Basic information
- CAS
87199-17-5- Standard SMILES
O=Cc1ccc(B(O)O)cc1- InChIKey
VXWBQOJISHAKKM-UHFFFAOYSA-N- Molecular formula
- C7H7BO3
- Average molar mass
- 149.94 g/mol
- Monoisotopic mass
- 150.04882448
Overview
structure in first source
Names & identifiers
- Preferred name
- 4-Formylphenylboronic Acid
- IUPAC
- (4-formylphenyl)boronic acid
- English name
- 4-Formylphenylboronic acid
- Molecular formula
- C7H7BO3
- Molecular weight
- 149.94
Names & synonyms
4-Formylphenylboronic acid87199-17-5Boronic acid, B-(4-formylphenyl)-p-formylphenylboronic acidZ4V1TO2DWRDTXSID6074887RefChem:570135DTXCID3048570438-670-5(4-formylphenyl)boronic acid4-Formylbenzeneboronic acidBoronic acid, (4-formylphenyl)-
Show more names
FPBAFormylphenylboronic acidp-Formylbenzeneboronic acidAKOS BRN-0111TIMTEC-BB SBB004077RARECHEM AH PB 01934-Formylphenylboroni4-Formylboronic acid
MFCD001518234-formylphenyl boronic acidCHEMBL1402544-Boronobenzaldehyde4-Formylphenylboronicacid4-formyl-phenylboronic acid4-(Dihydroxyboranyl)Benzaldehyde4-formylphenylborate
Database identifiers
- CAS
87199-17-5- PubChem CID
- 591073
- DTXSID
DTXSID6074887- ChEMBL
Properties
Computed structural properties
- Topological polar surface area
- 57.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 130
Physicochemical properties
- Melting point
- 237 · 237-242 °C (lit.)
- Boiling point
- 347.6 · 347.6±44.0 °C(Predicted)
- Density
- 1.24 · 1.24±0.1 g/cm3(Predicted)
- vapor pressure
- 0 Pa · 0Pa at 25℃
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- 10 g/l · <10g/l
- pka
- 7.34 · 7.34±0.10(Predicted)
- form
- Liquid
- color
- Clear colorless to yellow-orange
- PH
- 5.5 · 5.5 (1g/l, H2O, 20℃)
- Water Solubility
- Slightly Soluble in water.
- Sensitive
- Air Sensitive
- BRN
- 3030770 · 3030770
- InChI
- 1S/C7H7BO3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5,10-11H
- InChIKey
- VXWBQOJISHAKKM-UHFFFAOYSA-N
- SMILES
- OB(O)c1ccc(C=O)cc1
- LogP
- 1.36 at · 1.36 at 20℃
Safety & regulation
GHS classification
GHS Classification
Warning
H317: May cause an allergic skin reaction [Warning Sensitization, Skin]
P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)
Danger
H314 (66.9%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
P260, P261, P264, P272, P280, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P333+P317, P362+P364, P363, P405, and P501 (click each P-code to see the statement)
Hazard information
Regulatory Information
Chemical: 4-Formylphenylboronic Acid
PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.
Status: Active Update: 09-01-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/8924
4-formylphenylboronic acid: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and Categories
Skin Sens. 1 (100%)
Skin Corr. 1B (66.9%)
Skin sensitisation - category 1
Skin Sens. 1
Safety data
- F
- 10
- PPE
- Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 1759 8/PG 3
- hs_code
- 29163990
- risk_code
- 34-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
Chemistry & industry
Uses & manufacturing
Household ProductsInformation on 7 consumer products that contain 4-formylphenylboronic acid in the following categories is provided:
General Manufacturing InformationBoronic acid, B-(4-formylphenyl)-: ACTIVE
Applications
Usessuzuki reaction
Uses4-Formylbenzeneboronic acid acts as a reagent used for Palladium-catalyzed arylation Suzuki-Miyaura cross-coupling in water, copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides, ligand-free copper-catalyzed coupling of nitro arenes with arylboronic acids, triethylamine-catalyzed three-component Hantzsch condensations, copper-catalyzed nitrations, oxidative mono-cleavage of dialkenes catalyzed by Trametes hirsuta, palladacycle-catalyzed cross-coupling of arylboronic acids with carboxylic anhydrides or acyl chlorides, palladium-catalyzed aerobic oxidative cross-coupling reactions. It acts as a reagent used in preparation of sensitizers with dithiafulvenyl unit as electron donor for high-efficiency dye-sensitized solar cells, a novel protein synthesis inhibitor active against Gram-positive bacteria.
Uses4-Formylphenylboronic acid is a substrate for Suzuki cross-coupling reactions and it can be used as a reagent for:Palladium-catalyzed Suzuki-Miyaura cross-coupling in water. Copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides. Ligand-free copper-catalyzed coupling of nitro arenes with arylboronic acids. Triethylamine-catalyzed three-component Hantzsch condensations. Copper-catalyzed nitrations. Oxidative mono-cleavage of dialkenes catalyzed by Trametes hirsuta. Palladacycle-catalyzed cross-coupling of arylboronic acids with carboxylic anhydrides or acyl chlorides. Palladium-catalyzed aerobic oxidative cross-coupling reactions. The synthesis of sensitizers with dithiafulvenyl unit as electron donor for high-efficiency dye-sensitized solar cells.The synthesis of a novel protein synthesis inhibitor active against Gram-positive bacteria.The Suzuki aryl-aryl coupling of the upper rim of hexahomotrioxacalix[3]arene.A rhodium-catalyzed cyclization, converting 1,5-enynes to cyclopentenes and spiro-cyclopentenes.
Related reactions
507 records
Compound notes
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