[ CAS No. 5448-43-1 ]

Name: 5448-43-1|6-Chloroquinoxaline|98%
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SKU: A589327
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COA NMR CNMR HPLC LC-MS

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Alternatived Products of [ 5448-43-1 ]

Product Details of [ 5448-43-1 ]

CAS No. :	5448-43-1	MDL No. :	MFCD00047594
Formula :	C₈H₅ClN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	164.59 g/mol	Pubchem ID :	-
Synonyms :

Safety of [ 5448-43-1 ]

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 [ 5448-43-1 ]

* 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 [ 5448-43-1 ]
Downstream synthetic route of [ 5448-43-1 ]

[ 5448-43-1 ] Synthesis Path-Upstream 1~12

1
[ 6935-29-1 ]
[ 91-19-0 ]
[ 1448-87-9 ]
[ 5448-43-1 ]
[ 7483-33-2 ]

Reference： [1] Tetrahedron, 1989, vol. 45, # 24, p. 7795 - 7804

2
[ 6935-29-1 ]
[ 1448-87-9 ]
[ 5448-43-1 ]
[ 62163-09-1 ]
[ 1196-57-2 ]

Reference： [1] Tetrahedron, 1989, vol. 45, # 24, p. 7795 - 7804

3
[ 6935-29-1 ]
[ 1448-87-9 ]
[ 5448-43-1 ]

Reference： [1] Bulletin des Societes Chimiques Belges, 1986, vol. 95, # 8, p. 663 - 670

4
[ 5448-43-1 ]
[ 6298-37-9 ]

Reference： [1] Organic Letters, 2015, vol. 17, # 23, p. 5934 - 5937
[2] Angewandte Chemie - International Edition, 2015, vol. 54, # 12, p. 3773 - 3777[3] Angew. Chem., 2015, vol. 127, # 12, p. 3844 - 3848,5
[4] Angewandte Chemie - International Edition, 2015, vol. 54, # 12, p. 3768 - 3772[5] Angew. Chem., 2015, vol. 127, # 12, p. 3839 - 3843,5
[6] Organic Letters, 2014, vol. 16, # 17, p. 4388 - 4391

5
[ 5448-43-1 ]
[ 7467-91-6 ]

Reference： [1] Journal of the American Chemical Society, 2016, vol. 138, # 41, p. 13493 - 13496
[2] Organic Letters, 2012, vol. 14, # 14, p. 3688 - 3691
[3] Journal of Organic Chemistry, 2018, vol. 83, # 17, p. 9850 - 9857
[4] Organic Letters, 2017, vol. 19, # 11, p. 2853 - 2856

6
[ 6935-29-1 ]
[ 1448-87-9 ]
[ 5448-43-1 ]
[ 62163-09-1 ]
[ 1196-57-2 ]

Reference： [1] Tetrahedron, 1989, vol. 45, # 24, p. 7795 - 7804

7
[ 6935-29-1 ]
[ 7677-24-9 ]
[ 5448-43-1 ]
[ 62163-09-1 ]
[ 1196-57-2 ]
[ 7483-33-2 ]

Reference： [1] Tetrahedron, 1989, vol. 45, # 24, p. 7795 - 7804

8
[ 5448-43-1 ]
[ 6639-79-8 ]

Reference： [1] Journal of Organic Chemistry, 2013, vol. 78, # 21, p. 11096 - 11101

9
[ 5448-43-1 ]
[ 39267-11-3 ]
[ 6639-79-8 ]

Reference： [1] Journal of the Chemical Society, 1953, p. 2816,2819

10
[ 5448-43-1 ]
[ 7722-84-1 ]
[ 64-19-7 ]
[ 39267-11-3 ]
[ 6639-79-8 ]

Reference： [1] Journal of the Chemical Society, 1953, p. 2816,2819

11
[ 5448-43-1 ]
[ 64-18-6 ]
[ 7722-84-1 ]
[ 108-24-7 ]
[ 6639-80-1 ]
[ 6639-79-8 ]

Reference： [1] Journal of the Chemical Society, 1953, p. 2816,2819

12
[ 5448-43-1 ]
[ 73183-34-3 ]
[ 1167418-13-4 ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos In tetrahydrofuran at 20℃; for 0.0833333 h; Inert atmosphere Stage #2: at 70℃; for 5 h; Inert atmosphere	Under a nitrogen stream, 6-chloro-quinoxaline (5.15 g, 31.3 mmol), bi spinner cholate diborane (8.74 g, 34.4 mmol),in tetrahydrofuran (200 mL), tris (dibenzylideneacetone) dipalladium (287 mg, 0. 31 mmol), 2-dicyclohexylphosphino-2 ', 4', 6'-triisopropyl-biphenyl (597 mg, 1.25 mmol) was added to 300mL3 neck flask, and stirred at room temperature for 5 minutes. The solution to the potassium acetate (9.22g, 94.9mmol) was added, and the mixture was stirred for 5 hours at 70 ° C. Then, after cooling to room temperature, water was added to the reaction mixture and extracted. The organic layer was washed with saturated brine, and dried with anhydrous magnesium sulfate. Thereafter, the organic layer was concentrated by an evaporator. The resulting organic layer was concentrated The residue was purified by silica gel column chromatography (eluent = toluene / hexane), the desired product 2- (4,4,5,5-tetramethyl-1,3,2 dioxaborolan-2-yl) quinoxaline was obtained as a brown oil (yield 6.0 g, 75percent yield, LC 98.7percent purity). Compound identification was performed by H-NMR measurement

Reference： [1] Patent: JP2015/199681, 2015, A, . Location in patent: Paragraph 0105; 0106

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Yield	Reaction Conditions	Operation in experiment
90%	With [2,2]bipyridinyl; formic acid; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium formate In water at 80℃; for 5h;
89%	With tetrabutylammomium bromide; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In tetrahydrofuran at 60℃; for 63h; Inert atmosphere; Schlenk technique; Glovebox;
88%	With water; potassium hydroxide In 1,4-dioxane at 25℃; for 6h; Electrochemical reaction;	2.3.1. Electrochemical hydrogenation of quinoxalines using H2Oover a MoNi4 cathode General procedure: For the model reaction, electrochemical measurementswere performed in a divided cell consisting of a working electrode,a graphite rod counter electrode, and a Hg/HgO referenceelectrode. The cathodic cell (10 mL) and anodic cell (10mL) containing 7.0 mL of 1.0 M KOH solution were separatedby a membrane. First, 0.3 mmol of quinoxaline was added tothe cathodic cell and stirred to form a homogeneous solution.Chronoamperometry was carried out at a given constant potentialof -0.05 V vs. RHE, where the reaction mixture wasstirred until the starting materials disappeared. For the othersubstrates, electrochemical measurements were performed ina divided cell with a two-electrode system. The cathodic cell(10 mL) contained 1.0 M KOH solution (1.0 mL of dioxane and6.0 mL of H2O) and the anodic cell (10 mL) contained 7.0 mL of1.0 M KOH. The reactions were carried out at a constant currentof 25 mA. All experiments were performed at room temperature(RT, 25 °C).

81%	With ammonia borane; tris(pentafluorophenyl)borate In toluene at 80℃; for 8h; Schlenk technique; Inert atmosphere;
70%	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; potassium hydroxide; zinc In water; 1,2-dichloro-ethane at 50℃; Inert atmosphere; Schlenk technique;	3 Example 3 Under an argon atmosphere, [Rh(COD)Cl]2, Zn powder, KOH and 1.0 mL of 1,2-dichloroethane were added to a Schlenk tube equipped with a magnetic stirrer.A solution of 6-chloroquinoxaline in 1,2-dichloroethane (1.0 mL) was added to the above mixture.After adding H2O, the mixture was stirred at 50 ° C.Monitor by TLC until 6-chloroquinoxaline is completely consumed.The molar ratio of 6-chloroquinoxaline, [Rh (COD) Cl] 2, Zn powder, KOH and H2O is 1: 0.025: 3.5: 0.15: 10.The residue was purified by silica gel column chromatography,The desired product 6-chloro-1,2,3,4-tetrahydroquinoxaline was obtained.White solid, yield 70%,
70%	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; water; potassium hydroxide; zinc In toluene at 50℃; for 73h; Inert atmosphere;
	With lithium aluminium tetrahydride; diethyl ether
	With platinum; benzene Hydrogenation;
	With lithium aluminium tetrahydride In tetrahydrofuran for 3h; Reflux;

Yield	Reaction Conditions	Operation in experiment
85%	With bis(3,5-di-(tert-butyl)-2-hydroxyazobenzolato)nickel(II); potassium <i>tert</i>-butylate; oxygen In toluene at 80℃; for 8h; Sealed tube;
73%	In diethylene glycol dimethyl ether at 140℃; for 24h;	A generic experiment was as follows. In a two-neck roundbottomflask of 10 mL, 1,2-phenylenediamine (1a, 0.5 mmol),1,2-propyleneglycol (2a, 0.6 mmol), 1.5 mL of diethylene glycol dimethylether (diglyme), and an amount of catalyst were added.Subsequently, the reaction mixture was heated at 140 °C in a siliconebath that contains a magnetic stirrer and a temperature controller.

Yield	Reaction Conditions	Operation in experiment
98%	With hydrogen fluoride In water at 20℃; for 0.75h;
92%	In water at 20℃; for 0.5h; Green chemistry;
90%	In water at 20℃; for 1h;

[ CAS No. 5448-43-1 ]

Quality Control of [ 5448-43-1 ]

Related Doc. of [ 5448-43-1 ]

Product Details of [ 5448-43-1 ]

Safety of [ 5448-43-1 ]

Application In Synthesis of [ 5448-43-1 ]

[ 5448-43-1 ] Synthesis Path-Upstream 1~12

[ 5448-43-1 ] Synthesis Path-Downstream 1~42