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731374

Tri-n-butylphosphine

99%, liquid

Synonym(s):

Tributylphosphine, NSC 91700, P(n-Bu)3, TBP

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About This Item

Linear Formula:
[CH3(CH2)3]3P
CAS Number:
Molecular Weight:
202.32
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352128
EC Number:
213-651-2
MDL number:
Beilstein/REAXYS Number:
1738261
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Product Name

Tri-n-butylphosphine, 99%

vapor density

9 (vs air)

Quality Level

assay

99%

form

liquid

autoignition temp.

392 °F

reaction suitability

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

refractive index

n20/D 1.462 (lit.)

bp

150 °C/50 mmHg (lit.)

density

0.81 g/mL at 25 °C (lit.)

functional group

phosphine

SMILES string

CCCCP(CCCC)CCCC

InChI

1S/C12H27P/c1-4-7-10-13(11-8-5-2)12-9-6-3/h4-12H2,1-3H3

InChI key

TUQOTMZNTHZOKS-UHFFFAOYSA-N

Application

Catalyst for:
  • Domino reactions of activated conjugated dienes with β,γ−unsaturated-α-ketoesters[1]
  • [3+2]-Cycloadditions
  • Umpolung addition reactions
  • Reductive carbonylation
  • Allylation reactions

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1 of 1

This Item
T4948424704990827
reaction suitability

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

reaction suitability

-

reaction suitability

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

reaction suitability

reaction type: Acetylations, reagent type: ligand

assay

99%

assay

97%

assay

97%

assay

≥93.5% (Tri-N-butylphosphine, GC), ≥97% (Tri-N-butylphospine + isomers)

form

liquid

form

-

form

liquid

form

liquid

functional group

phosphine

functional group

phosphine

functional group

phosphine

functional group

phosphine

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

200

density

0.81 g/mL at 25 °C (lit.)

density

0.81 g/mL at 25 °C (lit.)

density

0.81 g/mL at 25 °C (lit.)

density

0.81 g/mL at 25 °C (lit.)


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signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Dam. 1 - Pyr. Liq. 1 - Skin Corr. 1A

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

flash_point_f

242.6 °F - closed cup

flash_point_c

117 °C - closed cup



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A. A. Vasil'ev, et al.,
Russian Chemical Bulletin, 59, 605-610 (2010)
A. S. Singh, et al.,
Tetrahedron Letters, 52, 2383-2386 (2011)
Substrate-controlled, phosphine-catalyzed domino reactions of activated conjugated dienes: highly diastereoselective synthesis of bicyclic skeletons.
Jianze Ma et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 17(27), 7418-7422 (2011-05-19)



Global Trade Item Number

SKUGTIN
731374-100G04061832865775
731374-25G04061832866833

Questions

1–2 of 2 Questions  
  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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