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731374

Sigma-Aldrich

Tri-n-butylphosphine

99%

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:
998-40-3
Molecular Weight:
202.32
Beilstein:
1738261
EC Number:
213-651-2
MDL number:
MFCD00009462
UNSPSC Code:
12352128
PubChem Substance ID:
329764649
NACRES:
NA.22
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vapor density

9 (vs air)

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

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Application

Catalyst for:
  • Domino reactions of activated conjugated dienes with β,γ−unsaturated-α-ketoesters[1]
  • [3+2]-Cycloadditions[2]
  • Umpolung addition reactions[3]
  • Reductive carbonylation[4]
  • Allylation reactions[5]

Signal Word

Danger

Hazard Statements

H250,H302,H314,H411

Hazard Classifications

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

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 2

Flash Point(F)

242.6 °F - closed cup

Flash Point(C)

117 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
SHBN7875
SHBN3708
SHBM4492
SHBM4051
SHBJ7035

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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)
X. Guan, et al.,
European Journal of Organic Chemistry, 14, 2673-2677 (2011)
A. S. Singh, et al.,
Tetrahedron Letters, 52, 2383-2386 (2011)
A. A. Vasil'ev, et al.,
Russian Chemical Bulletin, 59, 605-610 (2010)
Y. Zou, et al.,
Synlett, 7, 1000-1004 (2011)
View All Related Papers

Questions

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  1. 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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  2. 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/449/386/product-dating-information-mk.pdf

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