Basic information
- CAS
15128-82-2- Standard SMILES
O=[N+]([O-])c1ncccc1O- InChIKey
QBPDSKPWYWIHGA-UHFFFAOYSA-N- Molecular formula
- C5H4N2O3
- Average molar mass
- 140.1 g/mol
- Monoisotopic mass
- 140.02219199
Overview
structure in first source
Names & identifiers
- Preferred name
- 3-Hydroxy-2-nitropyridine
- IUPAC
- 2-nitropyridin-3-ol
- English name
- 3-Hydroxy-2-nitropyridine
- Molecular formula
- C5H4N2O3
- Molecular weight
- 140.1
Names & synonyms
Show more names
Database identifiers
- CAS
15128-82-2- PubChem CID
- 27057
- DTXSID
DTXSID6022264- UNII
- UU357X85YB
- EC Number
- 239-191-2、604-788-2
- Nikkaji
- J3.776A
Properties
Computed structural properties
- XLogP
- 1.2
- Topological polar surface area
- 78.9 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 0
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 133
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 69 · 69-71 °C (lit.)
- Boiling point
- 256.56 °C · 256.56°C (rough estimate)
- Density
- 1.5657 · 1.5657 (rough estimate)
- refractive index
- 1.48 · 1.4800 (estimate)
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- DMSO (Slightly), Methanol (Slightly, Heated)
- form
- Crystalline Powder
- pka
- 0.31 · 0.31±0.22(Predicted)
- color
- Yellow
- BRN
- 124473 · 124473
- InChI
- InChI=1S/C5H4N2O3/c8-4-2-1-3-6-5(4)7(9)10/h1-3,8H
- InChIKey
- QBPDSKPWYWIHGA-UHFFFAOYSA-N
- SMILES
- C1([N+]([O-])=O)=NC=CC=C1O
- CAS DataBase Reference
- 15128 · 15128-82-2(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 357 X85YB · UU357X85YB
- EPA Substance Registry System
- 3 · 3-Hydroxy-2-nitropyridine (15128-82-2)
- UNSPSC Code
- 12352100 · 12352100
- 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 · 26-37/39-36
- WGK Germany
- 3 · 3
- RTECS
- 7715000 · UU7715000
- Hazard Note
- Irritant
- HS Code
- 29333990 · 29333990
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Toxicity
- 50 · mouse,LD50,intravenous,180mg/kg (180mg/kg),U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#04089,
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 63 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- UU7715000
- hs_code
- 29333990
- Toxicity
- mouse,LD50,intravenous,180mg/kg (180mg/kg),U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#04089,
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 26-37/39-36
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Applications
Uses3-Hydroxy-2-nitropyridine may be used in the synthesis of novel sulfonates that are potent inhibitors of cell proliferation and tubulin polymerization.
Preparation methods
PreparationSynthesis of 3-hydroxy-2-nitropyridine: add 10g of 3-hydroxypyridine, 80ml of ethyl acetate, 4.2g of KNO3 and 21ml of acetic anhydride into a 250mL three-necked flask, and heat at 45°C with magnetic stirring After the reaction is completed, it is cooled to room temperature, filtered with suction, washed with a small amount of ethyl acetate for 1 to 2 times, the filtrate is taken to adjust the pH to neutrality with saturated NaOH solution, and extracted with ethyl acetate for 3 to 4 times. , take the extract and add activated carbon and heat under reflux for 1 hour, cool and filter, take the filtrate, dry with anhydrous magnesium sulfate, filter, concentrate on a rotary evaporator, and dry in a drying oven. 11.9 g of 3-hydroxy-2-nitropyridine was obtained with a yield of 81%.
Upstream & downstream products
Downstream products
Suppliers100 total
Related reactions
Compound notes
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