Basic information
- CAS
5332-24-1- Standard SMILES
Brc1cnc2ccccc2c1- InChIKey
ZGIKWINFUGEQEO-UHFFFAOYSA-N- Molecular formula
- C9H6BrN
- Average molar mass
- 208.05 g/mol
- Monoisotopic mass
- 206.96836129
Names & identifiers
- Preferred name
- 3-Bromoquinoline
- IUPAC
- 3-bromoquinoline
- English name
- 3-Bromoquinoline
- Molecular formula
- C9H6BrN
- Molecular weight
- 208.05
Names & synonyms
3-BROMOQUINOLINE5332-24-1Quinoline, 3-bromo-AI3-16560NSC 3995EINECS 226-237-1DTXSID0063787Quinoline, 3bromoRefChem:93267DTXCID6041399226-237-1InChI=1/C9H6BrN/c10-8-5-7-3-1-2-4-9(7)11-6-8/h1-6
Show more names
BromoquinolineCETH-0163-BromoquinoL3-bromo-quinolin3-Bromoquuinoline1-3-Bromoquinoline
ZGIKWINFUGEQEO-UHFFFAOYSA-N3-Bromo-quinolineMFCD000067673-BromoquinliineNSC-39953-Bromo quinoline3-bromoquinolin3-(bromo)quinoline
Database identifiers
- CAS
5332-24-1- PubChem CID
- 21413
- DTXSID
DTXSID0063787- ChEMBL
CHEMBL41490- UNII
- ZRP57JF73Z
- EC Number
- 226-237-1
- Nikkaji
- J208.079F
Properties
Computed structural properties
- XLogP
- 3.2
- Topological polar surface area
- 12.9 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 138
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Quinolines
SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy
LogP3.06
Vapor Pressure0.00147 [mmHg]
Physical DescriptionLight yellow liquid; mp = 13-15 deg C; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 13 · 13-15 °C (lit.)
- Boiling point
- 274 · 274-276 °C (lit.)
- Density
- 1.533 g/mL · 1.533 g/mL at 25 °C (lit.)
- vapor pressure
- 0.196 Pa · 0.196Pa at 25℃
- refractive index
- 20 · n20/D 1.664(lit.)
- Flash point
- 230 °F · >230 °F
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (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.
Hazard information
Regulatory Information
Status: Cease Manufacture Update: 22-11-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/21074
Quinoline, 3-bromo-: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryA skin and strong eye irritant; [Alfa Aesar MSDS] See Quinoline.
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- Eyeshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN2810
- hs_code
- 29334900
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36-37/39
- Storage Class
- 10 - Combustible liquids
Chemistry & industry
Uses & manufacturing
General Manufacturing InformationQuinoline, 3-bromo-: ACTIVE
Applications
UsesFor pharmaceuticals Medicine, pesticide intermediates
Uses3-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 Description3-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 methods
Preparation3-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.
Upstream & downstream products
Related reactions
309 records
Compound notes
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