHz, DMSO-d₆) δ 11.57 (br. s., 1H), 8.24 (dd, J=8.0, 0.8 Hz, 1H), 7.88-7.83 (m, 1H), 7.79-7.75 (m, 1H), 7.61 (ddd, J=8.0, 7.1, 1.1 Hz, 1H), 7.55 (s, 1H).

Reference： [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 4, p. 1299 - 1322
[2] Angewandte Chemie - International Edition, 2011, vol. 50, # 36, p. 8416 - 8419
[3] Synthetic Communications, 2007, vol. 37, # 23, p. 4199 - 4208
[4] Patent: US2014/206686, 2014, A1, . Location in patent: Paragraph 0497-0499
[5] Patent: WO2016/69976, 2016, A1, . Location in patent: Page/Page column 91

5
[ 491-30-5 ]
[ 3951-95-9 ]

Reference： [1] Patent: US6093731, 2000, A,

6
[ 491-30-5 ]
[ 256478-05-4 ]
[ 3951-95-9 ]

Reference： [1] Patent: EP1077945, 2003, B1,

7
[ 3749-21-1 ]
[ 3951-95-9 ]

Reference： [1] Chemistry Letters, 1983, p. 309 - 312

[ 3951-95-9 ] Synthesis Path-Downstream 1~64

1
[ 3749-21-1 ]
[ 3951-95-9 ]

Reference： [1]Chemistry Letters,1983,p. 309 - 312

Yield	Reaction Conditions	Operation in experiment
86%		Preparation 93 Ethyl 3-[(1,4-dichloro-7-isoquinolinyl)sulphonyl]amino}-2,2-dimethylpropanoate hydrochloride STR201 The title compound was obtained as a white solid (86%) from 1,4-dichlorosulphonyl chloride and ethyl 3-amino-2,2-dimethylpropanoate hydrochloride, following a similar procedure to that described in preparation 90. 1 H (CDCl3, 300 MHz) delta 1.25 (9H, m), 3.0 (2H, d), 4.1 (2H, q), 5.4 (1H, t), 8.2 (1H, d), 8.4 (1H, d), 8.5 (1H, s), 8.9 (1H, s) ppm. LRMS 404, 406 (MH+) Anal. found: C, 47.39; H, 4.44: N, 6.73. Calc. for C16 H18 Cl2 N2 O4 S: C, 47.42; H, 4.48; N, 6.91%.

3
[ 3951-95-9 ]
[ 624-92-0 ]
4-(methylthio)-1(2H)-isoquinolinone [ No CAS ]

Reference： [1]Synthetic Communications,2007,vol. 37,p. 4199 - 4208

4
[ 491-30-5 ]
[ 3951-95-9 ]

Yield	Reaction Conditions	Operation in experiment
68%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 2h;	Intermediate 6 4-bromoisoquinolin-1(2H)-one [0497] [0498] To a solution of isoquinolin-1(2H)-one (105 mg, 0.723 mmol) in DMF (2 mL), was added NBS (142 mg, 0.796 mmol). The mixture was stirred at rt for 2 h, then was concentrated. The crude product was purified via preparative HPLC to afford 110 mg (68%) of Intermediate 6. [0499] MS (ESI) m/z: 223.9 (M+H)+; 1H NMR (500 MHz, DMSO-d6) delta 11.57 (br. s., 1H), 8.24 (dd, J=8.0, 0.8 Hz, 1H), 7.88-7.83 (m, 1H), 7.79-7.75 (m, 1H), 7.61 (ddd, J=8.0, 7.1, 1.1 Hz, 1H), 7.55 (s, 1H).
	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 2h;	A. solution of isoquinoiin~ (2H)-one (150 rag, 1.03 mmol) in DMF (5 ml.) was treated with NBS (184 rag, 1 .03 mmol). The mixture was stirred at rt for 2 h and then poured into H20 (15 ml.). The formed precipitate was collected by filtration, washed with water and dried by lyophilization to give the title compound as a white solid.

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 1299 - 1322
[2]Angewandte Chemie - International Edition,2011,vol. 50,p. 8416 - 8419
[3]Synthetic Communications,2007,vol. 37,p. 4199 - 4208
[4]Patent: US2014/206686,2014,A1 .Location in patent: Paragraph 0497-0499
[5]Patent: WO2016/69976,2016,A1 .Location in patent: Page/Page column 91

5
[ 3951-95-9 ]
[ 66728-98-1 ]

Reference： [1]Synthetic Communications,2007,vol. 37,p. 4199 - 4208

6
[ 3951-95-9 ]
[ 68-12-2 ]
[ 63125-40-6 ]

Reference： [1]Synthetic Communications,2007,vol. 37,p. 4199 - 4208

7
[ 3951-95-9 ]
[ 124-38-9 ]
[ 34014-51-2 ]

Reference： [1]Synthetic Communications,2007,vol. 37,p. 4199 - 4208

8
[ 3951-95-9 ]
[ 74-88-4 ]
[ 77077-83-9 ]

Reference： [1]Synthetic Communications,2007,vol. 37,p. 4199 - 4208

9
[ 491-30-5 ]
[ 3951-95-9 ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; In acetonitrile;	Preparation 90 4-Bromo-1-chloro-7-isoquinolinesulphonyl chloride STR198 A suspension of isoquinolinol (10 g, 68.9 mmol) in MeCN (250 ml) at 50 C., was treated with N-bromosuccinimide (12.6 g, 70.8 mmol) whereupon almost complete solution occurred before a thick white precipitate was formed. After heating under reflux for 3 h, the reaction mixture was cooled in ice and the solid filtered, washed with MeCN, and dried to afford 4-bromo-1-(2H)-isoquinolone (7.6 g, 34.0 mmol). 1 H (DMSO-d6, 300 MHz) delta 7.55 (1H, s), 7.6 (1H, m), 7.75 (1H, d), 7.85 (1H, m), 8.2 (1H, d), 11.55 (1H, br s) ppm. LRMS 223, 225 (MH+).

Reference： [1]Patent: US6093731,2000,A

10
[ 3951-95-9 ]
[ 7440-44-0 ]
[ 108127-91-9 ]

Yield	Reaction Conditions	Operation in experiment
0.62 g (35%)	With hydrogenchloride In methanol; concentrated ammonia hydroxide; water	XXV 4-Amino-1(2H)-isoquinolinone monohydrochloride EXAMPLE XXV 4-Amino-1(2H)-isoquinolinone monohydrochloride A suspension of 2.0 g (8.92 mmol) of 4-bromo-1-isoquinolinol in 23 ml of concentrated ammonia hydroxide was heated in a sealed vessel for 16 hours at 120° C., then at 135° C. for one additional hour. The resulting yellow solution was diluted with 50 ml of water and then concentrated to 20 ml. The solid was collected, dissolved in methanol, treated with charcoal and filtered through celite. To this solution was added gaseous hydrochloric acid until a white precipitate appeared. The mixture was cooled and filtered to provide 0.62 g (35%) of the desired product; mp 275°-280° (dec).

Reference： [1]Current Patent Assignee: PFIZER INC; WAANAA RANBAATO - US5177075, 1993, A

11
withN-bromosuccinimide [ No CAS ]
[ 491-30-5 ]
[ 256478-05-4 ]
[ 3951-95-9 ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile;	Preparation 90 4-Bromo-1-chloro-7-isoquinolinesulphonyl chloride A suspension of isoquinolinol (10 g, 68.9 mmol) in MeCN (250 ml) at 50C, was treated withN-bromosuccinimide (12.6 g, 70.8 mmol) whereupon almost complete solution occurred before a thick white precipitate was formed. After heating under reflux for 3 h, the reaction mixture was cooled in ice and the solid filtered, washed with MeCN, and dried to afford 4-bromo-1-(2H)-isoquinolone (7.6 g, 34.0 mmol). 1H (DMSO-d6, 300MHz) delta 7.55 (1H, s), 7.6 (1H, m), 7.75 (1H, d), 7.85 (1H, m), 8.2 (1H, d), 11.55 (1H, br s) ppm. LRMS 223, 225 (MH+).

Reference： [1]Patent: EP1077945,2003,B1

12
[ 3951-95-9 ]
[ 1334432-85-7 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 8416 - 8419

13
[ 3951-95-9 ]
1-[tert-butyl(dimethyl)silyl]oxy}-1,2,3,4,4a,5,5a,6-octahydro-7Hbenzo[2,3]cyclobuta[1,2-c]isoquinolin-7-one [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 8416 - 8419

14
[ 3951-95-9 ]
[ 1334433-00-9 ]
(1R,4aR,5aR,11bS)-1-hydroxy-1,2,3,4,4a,5,5a,6-octahydro-7H-benzo[2,3]cyclobuta[1,2-c]isoquinolin-7-one [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 8416 - 8419

15
[ 3951-95-9 ]
[ 1334433-01-0 ]
[ 1334433-00-9 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 8416 - 8419

16
[ 3951-95-9 ]
[ 1334433-01-0 ]
4-(1-hydroxyhex-5-enyl)isoquinolin-1(2H)-one [ No CAS ]
[ 1334433-00-9 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 8416 - 8419

17
[ 3951-95-9 ]
[ 764-59-0 ]
[ 1334432-86-8 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 8416 - 8419

18
[ 3951-95-9 ]
[ 1119-51-3 ]
[ 1334432-78-8 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 8416 - 8419

19
[ 3951-95-9 ]
[ 100-39-0 ]
[ 33930-64-2 ]

Yield	Reaction Conditions	Operation in experiment
93%		Sodium hydride (60% dispersion in mineral oil, 0.656 g, 16.4 mmol) was carefully added to a solution of <strong>[3951-95-9]4-bromoisoquinolin-1(2H)-one</strong> (3.5 g, 15.6 mmol) in anhydrous DMF (60 mL) cooled to 0 C. The reaction was stirred at 0 C. for 30 min, then benzyl bromide (8.02 g, 46.9 mmol) was added slowly. The reaction was allowed to warm to rt and stirred for 17 h. After that time the reaction was diluted with water (200 mL) and extracted with ethyl acetate (3×200 mL). The organic phase was washed with water, brine, dried over Na2SO4 and concentrated under reduced pressure. The product was purified by flash column chromatography (silica gel, 90:10 hexanes/ethyl acetate to 75:25 hexanes/ ethyl acetate) to give 2-benzyl-<strong>[3951-95-9]4-bromoisoquinolin-1(2H)-one</strong> (4.55 g, 93%) as a white solid: 1H NMR (400 MHz, CDCl3) delta 8.49 (d, J=7.4 Hz, 1H), 7.79-7.84 (m, 1H), 7.71-7.79 (m, 1H), 7.53-7.60 (m, 1H), 7.29-7.38 (m, 6H), 5.21 (s, 2H); ESI MS m/z 314 [M+H]+ and 316 [M+H]+

Reference： [1]Patent: US2014/179648,2014,A1 .Location in patent: Paragraph 0927
[2]Journal of Medicinal Chemistry,2014,vol. 57,p. 1299 - 1322

20
[ 3951-95-9 ]
[ 1558050-02-4 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 1299 - 1322

21
[ 3951-95-9 ]
[ 1616401-67-2 ]

Reference： [1]Patent: US2014/179648,2014,A1

22
[ 3951-95-9 ]
[ 1616401-68-3 ]

Reference： [1]Patent: US2014/179648,2014,A1

23
[ 3951-95-9 ]
[ 1616401-69-4 ]

Reference： [1]Patent: US2014/179648,2014,A1

24
[ 3951-95-9 ]
[ 1616401-70-7 ]

Reference： [1]Patent: US2014/179648,2014,A1

25
[ 3951-95-9 ]
[ 1616401-73-0 ]

Reference： [1]Patent: US2014/179648,2014,A1

26
[ 3951-95-9 ]
4-(1-[(tert-butyldimethylsilyl)oxy]hepta-5,6-dien-1-yl)isoquinolin-1(2H)-one [ No CAS ]