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56553-60-7 - Sodium triacetoxyborohydride, 95% - STAB - B22060 - Alfa Aesar

B22060 Sodium triacetoxyborohydride, 95%

Numéro CAS
56553-60-7
Synonymes
STAB

Dimensions Prix ($) Quantité Disponibilité
5g 14,40
25g 38,70
100g 109,46
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Sodium triacetoxyborohydride, 95%

MDL
MFCD00012211
EINECS
000-000-0

Propriétés chimiques

Formule
Na(CH3CO2)3BH
Poids formulaire
211.94
Point de fusion
ca 110° dec.
Sensibilité
Moisture Sensitive
Solubilité
Soluble in dimethyl sulfoxide, methanol, benzene, toluene, terahydrofuran, dioxane and methylene chloride.

Applications

Sodium triacetoxyborohydride is used as a reagent in reductive amination of ketones, aldehydes and lactamization of carbonyl compounds with amines. It also serves as a reducing agent in organic synthesis.

Notes

Moisture sensitive. Incompatible with strong oxidizing agents, water, alcohols and acids.

Références bibliographiques

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 ß-hydroxy ketones diastereoselectively to anti-diols: J. Am. Chem. Soc., 110, 3560 (1988), and cyclic ß-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).

Tahara, Y. K.; Ito, M.; Kanyiva, K. S.; Shibata, T. Total Synthesis of cis-Clavicipitic Acid from Asparagine via Ir-Catalyzed C-H bond Activation as a Key Step. Chem. Eur. J. 2015, 21 (32), 11340-11343.

Kang, B.; Oh, J. A.; Lee, J. Y.; Rhim, H.; Yune, T. Y.; Choo, H. Y. P. 3-Benzamides and 3, 4, 5-trimethoxyphenyl amines as calcium channel blockers. Bioorg. Med. Chem 2015, 23 (18), 6166-6172.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H261-H228-H318-H315-H335

In contact with water releases flammable gas. Flammable solid. Causes serious eye damage. Causes skin irritation. May cause respiratory irritation.

Mentions de prudence: P210-P231+P232-P261-P280-P305+P351+P338-P304+P340-P310-P362-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Handle under inert gas. Protect from moisture. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician. Take off contaminated clothing and wash before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
4047608
Classe de danger
4.3
Groupe d'emballage
III
Code tarifaire harmonisé
2915.29
TSCA
Yes

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Consulté récemment

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Catalyseurs

Analytique et matériel de laboratoire