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B22060 Sodium triacetoxyborohydride, 95%

CAS Number
56553-60-7
Synonyms
STAB

Stock No. Size Price ($) Quantity Availability
B22060-06 5g 16.80
B22060-14 25g 43.60
B22060-22 100g 122.00
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Sodium triacetoxyborohydride, 95%

MDL
MFCD00012211
EINECS
000-000-0

Chemical Properties

Formula
Na(CH3CO2)3BH
Formula Weight
211.94
Melting point
ca 110° dec.
Storage & Sensitivity
Moisture Sensitive. Ambient temperatures.
Solubility
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.

Literature References

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H260-H315-H318

In contact with water releases flammable gases which may ignite spontaneously. Causes skin irritation. Causes serious eye damage.

Precautionary Statements: P223-P231+P232-P264b-P280-P302+P352-P305+P351+P338-P310-P332+P313-P335+P334-P362-P370+P378q-P501c

Keep away from any possible contact with water, because of violent reaction and possible flash fire. Handle under inert gas. Protect from moisture. Wash face, hands and any exposed skin thoroughly after handling Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. If skin irritation occurs: Get medical advice/attention. Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. Take off contaminated clothing and wash before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
4047608
Hazard Class
4.3
Packing Group
II
Harmonized Tariff Code
2915.29
TSCA
Yes

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