3D Mol Similar

X-PHOS

: Iupac Name：dicyclohexyl-[2-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphane; CAS No.: 564483-18-7; Molecular Weight：476.72; Modify Date.: 2022-10-29 02:50; Introduction: suzuki reaction View more+

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1. Names and Identifiers

: 1.1 Name; X-PHOS; 1.2 Synonyms; 2-(DICYCLOHEXYLPHOSPHINO)-2',4',6'-TRI-I-PROPYL-1,1'-BIPHENYL 2-(Dicyclohexylphosphino)-2',4',6'-triisopropylbiphenyl 2-Dicyclohexylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl, X-PHOS 2-DICYCLOHEXYLPHOSPHINO-2',4',6'-TRIISO-PROPYL-1,1'-BIPHENYL 2-DICYCLOHEXYLPHOSPHINO-2',4',6'-TRIISOPROPYLBIPHENYL 2-Dicyclohexylphosphino-2″,4″,6″-triisopropylbiphenyl 5-BROMO-4-CHLORO-3-INDOLYL PHOSPHATE -biphenyl]-2-yl]phosphane Dicyclohexyl(2',4',6'-triisopropyl-2-biphenylyl)phosphine Dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine dicyclohexyl[2',4',6'-tri(propan-2-yl)biphenyl-2-yl]phosphane Dicyclohexyl[2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine dicyclohexyl-[2-[2,4,6-tri(propan-2-yl)phenyl]phenyl]phosphane EINECS 270-588-3 L6TJ APR BR BY1&1 DY1&1 FY1&1&&- AL6TJ MFCD04117682 Phosphine, dicyclohexyl[2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]- XPhos; View all

1.3 CAS No.: 564483-18-7

1.4 CID: 11155794

1.5 EINECS(EC#): 611-387-6

1.6 Molecular Formula: C33H49P (isomer)

1.7 Inchi: InChI=1S/C33H49P/c1-23(2)26-21-30(24(3)4)33(31(22-26)25(5)6)29-19-13-14-20-32(29)34(27-15-9-7-10-16-27)28-17-11-8-12-18-28/h13-14,19-25,27-28H,7-12,15-18H2,1-6H3

1.8 InChIkey: UGOMMVLRQDMAQQ-UHFFFAOYSA-N

1.9 Canonical Smiles: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C

1.10 Isomers Smiles: CC(C)C1=CC(=C(C(=C1)C(C)C)C2=CC=CC=C2P(C3CCCCC3)C4CCCCC4)C(C)C

2. Properties

2.1 Melting point: 187-190℃

2.1 Boiling point: 569.8°C at 760 mmHg

2.1 Flash Point: 317.7°C

2.1 Precise Quality: 476.35700

2.1 PSA: 13.59000

2.1 logP: 10.49640

2.1 Appearance: White crystalline powder

2.2 Chemical Properties: White crystalline powder

2.3 Color/Form: white

2.4 StorageTemp: Inert atmosphere,Room Temperature

3. Use and Manufacturing

3.1 Usage: suzuki reaction

4. Safety and Handling

4.1 Symbol: GHS08;

4.1 Hazard Codes: Xn

4.1 Signal Word: Warning

4.1 Risk Statements: R22;R36/37/38

4.1 Safety Statements: S26;S37/39

4.1 Hazard Declaration: H351

4.1 RIDADR: NONH for all modes of transport

4.1 Caution Statement: P281

4.1 WGK Germany: 3

4.1 Safety: Hazard Codes: Xn
Risk Statements: 36/37/38-22-40
R36/37/38:Irritating to eyes, respiratory system and skin.
R22:Harmful if swallowed.
R40:Limited evidence of a carcinogenic effect.
Safety Statements: 37/39-26-36/37
S37/39:Wear suitable gloves and eye/face protection.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37:Wear suitable protective clothing and gloves.
WGK Germany: 3

4.2 Sensitive: Air Sensitive

4.3 Specification: 2-(Dicyclohexylphosphino)-2',4',6'-triisopropylbiphenyl , its cas register number is 564483-18-7. It also can be called X-Phos ; Dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine ; Dicyclohexyl[2',4',6'-tri(propan-2-yl)biphenyl-2-yl]phosphane ; Dicyclohexyl[2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]phosphine ; and Phosphine, dicyclohexyl[2',4',6'-tris(1-methylethyl)[1,1'-biphenyl]-2-yl]- .
2-(Dicyclohexylphosphino)-2',4',6'-triisopropylbiphenyl (CAS NO.564483-18-7) is stable. However, it is not compatible with strong oxidizing agents, halogens. And it also should avoid incompatible materials. Its hazardous decomposition productsare carbon monoxide, oxides of phosphorus, carbon dioxide. While, its hazardous polymerization will not occur.

4.4 Toxicity: 2-(Dicyclohexylphosphino)-2',4',6'-triisopropylbiphenyl (CAS NO.564483-18-7) hasn't been listed as a carcinogen by ACGIH, IARC, NTP, or CA Prop 65. And the toxicological properties have not been fully investigated.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

7. Synthesis Route

564483-18-7Total: 2 Synthesis Route

694-80-4 115 Suppliers

21524-34-5 100 Suppliers

16523-54-9 97 Suppliers

564483-18-7 201 Suppliers

Literatures:
Liu, Lei; Wu, Hai-Chen; Yu, Jin-Quan Chemistry - A European Journal, 2011 , vol. 17, # 39 p. 10828 - 10831
Yield: ~81%

694-80-4 115 Suppliers

21524-34-5 100 Suppliers

100384-03-0

564483-18-7 201 Suppliers

Literatures:
Liu, Lei; Wu, Hai-Chen; Yu, Jin-Quan Chemistry - A European Journal, 2011 , vol. 17, # 39 p. 10828 - 10831
Yield: ~84%

8. Precursor and Product

precursor:

100384-03-0

16523-54-9

694-80-4

21524-34-5

9. Other Information

9.0 Reaction

Exceptional ligands for Pd-catalyzed amination and amidation of aryl sulfonates.
Ligand used for the Pd-catalyzed Suzuki-Miyaura coupling reaction and carbonyl enolate coupling.
Ligand used for the chemoselective amination of aryl chlorides.
Ligand used for the Pd-catalyzed borylation of aryl chlorides, for the formation of trifluoroborates.
Ligand used for the Pd-catalyzed amination of vinyl halides and triflates.
Ligand used for the Pd-catalyzed three-component synthesis of indoles.
Ligand used for the Pt-catalyzed regioselective hydrosilylation of functionalized terminal arylalkynes.
Ligand used for the Pd-catalyzed synthesis of carbazoles.
Ligand used for the Pd-catalyzed Suzuki-Miyaura coupling of aryl chloride and NHC-boranes.
Ligand used for the direct arylation of picoline N-oxide.
Ligand used for the Negishi coupling of 2-heterocyclic organozinc reagents.
Catalyst for a phosphine-catalyzed Heine reaction.
Ligand used for the palladium-catalyzed oxidative coupling of indoles and heteroarenes.
Ligand used for the silver-catalyzed hydrogenation of aldehydes.
Ligand used for the palladium-catalyzed cyanation of heterycyclic halides.

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9.1 Chemical Properties: White crystalline powder

9.2 Uses: suzuki reaction

9.3 Uses: Exceptional ligands for Pd-catalyzed amination and amidation of aryl sulfonates. XPHOS is used as a regent in the synthesis of novel [1,2,4]triazolo[4,3-a]pyrazine derivatives as potential selective c-met inhibitors with improved pharmacokinetic properties.

9.4 Uses: XPHOS is used as a regent in the synthesis of novel [1,2,4]triazolo[4,3-a]pyrazine derivatives as potential selective c-met inhibitors with improved pharmacokinetic properties.

9.5 General Description: We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.

10. Computational chemical data

Molecular Weight: 476.72g/mol
Molecular Formula: C₃₃H₄₉P
Compound Is Canonicalized: True
XLogP3-AA: 10.1
Exact Mass: 476.35718856
Monoisotopic Mass: 476.35718856
Complexity: 545
Rotatable Bond Count: 7
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 0
Topological Polar Surface Area: 0
Heavy Atom Count: 34
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcfB8AAIAAAAAAAAAAAAAAAAAAAAAAAAwYMGAAAAAAAABQAAAGAgAAAAADQCIGAAyAIAAACCAAiBCAAACAAAgAAAIiAAAAIgIICKAERCAIAAggAAIiAcAgMAOwAACAAAQAACAAAQAACAAAAAAAAAAAA==

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Time: 2023/06/28

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2-Dicyclohexylphosphino-2’,4’,6’-tri-i-propyl-1,1’-biphenyl