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655325

Sigma-Aldrich

Tri-tert-butylphosphine solution

1.0 M in toluene

Synonym(s):

P(t-Bu)3, P(t-Bu)3

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About This Item

Empirical Formula (Hill Notation):
C12H27P
CAS Number:
13716-12-6
Molecular Weight:
202.32
MDL number:
MFCD00015006
UNSPSC Code:
12352128
PubChem Substance ID:
24884097
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

100

reaction suitability

reagent type: ligand
reaction type: Addition Reactions
reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reagent type: ligand
reaction type: Heck Reaction
reagent type: ligand
reaction type: Negishi Coupling
reagent type: ligand
reaction type: Sonogashira Coupling
reagent type: ligand
reaction type: Stille Coupling
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

concentration

1.0 M in toluene

density

0.861 g/mL at 25 °C

functional group

phosphine

SMILES string

CC(C)(C)P(C(C)(C)C)C(C)(C)C

InChI

1S/C12H27P/c1-10(2,3)13(11(4,5)6)12(7,8)9/h1-9H3

InChI key

BWHDROKFUHTORW-UHFFFAOYSA-N

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Application

Tri-tert-butylphosphine is a suitable ligand for palladium-catalyzed coupling reactions[1] such as:
  • Heck Reactions[2]
  • Negishi cross-coupling[3]
  • Stille reactions[4]
  • Sonogashira reactions[5]

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Signal Word

Danger

Hazard Classifications

Aquatic Chronic 3 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Repr. 2 - Skin Corr. 1B - STOT RE 2 - STOT SE 3

Target Organs

Central nervous system, Respiratory system

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 3

Flash Point(F)

39.9 °F

Flash Point(C)

4.4 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBK9948
STBK5826
STBH3330
SHBJ4695
STBG3582V

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Pd (PhCN) 2Cl2/P (t-Bu) 3: a versatile catalyst for Sonogashira reactions of aryl bromides at room temperature.
Hundertmark T, et al.
Organic Letters, 2(12), 1729-1731 (2000)
Heck reactions in the presence of P (t-Bu) 3: Expanded scope and milder reaction conditions for the coupling of aryl chlorides.
Littke A F, et al.
The Journal of Organic Chemistry, 64(1), 10-11 (1999)
Pd/P (t-Bu) 3: a mild and general catalyst for Stille reactions of aryl chlorides and aryl bromides
Littke A F, et al.
Journal of the American Chemical Society, 124(22), 6343-6348 (2002)
The first general method for palladium-catalyzed Negishi cross-coupling of aryl and vinyl chlorides: use of commercially available Pd (P (t-Bu) 3) 2 as a catalyst
Dai C, et al.
Journal of the American Chemical Society, 123(12), 2719-2724 (2001)
Gregory C Fu
Accounts of chemical research, 41(11), 1555-1564 (2008-10-25)
Metal-catalyzed coupling reactions of aryl electrophiles with organometallics and with olefins serve as unusually effective tools for forming new carbon-carbon bonds. By 1998, researchers had developed catalysts that achieved reactions of aryl iodides, bromides, and triflates. Nevertheless, many noteworthy challenges

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