tBuBrettPhos
Reaction- Product Name
- tBuBrettPhos
- CAS No.
- 1160861-53-9
- Chemical Name
- tBuBrettPhos
- Synonyms
- tBuBrettPhos;t-butylBrettPhos;2-(Di-tert-butylphosphino)-2′,4′,6′- triisopropyl-3,6-dimethoxy-1,1′-biphenyl;tBuBrettPhos 97%;tertButylBrettPhos;tert-ButylBrettPhos;-3,6-dimethoxybiphenyL;tBuBrettPhos ChemBeads;[3,6-Dimethoxy-2',4',6'-tr;phosphino)-3,6-dimethoxy-2',4',6'-tri-i-propyL
- CBNumber
- CB22521017
- Molecular Formula
- C31H49O2P
- Formula Weight
- 484.69
- MOL File
- 1160861-53-9.mol
tBuBrettPhos Property
- Melting point:
- 166-170°C
- Boiling point:
- 534.9±50.0 °C(Predicted)
- storage temp.
- 2-8°C, protect from light, stored under nitrogen
- form
- crystal
- color
- white
- InChI
- InChI=1S/C31H49O2P/c1-19(2)22-17-23(20(3)4)27(24(18-22)21(5)6)28-25(32-13)15-16-26(33-14)29(28)34(30(7,8)9)31(10,11)12/h15-21H,1-14H3
- InChIKey
- REWLCYPYZCHYSS-UHFFFAOYSA-N
- SMILES
- P(C1=C(OC)C=CC(OC)=C1C1=C(C(C)C)C=C(C(C)C)C=C1C(C)C)(C(C)(C)C)C(C)(C)C
Safety
- WGK Germany
- 3
- HS Code
- 2931.90.6000
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
- Precautionary statements
-
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P332+P313IF SKIN irritation occurs: Get medical advice/attention.
P337+P313IF eye irritation persists: Get medical advice/attention.
N-Bromosuccinimide Price
- Product number
- 730998
- Product name
- tBuBrettPhos
- Purity
- 97%
- Packaging
- 1g
- Price
- $280.58
- Updated
- 2025/07/31
- Product number
- 936758
- Product name
- tBuBrettPhos ChemBeads
- Packaging
- 1 unit
- Price
- $132.05
- Updated
- 2025/07/31
- Product number
- 730998
- Product name
- tBuBrettPhos
- Purity
- 97%
- Packaging
- 5g
- Price
- $1070
- Updated
- 2025/07/31
- Product number
- 936758
- Product name
- tBuBrettPhos ChemBeads
- Packaging
- 1G
- Price
- $276
- Updated
- 2024/03/01
- Product number
- D5663
- Product name
- Di-tert-butyl(2',4',6'-triisopropyl-3,6-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine
- Packaging
- 250MG
- Price
- $126
- Updated
- 2025/07/31
tBuBrettPhos Chemical Properties,Usage,Production
Reaction
- Ligand used in the Pd-catalyzed conversion of aryl and vinyl triflates to bromides and chlorides.
- Ligand used in the Pd-catalyzed O-arylation of ethyl acetohydroximates.
- Ligand used in the Pd-catalyzed conversion of aryl chlorides, triflates, and nonaflates to nitroaromatics.
- Ligand used in the Pd-catalyzed cross-coupling of amides and aryl mesylates.
Uses
Buchwald Phosphine Ligands for chemical Synthesis
General Description
tBuBrettPhos is a dialkylbiaryl phosphine ligand developed by the Buchwald group. It promotes cross-coupling reactions more efficiently and exhibits improved reactivity compared to other catalytic systems.
reaction suitability
reaction type: Cross Couplings
reagent type: ligand
reaction type: Arylations
reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reagent type: ligand
reaction type: C-X Bond Formation
reagent type: ligand
reaction type: Fluorinations
Synthesis
13716-10-4
21524-34-5
82830-49-7
1160861-53-9
Example 3: Synthesis of Ligand 6; A reflux condenser, glass stopper and rubber septum were assembled to an oven-dried, three-necked, 100 mL round-bottomed flask equipped with a magnetic stir bar. After addition of magnesium chips (360 mg, 15.36 mmol), the flask was evacuated and backfilled with argon (this process was repeated three times). THF (40 mL) and 2,4,6-triisopropylbromobenzene (3.62 g, 12.8 mmol) were added via syringe, heated to reflux and 1,2-dibromomethane (40 μL) was added dropwise. The reaction mixture was stirred at reflux for 1 h and cooled to room temperature. In another oven-dried 500 mL Schlenk flask, a magnetic stir bar and septum were added, evacuated and backfilled with argon (repeated 3 times). THF (160mL) and 1,4-dimethoxy-2-fluorobenzene (2g, 12.8mmol) were added via syringe and cooled to -78°C. n-BuLi (2.5 M hexane solution, 5.12 mL, 12.8 mmol) was added dropwise over 15 min with stirring for 30 min. The previously prepared Grignard reagent was added by cannula transfer and stirred at -78 °C for 1 hour. Slowly warmed to room temperature and continued stirring for 3 hours. Anhydrous CuCl (1.267 g, 12.8 mmol) was added rapidly under argon protection, followed by ClP(t-Bu)2 (2.44 mL, 12.8 mmol) via syringe, and the Schlenk tube was sealed with a PTFE screw cap. The reaction mixture was heated to 75 °C, kept for 48 h and then cooled to room temperature. The reaction was quenched with 30% NH4OH aqueous solution (100 mL) and extracted with EtOAc (200 mL). The organic layer was washed sequentially with 30% aqueous NH4OH (3 x 100 mL) and brine (100 mL), dried over MgSO4, filtered and concentrated to give a yellow oil. The crude product was dissolved in a minimal amount of hot MeOH and crystallized overnight at -25 °C in a refrigerator to give 1.11 g of white crystals (18% yield).
References
[1] Patent: WO2009/76622, 2009, A2. Location in patent: Page/Page column 116
tBuBrettPhos Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from tBuBrettPhos manufacturers
- Product
- 2-(Di-t-butylphosphino)-3,6-dimethoxy-2'-4'-6'-tri-i-propyl-1,1'-biphenyl, min. 98% t-butylBrettPhos 1160861-53-9
- Price
- US $0.00-0.00/KG
- Min. Order
- 5KG
- Purity
- 98%
- Supply Ability
- 25KG
- Release date
- 2024-01-05
- Product
- 2-(Di-t-butylphosphino)-3,6-dimethoxy-2'-4'-6'-tri-i-propyl-1,1'-biphenyl,t-butylBrettPhos 1160861-53-9
- Price
- US $0.00/kg
- Min. Order
- 20kg
- Purity
- 99%
- Supply Ability
- 20 tons
- Release date
- 2024-10-15
- Product
- 2-(Di-t-butylphosphino)-3,6-dimethoxy-2'-4'-6'-tri-i-propyl-1,1'-biphenyl, min. 98% t-butylBrettPhos 1160861-53-9
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 98%
- Supply Ability
- 1ton
- Release date
- 2022-09-30