Phenylboronic acid pinacol ester
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Basic information
- CAS
24388-23-6- Standard SMILES
CC1(C)OB(c2ccccc2)OC1(C)C- InChIKey
KKLCYBZPQDOFQK-UHFFFAOYSA-N- Molecular formula
- C12H17BO2
- Average molar mass
- 204.08 g/mol
- Monoisotopic mass
- 204.1321599
Names & identifiers
- Preferred name
- Phenylboronic acid pinacol ester
- IUPAC
- 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane
- English name
- (4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZENE
- Molecular formula
- C12H17BO2
- Molecular weight
- 204.07
Names & synonyms
Phenylboronic acid pinacol esterRefChem:861718629-233-124388-23-64,4,5,5-Tetramethyl-2-phenyl-1,3,2-dioxaborolane(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzenephenylboronic acid, pinacol esterMFCD00966985benzeneboronic acid, pinacol ester2-Phenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolanephenylboronic pinacol esterSCHEMBL90476
Show more names
Phenylboronic acid pinacol ester 97%2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzene, 2-Phenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneM7121PhenylpinacolboranePinaryl phenylboronic acidPHENYL-BORONIC ACID PINACOL ESTER
1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-phenyl-OSM-S-460AKOS0159511244,4,5,5-tetramethyl-1,3,2-dioxaborolylbenzeneSY246300Pinacolborane Impurity 4(PINACOLBORYL)BENZENEPINACOL PHENYLBORONATE
Database identifiers
- CAS
24388-23-6- PubChem CID
- 570673
- DTXSID
DTXSID50341152- EC Number
- 629-233-1
- Nikkaji
- J700.119C
Properties
Computed structural propertiesFilling in
- Topological polar surface area
- 18.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 216
Physicochemical properties
- Melting point
- 27 · 27-31 °C(lit.)
- Boiling point
- 130 °C/20mmHg · 130°C/20mmHg(lit.)
- Density
- 0.99 · 0.99±0.1 g/cm3(Predicted)
- Flash point
- 225 °F · 225 °F
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- form
- powder to lump
- color
- White to Almost white
- InChI
- 1S/C12H17BO2/c1-11(2)12(3,4)15-13(14-11)10-8-6-5-7-9-10/h5-9H,1-4H3
- InChIKey
- KKLCYBZPQDOFQK-UHFFFAOYSA-N
- SMILES
- CC1(C)OB(OC1(C)C)c2ccccc2
- CAS DataBase Reference
- 24388 · 24388-23-6(CAS DataBase Reference)
- UNSPSC Code
- 12352103 · 12352103
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
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
Warning
H302 (97.7%): Harmful if swallowed [Warning Acute toxicity, oral]；H315 (97.7%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (97.7%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (97.7%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
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 43 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (97.7%)；Skin Irrit. 2 (97.7%)；Eye Irrit. 2 (97.7%)；STOT SE 3 (97.7%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- hs_code
- 29319090
- risk_code
- 22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,Xi
- hazard_note
- Irritant
Chemistry & industry
Applications
Usessuzuki reaction
UsesPhenylboronic acid pinacol ester can be used:To prepare sulfinamide derivatives by reacting with diethylaminosulfur trifluoride (DAST) and potassium phenyltrifluoroborate.As a substrate in the study of Suzuki–Miyaura coupling of various aryl iodides over SiliaCatPd(0).
General DescriptionPhenylboronic acid, pinacol ester, also known as boronate ester, is generally used in metal-catalyzed C-C bond formation reactions like Suzuki–Miyaurareaction.
Upstream & downstream products
Downstream products
Related reactions
467 records
Compound notes
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