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224311-51-7 molecular structure
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di-tert-butyl(2-phenylphenyl)phosphane

ChemBase ID: 10385
Molecular Formular: C20H27P
Molecular Mass: 298.402141
Monoisotopic Mass: 298.18503749
SMILES and InChIs

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

Cite this record

CBID:10385 http://www.chembase.cn/molecule-10385.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
224311-51-7
MDL Number
MFCD01862440
Beilstein Number
8322131
PubChem SID
160973692
24882938
24890234
PubChem CID
2734215

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
H Acceptors H Donor
LogD (pH = 5.5) 4.645715  LogD (pH = 7.4) 4.922454 
Log P 5.0952  Molar Refractivity 94.8151 cm3
Polarizability 38.924267 Å3 Polar Surface Area 0.0 Å2
Rotatable Bonds Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Melting Point
85°C expand Show data source
86-88 °C(lit.) expand Show data source
Ligand For
Buchwald-Hartwig Cross Coupling Reaction expand Show data source
C-X Bond Formation expand Show data source
Heck Reaction expand Show data source
Suzuki-Miyaura Coupling expand Show data source
Storage Warning
AIR SENSITIVE expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
TSCA Listed
false expand Show data source
GHS Hazard statements
H413 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Purity
≥97.0% (GC) expand Show data source
95% expand Show data source
97% expand Show data source
99% expand Show data source
Grade
purum expand Show data source
Linear Formula
C6H5C6H4P[C(CH3)3]2 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 638439 external link
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 external link
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

REFERENCES

REFERENCES

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PATENTS

PATENTS

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