sodium bis(acetyloxy)boranuidyl acetate

• ChemBase ID: 85625
• Molecular Formular: C6H9BNaO6
• Molecular Mass: 210.93283
• Monoisotopic Mass: 211.03898769
• SMILES: [B-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]
• Canonical SMILES: CC(=O)O[B-](OC(=O)C)OC(=O)C.[Na+]
• InChI: InChI=1S/C6H9BO6.Na/c1-4(8)11-7(12-5(2)9)13-6(3)10;/h1-3H3;/q-1;+1
• InChIKey: AGGHKNBCHLWKHY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium bis(acetyloxy)boranuidyl acetate; sodium bis(acetyloxy)-$l^{2}-boranuidyl acetate
• IUPAC Traditional name: sodium bis(acetyloxy)boranuidyl acetate; sodium bis(acetyloxy)-$l^{2}-boranuidyl acetate
• Synonyms: STAB; Sodium triacetoxyborohydride; Sodium triacetoxy borohydride; Sodium tris(acetoxy)borohydride; Tris(acetoxy)hydroborate sodium salt; Sodium tris(acetoxy)hydroborate 97%; 三乙酰氧基硼氢化钠

Database IDs

• CAS Number: 56553-60-7
• EC Number: 000-000-0
• MDL Number: MFCD00012211
• Beilstein Number: 4047608
• PubChem SID: 24859012; 24886353; 162072741
• PubChem CID: 23676153

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): -0.9961
• LogD (pH = 7.4): -0.9961
• Log P: -0.9961
• Molar Refractivity: 35.9483 cm^3
• Polarizability: 16.623045 Å^3
• Polar Surface Area: 78.9 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 116-120 °C (dec.)(lit.); 116-120(dec.)°C; ca 110°C dec.
• Density: 1.43

Safety Information

• Storage Warning: Highly Flammable/Irritant/Moisture Sensitive/Store under Argon; Moisture Sensitive
• European Hazard Symbols: Flammable (F); Irritant (Xi)
• UN Number: 1409; UN3396
• German water hazard class: 3
• Hazard Class: 4.3
• Packing Group: 2; III
• Risk Statements: 11-15-37/38-41; 15
• Safety Statements: 7/8-26-33-37/39-43-60; 7/8-43
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H261; H261-H228-H318-H315-H335
• GHS Precautionary statements: P210-P231+P232-P241-P305+P351+P338-P405-P501A; P231 + P232-P422
• RID/ADR: UN 1409 4.3/PG 2

Product Information

• Purity: ≥90% (gas-volumetric); 95%
• Grade: technical
• Linear Formula: (CH3COO)3BHNa

DETAILS

Sigma Aldrich - 316393

Frequently Asked Questions
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Packaging
1, 10, 25 kg in steel drum
25, 100 g in poly bottle
Application
Reagent used in reductive amination of ketones and aldehydes1,2 and reductive amination/lactamization of carbonyl compounds with amines.2,3Reagent for the reductive amination of aryl aldehydes.4

Sigma Aldrich - 72062

Other Notes
Mild, stereoselective reducing agent1

REFERENCES

• Selective reducing agent; review: Org. Prep. Proced. Int., 17, 317 (1985). Reduces aldehydes in the presence of ketones: J. Chem. Soc., Chem. Commun., 535 (1975). For stereoselective reduction of ketones in AcOH, see: Tetrahedron Lett., 273 (1983). Reduces ?-hydroxy ketones diastereoselectively to anti-diols: J. Am. Chem. Soc., 110, 3560 (1988), and cyclic ?-enamino esters selectively to the cis-amino esters: J. Org. Chem., 59, 5328 (1994); Tetrahedron: Asymmetry, 5, 1455 (1994).
• Excellent reagent for reductive amination of aldehydes and ketones with a wide variety of amines: J. Org. Chem., 61, 3849 (1996); Tetrahedron Lett., 37, 3977 (1996); review: A.C.S. Symp. Ser., 641, 201 (1996).