3-Bromoquinoline
Bromoquinoline · Quinoline, 3-bromo- · NSC 3995 · CETH-016 · 3-BromoquinoL · 3-BROMOQUINOLINE · 3-BROMOQUINLIINE · 3-bromo-quinolin
Identifiers & Physical Properties
| CAS No. | 5332-24-1 |
|---|---|
| Molecular formula | C9H6BrN |
| Average molar mass | 208.05 g/mol |
| Monoisotopic mass | 206.96836129 g/mol |
| SMILES | Brc1cnc2ccccc2c1 |
| InChIKey | ZGIKWINFUGEQEO-UHFFFAOYSA-N |
| PubChem CID | 21413 |
| ChEMBL | CHEMBL41490 |
| EC No. | 226-237-1 |
| DTXSID | DTXSID0063787 |
Chemical & Physical Properties
| XLogP | 3.2 |
|---|---|
| Topological polar surface area | 12.9 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 1 |
| Rotatable bonds | 0 |
| Heavy atoms | 11 |
| Formal charge | 0 |
| Complexity | 138 |
| Chemical classes | Nitrogen Compounds -> Quinolines |
| SpringerMaterials Properties | Nuclear quadrupole resonance spectroscopy |
| LogP (partition coefficient) | 3.06 |
| Vapor pressure | 0.00147 [mmHg]0.196Pa at 25℃ |
| Physical Description | Light yellow liquidmp = 13-15 deg C[Alfa Aesar MSDS] |
| Melting point | 13-15 °C (lit.) |
| Boiling point | 274-276 °C (lit.) |
| Density | 1.533 g/mL at 25 °C (lit.) |
| Refractive index | n20/D 1.664(lit.) |
| Flash point | >230 °F |
| Storage conditions | Keep in dark place,Inert atmosphere,Room temperature |
| pKa (acidity coefficient) | 2.69(at 25℃) |
| Physical state | Liquid |
| Color | Clear colorless to yellow |
| Solubility | 103mg/L at 25℃ |
| BRN | 112939 |
| InChI | 1S/C9H6BrN/c10-8-5-7-3-1-2-4-9(7)11-6-8/h1-6H |
| InChIKey | ZGIKWINFUGEQEO-UHFFFAOYSA-N |
| SMILES | Brc1cnc2ccccc2c1 |
| LogP (partition coefficient) | 3.03 |
| CAS DataBase Reference | 5332-24-1(CAS DataBase Reference) |
| FDA UNII | ZRP57JF73Z |
| NIST Chemistry Reference | Quinoline, 3-bromo-(5332-24-1) |
| EPA Substance Registry System | Quinoline, 3-bromo- (5332-24-1) |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315-H319-H335 |
| GHS precautionary statements | P261-P264-P271-P280-P302+P352-P305+P351+P338 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type ABEK (EN14387) respirator filter |
| Hazard symbols | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 26-36-37/39 |
| UN transport number | UN2810 |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| Customs code | 29334900 |
| Storage class | 10 - Combustible liquids |
| Hazard class | Eye Irrit. 2Skin Irrit. 2 |
| REACH registrations | Inactive |
Safety & Regulations
| GHS classification | WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 47 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | Status: Cease Manufacture Update: 22-11-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/21074Quinoline, 3-bromo-: Does not have an individual approval but may be used under an appropriate group standard |
| Hazards summary | A skin and strong eye irritant[Alfa Aesar MSDS] See Quinoline. |
| Hazard Classes and Categories | Skin Irrit. 2 (100%) |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type ABEK (EN14387) respirator filter |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| UN transport number | UN2810 |
| Customs code | 29334900 |
| Risk statements (R) | 36/37/38 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xi |
| Safety statements (S) | 26-36-37/39 |
| Storage class | 10 - Combustible liquids |
| GHS hazard statements | H315-H319-H335 |
| REACH registrations | Inactive |
| Hazard class |
Applications & Uses
Uses
For pharmaceuticals Medicine, pesticide intermediates
Uses
3-Bromoquinoline undergoes bromine-magnesium exchange reaction with lithium tributylmagnesate in toluene at -10°C, which is quenched by various electrophiles to yield functionalized quinolines.
General Description
3-Bromoquinoline undergoes bromine-magnesium exchange reaction with lithium tributylmagnesate in toluene at -10°C, which is quenched by various electrophiles to yield functionalized quinolines.
Preparation & Synthesis
Preparation
3-Bromoquinoline reacts with mixed acids to form 3-bromo-5-nitroquinoline, which is then oxidized to 5-bromo-2,3-pyridinedicarboxylic acid upon heating with potassium permanganate. 6-Bromoquinoline reacts with nitric acid upon heating to form 6-bromo-8-nitroquinoline, which is then oxidized to 2,3-pyridinedicarboxylic acid upon reaction with potassium permanganate. 2-Bromoquinoline is prepared by reacting 2-hydroxyquinoline with phosphorus pentabromide. 3-Bromoquinoline is prepared by heating quinoline perbromide at 180°C. 4-Bromoquinoline is prepared by heating 4-hydroxyquinoline with phosphorus pentabromide, or by diazotizing 4-aminoquinoline. 5-Bromoquinoline is prepared by heating m-bromoaniline, glycerol, m-bromonitrobenzene, and concentrated sulfuric acid, or by diazotizing 5-aminoquinoline. 6-Bromoquinoline is prepared by heating p-bromoaniline with glycerol, concentrated sulfuric acid, and p-bromonitrobenzene. 7-Bromoquinoline is prepared by diazotization of 7-aminoquinoline. 8-Bromoquinoline is prepared by heating o-bromoaniline, glycerol, concentrated sulfuric acid, and o-bromonitrobenzene. Uses: As a reagent in organic synthesis.