6-Bromoquinoxaline
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6-Bromoquinoxaline
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CAS No:
50998-17-9
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Formula:
C8H5BrN2
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Chemical Name:
6-Bromoquinoxaline
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Synonyms:
Quinoxaline, 6-broMo-;6-Bromo-1,4-benzodiazine;6-BROMOQUINOXALINE;6-BROMOBENZOPYRAZINE;6-BROMOQUINOXALINE ,98%
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CAS No:
Safety Information
NONH for all modes of transport
3
22-41
26
Xi,Xn
Irritant
P280-P305 + P351 + P338
H302-H318
|Danger|H302 (97.5%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P280, P301+P312, P305+P351+P338, P310, P330, and P501|Aggregated GHS information provided by 40 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
6-Bromoquinoxaline Use and Manufacturing
General procedure: To a 250 ml three-necked flask was added 3.91 g (molecular weight 186, 0.021 mol) of 4-bromo-o-phenylenediamine, Tetraphenyl ethyl ketone 4.41 g (molecular weight 210, 0.021 mol), Ethanol (40 ml), Under stirring conditions, 3min dropping 0.2 grams of concentrated sulfuric acid, The reaction was carried out at 65 C for 4 hours, After completion of the reaction, the mixture was cooled to room temperature, filtered, washed successively with 50 ml of ethanol and 50 ml of petroleum ether, To obtain 6.66 g (molecular weight 360) of the intermediate compound 6-bromo-2, 3-diphenylquinoxaline in 88.1% yield.General procedure: To a solution of compound 6r (401.3 mg, 1 mmol), Pd(OAc)2 (22.5 mg, 0.1 mmol), P(O-Tolyl)3 (60.9 mg, 0.2 mmol), Et3N (303.6 mg, 417 muL, 3 mmol) in ACN (10 mL) was added a solution of R2X (heteroaryl or aryl halides, X=Br, I; 1.5 mmol) in ACN (5 mL) dropwise under an argon atmosphere in a sealed tube. The mixture was stirred under an argon atmosphere at 40 C for 16-48 h. The reaction mixture was then cooled, concentrated under vacuum and re-dissolved in CH2Cl2. After filtering, the filtrate was washed with saturated NaCl aqueous solution, dried with MgSO4 and concentrated under vacuum. The crude material was purified by column chromatography (PE/EA) on silica gel to afford compound 6ra-rt.This reaction showed high stereo- and regioselectivity.
Computed Properties
Molecular Weight:209.04
XLogP3:2.2
Hydrogen Bond Acceptor Count:2
Exact Mass:207.96361
Monoisotopic Mass:207.96361
Topological Polar Surface Area:25.8
Heavy Atom Count:11
Complexity:140
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
