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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
316393
Triacétoxyborohydrure de sodium
97%
Synonyme(s) :
STAB
About This Item
Produits recommandés
Niveau de qualité
Essai
97%
Pertinence de la réaction
reagent type: reductant
Score du produit alternatif plus écologique
old score: 5
new score: 1
Find out more about DOZN™ Scoring
Caractéristiques du produit alternatif plus écologique
Waste Prevention
Design for Energy Efficiency
Use of Renewable Feedstocks
Learn more about the Principles of Green Chemistry.
sustainability
Greener Alternative Product
Pf
116-120 °C (dec.) (lit.)
Autre catégorie plus écologique
Chaîne SMILES
[Na+].CC(=O)O[BH-](OC(C)=O)OC(C)=O
InChI
1S/C6H10BO6.Na/c1-4(8)11-7(12-5(2)9)13-6(3)10;/h7H,1-3H3;/q-1;+1
Clé InChI
HHYFEYBWNZJVFQ-UHFFFAOYSA-N
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Catégories apparentées
Description générale
Application
- dans l'amination réductrice de cétones et d'aldéhydes[2][3]
- pour préparer du N-benzyl-γ-valérolactame en le faisant réagir avec du 4-oxopentanoate de méthyle et de la benzylamine par amination/lactamisation réductrice[3]
- pour réduire des imines et des énamines en amines correspondantes[2]
- pour réduire des quinoléines et des isoquinoléines en dérivés tétrahydro correspondants[2]
- dans l'hydroboration d'alcènes[4]
- pour synthétiser des biradicaux nitroxyde afin de créer des groupements terminaux de haute relaxivité capables de se lier à des dendrimères[5].
Produit(s) apparenté(s)
Mention d'avertissement
Danger
Mentions de danger
Conseils de prudence
Classification des risques
Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Sol. 1 - Repr. 1B - Water-react 1
Risques supp
Code de la classe de stockage
4.3 - Hazardous materials which set free flammable gases upon contact with water
Classe de danger pour l'eau (WGK)
WGK 2
Point d'éclair (°F)
Not applicable
Point d'éclair (°C)
Not applicable
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Certificats d'analyse (COA)
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Articles
Sodium triacetoxyborohydride
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How is shipping temperature determined? And how is it related to the product storage temperature?
1 answer-
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How can I determine the shelf life / expiration / retest date of this product?
1 answer-
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.pdfHelpful?
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How else can Product 316393, Sodium triacetoxyborohydride, be used as a reducing agent?
1 answer-
Recently, sodium triacetoxyborohydride was used to stereoselectively reduce 4-ketoprolines to the corresponding trans-hydroxy-proline in excellent yields. By comparison, reduction of the 4-ketoproline esters failed to provide any product.
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What is the Department of Transportation shipping information for this product?
1 answer-
Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
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What is Product 316393, Sodium triacetoxyborohydride, used for?
1 answer-
Sodium triacetoxyborohydride (NaBH(OAc)3) is particularly effective in reductive aminations due to its large scope, mildness, and selectivity.
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Which is better to use, Product 316393, Sodium triacetoxyborohydride, or sodium cyanoborohydride?
1 answer-
It is preferred to sodium cyanoborohydride (NaBH3CN) in many applications due to reduced toxicity of the side products formed, and better yields and reproducibility during synthesis. (See Chemfiles, vol 5, no. 9). The reductive aminations of complex substrates also proceed smoothly using sodium triacetoxyborohydride.
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