[ CAS No. 876-88-0 ] {[proInfo.proName]}

Name: 876-88-0|6-Bromocinnolin-4-ol|98%
Brand: Ambeed
SKU: A254470
Price: 20.0 USD
Availability: InStock
Rating: 98 (35 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

DV 2D 3D

3d Animation Molecule Structure of 876-88-0

Structure of 876-88-0 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 876-88-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 876-88-0 ]

SDS Specification

Alternatived Products of [ 876-88-0 ]

Product Details of [ 876-88-0 ]

CAS No. :	876-88-0	MDL No. :	MFCD09834642
Formula :	C₈H₅BrN₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VWMHMZLZLNLBPB-UHFFFAOYSA-N
M.W :	225.04	Pubchem ID :	270902
Synonyms :

Safety of [ 876-88-0 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P302+P352-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 876-88-0 ]

* 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 [ 876-88-0 ]
Downstream synthetic route of [ 876-88-0 ]

[ 876-88-0 ] Synthesis Path-Upstream 1~4

1
[ 876-88-0 ]
[ 318276-72-1 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 20, p. 6832 - 6846

2
[ 876-88-0 ]
[ 68211-15-4 ]

Yield	Reaction Conditions	Operation in experiment
89%	With thionyl chloride In N,N-dimethyl-formamide for 0.5 h; Reflux	Thionyl chloride (3 mL) and N, N-dimethylformamide (30 μL) were added to 6-bromocinnolin-4 (1 H) -one (300 mg, 1.33 mmol) and the mixture was heated under reflux for 30 minutes. The reaction solution was concentrated,Saturated multilayer water was added to the obtained residue,And extracted with ethyl acetate. The organic layer was washed with saturated brine,After drying over anhydrous magnesium sulfate, filtration,The solvent was distilled off. The resulting residue was purified by silica gel column chromatography (hexane / ethyl acetate)To give the title compound (288 mg, 89percent). Yellow solid
85%	With trichlorophosphate In tetrahydrofuran for 1 h; Reflux	6-l3romo-4-chlorocinnoline (8a) In a flame dried250 mE round bottom flask was added 6-bromocinnolin-4 (1H)-one (1.00 g, 4.44 mmol), anhydrous tetrahydrofuran (45 mE), and phosphorus oxychloride (1.25 mE, 13.41 mmol). The mixture was refluxed for 1 hour at which point a deep greenlblue solution had resulted. The solution was cooled to 0° C. and was quenched by the dropwise addition of sat. aq. NaHCO3 (70 mE). The mixture was allowed to warm to room temperature and stir for an additional 1 hout Water (50 mE) was added and the mixture was extracted with dichloromethane (3x100 mE). The combined organic layers were washed with sat. aq. NaHCO3 (50 mE), washedwith brine (50 mE), dried over Na2SO4, and concentrated on to silica, and purified by flash column chromatography using a gradient of 1-5percent methanol in dichloromethane to yield an inseparable10:1 mixture of 8a and 8b as a brown solid in 85percent yield. ‘H NMR (500 MHz, CDC13) ö 9.36 (s, 1H), 8.43 (d, J=8.8 Hz, 1H), 8.36 (d, J=2.0 Hz, 1H), 7.98 (dd, J=9.3, 2.0 Hz, 1H). ECMS found 242.9/199.0 [M+H].

Reference： [1] Patent: JP6378918, 2018, B2, . Location in patent: Paragraph 0721; 0724
[2] Patent: US2015/259331, 2015, A1, . Location in patent: Paragraph 0192
[3] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 20, p. 6832 - 6846
[4] Patent: US2003/187026, 2003, A1,
[5] Journal of the Chemical Society, 1950, p. 384,389
[6] Journal of Organic Chemistry, 1946, vol. 11, p. 405,412
[7] Journal of the Chemical Society, 1947, p. 917,920

3
[ 876-88-0 ]
[ 68211-15-4 ]

Reference： [1] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 4, p. 434 - 438

4
[ 876-88-0 ]
[ 68211-13-2 ]
[ 68211-15-4 ]

Reference： [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 14, p. 5522 - 5537

Same Skeleton Products

Related Products

Historical Records

Related Functional Groups of
[ 876-88-0 ]

Bromides

[ 885518-77-4 ]

6-Bromo-1H-indazol-4-ol

Similarity: 0.84

[ 885519-21-1 ]

6-Bromo-4-methoxy-1H-indazole

Similarity: 0.81

[ 885518-75-2 ]

4-Bromo-1H-indazol-6-ol

Similarity: 0.80

[ 1227270-50-9 ]

5-Bromo-1H-indazol-6-ol

Similarity: 0.80

Alcohols

[ 885518-77-4 ]

6-Bromo-1H-indazol-4-ol

Similarity: 0.84

[ 875-66-1 ]

Cinnolin-4-ol

Similarity: 0.83

[ 885518-75-2 ]

4-Bromo-1H-indazol-6-ol

Similarity: 0.80

[ 1227270-50-9 ]

5-Bromo-1H-indazol-6-ol

Similarity: 0.80

Related Parent Nucleus of
[ 876-88-0 ]

Cinnolines

[ 875-66-1 ]

Cinnolin-4-ol

Similarity: 0.83

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

Yield	Reaction Conditions	Operation in experiment
34.8%	Stage #1: N-(2-acetyl-4-bromophenyl)acetamide With hydrogenchloride In tetrahydrofuran; water at 85℃; for 1.5h; Stage #2: With hydrogenchloride; sodium nitrite In water at 100℃; for 3h;
	Stage #1: N-(2-acetyl-4-bromophenyl)acetamide With hydrogenchloride In tetrahydrofuran for 1h; Inert atmosphere; Reflux; Stage #2: With hydrogenchloride; sodium nitrite In water at 0 - 20℃; for 21h; Reflux;	12 Under N2, a mixture of N-(2-acetyl-4-bromophenyl)acetamide (35 g, 137 mmol) and HCI (100 mL, 600 mmol) in THF (400 mL) was heated to reflux for 1 h. After being concentrated under vacuum to remove the solvent, the mixture was treated with EtOAc( 100 mL). The aqueous layer was concentrated to remove THF, and 6N HCI (100 mL, 600 mmol) was added at room temperature. After cooling to 0°C, the resulting mixture was treated dropwise with NaNO2 (9.43 g, 137 mmol) in 20 mL H2O. The reaction mixture was then stirred at r.t. for 15 h. Then the resulting mixture was heated to reflux for another 6 h. The mixture was cooled to r.t. The solid was collected and dried in vacuo, to afford the desired product as a white solid. The crude product was used directly in next step without further purification. (19.5g, yield 63.4%) MS (m/z): 227 (M+H)+
	Stage #1: N-(2-acetyl-4-bromophenyl)acetamide With hydrogenchloride In tetrahydrofuran for 1h; Inert atmosphere; Reflux; Stage #2: With sodium nitrite In water at 0 - 20℃; for 15h;	12 EXAMPLE 12 Synthesis of Compounds 183 and 184 Compound 183 2-(4-(8-(6-amino-5-(trifluoromethyl)pyridin-3-yl)-1H-imidazo[4,5-c]cinnolin-1-yl)phenyl)-2-methylpropanenitrile Under N2, a mixture of N-(2-acetyl-4-bromophenyl)acetamide (35 g, 137 mmol) and HCl (100 mL, 600 mmol) in THF (400 mL) was heated to reflux for 1 h. After being concentrated under vacuum to remove the solvent, the mixture was treated with EtOAc (100 mL). The aqueous layer was concentrated to remove THF, and 6N HCl (100 mL, 600 mmol) was added at room temperature. After cooling to 0° C., the resulting mixture was treated dropwise with NaNO2 (9.43 g, 137 mmol) in 20 mL H2O. The reaction mixture was then stirred at r.t. for 15 h. Then the resulting mixture was heated to reflux for another 6 h. The mixture was cooled to r.t. The solid was collected and dried in vacuo, to afford the desired product as a white solid. The crude product was used directly in next step without further purification. (19.5 g, yield 63.4%) MS (m/z): 227 (M+H)+

Yield	Reaction Conditions	Operation in experiment
58.6%	With sulfuric acid; nitric acid at 0 - 60℃; for 3h; Inert atmosphere;	12 Under N2, an orange solution of 6-bromocinnolin-4-ol (18.5 g, 82 mmol) in HNO3 (90 ml_, 82 mmol) was cooled to 0°C, and H2SO4 (30 ml_) was added. The resulting mixture was then heated at 60°C for 3h. After the reaction went to completion as monitored by LC-MS, the reaction mixture was cooled to 0°C, and was then quenched with H2O (20 ml_). The mixture was diluted with EtOAc (25 ml_). Following general workup procedures, the crude residue was added to silica gel, and eluted with PE/EtOAc to give 6-bromo-3-nitrocinnolin-4-ol as a pale yellow solid (13 g, yield58.6%).
58.6%	With sulfuric acid; nitric acid at 0 - 60℃; for 3h;	12 EXAMPLE 12 Synthesis of Compounds 183 and 184 Compound 183 2-(4-(8-(6-amino-5-(trifluoromethyl)pyridin-3-yl)-1H-imidazo[4,5-c]cinnolin-1-yl)phenyl)-2-methylpropanenitrile Under N2, an orange solution of 6-bromocinnolin-4-ol (18.5 g, 82 mmol) in HNO3 (90 mL, 82 mmol) was cooled to 0° C., and H2SO4 (30 mL) was added. The resulting mixture was then heated at 60° C. for 3 h. After the reaction went to completion as monitored by LC-MS, the reaction mixture was cooled to 0° C., and was then quenched with H2O (20 mL). The mixture was diluted with EtOAc (25 mL). Following general workup procedures, the crude residue was added to silica gel, and eluted with PE/EtOAc to give 6-bromo-3-nitrocinnolin-4-ol as a pale yellow solid (13 g, yield 58.6%).

Yield	Reaction Conditions	Operation in experiment
61%	With trichlorophosphate In tetrahydrofuran for 0.5h; Reflux;	I-1-2 Preparation I-1-2: 4-chloro-6-bromocinnoline 10.0 g (0.044 mol) 4-hydroxy-6-bromocinnoline and 80 mL THF were added to a 500 mL flask and refluxed, and 10.2 g (0.066 mol, 1.5 eq) POCl3 was added dropwise.About 30 minutes later, TLC confirmed that the reaction was complete,Rotary evaporation to remove THF, add DCM until most of it is dissolved, wash with a large amount of saturated NaHCO3 to pH=78, separate the DCM layer, filter with silica gel (developing solvent is DCM)Obtained 4-chloro-6-bromocinnoline(6.6 g, 0.027 mol, 61%).
61%	Stage #1: 6-bromocinnolin-4-ol In tetrahydrofuran for 0.166667h; Reflux; Stage #2: With trichlorophosphate In tetrahydrofuran for 0.5h;	Compound 32 (10 g, 0.044 mol) and THF (80 mL) were stirred at reflux for 10 min before POCl3 (10 g, 0.065 mol) was added, then was stirred for a further 30 min until TLC showed completion of the reaction. The mixture was concentrated, solved by DCM, then washed with saturated NaHCO3 to adjust pH to 7~8. The organic layer was concentrated, then purified by column chromatography to get 33 (6.6 g, 61%). 1H-NMR (400 MHz, CDCl3): δ ppm 8.02 (d, J = 9.04 Hz, 1H), 8.40 (s, 1H), 8.48 (d, J = 8.56 Hz, 1H), 9.38 (s, 1H).
54.7%	With trichlorophosphate at 85℃; for 3.5h;

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: 1-(2-amino-5-bromophenyl)ethanone With hydrogenchloride In water at 0℃; for 0.333333h; Stage #2: With sodium nitrite In water at 0℃; Reflux;	I-1-1 Preparation I-1-1: 4-hydroxy-6-bromocinnoline 20.0 g (0.093 mol) of 2-amino-5-bromoacetophenone and 40 mL of water were added to a 500 mL flask, 40 mL of concentrated hydrochloric acid was added with stirring at 0° C., and stirring was continued for 20 min.A solution of 6.7g (0.097mol, 1.04eq.) NaNO2 dissolved in 50mL water was slowly added dropwise at 02.After dripping, return to room temperature and stir for 1 hour, then reflux for 6 hours, and overnight at room temperature.It was filtered to obtain 4-hydroxy-6-bromocinnoline(18.4 g, 0.082 mol, 88%).
88%	With hydrogenchloride; sodium nitrite In water at 0 - 20℃; for 7h; Reflux;	Compound 31 (20 g, 0.093 mol) and water (40 mL) were stirred for 10 min at 0 oC before conc. HCl (40 mL) was added. To the mixture was added a solution of NaNO2 (6.7 g, 0.097 mol) in water (50 mL), slowly and dropwise. After the addition, the reaction was warmed to room temperature and stirred for a further 1 h, following by a reflux of 6 h. The mixture was then filtered, filter cake washed with water and MTBE to get 32 (18 g, 88%). 1H-NMR (400 MHz, MeOD): δ ppm 7.58 (d, J = 9.00 Hz, 1H), 7.89 (s, 1H), 7.94 (d, J = 9.12 Hz, 1H), 8.31 (s, 1H).
75.1%	With hydrogenchloride; sodium nitrite In water at 0 - 85℃; for 1.25h;	2-1 Step 2-1, preparation of 6-bromo-cinnolin-4-ol: To a suspension of 1-(2-amino-5-bromo-phenyl)-ethanone (5.000 g, 23.35 mmol) in 5 N HCl (aq) (70 mL) at 0° C. was slowly added a solution of sodium nitrite (1.933 g, 28.01 mmol) in H2O (5 mL). After stirring at 0° C. for 15 min, the reaction solution was heated at 85° C. for 1 hr. The mixture was cooled to RT and the solid was collected by vacuum filtration and washed with water to afford the title compound (3.947 g, 75.1% yield) as a brown solid. MS (M+H)-=225.2.

[ CAS No. 876-88-0 ] {[proInfo.proName]}

Quality Control of [ 876-88-0 ]

Related Doc. of [ 876-88-0 ]

Product Details of [ 876-88-0 ]

Safety of [ 876-88-0 ]