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316393
Sodium triacetoxyborohydride
97%
Synonym(s):
STAB
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About This Item
Recommended Products
Quality Level
Assay
97%
reaction suitability
reagent type: reductant
mp
116-120 °C (dec.) (lit.)
SMILES string
[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
InChI key
HHYFEYBWNZJVFQ-UHFFFAOYSA-N
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General description
Application
- In the reductive amination of ketones and aldehydes.[2][3]
- To prepare N-benzyl-γ-valerolactam by reacting with methyl 4-oxopentanoate and benzylamine via reductive amination/lactamization.[3]
- To reduce imines and enamines to corresponding amines.[2]
- To reduce quinolines and isoquinolines to corresponding tetrahydro derivatives.[2]
- In the hydroboration of alkenes.[4]
- To synthesize nitroxide biradicals for creating high relaxivity terminal groups linkage to dendrimers.[5]
related product
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Sol. 1 - Repr. 1B - Water-react 1
Supplementary Hazards
Storage Class Code
4.3 - Hazardous materials which set free flammable gases upon contact with water
WGK
WGK 2
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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Sodium triacetoxyborohydride
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How is shipping temperature determined? And how is it related to the product storage temperature?
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How can I determine the shelf life / expiration / retest date of this product?
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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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What is the Department of Transportation shipping information for this product?
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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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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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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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