3D Mol Similar

6-Bromoquinoline

Iupac Name：6-bromoquinoline

CAS No.: 5332-25-2

Molecular Weight：208.058

Modify Date.: 2022-11-29 08:24

Introduction:

Thick Oil

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1. Names and Identifiers

1.1 Name: 6-Bromoquinoline
1.2 Synonyms: 6-Bromo-1-azanaphthalene 6-BROMOOQUINOLINE 6-bromo-quinolin 6-Br-quinoline NSC 3996 Quinoline, 6-bromo- TIMTEC-BB SBB001559

1.3 CAS No.: 5332-25-2

1.4 CID: 79243

1.5 EINECS(EC#): 226-238-7

1.6 Molecular Formula: C9H6BrN (isomer)

1.7 Inchi: InChI=1S/C9H6BrN/c10-8-3-4-9-7(6-8)2-1-5-11-9/h1-6H

1.8 InChkey: IFIHYLCUKYCKRH-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC2=C(C=CC(=C2)Br)N=C1

1.10 Isomers Smiles: C1=CC2=C(C=CC(=C2)Br)N=C1

2. Properties

2.1 Density: 1.564

2.1 Melting point: 19°C

2.1 Boiling point: 278 °C at 760 mmHg

2.1 Refractive index: n20/D 1.663

2.1 Flash Point: 132.8 °C

2.1 Precise Quality: 206.96800

2.1 PSA: 12.89000

2.1 logP: 2.99730

2.1 Solubility: Soluble in acetone, acetonitrile, dichloromethane, ethyl acetate and THF.

2.2 Appearance: Light Yellow Colour Liquid

2.3 Storage: Ambient temperatures.

2.4 Chemical Properties: Thick Oil 6-Bromoquinoline Preparation Products And Raw materials Raw materials

2.5 pKa: 4.18±0.10(Predicted)

2.6 Water Solubility: soluble in acetone, acetonitrile, dichloromethane, ethyl acetate and THF.

2.7 StorageTemp: Refrigerator

3. Use and Manufacturing

3.1 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.

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S26;S37/39

4.1 Hazard Class: IRRITANT

4.1 Hazard Declaration: H302-H315-H318-H335

4.1 RIDADR: NONH for all modes of transport

4.1 Caution Statement: P261-P280-P305 + P351 + P338

4.1 WGK Germany: 3

4.1 Safety: Safety Information of 6-Bromoquinoline (CAS NO.5332-25-2):
Hazard Codes: Xi,Xn
Risk Statements: 36/37/38-41-37/38-22-20/21/22??
R36/37/38:Irritating to eyes, respiratory system and skin.?
R41:Risk of serious damage to the eyes.?
R37/38:Irritating to respiratory system and skin.?
R22:Harmful if swallowed.?
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-37/39-39-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S37/39:Wear suitable gloves and eye/face protection.?
S39:Wear eye / face protection.?
S36:Wear suitable protective clothing.
Hazard Note: Irritant
HazardClass: IRRITANT?

4.2 Specification: ?6-Bromoquinoline , its CAS NO. is 5332-25-2, the synonyms are NSC 3996 ; Quinoline, 6-bromo- .??

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin irritation, Category 2

Serious eye damage, Category 1

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H302 Harmful if swallowed H315 Causes skin irritation H318 Causes serious eye damage H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P310 Immediately call a POISON CENTER/doctor/\u2026 P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in CDCl3

13C NMR : Predict

1H NMR : 400 MHz in CDCl3

1H NMR : Predict

Predict 1H proton NMR

7. Other Information

7.0 Usage: 6-Bromoquinoline is used as fine chemical and pharmaceutical intermediate, used as the coupling reagent.

7.1 Storage Conditions: 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.

7.2 Manufacturing Info: Quinoline, 6-bromo-: INACTIVE

8. Computational chemical data

Molecular Weight: 208.058g/mol
Molecular Formula: C₉H₆BrN
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 206.96836
Monoisotopic Mass: 206.96836
Complexity: 138
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 1
Topological Polar Surface Area: 12.9
Heavy Atom Count: 11
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcYByAAAAEAAAAAAAAAAAAAAAAAAAAAA8QAAAAAAAAACx8AAAHABAAAABrAjBHgQ8wPIIEACgAzRnRACCgCAxAiQI2CA4ZLgIIOLAkZGEIAhggADIyhcQgIAOAAAgEAACAAAAAEAgAAQAAAAAAAAAAA==

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6-Bromoquinoline