Basic information
- CAS
24067-17-2- Standard SMILES
O=[N+]([O-])c1ccc(B(O)O)cc1- InChIKey
NSFJAFZHYOAMHL-UHFFFAOYSA-N- Molecular formula
- C6H6BNO4
- Average molar mass
- 166.93 g/mol
- Monoisotopic mass
- 167.03898807
Names & identifiers
- Preferred name
- 4-Nitrophenylboronic acid
- IUPAC
- (4-nitrophenyl)boronic acid
- English name
- 4-Nitrophenylboronic acid
- Molecular formula
- C6H6BNO4
- Molecular weight
- 166.93
Names & synonyms
Show more names
Database identifiers
- CAS
24067-17-2- PubChem CID
- 2773552
- DTXSID
DTXSID50378549- ChEMBL
CHEMBL91108- EC Number
- 627-647-7
- Nikkaji
- J639.570H
Properties
Computed structural properties
- Topological polar surface area
- 86.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 161
Physicochemical properties
- Melting point
- 285 · 285-290°C (dec.)
- Boiling point
- 373.7 · 373.7±44.0 °C(Predicted)
- Density
- 1.4 · 1.40±0.1 g/cm3(Predicted)
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- 15 mg/ml; · DMF: 15 mg/ml; DMSO: 15 mg/ml; Ethanol: 15 mg/ml; Ethanol:PBS (pH 7.2) (1:5): 0.16 mg/ml
- pka
- 7.04 · 7.04±0.10(Predicted)
- form
- Crystalline Powder
- color
- White to yellow
- Water Solubility
- Slightly soluble in water.
- InChI
- InChI=1S/C6H6BNO4/c9-7(10)5-1-3-6(4-2-5)8(11)12/h1-4,9-10H
- InChIKey
- NSFJAFZHYOAMHL-UHFFFAOYSA-N
- SMILES
- B(C1=CC=C([N+]([O-])=O)C=C1)(O)O
- CAS DataBase Reference
- 24067 · 24067-17-2(CAS DataBase Reference)
- UNSPSC Code
- 12352103 · 12352103
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335-H302
- Precautionary statements
- 261 · P261-P280a-P304+P340-P305+P351+P338-P405-P501a
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xn
- Risk Statements
- 22 · 22
- Safety Statements
- 26 · 26-36/37/39-24/25
- WGK Germany
- 3 · 3
- Hazard Note
- Harmful
- HS Code
- 29319090 · 29319090
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 Oral · Acute Tox. 4 Oral
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (87.5%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, 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 48 reports by companies from 7 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
- hs_code
- 29319090
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- hazard_note
- Harmful
- safety_code
- 26-36/37/39-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335-H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Chemistry & industry
Applications
Description4-Nitrobenzeneboronic acid is an arylboronic acid building block that has been used in the synthesis of phenols.
Uses4-Nitrophenylboronic Acid is a useful synthetic intermediate. It is a reagent used for ligand-free palladium-catalyzed Suzuki-Miyaura cross-couplings, Ruthenium catalyzed direct arylation of benzylic sp3 carbons of acyclic amines and Diels-Alder or C-H activation reactions.
UsesReagent used forLigand-free palladium-catalyzed Suzuki-Miyaura cross-couplings Ruthenium catalyzed direct arylation of benzylic sp3 carbons of acyclic amines Diels-Alder or C-H activation reactions Regioselective Suzuki-Miyaura coupling and tandem palladium-catalyzed intramolecular aminocarbonylation and annulationsN-arylation of phenylurea using copper acetylacetonate catalyst Environmentally benign one-pot synthesis through a double arylation process Copper-mediated cyanations copper-catalyzed arylations Regioselective glycosylations Suzuki couplings followed by arylations X-ray absorption on rhodium-grafted hydrotalcite catalyst for heterogeneous 1,4-addition reaction of organoboron reagents to electron deficient olefins Reagent used in Preparation ofCombretastatin analogs as potential antitumor agents Human immunodeficiency virus (HIV) protease inhibitors with antiviral activities against drug-resistant viruses
Usessuzuki reaction
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
Related reactions
Compound notes
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