Basic information
- 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 properties
- 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
- UNSPSC Code
- 12352103 · 12352103
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302
- Precautionary statements
- 301 · P301+P312+P330
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xn,Xi
- Risk Statements
- 20 · 20/21/22-36/37/38
- Safety Statements
- 36 · 36-37/39-26
- WGK Germany
- 3 · 3
- RTECS
- 8950000 · CY8950000
- TSCA
- No
- HazardClass
- IRRITANT
- HS Code
- 29319090 · 29319090
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 Oral · Acute Tox. 4 Oral
- REACH Registrations
- Active
Safety & regulation
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
- 29319090
- 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
- Hazard statements
- H302
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P301+P312+P330
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
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Related reactions
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