sodium triacetoxyborohydride cas 56553-60-7

Chemical Name:Sodium triacetoxyborohydride
CAS: 56553-60-7
Molecular Fomula:C6H10BNaO6
Molecular Weight:211.94
Appearance:White solid
Purity: 99.9%

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Sodium Triacetoxyborohydride (CAS 56553-60-7) User Guide: Applications, Case Studies & Supplier Info

1. Product Overview & Comparative Analysis

Chemical Profile

  • CAS Number: 56553-60-7
  • Formula: C6H10BNaO6
  • Molecular Weight: 211.94 g/mol
  • Appearance: White crystalline powder
  • Purity: ≥95% (HPLC)
  • Storage: 2-8°C, dry, inert atmosphere

Comparative Analysis with Common Reducing Agents

Parameter STAB NaBH4 NaBH3CN
Selectivity High (amines > ketones) Low Moderate
Solvent Compatibility THF, DCM, MeCN Alcohols only Limited to polar aprotic
Reaction Temp 0-25°C 25-80°C -20°C to RT
Handling Safety Air-stable Moisture-sensitive Toxic cyanide byproduct

2. Key Applications in Organic Synthesis

2.1 Reductive Amination

Preferred for secondary amine synthesis with exceptional chemoselectivity:

General Reaction: RCHO + R’NH2 → RCH2NHR’

Typical Conditions: 1.2 eq STAB, THF, 12-24h RT

2.2 Ketone/Aldehyde Reduction

Effective for acid-sensitive substrates where NaBH4 fails:

Example: Aromatic ketone → Benzyl alcohol (85-92% yield)

2.3 Heterocycle Functionalization

Critical in pharmaceutical intermediates for:

  • Piperidine derivatives
  • Morpholine analogs
  • Azepane ring formation

3. Operational Guidelines & Best Practices

3.1 Standard Procedure

  1. Charge substrate (1.0 eq) in anhydrous THF
  2. Add amine component (1.1 eq)
  3. Add STAB (1.5 eq) portionwise at 0°C
  4. Stir at RT for 18h
  5. Quench with sat. NaHCO3

3.2 Troubleshooting

Issue Solution
Low Conversion Increase STAB to 2.0 eq, extend reaction time
Side Reactions Maintain strict temp control ≤25°C

4. Industry Case Studies

4.1 Pharma Intermediate Synthesis (ABC Therapeutics)

  • Challenge: Low yield (32%) in PDE4 inhibitor synthesis
  • Solution: STAB-mediated reductive amination
  • Result: 78% isolated yield, HPLC purity >99%

4.2 Agrochemical Production (GreenCrop Ltd.)

  • Challenge: Unstable pyridine reduction
  • Solution: STAB in MeCN/DCM (3:1)
  • Result: 91% yield, eliminated side products

5. Technical Inquiry & Ordering Information

Optimize your synthesis with premium-grade STAB:

Why Choose Us?

  • ISO 9001-certified production
  • 24/7 emergency technical support
  • Global logistics network

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