2-Bromopyridine
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Basic information
- CAS
109-04-6- Standard SMILES
Brc1ccccn1- InChIKey
IMRWILPUOVGIMU-UHFFFAOYSA-N- Molecular formula
- C5H4BrN
- Average molar mass
- 158 g/mol
- Monoisotopic mass
- 156.95271123
Overview
2-bromopyridine is a monobromopyridine.
Names & identifiers
- Preferred name
- 2-Bromopyridine
- IUPAC
- 2-bromopyridine
- English name
- 2-Bromopyridine
- Molecular formula
- C5H4BrN
- Molecular weight
- 158
Names & synonyms
2-BROMOPYRIDINE109-04-6o-Bromopyridine2-Pyridyl bromidePyridine, 2-bromo-2-bromopyridinbeta-Bromopyridinealpha-BromopyridinePyridine, 2-bromo-,.beta.-Bromopyridine7Z7MLC4VD8NSC 8031
Show more names
-BromopyridinePyridine,2-bromo-2-BROMOPYRIDINE FOR SYNTHESIS-Bromoazine2-Brompyridin2-bromo-pyridin2-pyridylbromideAKOS BBS-00004324
.alpha.-BromopyridinePyridin-2-yl bromideDTXSID6051564CHEBI:51574UNII-7Z7MLC4VD8NSC-8031EINECS 203-641-6BRN 0105789
Database identifiers
- CAS
109-04-6- PubChem CID
- 7973
- DTXSID
DTXSID6051564- ChEMBL
CHEMBL331374- ChEBI
CHEBI:51574- UNII
- 7Z7MLC4VD8
- EC Number
- 203-641-6
- Nikkaji
- J32.655K
Properties
Computed structural propertiesFilling in
- XLogP
- 1.4
- Topological polar surface area
- 12.9 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 56
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Pyridines
SpringerMaterials Properties15N nuclear magnetic resonance spectrum
LogP1.42
Vapor Pressure1.0 [mmHg]
Physical DescriptionColorless oily liquid; [EPA - PPRTV] Pale yellow or colorless liquid; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 193 °C · 193°C
- Boiling point
- 192 · 192-194 °C (lit.)
- Density
- 1.657 g/mL · 1.657 g/mL at 25 °C (lit.)
- refractive index
- 20 · n20/D 1.572(lit.)
- Flash point
- 130 °F · 130 °F
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H226 (16.7%): Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P316, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 60 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Pyridine, 2-bromo-
Status: Active Update: 16-06-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/18620
2-Bromopyridine: HSNO Approval: HSR006014 Approved with controls
Hazards SummaryA skin and strong eye irritant; Toxic by ingestion; Highly toxic by skin absorption; [Alfa Aesar MSDS]
Hazard Classes and CategoriesFlam. Liq. 3 (16.7%)
Toxicology
Toxicity DataLC50 (rat) < 200,000 mg/m3/1hr
EPA Provisional Peer-Reviewed Toxicity Values
2-Bromopyridine
PDF Document
2011
Safety data
Chemistry & industry
Uses & manufacturing
UsesUsed to make pharmaceuticals, agricultural chemicals, pyrithione-based biocides, and other organic chemicals; [ExPub: EPA - PPRTV]
General Manufacturing InformationPyridine, 2-bromo-: ACTIVE
Applications
Uses2-Bromopyridine is a 2-halogenated pyridine used in the preparation of a variety of biologically active compounds such as antimalarial agents and beta-adrenoceptor agonist.
Preparation methods
Preparation2-Bromopyridine is synthesized from 2-aminopyridine by bromination. In industrial production, hydrobromic acid (over 48%) is first cooled to below 0°C, 2-aminopyridine is slowly added, and then liquid bromine is added dropwise in a salt bath under freezing, and the rate of addition is to control the reaction temperature below -5°C appropriate. After adding, add sodium nitrite aqueous solution dropwise, control the reaction temperature to be below 0°C, stir for 20-30min, dropwise add 50% sodium hydroxide solution, extract the reaction solution with ether, wash with water, dry with anhydrous sodium sulfate, filter, and recover Diethyl ether, the residue was distilled under reduced pressure, and the 88°C-94°C/3333Pa fraction was collected to obtain the finished product of 2-bromopyridine with a yield of 83.8%.
Upstream & downstream products
Upstream raw materials
Related reactions
1,619 records
Compound notes
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