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257192

Triethylborane

≥95%

Synonym(s):

Triethylboron

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About This Item

Linear Formula:
(C2H5)3B
CAS Number:
97-94-9
Molecular Weight:
97.99
NACRES:
NA.22
PubChem Substance ID:
24855572
UNSPSC Code:
12352001
EC Number:
202-620-9
MDL number:
MFCD00009022
Assay:
≥95%

Key Documents

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InChI key

LALRXNPLTWZJIJ-UHFFFAOYSA-N

InChI

1S/C6H15B/c1-4-7(5-2)6-3/h4-6H2,1-3H3

SMILES string

CCB(CC)CC

assay

≥95%

reaction suitability

reagent type: reductant

refractive index

n20/D 1.397 (lit.)

bp

95 °C (lit.)

mp

−93 °C (lit.)

density

0.677 g/mL at 25 °C (lit.)

Quality Level

100

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Show Differences

1 of 4

This Item
195030179701257222
Triethylborane ≥95%

Sigma-Aldrich

257192

Triethylborane

Triethylborane solution 1.0 M in hexanes

Sigma-Aldrich

195030

Triethylborane solution

Triethylborane solution 1.0 M in THF

Sigma-Aldrich

179701

Triethylborane solution

Trimethylaluminum 97%

Sigma-Aldrich

257222

Trimethylaluminum

assay

≥95%

assay

-

assay

-

assay

97%

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

200

reaction suitability

reagent type: reductant

reaction suitability

reagent type: reductant

reaction suitability

reagent type: reductant

reaction suitability

-

density

0.677 g/mL at 25 °C (lit.)

density

0.675 g/mL at 25 °C

density

0.865 g/mL at 25 °C

density

0.752 g/mL at 25 °C (lit.)

mp

−93 °C (lit.)

mp

-

mp

-

mp

15 °C (lit.)

bp

95 °C (lit.)

bp

-

bp

-

bp

125-126 °C (lit.), 127 °C/760 mmHg, 20 °C/8 mmHg, 56 °C/50 mmHg

Application

Reagent for:
  • Enantioselective umpolung allylation of aldehydes
  • Preparation of tetramethylammonium trialkylphenylborate salts

Catalyst for:
  • Radical reductions of alkyl bromides and iodides bearing electron withdrawing groups with N-heterocyclic carbene boranes
  • Synthesis of 1-substituted pyrrolines by N-diallylation of amines and ring-closing metathesis
  • Decarboxylative C-C bond cleavage reactions
  • Alkene hydrogenations
  • Aminyl radical cyclizations onto silyl enol ethers

Modifier for single-site organochromium ethylene polymerization catalysts
Used with lithium tri-tert-butoxyaluminohydride (cat. no. L2904) in the reductive cleavage of ethers and epoxides.[1] Used in the deoxygenation of primary and secondary alcohols.[2]

General description

Triethylborane (Et3B) is an organoborane pyrophoric liquid. It is prepared on the plant scale by the reaction of AlEt3 and KBF4.[3] Et3B is widely used as a precursor for the preparation of reducing agents such as lithium triethylborohydride and sodium triethylborohydride. It can also be utilized as an initiator in radical cyclization reactions.[4]

Packaging

Supplied in a Sure/Pac™ cylinder and has a 1/4-turn bronze ball valve with a female 1/4" NPT outlet thread (Z122661) installed. Before using the cylinder, ensure that the valve is closed, then remove carbon steel plug that seals the outlet valve.

Compatible with the following:For instructions please refer to technical bulletin AL-136: The Aldrich Sure/Pac™ Cylinder System

Legal Information

Aldrich is a registered trademark of Sigma-Aldrich Co. LLC
Sure/Pac is a trademark of Sigma-Aldrich Co. LLC

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Danger

Hazard Classifications

Acute Tox. 3 Oral - Eye Dam. 1 - Pyr. Liq. 1 - Skin Corr. 1A

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk

WGK 1

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
SHBS4673
SHBQ6705
SHBL4002
SHBK8092
SHBJ4615

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Masafumi Ueda et al.
Organic letters, 11(20), 4632-4635 (2009-10-09)
Intermolecular hydroxyalkylation of alpha,beta-unsaturated imines involving Et3B-mediated regioselective alkyl radical addition and subsequent hydroxylation with molecular oxygen has been developed, in which N-borylenamine generated by trapping of the enaminyl radical with Et3B was a key intermediate in the proposed aerobic
A Convenient Preparation of Trimethylborane and Triethylborane
Koster, R, et al.
Synth. React. Inorg. Met.-Org. Chem. , 3(4), 359-367 (1973)
Tetrahedron, 49, 7193-7193 (1993)
Aldrichimica Acta, 6, 21-21 (1973)
Triethylborane-mediated atom transfer radical cyclization reaction in water
Yorimitsu H, et al.
The Journal of Organic Chemistry, 63(23), 8604-8605 (1998)
View All Related Papers

Questions

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  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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