Basic information
- CAS
39856-50-3- Standard SMILES
O=[N+]([O-])c1ccc(Br)cn1- InChIKey
ATXXLNCPVSUCNK-UHFFFAOYSA-N- Molecular formula
- C5H3BrN2O2
- Average molar mass
- 202.99 g/mol
- Monoisotopic mass
- 201.93778944
Overview
used as a reagent; structure in first source
Names & identifiers
- Preferred name
- 5-Bromo-2-nitropyridine
- IUPAC
- 5-bromo-2-nitropyridine
- English name
- 5-Bromo-2-nitropyridine
- Molecular formula
- C5H3BrN2O2
- Molecular weight
- 202.99
Names & synonyms
5-Bromo-2-nitropyridine39856-50-3DTXSID20355827MA6LUF3NL7RefChem:102151DTXCID90306886609-748-82-Nitro-5-bromopyridinePYRIDINE, 5-BROMO-2-NITRO-2-Nitro-5-bromo pyridineMFCD001604113-bromo-6-nitro pyridine
Show more names
AKOS BBS-000013305-Bromo-2-nitropyridRisdiplam Impurity 83-BROMO-6-NITROPYRIDINE5-Bromo-2-notropyridine2-Nitro-5-borMopyridinePalbociclib impurity A
5-bromo-2-nitro pyridine5-Bromo-2-nitropyridine, 99%CS-D1019AC-3148HY-59228SY004047Palbociclib Impurity AEN300-80262
Database identifiers
- CAS
39856-50-3- PubChem CID
- 817620
- DTXSID
DTXSID20355827- UNII
- MA6LUF3NL7
- EC Number
- 609-748-8
- Nikkaji
- J1.215.692H
Properties
Computed structural properties
- XLogP
- 1.7
- Topological polar surface area
- 58.7 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 136
Physicochemical properties
- Melting point
- 148 · 148-150 °C (lit.)
- Boiling point
- 292.3 · 292.3±20.0 °C(Predicted)
- Density
- 1.833 · 1.833±0.06 g/cm3(Predicted)
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- -4.95 · -4.95±0.22(Predicted)
- color
- White to yellow to beige powder or crystal or chunks
- BRN
- 120878 · 120878
- InChI
- InChI=1S/C5H3BrN2O2/c6-4-1-2-5(7-3-4)8(9)10/h1-3H
- InChIKey
- ATXXLNCPVSUCNK-UHFFFAOYSA-N
- SMILES
- C1([N+]([O-])=O)=NC=C(Br)C=C1
- CAS DataBase Reference
- 39856 · 39856-50-3(CAS DataBase Reference)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36/37
- WGK Germany
- 3 · 3
- HazardClass
- IRRITANT
- PackingGroup
- III
- HS Code
- 29339900 · 29339900
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
- REACH Registrations
- Active
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 57 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationStatus: Active Update: 03-09-2015 https://echa.europa.eu/registration-dossier/-/registered-dossier/16537
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- hs_code
- 29339900
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36/37
- hazard_class
- IRRITANT
- Storage Class
- 11 - Combustible Solids
- packing_group
- III
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- REACH Registrations
- Active
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Applications
Uses5-Bromo-2-nitropyridine is employed as a reagent in the synthesis of novel benzinidazoles, potent inhibitors of TIE-2 and VEGFR-2 Tyrosine (T899975) kinase receptors.
Preparation methods
Preparation5-Bromo-2-nitropyridine was prepared from the corresponding amine via hydrogen peroxide oxidation in large scale production. N-Bromosuccinimide (NBS) bromination of 2-aminopyridine in acetonitrile at 0-5 °C delivered 5-bromo-2- aminopyridine with good regioselectivity (>20:1). The brominated amino-pyridine was then reacted with the oxidant mixture, yielding 5-Bromo-2-nitropyridine after dilution with water and isopropanol[1].
Upstream & downstream products
Upstream raw materials
Downstream products
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Related reactions
327 records
Compound notes
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