4,4,5,5-tetramethyl-1,3,2-dioxaborolane

• ChemBase ID: 91429
• Molecular Formular: C6H13BO2
• Molecular Mass: 127.97722
• Monoisotopic Mass: 128.10086006
• SMILES: B1OC(C)(C)C(O1)(C)C
• Canonical SMILES: CC1(C)OBOC1(C)C
• InChI: InChI=1S/C6H13BO2/c1-5(2)6(3,4)9-7-8-5/h7H,1-4H3
• InChIKey: UCFSYHMCKWNKAH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• IUPAC Traditional name: 4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Synonyms: 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane solution; 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane; Pinacolborane; 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane; Pinacolborane; 4,4,5,5-Tetramethyl-1,3,2-dioxaborolane; Pinacolatoborane; Pinacolborane; 4,4,5,5-四甲基-1,3,2-二杂氧戊硼烷 溶液; 频哪醇硼烷; 4,4,5,5-四甲基-1,3,2-二杂氧戊硼烷; 频那醇硼烷（PINB）; 凤梨醇硼烷

Database IDs

• CAS Number: 25015-63-8
• MDL Number: MFCD00674030
• Beilstein Number: 7802871
• PubChem SID: 24869184; 24869353; 162078128; 24884127
• PubChem CID: 6364989

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.9622
• LogD (pH = 7.4): 1.9622
• Log P: 1.9622
• Molar Refractivity: 31.0388 cm^3
• Polarizability: 14.41995 Å^3
• Polar Surface Area: 18.46 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 42-43 °C/50 mmHg(lit.); 42-43°C/50mm; 42-43°C/50mm; 65-67 °C
• Flash Point: -13 °F; -25 °C; 41 °F; 5 °C; 5°C; 5°C(41°F)
• Density: 0.882; 0.882 g/mL at 25 °C(lit.); 0.887 g/mL at 25 °C
• Refractive Index: 1.3970; n20/D 1.396(lit.)

Safety Information

• Storage Warning: Air Sensitive; Highly Flammable/Moisture Sensitive/Air Sensitive/Keep Cold/Store under Argon
• European Hazard Symbols: Flammable (F); Irritant (Xi)
• UN Number: 3398; 3399; UN3399
• German water hazard class: 3
• Hazard Class: 4.3
• Packing Group: 2; II
• Risk Statements: 11-15; 11-15-19-36/37
• Safety Statements: 16-26-43; 16-43; 7/8-9-16-33-43
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H261; H225-H261-H319-H335
• GHS Precautionary statements: P210-P231 + P232-P261-P305 + P351 + P338-P422; P210-P231 + P232-P422; P210-P231+P232-P241-P303+P361+P353-P403+P235-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3398 4.3/PG 2; UN 3399 4.3/PG 2
• Supplemental Hazard Statements: May form explosive peroxides.
• Storage Temperature: 2-8°C

Product Information

• Purity: 97%
• Concentration: 1.0 M in THF
• Empirical Formula (Hill Notation): C6H13BO2

DETAILS

Apollo Scientific Ltd - OR7123

Reportedly couples with aryl halides to produce aryl boronates:J.Org.Chem.(1997)62,6458-6459.

Sigma Aldrich - 458945

Packaging
25, 4×25, 100 mL in Sure/Seal™

Sigma Aldrich - 456462

Application
Borylation reagent recently used to prepare 2-borylpyrroles from 2-iodopyrroles via palladium catalysis.1 Also used to borylate aryl bromides and chlorides with Pd(dba)2 and di-tert-butylphosphinophenyl ether.2
Pinacolborane; reagent for selective reduction, hydroboration, and for the preparation of boronates for Suzuki-type couplings.
Packaging
25, 100 mL in Sure/Seal™

Sigma Aldrich - 655856

Packaging
25, 100, 500 g in Sure/Seal™
5 g in glass bottle

Toronto Research Chemicals - P457500

It is used for synthesis of unsymmetrical biaryls via aromatic C-H borylation-cross-coupling sequence.

REFERENCES

• Precursor of boronic esters by hydroboration or coupling reactions. Hydroboration of alkynes, in the presence of Rh or Ni catalysts, yields alkenylboronates: Tetrahedron Lett., 37, 3283 (1996). Hydroboration of alkenes in the presence of Chlorotris(triphenylphosphine)rhodium(I), 10468, affords the alkylboronate: Tetrahedron Lett., 37, 3283 (1996); with phosphine-free catalyst Chloro(1,5-cyclooctadiene)rhodium(I) dimer, 10466, dehydrogenative borylation predominates to give the alkenylboronate: Tetrahedron Lett., 40, 213 (1999); Bull. Chem. Soc. Jpn., 75, 825 (2002):
  
• Coupling aryl iodides and bromides, catalyzed by [1,1'-Bis(diphenylphosphino)ferrocene]palladium(II) chloride, 41225, gives the aryl pinacolboronates: J. Org. Chem., 62, 6458 (1997); 65, 164 (2000). In the presence of triphenylarsine, Pd-catalyzed coupling with alkenyl triflates and iodides affords vinylboronates: Synthesis, 778 (2000). For a brief review of uses of pinacolborane, see: Synlett, 1210 (2000).