3,5-Dibromopyridine
Basic information
- CAS
625-92-3- Standard SMILES
Brc1cncc(Br)c1- InChIKey
SOSPMXMEOFGPIM-UHFFFAOYSA-N- Molecular formula
- C5H3Br2N
- Average molar mass
- 236.89 g/mol
- Monoisotopic mass
- 234.86322
Overview
3,5-dibromopyridine is a dibromopyridine.
Names & identifiers
- Preferred name
- 3,5-Dibromopyridine
- IUPAC
- 3,5-dibromopyridine
- English name
- 3,5-Dibromopyridine
- Molecular formula
- C5H3Br2N
- Molecular weight
- 236.89
Names & synonyms
3,5-Dibromopyridine625-92-3CHEBI:51593DTXSID3073921RefChem:486667DTXCID2043377210-916-4Pyridine, 3,5-dibromo-3,5-dibromopyridinMFCD000146343,5-dibromo-pyridine3,5-dibromo pyridine
Show more names
NSC 62093,5-DibrompyridinIFLAB-BB F1995-01903,5-dibormopyridineTIMTEC-BB SBB0032373,5-Dibromopyridine>Perampanel Impurity 123,5-Dibromopyridine,99%
3.5-Dibromopyridine3,5-dibromo-pyridinHY-Y0491CS-W019948PS-4092AC-907/30002039F1995-0190Z57070461
Database identifiers
- CAS
625-92-3- PubChem CID
- 69369
- DTXSID
DTXSID3073921- ChEBI
CHEBI:51593- EC Number
- 210-916-4
- Nikkaji
- J79.765K
Properties
Computed structural properties
- XLogP
- 2.2
- 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
- 68.8
Experimental & physicochemical properties
SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy
Physicochemical properties
- Melting point
- 110 · 110-115 °C (lit.)
- Boiling point
- 222 °C · 222 °C
- Density
- 2.0383 · 2.0383 (rough estimate)
- refractive index
- 1.58 · 1.5800 (estimate)
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- DMSO (Slightly, Heated), Methanol (Slightly)
- pka
- 0.52 · 0.52±0.20(Predicted)
- form
- Needle-Like Crystals
- color
- White to light beige
- Water Solubility
- Soluble in Chloroform and Methanol. Insoluble in water.
- BRN
- 108477 · 108477
- InChI
- 1S/C5H3Br2N/c6-4-1-5(7)3-8-2-4/h1-3H
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
Warning
H302 (18.9%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 53 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information3,5-Dibromopyridine: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesAcute Tox. 4 (18.9%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- ridadr
- UN2811
- hs_code
- 2933399090
- risk_code
- 36/37/38-20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,Xn
- safety_code
- 26-36-36/37/39
- hazard_class
- IRRITANT
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319
Chemistry & industry
Applications
Uses3-Acetylamino-5-ethoxypyridine was prepared by converting 3, 5-dibromopyridine with sodium ethylate into 3-bromo-5-ethoxypyridine, allowing this substance to interact with ammonia and acetylating the aminoethoxypyridine thus formed with acetic anhydride. Lithiation of 3, 5-dibromopyridine with LDA and subsequent reaction with electrophiles provided 4-alkyl-3, 5-dibromopyridines 2 in high yield. Ligand was prepared by a Pd(0)-catalyzed cross-coupling reaction of 3,5-dibromopyridine and 5-tributylstannyl-3,3-bipyridine. The synthesis of 3, 5-bis (2-indolyl) pyridine and 3-[(2-indolyl)-5-phenyl] pyridine derivatives as includes Stille or Suzuki type reactions, which were realized on the 3,5-dibromopyridine.
General Description3,5-Dibromopyridine undergoes lithiation with lithium diisopropylamide and on subsequent reaction with electrophiles yields 4-alkyl-3,5-dibromopyridines.
Upstream & downstream products
Downstream products
Related reactions
492 records
Compound notes
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