[ CAS No. 81045-39-8 ] {[proInfo.proName]}

Name: 81045-39-8|5,8-Dibromoisoquinoline|98%
Brand: Ambeed
SKU: A100869
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Quality Control of [ 81045-39-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 81045-39-8 ]

Product Details of [ 81045-39-8 ]

CAS No. :	81045-39-8	MDL No. :	MFCD03109888
Formula :	C₉H₅Br₂N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KNBALCRXZUTMBP-UHFFFAOYSA-N
M.W :	286.95	Pubchem ID :	271281
Synonyms :

Calculated chemistry of [ 81045-39-8 ]

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 :	0.0
Molar Refractivity :	57.14
TPSA :	12.89 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.58 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.34
Log Po/w (XLOGP3) :	3.48
Log Po/w (WLOGP) :	3.76
Log Po/w (MLOGP) :	2.99
Log Po/w (SILICOS-IT) :	3.79
Consensus Log Po/w :	3.27

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-4.43
Solubility :	0.0107 mg/ml ; 0.0000373 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.43
Solubility :	0.106 mg/ml ; 0.000369 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.4
Solubility :	0.00115 mg/ml ; 0.00000399 mol/l
Class :	Moderately soluble

Medicinal Chemistry

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

Safety of [ 81045-39-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 81045-39-8 ]

* 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 [ 81045-39-8 ]
Downstream synthetic route of [ 81045-39-8 ]

[ 81045-39-8 ] Synthesis Path-Upstream 1~6

1
[ 119-65-3 ]
[ 34784-04-8 ]
[ 81045-39-8 ]

Reference： [1] Helvetica Chimica Acta, 1985, vol. 68, p. 1828 - 1834
[2] Helvetica Chimica Acta, 1985, vol. 68, p. 1828 - 1834
[3] Journal of Medicinal Chemistry, 2005, vol. 48, # 3, p. 744 - 752

2
[ 119-65-3 ]
[ 34784-04-8 ]
[ 63927-22-0 ]
[ 81045-39-8 ]

Reference： [1] Synthesis, 2002, # 1, p. 83 - 86

3
[ 119-65-3 ]
[ 34784-04-8 ]
[ 63927-22-0 ]
[ 81045-39-8 ]

Reference： [1] Synthesis, 2002, # 1, p. 83 - 86

4
[ 119-65-3 ]
[ 81045-39-8 ]

Yield	Reaction Conditions	Operation in experiment
56%	Stage #1: at 0℃; Stage #2: at -25 - 20℃; Stage #3: at 0℃; for 1 h;	Isoquinoline ( 13a) (1.83 ml, 15.50 mmol) was added slowly to concentrated H2SO4 ( 17 ml) at 0°C under stirring. The mixture was cooled at -25°C and sodium borohydride (6.34 g, 35.65 mmol) was added at a rate such that the reaction temperature was maintained between -25°C to -20°C. The resulting reaction was continued for 1 hour at the said temperature and then allowed to reach at room temperature. The reaction mixture was poured into crushed ice and the pH was adjusted to 7.0 using concentrated aqueous N¾. The resulting slurry was stirred for 1 hour at 0°C after which it was filtered and washed with ice-cold water. The crude product so obtained was air dried and purified by column chromatography to afford (2.5 g, 56percent) 5,8-dibromoisoquinoline (13b). MS (EI) rn/z: 286 (M+l). Ή NMR (400 MHz, DMSO-d₆): 8 9.48 (s, 1H), 8.78 (d, J = 6 Hz, 1H), 8.06 (d, J = 8 Hz, 1H), 7.98 (dd, J = 6 Hz, J = 8 Hz, 2H).

Reference： [1] Organic Letters, 2017, vol. 19, # 1, p. 262 - 265
[2] Journal of Materials Chemistry C, 2015, vol. 3, # 22, p. 5835 - 5843
[3] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 16, p. 4026 - 4030
[4] Patent: WO2013/5157, 2013, A1, . Location in patent: Page/Page column 36; 37
[5] Polymer, 2011, vol. 52, # 26, p. 6029 - 6036
[6] Reactive and Functional Polymers, 2011, vol. 71, # 8, p. 849 - 856

5
[ 119-65-3 ]
[ 34784-04-8 ]
[ 81045-39-8 ]

6
[ 119-65-3 ]
[ 34784-04-8 ]
[ 63927-22-0 ]
[ 81045-39-8 ]

Reference： [1] Synthesis, 2002, # 1, p. 83 - 86

[ 81045-39-8 ] Synthesis Path-Downstream 1~50

1
[ 119-65-3 ]
[ 34784-04-8 ]
[ 81045-39-8 ]

Reference： [1]Helvetica Chimica Acta,1985,vol. 68,p. 1828 - 1834
[2]Helvetica Chimica Acta,1985,vol. 68,p. 1828 - 1834
[3]Journal of Medicinal Chemistry,2005,vol. 48,p. 744 - 752

3
[ 81045-39-8 ]
[ 81171-44-0 ]
[ 244250-20-2 ]
benzyl 5,8-dibromo-1,2-dihydro-2-[N-(p-nitrophenyl)sulfonyl-(S)-alanyl]isoquinolin-1-ylacetate [ No CAS ]
benzyl 5,8-dibromo-1,2-dihydro-2-[N-(p-nitrophenyl)sulfonyl-(S)-alanyl]isoquinolin-1-ylacetate [ No CAS ]

Reference： [1]Tetrahedron,2001,vol. 57,p. 8827 - 8839

4
[ 81045-39-8 ]
[ 24850-33-7 ]
[ 53701-47-6 ]
1-allyl-5,8-dibromo-1,2-dihydro-2-[N-phthaloylalanyl]isoquinoline [ No CAS ]
1-allyl-5,8-dibromo-1,2-dihydro-2-[N-phthaloylalanyl]isoquinoline [ No CAS ]

Reference： [1]Tetrahedron,2001,vol. 57,p. 8827 - 8839

5
[ 81045-39-8 ]
[ 111061-31-5 ]
[ 53701-47-6 ]
phenyl 5,8-dibromo-1,2-dihydro-2-[N-phthaloylalanyl]isoquinolin-1-ylacetate [ No CAS ]
phenyl 5,8-dibromo-1,2-dihydro-2-[N-phthaloylalanyl]isoquinolin-1-ylacetate [ No CAS ]

Reference： [1]Tetrahedron,2001,vol. 57,p. 8827 - 8839

6
[ 81045-39-8 ]
[ 81171-44-0 ]
[ 53701-47-6 ]
benzyl 5,8-dibromo-1,2-dihydro-2-[N-phthaloylalanyl]isoquinolin-1-ylacetate [ No CAS ]
benzyl 5,8-dibromo-1,2-dihydro-2-[N-phthaloylalanyl]isoquinolin-1-ylacetate [ No CAS ]

Reference： [1]Tetrahedron,2001,vol. 57,p. 8827 - 8839

7
[ 13735-81-4 ]
[ 81045-39-8 ]
[ 4306-25-6 ]
5,8-dibromo-1,2-dihydro-1-phenacyl-2-[N-phthaloyl-(S)-alanyl]isoquinoline [ No CAS ]
5,8-dibromo-1,2-dihydro-1-phenacyl-2-[N-phthaloyl-(S)-alanyl]isoquinoline [ No CAS ]

Reference： [1]Tetrahedron,2001,vol. 57,p. 8827 - 8839

8
[ 119-65-3 ]
[ 34784-04-8 ]
[ 63927-22-0 ]
[ 81045-39-8 ]

Reference： [1]Synthesis,2002,p. 83 - 86

9
[ 688-61-9 ]
[ 81045-39-8 ]
(1S,3S)-1,3-Diallyl-5,8-dibromo-1,2,3,4-tetrahydro-isoquinoline [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,2002,vol. 657,p. 123 - 128

10
[ 81045-39-8 ]
[ 24850-33-7 ]
[ 4306-25-6 ]
[ 496910-19-1 ]
2-[(S)-2-((S)-1-Allyl-5,8-dibromo-1H-isoquinolin-2-yl)-1-methyl-2-oxo-ethyl]-isoindole-1,3-dione [ No CAS ]

Reference： [1]Heterocycles,2002,vol. 58,p. 115 - 118

11
[ 81045-39-8 ]
[ 24850-33-7 ]
[ 4306-25-6 ]
1-(R)-allyl-5,8-dibromo-1,2-dihydro-2-[N-phthaloyl-(S)-alanyl]isoquinoline [ No CAS ]

Reference： [1]Chemical and pharmaceutical bulletin,2003,vol. 51,p. 951 - 955

12
[ 81045-39-8 ]
[ 2826-79-1 ]

Reference： [1]Chemical and pharmaceutical bulletin,2003,vol. 51,p. 951 - 955
[2]Heterocycles,2002,vol. 58,p. 115 - 118
[3]Heterocycles,2002,vol. 58,p. 115 - 118

13
[ 81045-39-8 ]
[ 496910-23-7 ]

Reference： [1]Chemical and pharmaceutical bulletin,2003,vol. 51,p. 951 - 955
[2]Heterocycles,2002,vol. 58,p. 115 - 118
[3]Heterocycles,2002,vol. 58,p. 115 - 118

14
[ 81045-39-8 ]
[ 496910-21-5 ]

Reference： [1]Chemical and pharmaceutical bulletin,2003,vol. 51,p. 951 - 955
[2]Heterocycles,2002,vol. 58,p. 115 - 118

15
[ 81045-39-8 ]
[ 496910-22-6 ]

Reference： [1]Chemical and pharmaceutical bulletin,2003,vol. 51,p. 951 - 955
[2]Heterocycles,2002,vol. 58,p. 115 - 118
[3]Heterocycles,2002,vol. 58,p. 115 - 118

16
[ 81045-39-8 ]
[ 496910-20-4 ]

Reference： [1]Chemical and pharmaceutical bulletin,2003,vol. 51,p. 951 - 955
[2]Heterocycles,2002,vol. 58,p. 115 - 118

17
[ 81045-39-8 ]
[ 68263-23-0 ]

Reference： [1]Tetrahedron,2001,vol. 57,p. 8827 - 8839

18
[ 81045-39-8 ]
1,2,3,4-tetrahydro-2-[methoxy(trifluoromethyl)phenylacetyl]-1-(2-phenethyl)isoquinoline [ No CAS ]

Reference： [1]Tetrahedron,2001,vol. 57,p. 8827 - 8839

19
[ 81045-39-8 ]
1,2,3,4-tetrahydro-1-phenetyl-2-[N-phthaloyl-(S)-alanyl]isoquinoline [ No CAS ]

Reference： [1]Tetrahedron,2001,vol. 57,p. 8827 - 8839

20
[ 81045-39-8 ]
[ 68-12-2 ]
[ 943847-29-8 ]
[ 943847-30-1 ]

Yield	Reaction Conditions	Operation in experiment
		To a stirred mixture of <strong>[81045-39-8]5,8-dibromoisoquinoline</strong> (4.0 g. 13.9 mmol) in tetrahydrofuran (120 mL) at -78 0C under nitrogen atmosphere was added dropwise a solution of rc-butyllithium (2.3 M in hexane, 7.3 mL, 16.8 mmol). The reaction mixture turned dark. After stirring for 15 minutes, the reaction mixture was quenched by adding lambdazetaiV-dimethylformamide (4.0 mL). After stirring at -78 0C for an additional 1 h, the reaction mixture was quenched with water, extracted with mixture of ethyl acetate/hexane (2:8), washed with water and brine, dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using hexanes/ethyl acetate as eluent to afford the 8-bromo-5-isoquinolinecarboxaldehyde (0.10 g), followed by 5-bromo-8-isoquinoIinecarboxaldehyde (1.0 g) as white solids.1H NMR (CDCl3) of S-bromo-5-isoquinolinecarboxaldehyde: 10.36 (s, IH), 9.72 (s, IH), 9.00 (d, IH), 8.79 (d, IH), 8.04 (d, IH), 8.01 (dd, IH); and1H NMR (CDCl3) of S-bromo-S-isoquinolinecarboxaldehyde: 10.57 (s, IH), 10.41 (s, IH), * 8.81 (d, IH), 8.18 (d, IH), 8.11 (d, IH), 7.94 (d, IH).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 4026 - 4030
[2]Patent: WO2007/79162,2007,A1 .Location in patent: Page/Page column 33-34

21
[ 81045-39-8 ]
[ 761446-44-0 ]
[ 1353970-23-6 ]
[ 1353970-21-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate tribasic trihydrate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; at 80℃; for 18h;Inert atmosphere;	A suspension of 573 mg (2.0 mmol) <strong>[81045-39-8]5,8-dibromoisoquinoline</strong>, 458 mg (2.2 mmol) 1- methyM^^.S.S-tetramethyl-fl .S^ldioxaborolan^-y -I H-pyrazole, 849 mg (4.0 mmol) tri-potassium-phosphate trihydrate and 140 mg (0.20 mmol) bis- (triphenylphosphine)-palladium(ll)-chloride in 4 ml 1 ,2-dimethoxyethane were stirred for 18 hours at 80 C under nitrogen. The reaction mixture was cooled to room temperature, diluted with THF and filtered. The filtrate was evaporated and the residue was chromatographed on a silica gel column with ethylacetate/methanol as eluent. The two isomers were obtained separately.First eluted isomer: 8-bromo-5-(1-methyl-1 H-pyrazol-4-yl)-isoquinoline as colourless crystals; HPLC/MS 1.90 min, [M+H] = 288/290.Second eluted isomer: 5-bromo-8-(1-methyl-1 H-pyrazol-4-yl)-isoquinoline as yellow crystals; HPLC/MS (A) 2.02 min, [M+H] = 288/290.
	With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate tribasic trihydrate; In 1,2-dimethoxyethane; at 80℃; for 18h;Inert atmosphere;	1. A suspension of 573 mg (2.0 mmol) <strong>[81045-39-8]5,8-dibromoisoquinoline</strong>, 458 mg (2.2 mmol) 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole, 849 mg (4.0 mmol) tri-potassium-phosphate trihydrate and 140 mg (0.20 mmol) bis-(triphenylphosphine)-palladium(II)-chloride in 4 ml 1,2-dimethoxyethane were stirred for 18 hours at 80 C. under nitrogen. The reaction mixture was cooled to room temperature, diluted with THF and filtered. The filtrate was evaporated and the residue was chromatographed on a silica gel column with ethylacetate/methanol as eluent. The two isomers were obtained separately.[0446]First eluted isomer: 8-bromo-5-(1-methyl-1H-pyrazol-4-yl)-isoquinoline as colourless crystals; HPLC/MS 1.90 min, [M+H]=288/290.[0447]Second eluted isomer: 5-bromo-8-(1-methyl-1H-pyrazol-4-yl)-isoquinoline as yellow crystals; HPLC/MS (A) 2.02 min, [M+H]=288/290.

Reference： [1]Patent: WO2012/595,2012,A1 .Location in patent: Page/Page column 102-103
[2]Patent: US2013/102603,2013,A1 .Location in patent: Paragraph 0444; 0445; 0446; 0447

22
[ 81045-39-8 ]
[ 1323919-50-1 ]
[ 761446-44-0 ]
[ 1353967-97-1 ]
[ 1353968-20-3 ]

Yield	Reaction Conditions	Operation in experiment
		A suspension of 573 mg (2.0 mmol) <strong>[81045-39-8]5,8-dibromoisoquinoline</strong>, 458 mg (2.2 mmol) 1- methyM^^.S.S-tetramethyl-fl .S^ldioxaborolan^-y -I H-pyrazole, 849 mg (4.0 mmol) tri-potassium-phosphate trihydrate and 140 mg (0.20 mmol) bis- (triphenylphosphine)-palladium(ll)-chloride in 4 ml 1 ,2-dimethoxyethane were stirred for 18 hours at 80 C under nitrogen. The reaction mixture was cooled to room temperature, diluted with THF and filtered. The filtrate was evaporated and the residue was chromatographed on a silica gel column with ethylacetate/methanol as eluent. The two isomers were obtained separately.First eluted isomer: 8-bromo-5-(1-methyl-1 H-pyrazol-4-yl)-isoquinoline as colourless crystals; HPLC/MS 1.90 min, [M+H] = 288/290.Second eluted isomer: 5-bromo-8-(1-methyl-1 H-pyrazol-4-yl)-isoquinoline as yellow crystals; HPLC/MS (A) 2.02 min, [M+H] = 288/290.; A suspension of 135 mg (0.47 mmol) 8-bromo-5-(1-methyl-1H-pyrazol-4-yl)- isoquinoline, 126 mg (0.47 mmol) 2-(2-fluoro-phenyl)-[1,8]naphthyridine-4-boronic acid and 47.4 mg (0.56 mmol) sodium hydrogen carbonate in 1.2 ml DMF and 0.6 ml water was heated to 80 C under nitrogen. Then 6.6 mg (0.009 mmol) bis- (triphenylphosphine)-palladium(ll)-chloride were added. The reaction mixture was stirred for 18 hours at 80 C. The reaction mixture was cooled to room temperature and partitioned between water and dichloromethane. The organic phase was dried over sodium sulfate and evaporated. The residue was chromatographed on a silica gel column with ethyl acetate/methanol as eluent yielding 2-(2-fluoro-phenyl)-4-[5- (1-methyl-1H-pyrazol-4-yl)-isoquinolin-8-yl]-[1,8]naphthyridine as colourless solid; HPLC/MS (A): 1.87 min, [M+H] 432.1H NMR (400 MHz, DMSO) delta = 9.19 (dd, J=4.1, 1.9, 1H), 8.83 (d, J=0.9, 1H), 8.60 (d, J=6.0, 1H), 8.27 (s, 1H), 8.23 (td, J=7.9, 1.8, 1H), 8.17 (dd, J=6.0, 0.9, 1H), 8.11 (d, J=2A, 1H), 7.95 (d, J=7.4, 1H), 7.91 (m, 2H), 7.80 (d, J=7A, 1H), 7.62 (m, 1H), 7.57 (dd, J=8.4, 4.1, 1H), 7.47 (td, J=7.6, 1.1, 1H), 7.41 (ddd, J=11.6, 8.3, 1.0, 1H), 4.01 (s, 3H). Similarly was prepared: 2-(2-Fluoro-phenyl)-4-[8-(1-methyl-1H-pyrazol-4-yl)- isoquinolin-5-yl]-[1,8]naphthyridine as yellow solid; HPLC/MS (A): 1.84 min, [M+H] 432.1H NMR (400 MHz, DMSO) delta = 9.66 (d, J=0.9, 1H), 9.18 (dd, J=4.1, 1.9, 1H), 8.45 (d, J=5.9, 1H), 8.33 (s, 1H), 8.22 (td, J=7.9, 1.8, 1H), 8.06 (d, J=2.3, 1H), 7.95 (d, J=0.8, 1H), 7.93 (d, J=7.4, 1H), 7.87 (dd, J=8.4, 1.9, 1H), 7.83 (d, J=7.4, 1H), 7.62 (dddd, J=8.2, 7.2, 5.1, 1.9, 1H), 7.56 (dd, J=8A, 4.1, 1H), 7.47 (td, J=7.6, 1.1, 1H), 7.41 (ddd, .7=11.7, 8.3, 1.0, 1H), 7.29 (dd, .7=5.9, 0.9, 1H), 4.02 (s, 3H).

Reference： [1]Patent: WO2012/595,2012,A1 .Location in patent: Page/Page column 102-103

23
[ 119-65-3 ]
[ 81045-39-8 ]

Yield	Reaction Conditions	Operation in experiment
56%		Isoquinoline ( 13a) (1.83 ml, 15.50 mmol) was added slowly to concentrated H2SO4 ( 17 ml) at 0C under stirring. The mixture was cooled at -25C and sodium borohydride (6.34 g, 35.65 mmol) was added at a rate such that the reaction temperature was maintained between -25C to -20C. The resulting reaction was continued for 1 hour at the said temperature and then allowed to reach at room temperature. The reaction mixture was poured into crushed ice and the pH was adjusted to 7.0 using concentrated aqueous N¾. The resulting slurry was stirred for 1 hour at 0C after which it was filtered and washed with ice-cold water. The crude product so obtained was air dried and purified by column chromatography to afford (2.5 g, 56%) 5,8-dibromoisoquinoline (13b). MS (EI) rn/z: 286 (M+l). ? NMR (400 MHz, DMSO-d6): 8 9.48 (s, 1H), 8.78 (d, J = 6 Hz, 1H), 8.06 (d, J = 8 Hz, 1H), 7.98 (dd, J = 6 Hz, J = 8 Hz, 2H).

Reference： [1]Organic Letters,2017,vol. 19,p. 262 - 265
[2]Journal of Materials Chemistry C,2015,vol. 3,p. 5835 - 5843
[3]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 4026 - 4030
[4]Patent: WO2013/5157,2013,A1 .Location in patent: Page/Page column 36; 37
[5]Polymer,2011,vol. 52,p. 6029 - 6036
[6]Reactive and functional polymers,2011,vol. 71,p. 849 - 856

24
[ 81045-39-8 ]
[ 913558-64-2 ]

Reference： [1]Polymer,2011,vol. 52,p. 6029 - 6036

25
[ 81045-39-8 ]
[ 1353436-09-5 ]

Reference： [1]Polymer,2011,vol. 52,p. 6029 - 6036

26
[ 81045-39-8 ]
[ 1312759-04-8 ]

Reference： [1]Reactive and functional polymers,2011,vol. 71,p. 849 - 856

27
[ 81045-39-8 ]
[ 569343-09-5 ]
[ 1312758-98-7 ]

Reference： [1]Reactive and functional polymers,2011,vol. 71,p. 849 - 856

28
[ 81045-39-8 ]
[ 1353968-20-3 ]

Reference： [1]Patent: US2013/102603,2013,A1

29
[ 81045-39-8 ]
[ 1622863-84-6 ]