ナトリウムトリアセトキシボロヒドリド

危険有害性情報のコード(GHS)

• 絵表示(GHS)

  

• 注意喚起語

  Danger

• 危険有害性情報

  H228：可燃性固体

  H260：水に触れると自然発火するおそれのある可燃性 /引火性ガスを発生

  H302：飲み込むと有害

  H318：重篤な眼の損傷

• 注意書き

  P210：熱/火花/裸火/高温のもののような着火源から遠ざ けること。－禁煙。

  P231+P232：湿気を遮断し、不活性ガス下で取り扱うこと。

  P280：保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。

  P301+P312：飲み込んだ場合：気分が悪い時は医師に連絡する こと。

  P305+P351+P338：眼に入った場合：水で数分間注意深く洗うこと。次にコ ンタクトレンズを着用していて容易に外せる場合は外す こと。その後も洗浄を続けること。

  P308+P313：暴露または暴露の懸念がある場合：医師の診断/手当てを 受けること。

ナトリウムトリアセトキシボロヒドリド 価格

MSDS Information

• STAB

ナトリウムトリアセトキシボロヒドリド 化学特性,用途語,生産方法

• 外観

  白色粉末～結晶

• 化学的特性

  Sodium triacetoxyborohydride (STAB-H) is commercially available as a hygroscopic white powder with a melting point of 116-120 °C. freely soluble in benzene. It is prepared by the reaction of NaBH4 with excess acetic acid in benzene or toluene.

• 使用

  Sodium Triacetoxyborohydride(STAB) is a hydride reagent used in stereoselective reductive amination. It is able to replace toxic sodium cyanoborohydride under most conditions. It is selective in reducing aldehydes to alcohols in the presence of ketones. STAB is also stable in anhydrous acids, which enables reductive amination of aldehydes and ketones. It used in reductive amination of ketones and aldehydes and reductive amination/lactamization of carbonyl compounds with amines. The advantage of STAB compared to sodium cyanoborohydride is evident. STAB, being non-toxic, is easier to handle and forms no toxic by-products, making the treatment of process waste after the reaction simple and less costly.

• 主な応用

  Sodium triacetoxyborohydride is a mild reagent that exhibits remarkable selectivity as a reducing agent. It reduces aldehydes but not ketones; however, beta-hydroxyketones can be reduced selectively to give 1,3-trans diols.The steric and the electron-withdrawing effects of the three acetoxy groups stabilize the boron-hydrogen bond and are responsible for its mild reducing properties.
  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.

• 反応性

  Sodium Triacetoxyborohydride is selective reducing agent in organic synthesis. It is especially suitable for reductive aminations. Since the reaction rate for the reduction of iminium ions is much faster than for ketones or even aldehydes, the reductive amination can be carried out as a one-pot procedure by introducing the reducing agent into a mixture of the amine and carbonyl compound. The presence of a stoichiometric amount of acetic acid, which catalyzes the imine formation and provides the iminium ion, doesn't present any problem under these conditions.
  
  Reductive amination (simplified)

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