tetrafluoroboranuide; tri-tert-butylphosphanium

• ChemBase ID: 153051
• Molecular Formular: C12H27BF4P
• Molecular Mass: 289.1211538
• Monoisotopic Mass: 289.18795577
• SMILES: [B-](F)(F)(F)F.CC(C)(C)[P+](C(C)(C)C)C(C)(C)C
• Canonical SMILES: CC([P+](C(C)(C)C)C(C)(C)C)(C)C.F[B-](F)(F)F
• InChI: InChI=1S/C12H27P.BF4/c1-10(2,3)13(11(4,5)6)12(7,8)9;2-1(3,4)5/h1-9H3;/q;-1/p+1
• InChIKey: YTJUCJAUJCXFTN-UHFFFAOYSA-O

NAMES AND DATABASE IDS

Names

• IUPAC name: tetrafluoroboranuide; tri-tert-butylphosphanium
• IUPAC Traditional name: tri-tert-butylphosphanium tetrafluoroborate
• Synonyms: Tri-tert-butylphosphonium tetrafluoroborate; Fluoroboric acid tri-tert-butylphosphine adduct; Tri-tert-butylphosphine fluoroboric acid adduct; TTBP · HBF4; [(t-Bu)3PH]BF4; Tri-tert-butylphosphonium tetrafluoroborate; 三叔丁基磷四氟硼酸盐; 四氟硼酸三叔丁基膦

Database IDs

• CAS Number: 131274-22-1
• EC Number: 000-000-0
• MDL Number: MFCD04039975; MFCD07189501
• Beilstein Number: 8813613
• PubChem SID: 162247191; 24880961
• PubChem CID: 2734635

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.3845654
• LogD (pH = 7.4): 2.3847759
• Log P: 2.5937
• Molar Refractivity: 64.5069 cm^3
• Polarizability: 25.961126 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 261 °C(lit.); ca 260°C dec.
• Ligand For: Addition Reactions; Buchwald-Hartwig Cross Coupling Reaction; Carbonylations; Heck Reaction; Negishi Coupling; Sonogashira Coupling; Stille Coupling; Suzuki-Miyaura Coupling

Safety Information

• Storage Warning: Hygroscopic
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 97%
• Linear Formula: [[(CH3)3C]3PH]BF4

DETAILS

Sigma Aldrich - 578940

Application
Hindered Phosphine salt employed with a Pd(0)-15-membered, triolefinic, macrocyle in Suzuki cross-coupling reactions of aryl bromides and chlorides.1 Also used in Heck coupling of non-activated vinyl tosylates with electron deficient olefins.2
Ligand used in the Pd-catalyzed enantioselective α-arylation of N-boc-pyrrolidine.
Packaging
1, 5 g in glass bottle

REFERENCES

• Convenient, air-stable replacement for tri-tert-butylphosphine, e.g. in Suzuki, Heck, Stille and Sonogashira coupling reactions: Org. Lett., 3, 4295 (2001).