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6-Bromoquinoline

6-Bromoquinoline structure

CAS No:
5332-25-2
Formula:
C9H6BrN
Chemical Name:
6-Bromoquinoline
Synonyms:
Quinoline,6-bromo-;6-Bromoquinoline;NSC 3996
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

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Description

Thick Oil

6-Bromoquinoline Basic Attributes

Molecular Weight：

208.05

Exact Mass：

208.05

EC Number：

206-363-3

UNII：

KS7HD5UJ94

NSC Number：

3996

DSSTox ID：

DTXSID5063788

HScode：

2933499090

Characteristics

PSA：

12.9

XLogP3：

2.8

Appearance：

Light Yellow Colour Liquid

Density：

1.55

Melting Point：

24 °C

Boiling Point：

281 °C

Flash Point：

19 °C

Refractive Index：

n20/D1.663

Water Solubility：

soluble in acetone, acetonitrile, dichloromethane, ethyl acetate and THF.

Storage Conditions：

Refrigerator

Safety Information

Hazard category：

IRRITANT

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38-41-37/38-22-20/21/22

safety instructions：

26-37/39-39-36

Marks：

Xi,Xn

Hazard note：

Irritant

Precautionary statement(s)：

P261-P280-P305 + P351 + P338

Hazard Statements：

H302-H315-H318-H335

GHS Classification：

|Danger|H302 (97.62%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 42 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

6-Bromoquinoline Use and Manufacturing

Methods of Manufacturing

General procedure: All the reactions were carried out in a 50 mL stainless steel autoclave (Scheme 1). A mixture of glycerol (1 g, 1 equiv.), aniline (0.58 g, 0.5 equiv.), water (2.5 mL) and W-KIT-6 (100 mg) was charged in to the autoclave simultaneously and finally heated to 200 °C with stirring for 3 h. On completion of the reaction (monitored by TLC), the autoclave was cooled to room temperature and the catalyst was removed by filtration. Ethyl acetate (10 mL) and water (5 mL) were added to the reaction mixture and stirred well for few minutes. The organic layer was dried over anhydrous Na2SO4 and the crude was purified by column chromatography using 60-120 mesh silica with ethylacetate/hexane as eluent to afford the desired product in good yield. The product was analyzed and confirmed with GC-MS and 1H NMR and 13C NMR spectroscopy (Table 1 and Figs S1-S5, Supplementary Data).Step 1.Glycerol (60.0mL, 0.82mol), FeSOGeneral procedure: To a 10 mL round bottom flask equipped with a magnetic stir bar, 1, 2, 3, 4-tetrahydroquinoline (0.5 mmol), DEAD solution 40 wtpercent in toluene (2.2 eq, 1.1 mmol, 0.5 mL), and CHClGeneral procedure: N-Heterocyclic amine (0.50 mmol), CoTPP (10 mg) and DMF (2 mL) were mixed in a carousel reaction tube. The reaction mixture was stirred at 120 C under oxygen atmosphere, the reaction was sampled periodically and monitored by TLC (petroleum ether/ethyl acetate (10:1 v/v)). After the reaction, the reaction mixture was then cooled to room temperature and purified using flash chromatography to give the corresponding product. All the dehydrogenation products are known, and their NMR spectra were consistent with the literature. NMR spectra were recorded at 25 C on an Bruker AVANCE III 400-NMR spectrometer at 400 MHz for General procedure: To a Schlenk tube equipped with a magnetic stir bar were added8-methyl-1, 2, 3, 4-tetrohydroquinoline (0.50 mmol), FeCl2 (1.9mg, 1.5·10–2 mmol), DMSO (31.2 mg, 0.4 mmol), and p-xylene (1mL). The reaction mixture was stirred at 110 °C under anoxygen atmosphere using a balloon and monitored by TLC. Afterthe reaction, the mixture was cooled to room temperature andpurified using flash chromatography (hexane–EtOAc, 10:1) togive the corresponding product 8-methylquinoline in 70percent yield.8-MethylquinolineColorless oil. 1H NMR (400 MHz, CDCl3): δ = 8.93 (m, 1 H), 8.10(m, 1 H), 7.64 (d, J = 4.0 Hz, 1 H), 7.54 (m, 1 H), 7.43–7.35 (m, 2H) 2.82 (s, 3 H). 13C NMR (100 MHz, CDCl3): δ = 149.2, 147.3, 137.1, 136.3, 129.6, 128.3, 126.3, 125.9, 120.8, 18.2. HRMS: m/zcalcd for [C10H9N + H+]: 144.0813; found: 144.0813.

Manufacturing Info：

Quinoline, 6-bromo-: INACTIVE

Computed Properties

Molecular Weight:208.05
XLogP3:2.8
Hydrogen Bond Acceptor Count:1
Exact Mass:206.96836
Monoisotopic Mass:206.96836
Topological Polar Surface Area:12.9
Heavy Atom Count:11
Complexity:138
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Toluene

Tetrahydrofuran

Sodium hydroxide

Glycerol

1-Butanol

Zinc chloride

Sulfuric acid

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