Basic information
- Standard SMILES
Brc1ccc(Br)nc1- InChIKey
ZHXUWDPHUQHFOV-UHFFFAOYSA-N- Molecular formula
- C5H3Br2N
- Average molar mass
- 236.89 g/mol
- Monoisotopic mass
- 234.8632233
Names & identifiers
- Preferred name
- 2,5-Dibromopyridine
- IUPAC
- 2,5-dibromopyridine
- English name
- 2,5-Dibromopyridine
- Molecular formula
- C5H3Br2N
- Molecular weight
- 236.89
Names & synonyms
Show more names
Database identifiers
- CAS
624-28-2- PubChem CID
- 69353
- DTXSID
DTXSID00211452- UNII
- V4W4Z4K29X
- EC Number
- 210-839-6
- Nikkaji
- J79.763D
Properties
Computed structural properties
- XLogP
- 2.6
- Topological polar surface area
- 12.9 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 76.8
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 92 · 92-95 °C (lit.)
- Boiling point
- 235 °C · 235 °C / 772mmHg
- Density
- 2.0383 · 2.0383 (rough estimate)
- refractive index
- 1.58 · 1.5800 (estimate)
- Flash point
- 62 ℃ · 62℃
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- pka
- -1.57 · -1.57±0.10(Predicted)
- form
- Crystalline Powder
- color
- Almost white or light beige to brown
- Water Solubility
- insoluble
- BRN
- 109099 · 109099
- InChI
- InChI=1S/C5H3Br2N/c6-4-1-2-5(7)8-3-4/h1-3H
- InChIKey
- ZHXUWDPHUQHFOV-UHFFFAOYSA-N
- SMILES
- C1(Br)=NC=C(Br)C=C1
- CAS DataBase Reference
- 624 · 624-28-2(CAS DataBase Reference)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 335 · H335-H302+H312+H332-H315-H319
- Precautionary statements
- 280 a-P304+P340-P305+P351+P338-P405-P501a-P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312+P362+P364-P304+P340+P312-P305+P351+P338+P337+P313-P501 · P280a-P304+P340-P305+P351+P338-P405-P501a-P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312+P362+P364-P304+P340+P312-P305+P351+P338+P337+P313-P501
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi,Xn
- Risk Statements
- 36 · 36/37/38-20/21/22
- Safety Statements
- 26 · 26-37/39-36/37/39-36
- RIDADR
- 2811 · UN2811
- WGK Germany
- 3 · 3
- HazardClass
- IRRITANT
- HS Code
- 29333999 · 29333999
- Storage Class
- 11 · 11 - Combustible Solids
- REACH Registrations
- Inactive
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 48 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Status: No longer Valid Update: 17-10-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/30054
2,5-Dibromopyridine: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- ridadr
- UN2811
- hs_code
- 29333999
- risk_code
- 36/37/38-20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,Xn
- safety_code
- 26-37/39-36/37/39-36
- hazard_class
- IRRITANT
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H335-H302+H312+H332-H315-H319
- REACH Registrations
- Inactive
- Precautionary statements
- P280a-P304+P340-P305+P351+P338-P405-P501a-P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312+P362+P364-P304+P340+P312-P305+P351+P338+P337+P313-P501
Chemistry & industry
Applications
DescriptionPyridine and its derivatives are distributed widely by nature. Many plant constituents are as contain pyridine ring compounds in the structure of alkaloids, etc.; they are the bases producing many vital compounds and are indispensable raw materials during medicine, agricultural chemicals, dyestuff, tension-active agents, rubber ingredients, fodder additives, foodstuff additives, tackiness agents, etc. are produced.2,5-dibromo pyridine is an important intermediate of organic synthesis and is mainly used in medicine intermediate, organic synthesis, and organic solvent, can also be applicable to aspects such as DYE PRODUCTION, pesticide production and spices. Selective monolithiation of 2,5-dibromopyridine at either the 2-position or the 5-position is reported. Solvent and concentration strongly influence the selectivity. Coordinating solvents and higher concentration favour the 5-position, while non-coordinating solvents and lower concentration favour the 2-position[1].
Uses2,5-Dibromopyridine (cas# 624-28-2) is a compound useful in organic synthesis.
Preparation methods
PreparationTo synthesize 2,5-dibromopyridine, follow these steps:Add 2-amino-5-bromopyridine (13.0 kg) into a water-cooled solution at 10 °C.Slowly add 47% aqueous hydrogen bromide (37 L) to the mixture.Introduce liquid bromine (11 L) into the mixture.Maintain the reaction temperature below 10 °C.Prepare a solution of NaNO2 (16.1 kg) and H2O (19 L) and add it dropwise to the mixture while keeping the temperature between 0-5 °C.Stir the reaction mixture for 30 minutes.Treat the mixture with a solution of NaOH (28.0 kg) in water (30 L) at a controlled rate below 20-25 °C.Extract the reaction mixture with diethyl ether (3 × 40 L).Dry the organic layer with anhydrous Na2SO4.Remove the desiccant by filtration.Evaporate the resulting filtrate under reduced pressure to dryness.Suspend the residue in heptane (10 L).Collect the target product molecule, 2,5-dibromopyridine, by filtration.Synthesis method of 2,5-dibromopyridine
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Related reactions
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