[ CAS No. 22615-00-5 ] {[proInfo.proName]}

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Quality Control of [ 22615-00-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 22615-00-5 ]

Product Details of [ 22615-00-5 ]

CAS No. :	22615-00-5	MDL No. :	MFCD01646407
Formula :	C₉H₆BrNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LANTXZGXVINCPP-UHFFFAOYSA-N
M.W :	224.05	Pubchem ID :	818076
Synonyms :

Safety of [ 22615-00-5 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H320-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 22615-00-5 ]

* 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 [ 22615-00-5 ]
Downstream synthetic route of [ 22615-00-5 ]

[ 22615-00-5 ] Synthesis Path-Upstream 1~4

1
[ 22615-00-5 ]
[ 5332-24-1 ]

Reference： [1] Tetrahedron Letters, 1997, vol. 38, # 5, p. 845 - 848
[2] Chemical Communications, 2015, vol. 51, # 32, p. 7035 - 7038
[3] Organic Letters, 2018, vol. 20, # 23, p. 7712 - 7716

2
[ 22615-00-5 ]
[ 613-18-3 ]

Reference： [1] Synthetic Communications, 2000, vol. 30, # 3, p. 427 - 432

3
[ 22615-00-5 ]
[ 101870-60-4 ]

Reference： [1] European Journal of Organic Chemistry, 2016, vol. 2016, # 8, p. 1606 - 1611
[2] Heterocycles, 1991, vol. 32, # 8, p. 1579 - 1586
[3] Synlett, 2004, # 11, p. 2000 - 2004
[4] Chemical and Pharmaceutical Bulletin, 1959, vol. 7, p. 273,275
[5] Synthetic Communications, 2000, vol. 30, # 3, p. 427 - 432
[6] Patent: US5372813, 1994, A,
[7] Tetrahedron, 2013, vol. 69, # 45, p. 9512 - 9519

4
[ 22615-00-5 ]
[ 13721-00-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	With N,N-dimethyl-formamide; phosphorus(V) oxybromide In dichloromethane at 0 - 25℃; for 6 h; Inert atmosphere	General procedure: To a stirred solution of the appropriate azine N-oxides in anhydrous CH₂Cl₂ (0.1 M) at 0 °C is added POBr₃ (1.2 equiv) followed by dropwise addition of DMF (0.5 equiv) under argon. The resulting reaction mixture was warmed to 25 °C and stirred for several hours until the reaction is complete as indicated by TLC. Saturated aqueous sodium carbonate solution is added to the reaction mixture slowly to adjust the pH to 7–8. The resulting mixture is separated and the aqueous phase is extracted with CH₂Cl₂ thoroughly. The organic phase is combined and washed with brine, dried over Na₂SO₄, filtered and concentrated under reduced pressure to afford the crude product, which is purified by flash column chromatography using PE/EA (100:1) as eluent.

Reference： [1] Tetrahedron, 2016, vol. 72, # 38, p. 5762 - 5768

[ 22615-00-5 ] Synthesis Path-Downstream 1~11

1
[ 22615-00-5 ]
[ 101870-60-4 ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate;	3-Bromo-2-chloroquinoline (7). To POCl3 (7.5 ml, 80 mmol) was added in portions solid 6 (2.25 g, 10 mmol). The mixture was stirred at room temperature for 30 min and then 60 C. for 10 min. The mixture was then poured into cold 1M NaOH extracted with CH2 C2. The combined extracts were dried (K2 CO3) and concentrated to a residue which was purified by flash chromatography (EtOAc) to afford 3-Bromo-2-chloroquinoline 7 (1.95 g, 80%). 1 H NMR d (ppm): 7.6 dd (CH atom), 7.7 m (2 CH atom), 8.0 d (CH atom), 8.5 s (CH arom)

Reference： [1]European Journal of Organic Chemistry,2016,vol. 2016,p. 1606 - 1611
[2]Heterocycles,1991,vol. 32,p. 1579 - 1586
[3]Synlett,2004,p. 2000 - 2004
[4]Chemical and pharmaceutical bulletin,1959,vol. 7,p. 273,275
[5]Synthetic Communications,2000,vol. 30,p. 427 - 432
[6]Patent: US5372813,1994,A
[7]Tetrahedron,2013,vol. 69,p. 9512 - 9519

2
[ 22615-00-5 ]
[ 613-18-3 ]

Reference： [1]Synthetic Communications,2000,vol. 30,p. 427 - 432

3
[ 22615-00-5 ]
[ 941-91-3 ]

Reference： [1]Synlett,1997,vol. 1997,p. 1067 - 1068
[2]Patent: WO2019/140387,2019,A1

4
[ 22615-00-5 ]
[ 2232-08-8 ]
[ 1544536-11-9 ]

Reference： [1]Bulletin of the Korean Chemical Society,2013,vol. 34,p. 3459 - 3462

5
[ 22615-00-5 ]
[ 4426-47-5 ]
[ 1607440-02-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; at 90℃; for 12h;Inert atmosphere;	General procedure for the synthesis of 3-Butylquinoline 1-oxide (Compound 13a): To a stirred solution of substrate Compound 1 1 (100 mg, 0.446 mmol) in 1 ,4-dioxane was added <strong>[4426-47-5]butylboronic acid</strong> (91 mg, 0.892 mmol), Pd(PPh3)4 (25 mg, 0.0228 mmol) and K2C03 (184 mg, 1.33 mmol). The resulting reaction mixture was stirred at 90 C under nitrogen atmosphere for 12 h. After completion of reaction (monitored by TLC), the reaction mixture was diluted with water and extracted with ethyl acetate (3 x 10 mL). The combined organic layer was dried over Na2S04 and concentrated under reduced pressure, crude material was purified by flash chromatography using CH2Cl2:MeOH as an eluent to obtain Compound 13a as a white solid (72 mg, 80%).

Reference： [1]ChemMedChem,2014,vol. 9,p. 719 - 723
[2]Patent: WO2015/95780,2015,A1 .Location in patent: Page/Page column 19; 34

6
[ 22615-00-5 ]
[ 4737-50-2 ]
[ 1607440-03-8 ]

Reference： [1]ChemMedChem,2014,vol. 9,p. 719 - 723

7
[ 22615-00-5 ]
[ 16343-08-1 ]
[ 1607440-04-9 ]

Yield	Reaction Conditions	Operation in experiment
78%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,4-dioxane at 90℃; for 12h; Inert atmosphere;

Reference： [1]Kokatla, Hari Prasad; Sil, Diptesh; Tanji, Hiromi; Ohto, Umeharu; Malladi, Subbalakshmi S.; Fox, Lauren M.; Shimizu, Toshiyoki; David, Sunil A. [ChemMedChem, 2014, vol. 9, # 4, p. 719 - 723]

8
[ 22615-00-5 ]
[ 886747-03-1 ]
[ 1607440-06-1 ]

Reference： [1]ChemMedChem,2014,vol. 9,p. 719 - 723

9
[ 22615-00-5 ]
[ 13721-00-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	With N,N-dimethyl-formamide; phosphorus(V) oxybromide; In dichloromethane; at 0 - 25℃; for 6h;Inert atmosphere;	General procedure: To a stirred solution of the appropriate azine N-oxides in anhydrous CH2Cl2 (0.1 M) at 0 C is added POBr3 (1.2 equiv) followed by dropwise addition of DMF (0.5 equiv) under argon. The resulting reaction mixture was warmed to 25 C and stirred for several hours until the reaction is complete as indicated by TLC. Saturated aqueous sodium carbonate solution is added to the reaction mixture slowly to adjust the pH to 7-8. The resulting mixture is separated and the aqueous phase is extracted with CH2Cl2 thoroughly. The organic phase is combined and washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford the crude product, which is purified by flash column chromatography using PE/EA (100:1) as eluent.

Reference： [1]Tetrahedron,2016,vol. 72,p. 5762 - 5768

10
[ 22615-00-5 ]
[ 873-55-2 ]
[ 117620-35-6 ]

Yield	Reaction Conditions	Operation in experiment
48%	With ferric nitrate In dimethyl sulfoxide at 120℃; for 0.333333h; Microwave irradiation; regioselective reaction;	Synthesis of 2-arylsulfonyl quinolines (3a-c); general procedure General procedure: Quinoline N-oxides 1 (0.3 mmol), sodium arylsulfinates 2 (0.45 mmol) and Fe(NO3)3 (0.09 mmol) in DMSO (3.0 mL) were added to a microwave reaction tube (5.0 mL). The reaction mixture was heated at 120 °C for 20 min under microwave irradiation. After reaction completion, the solvent was distilled under vacuum. Ethyl acetate (10 mL) was added to the residue, and washed with saturated sodium chloride solution (3 × 30 mL). The organic phase was dried over anhydrous NaSO4 and concentrated under vacuum. The crude product was purified by silica gel column chromatography to give the desired products 3 using ethyl acetate/petroleum ether (1:10 to 1:5) as the eluent. All compounds were confirmedby IR, 1H NMR, 13C NMR and MS.

Reference： [1]Mai, Wenpeng; Lv, Mingxiu; Zhang, Xiaofeng; Lu, Kui [Journal of Chemical Research, 2017, vol. 41, # 12, p. 705 - 708]

11
[ 22615-00-5 ]
[ 354-38-1 ]
3-bromo-8-trifluoroacetaminoquinoline oxide [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 4728 - 4733

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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
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P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
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[ CAS No. 22615-00-5 ] {[proInfo.proName]}

Quality Control of [ 22615-00-5 ]

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Safety of [ 22615-00-5 ]

Application In Synthesis of [ 22615-00-5 ]

[ 22615-00-5 ] Synthesis Path-Upstream 1~4

[ 22615-00-5 ] Synthesis Path-Downstream 1~11

Precautionary Statements-General

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