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+]
• General Description: Sodium triacetoxyborohydride (STAB) is a selective reducing agent used in organic synthesis, particularly for the reduction of iminium ions and carbon-carbon double bonds in complex molecules, often yielding diastereoselective products. It is synthesized from sodium borohydride and acetic acid, though the process requires careful thermal management to avoid hazardous hydrogen gas release and uncontrolled exotherms. STAB is employed in multistep reactions, such as the reduction of indoloquinolizines or β-aminoesters, where it facilitates the formation of stereogenic centers while maintaining high diastereoselectivity. Its controlled reactivity makes it valuable for constructing densely functionalized cyclic structures.

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

(2S,3S)-<1-(1(S)-phenylethyl)-2-methylpyrrolidin-3-yl>carboxylic acid methyl ester

N-(4-chlorophenyl)-4-piperidinamine

4-(4-fluorophenylamino)-piperidine

Refernces

Discovery of liver selective non-steroidal glucocorticoid receptor antagonist as novel antidiabetic agents

10.1016/j.bmcl.2012.07.078

The study focused on a series of benzyl-phenoxybenzyl amino-phenyl acid derivatives (8a–q), with compound 8g emerging as the lead candidate. This compound demonstrated excellent binding affinity to the human GR, potent antagonistic activity in vitro, and significant oral antidiabetic and antihyperlipidemic effects in vivo, while exhibiting liver selectivity. The research concluded that compound 8g, a passive GR antagonist, could be a promising and safe therapeutic approach for T2DM due to its minimal impact on the hypothalamic-pituitary-adrenal (HPA) axis. The chemicals used in the synthesis and testing of these compounds included various benzyl and phenyl derivatives, sodium triacetoxyborohydride, lithium hydroxide, and other reagents for the synthesis of the target compounds, as well as radioligands and cell lines for in vitro assays.

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