di-tert-butyl(2-phenylphenyl)phosphane

• ChemBase ID: 10385
• Molecular Formular: C20H27P
• Molecular Mass: 298.402141
• Monoisotopic Mass: 298.18503749
• SMILES: c1(c2ccccc2)c(cccc1)P(C(C)(C)C)C(C)(C)C
• Canonical SMILES: CC(P(C(C)(C)C)c1ccccc1c1ccccc1)(C)C
• InChI: InChI=1S/C20H27P/c1-19(2,3)21(20(4,5)6)18-15-11-10-14-17(18)16-12-8-7-9-13-16/h7-15H,1-6H3
• InChIKey: CNXMDTWQWLGCPE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: di-tert-butyl(2-phenylphenyl)phosphane
• IUPAC Traditional name: di-tert-butyl(2-phenylphenyl)phosphane
• Synonyms: 2-(Di-tert-Butylphosphino)biphenyl; 2-(Di-t-butylphosphino)biphenyl; JohnPhos; (2-Biphenylyl)di-tert-butylphosphine; 2-(Di-tert-butylphosphino)biphenyl; (2-Biphenyl)di-tert-butylphosphine; (2-联苯基)二-叔丁基膦; 2-(二-叔-丁基膦基)联苯; 2-(二叔丁基膦)联苯

Database IDs

• CAS Number: 224311-51-7
• MDL Number: MFCD01862440
• Beilstein Number: 8322131
• PubChem SID: 24882938; 24890234; 160973692
• PubChem CID: 2734215

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 4.645715
• LogD (pH = 7.4): 4.922454
• Log P: 5.0952
• Molar Refractivity: 94.8151 cm^3
• Polarizability: 38.924267 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 85°C; 86-88 °C(lit.)
• Ligand For: Buchwald-Hartwig Cross Coupling Reaction; C-X Bond Formation; Heck Reaction; Suzuki-Miyaura Coupling

Safety Information

• Storage Warning: AIR SENSITIVE
• German water hazard class: 3
• TSCA Listed: false
• GHS Hazard statements: H413
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥97.0% (GC); 95%; 97%; 99%
• Grade: purum
• Linear Formula: C6H5C6H4P[C(CH3)3]2

DETAILS

Sigma Aldrich - 638439

Application
Bulky biarylphosphine ligand utilized in the palladium catalyzed Stille cross-coupling reaction.8
Bulky phosphine ligand used in a Pd-catalyzed 2,3-diarylation of α,α-disubstituted-3-thiophenemethanols via cleavage of C-H and C-C bonds.
Ligand utilized in amination of aryl halides and aryl triflates.1Catalyst for:
• Decarboxylative cross-coupling of dialkoxybenzoic acids with diaryl disulfides or diaryl diselenides2
• Stereoselective preparation of imidazolidinones via intramolecular hydroamination of N-allylic-N-arylureas3
• Regioselective arylation of olefins with aryl chlorides4
• Cross-coupling reaction for the synthesis of polyunsaturated macrolactones5
• Regioselective O-alkylation reactions6
• Sonogashira-type cross coupling7
Packaging
1, 5, 25, 100 g in glass bottle

Sigma Aldrich - 96004

Other Notes
Optimal ligand for a novel amination reaction (Buchwald reaction)1
Application
Ligand utilized in amination of aryl halides and aryl triflates.1Catalyst for:
• Decarboxylative cross-coupling of dialkoxybenzoic acids with diaryl disulfides or diaryl diselenides2
• Stereoselective preparation of imidazolidinones via intramolecular hydroamination of N-allylic-N-arylureas3
• Regioselective arylation of olefins with aryl chlorides4
• Cross-coupling reaction for the synthesis of polyunsaturated macrolactones5
• Regioselective O-alkylation reactions6
• Sonogashira-type cross coupling7