4-Chlorophenylboronic acid
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Basic information
- CAS
1679-18-1- Standard SMILES
OB(O)c1ccc(Cl)cc1- InChIKey
CAYQIZIAYYNFCS-UHFFFAOYSA-N- Molecular formula
- C6H6BClO2
- Average molar mass
- 156.38 g/mol
- Monoisotopic mass
- 156.01493751
Names & identifiers
- Preferred name
- 4-Chlorophenylboronic acid
- IUPAC
- (4-chlorophenyl)boronic acid
- English name
- 4-Chlorophenylboronic acid
- Molecular formula
- C6H6BClO2
- Molecular weight
- 156.37
Names & synonyms
4-Chlorophenylboronic acid1679-18-1(4-chlorophenyl)boronic acidp-Chlorophenylboronic acidBoronic acid, (4-chlorophenyl)-p-Chlorobenzeneboronic acidBenzeneboronic acid, p-chloro-Boronic acid, p-chlorophenyl(p-Chlorophenyl)metaboric acidNSC 25408EINECS 216-845-5AB2T8N4T4C
Show more names
4-CHLOROBENZENEBORONIC ACIDAC 34441WLN: QBQR DGAKOS BRN-0011RARECHEM AH PB 0178orobenzeneboronic Acid4-Chlorophenylboric acidp-chlorophenylboronic aci
BRN 2936346AI3-32764(P-CHLOROPHENYL)BORONIC ACIDNSC-254084-16-00-01667 (Beilstein Handbook Reference)B-(4-CHLOROPHENYL)BORONIC ACIDDTXSID50168427BORONIC ACID, B-(4-CHLOROPHENYL)-
Database identifiers
- CAS
1679-18-1- PubChem CID
- 74299
- DTXSID
DTXSID50168427- ChEMBL
CHEMBL1209679- UNII
- AB2T8N4T4C
- EC Number
- 216-845-5
- Nikkaji
- J54.863D
Properties
Computed structural propertiesFilling in
- Topological polar surface area
- 40.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 102
Physicochemical properties
- Melting point
- 284 · 284-289 °C(lit.)
- Boiling point
- 295.4 · 295.4±42.0 °C(Predicted)
- Density
- 1.32 · 1.32±0.1 g/cm3(Predicted)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- DMSO
- pka
- 8.39 · 8.39±0.10(Predicted)
- form
- Crystalline Powder
- color
- Off-white to beige
- Water Solubility
- 2.5 g/100 · 2.5 g/100 mL
- BRN
- 2936346 · 2936346
- InChI
- InChI=1S/C6H6BClO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4,9-10H
- InChIKey
- CAYQIZIAYYNFCS-UHFFFAOYSA-N
- SMILES
- B(C1=CC=C(Cl)C=C1)(O)O
- CAS DataBase Reference
- 1679 · 1679-18-1(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 2 T8N4T4C · AB2T8N4T4C
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
This chemical does not meet GHS hazard criteria for 9.7% (6 of 62) of reports.
Warning
H302 (77.4%): 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 62 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationStatus: Active Update: 24-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24375
Hazard Classes and CategoriesAcute Tox. 4 (77.4%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- No
- rtecs
- CY8950000
- hs_code
- 2931900090
- risk_code
- 20/21/22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,Xi
- safety_code
- 36-37/39-26
- hazard_class
- IRRITANT
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
Uses4-Chlorobenzeneboronic Acid is used as a catalyst for the preparation of 4-hydroxycoumarin derivatives which display antitrypanosomal and antioxidant properties. It is also used as a catalyst for the asymmetric borane reduction of electron-deficient ketones.
Uses4-Chlorophenylboronic acid can be used as a reactant in:Palladium-catalyzed direct arylation.Cyclopalladation. Tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation. Copper-mediated ligandless aerobic fluoroalkylation. Pd-catalyzed arylative cyclization. Ruthenium catalyzed direct arylation. Ligand-free copper-catalyzed coupling reactions. Regioselective arylation and alkynylation by Suzuki-Miyaura and Sonogashira cross-coupling reactions. It can also be used to prepare: Substituted diarylmethylidenefluorenes via Suzuki coupling reaction.Baclofen lactam by Suzuki coupling of a pyrrolinyl tosylate, followed by hydrogenation reaction.Palladium(II) thiocarboxamide complexes as Suzuki coupling catalysts. Biaryls by Suzuki reactions of aryl chlorides, bromides, and iodides with arylboronic acids.
Upstream & downstream products
Upstream raw materials
Downstream products
Related reactions
1,273 records
Compound notes
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