Basic information
- CAS
564483-19-8- Standard SMILES
CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)C(C)(C)C)c(C(C)C)c1- InChIKey
SACNIGZYDTUHKB-UHFFFAOYSA-N- Molecular formula
- C29H45P
- Average molar mass
- 424.6 g/mol
- Monoisotopic mass
- 424.32588807
Names & identifiers
- Preferred name
- Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphane
- IUPAC
- ditert-butyl-[2-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphane
- English name
- 2-Di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl
- Molecular formula
- C29H45P
- Molecular weight
- 424.64
Names & synonyms
di-tert-butyl[2',4',6'-tris(propan-2-yl)-[1,1'-biphenyl]-2-yl]phosphaneDi-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneRefChem:586116639-817-8564483-19-82-Di-tert-butylphosphino-2',4',6'-triisopropylbiphenylDi-tert-butyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphinetBuXPhos2-DI-T-BUTYLPHOSPHINO-2',4',6'-TRI-I-PROPYL-1,1'-BIPHENYLtert-Butyl XPhost-Bu XPhosMFCD06411306
Show more names
2-Di-tert-butylphosphino-2',4',6'-trisopropylbinphenylTERT-BUTYL X-PHOSDi-tert-butyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphinetBuXPhos 97%di-t-Bu-XPhos2&lsquo
t-butyl-Xphost-BuXPhosditert-butyl-[2-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphanedi-tert-butyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphaneditert-butyl-[2-(2,4,6-triisopropylphenyl)phenyl]phosphaneC29H45P2-di-t-butylphosphino-2',4',6'-triisopropylbiphenyl2-di-t-butylphosphino-2',4',6'-tri-i-propyl-1,1'biphenyl
Properties
Computed structural properties
- XLogP
- 8.5
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 7
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 485
Physicochemical properties
- Melting point
- 148 · 148-151 °C(lit.)
- Boiling point
- 493.5 · 493.5±45.0 °C(Predicted)
- storage temp.
- 2 · 2-8°C, protect from light, stored under nitrogen
- solubility
- soluble in Toluene
- form
- Crystalline Powder
- color
- White
- InChI
- InChI=1S/C29H45P/c1-19(2)22-17-24(20(3)4)27(25(18-22)21(5)6)23-15-13-14-16-26(23)30(28(7,8)9)29(10,11)12/h13-21H,1-12H3
- InChIKey
- SACNIGZYDTUHKB-UHFFFAOYSA-N
- SMILES
- P(C(C)(C)C)(C(C)(C)C)C1=CC=CC=C1C1=C(C(C)C)C=C(C(C)C)C=C1C(C)C
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P280-P305+P351+P338-P304+P340-P405-P501A
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (97.4%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 78 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (97.4%)
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- No
- hs_code
- 29310099
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36/37/39
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P280-P305+P351+P338-P304+P340-P405-P501A
Chemistry & industry
Applications
UsestBuXPhos [2-Di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl] is an air-stable, electron-rich biaryl phosphine ligand developed by the Buchwald group to enhance the reactivity of palladium catalysis during cross-coupling reactions. tBuXPhos has been used in the preparation of [tBuXPhosAu(MeCN)]BAr4F, a gold catalyst for the intermolecular [2+2] cycloaddition of terminal arylalkynes with substituted alkenes to form functionalized cyclobutenes with high regioselectivity. tBuXPhos is a ligand for Pd-catalyzed C-O and C-N bond formation. It can be used in the following reactions: • Palladium-catalyzed Tsuji-Trost substitution and cross-coupling of benzylic fluorides. • Palladium-catalyzed C-N cross-coupling of sulfinamides and aryl halides. • Palladium-catalyzed rapid methoxylation and deuteriomethoxylation of bromo-chalcones.
UsesEffective ligand for the Pd-catalyzed arylation of pyrazoles, indazoles and amino heterocycles
UsestBuXPhos is a ligand for Pd-catalyzed C-O and C-N bond formation.It can be used in the following reactions:Palladium-catalyzed Tsuji-Trost substitution and cross-coupling of benzylic fluorides.Palladium-catalyzed C-N cross-coupling of sulfinamides and aryl halides.Palladium-catalyzed rapid methoxylation and deuteriomethoxylation of bromo-chalcones.
Usessuzuki reaction
General DescriptiontBuXPhos [2-Di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl] is an air-stable, electron-rich biaryl phosphine ligand developed by the Buchwald group to enhance the reactivity of palladium catalysis during cross-coupling reactions.
Upstream & downstream products
Upstream raw materials
Related reactions
1,067 records
Compound notes
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