Sodium triacetoxy-borohydride

Base Information

• Chemical Name: Sodium triacetoxy-borohydride
• CAS No.: 56553-60-7
• Molecular Formula: C6H10BNaO6
• Molecular Weight: 211.943
• Hs Code.: 2850.00
• Nikkaji Number: J1.884.353F,J2.805.651F
• Wikidata: Q7553383
• Mol file: 56553-60-7.mol

Synonyms:sodium trisacetoxyborohydride;sodium triacetoxy-borohydride;Na(OAc)3BH;NaB(OAc)3H;NaBH(AcO)3;NaBH(OAc)3;sodium tnacetoxyborohydnde;UNII-4VU0JE4YSK;sodium tnacetoxyborohydride;sodium triacetoxyborohydnde;sodium triactoxyborohydride;sodiumtrisacetoxyborohydride;sodium triacetoxvborohydride;sodium triacetoxyhydroborate;sodium triacteoxyborohydride;sodiumtriacetoxy borohydride;sodiumtriacetoxy-borohydride;C6H10BNaO6;Sodium triacetoxiborohydride;sodium triacetoxyboro hydrid;sodium triacetoxylborohydride;sodium tri-acetoxyborohydride;sodium triacetoxyboro hydride;sodium triacetoxyboro-hydride;sodium triacetoxyborohyd ride;sodium(triacetoxy)borohydride;Sodium triacetoxy borohydride;Sodium triacetoxyl borohydride;Sodium triacetoxyl-borohydride;Sodium tris-acetoxyborohydride;sodium trisacetoxy borohydride;sodium (triacetoxy)borohydride;sodium tri acetoxy borohydride;sodium tri(acetoxy)borohydride;sodium tri-acetoxy borohydride;sodium tri-acetoxy-borohydride;sodium(triacetoxy)-borohydride;sodium triacetyloxy borohydride;Sodium tris(acetoxy)borohydride;Sodium tris(acetoxy)hydroborate;sodium (triacetoxy)-borohydride;DTXSID8074368;sodium tris(acetoxy) borohydride;HHYFEYBWNZJVFQ-UHFFFAOYSA-N;BP-31215;NS00123020;Sodium Triacetoxyborohydride (Technical Grade);D77878;Q7553383

Chemical Property of Sodium triacetoxy-borohydride

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0Pa at 25℃
• Melting Point: 116-120 °C (dec.)(lit.)
• Boiling Point: 111.1℃[at 101 325 Pa]
• PSA: 78.90000
• Density: 1.36[at 20℃]
• LogP: -0.60710
• Storage Temp.: Flammables + water-Freezer (-20°C)e area
• Sensitive.: Moisture Sensitive
• Solubility.: Soluble in dimethyl sulfoxide, methanol, benzene, toluene, terah
• Water Solubility.: reacts
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 212.0468125
• Heavy Atom Count: 14
• Complexity: 192

Purity/Quality:

99% ^*data from raw suppliers

Sodium triacetoxyborohydride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F, Xi, C
• Hazard Codes: F,Xi,C
• Statements: 15-34-14/15-37/38-11
• Safety Statements: 43-7/8-45-36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: [BH-](OC(=O)C)(OC(=O)C)OC(=O)C.[Na+]
• Uses: 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.

Technology Process of Sodium triacetoxy-borohydride

There total 7 articles about Sodium triacetoxy-borohydride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.2%

→ sodium tris(acetoxy)borohydride (56553-60-7)

Guidance literature:

Reference yield: 92.0%

sodium tetrahydroborate (16940-66-2) → sodium tris(acetoxy)borohydride (56553-60-7)

Guidance literature:

With acetic acid; In benzene; byproducts: H2; under N2-atmosphere; slurry of NaBH4 in benzene cooled (10°C); CH3COOH added dropwise (temp. < 20°C); mixt. warmed (ambient temp.) and stirred for 8h;; filtration; white powder washed (ether) and held under vacuum over night; elem. anal.;;

DOI:10.1021/ja00219a035

Reference yield: 75.0%

→ 2'-O-(triethylsilyl)-6β-hydroxypaclitaxel + sodium tris(acetoxy)borohydride (56553-60-7)

Guidance literature:

upstream raw materials:

acetic acid

triacetoxyborane

sodium hydride

sodium tetrahydroborate

Downstream raw materials:

8-(p-azido-N-ethyl-tetrafluoroaniline)-3,7-dimethyl-1-acetoxyl-2,6-octadiene

5-(2,4-difluoro-benzyl)-hexahydro-pyrrolo[3.4-c]pyrrole-2-carboxylic Acid Tert-Butyl Ester

N-(4-chlorophenyl)-4-piperidinamine

4-(4-fluorophenylamino)-piperidine

Refernces

• 1、 Suryavanshi, Padmakar A.,Sridharan, Vellaisamy,Menéndez, J. Carlos. "A β-enaminone-initiated multicomponent domino reaction for the synthesis of indoloquinolizines and benzoquinolizines from acyclic precursors". . p. 13207 - 13215. Retrieved 2013.
• 2、 Lam, Thientu T.,Bagner, Carl,Tuma, Linda. "Application of thermal analytical techniques in development of a safe and robust process for production of triacetoxyborohydride (STAB)". . p. 109 - 113. Retrieved 2005.
• 3、 Nakayama, Yasuaki,Maser, Michael R.,Okita, Tatsuya,Dubrovskiy, Anton V.,Campbell, Taryn L.,Reisman, Sarah E.. "Total Synthesis of Ritterazine B". supporting information. p. 4187 - 4192. Retrieved 2021/04/06.
• 4、 Maiti, Swarupananda,Leonardi, Marco,Cores, ángel,Tenti, Giammarco,Ramos, M. Teresa,Villacampa, Mercedes,Menéndez, J. Carlos. "Synthesis of 1,4-Diazepanes and Benzo[ b][1,4]diazepines by a Domino Process Involving the in Situ Generation of an Aza-Nazarov Reagent". . p. 11924 - 11933. Retrieved 2020/10/23.