Basic information
- 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
Show more names
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 properties
- 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
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
- solubility
- 20 g/l · 20g/l
- form
- Liquid
- pka
- 1 · pK1: 0.71(+1) (25°C)
- color
- Clear colorless to pale brown
- Water Solubility
- Slightly miscible with water.
- BRN
- 105789 · 105789
- Henry's Law Constant
- 1.3 · 1.3×100 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- Dielectric constant
- 24.02 · 24.02
- Stability
- Stable. Flammable. Incompatible with strong oxidizing agents, strong acids, acid chlorides.
- InChI
- 1S/C5H4BrN/c6-5-3-1-2-4-7-5/h1-4H
- InChIKey
- IMRWILPUOVGIMU-UHFFFAOYSA-N
- SMILES
- Brc1ccccn1
- LogP
- 1.42 · 1.42
- CAS DataBase Reference
- 109 · 109-04-6(CAS DataBase Reference)
- FDA UNII
- 7 Z7MLC4VD8 · 7Z7MLC4VD8
- NIST Chemistry Reference
- 2 · Pyridine, 2-bromo-(109-04-6)
- EPA Substance Registry System
- 2 · Pyridine, 2-bromo- (109-04-6)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 301 · H301-H310-H315-H319-H335
- Precautionary statements
- 262 · P262-P280-P301+P310+P330-P302+P352+P310-P305+P351+P338
- target organs
- Respiratory system
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- T,Xn,F
- Risk Statements
- 10 · 10-24/25-36/37/38-23/24/25-20/21/22
- Safety Statements
- 16 · 16-36/37-45-38-36/37/39-28A-26
- RIDADR
- 2929 · UN 2929 6.1/PG 2
- WGK Germany
- 3 · 3
- RTECS
- 3850000 · US3850000
- F
- 8 · 8
- Hazard Note
- Toxic
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1
- PackingGroup
- II
- HS Code
- 29333999 · 29333999
- Storage Class
- 6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- Hazard Classifications
- 2 DermalAcute · Acute Tox. 2 DermalAcute Tox. 3 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- REACH Registrations
- Active
Safety & regulation
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
Toxicology
EPA Provisional Peer-Reviewed Toxicity Values
2-Bromopyridine
PDF Document
2011
Safety data
- F
- 8
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- US3850000
- ridadr
- UN 2929 6.1/PG 2
- hs_code
- 29333999
- risk_code
- 10-24/25-36/37/38-23/24/25-20/21/22
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- T,Xn,F
- hazard_note
- Toxic
- safety_code
- 16-36/37-45-38-36/37/39-28A-26
- hazard_class
- 6.1
- Storage Class
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- packing_group
- II
- target organs
- Respiratory system
- Hazard statements
- H301-H310-H315-H319-H335
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 2 DermalAcute Tox. 3 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P262-P280-P301+P310+P330-P302+P352+P310-P305+P351+P338
Chemistry & industry
Uses & manufacturing
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
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: 2-bromopyridine is a monobromopyridine.
Related reactions
Linked notes
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