316393
Sodium triacetoxyborohydride
>95%
Sustainability features
Synonym(s):
STAB
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About This Item
Linear Formula:
(CH3COO)3BHNa
CAS Number:
Molecular Weight:
211.94
UNSPSC Code:
12352302
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
4047608
Assay:
>95%
Quality Segment
assay
>95%
reaction suitability
reagent type: reductant
greener alternative product score
old score: 5
new score: 1
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sustainability
Sustainability features
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
General description
Sodium triacetoxyborohydride (NaBH(OAc)3) is particularly effective in reductive aminations due to its large scope, mildness, and selectivity. 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.
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Application
Sodium triacetoxyborohydride or [NaBH(OAc)3] can be used as a reagent:
- 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.
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Signal Word
Danger
Hazard Codes
Precautionary Statements
supp_hazards
Storage Class
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
Hazard Classifications
Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Sol. 1 - Repr. 1B - Water-react. 1
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