316393
Sodium triacetoxyborohydride
>95%
Synonym(s):
STAB
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About This Item
Quality Level
Assay
>95%
reaction suitability
reagent type: reductant
greener alternative product score
old score: 5
new score: 1
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mp
116-120 °C (dec.) (lit.)
greener alternative category
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.
- To prepare N-benzyl-γ-valerolactam by reacting with methyl 4-oxopentanoate and benzylamine via reductive amination/lactamization.
- To reduce imines and enamines to corresponding amines.
- To reduce quinolines and isoquinolines to corresponding tetrahydro derivatives.
- In the hydroboration of alkenes.
- To synthesize nitroxide biradicals for creating high relaxivity terminal groups linkage to dendrimers.
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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If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.
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The lot specific COA document can be found by entering the lot number above under the "Documents" section.
What is Product 316393, Sodium triacetoxyborohydride, used for?
Sodium triacetoxyborohydride (NaBH(OAc)3) is particularly effective in reductive aminations due to its large scope, mildness, and selectivity.
Which is better to use, Product 316393, Sodium triacetoxyborohydride, or sodium cyanoborohydride?
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.
How else can Product 316393, Sodium triacetoxyborohydride, be used as a reducing agent?
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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