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14044-65-6 - Borane-tetrahydrofuran complex, 1M soln. in THF, stab. with 5mmol NaBH4 - BTHF - L13961 - Alfa Aesar

L13961 Borane-tetrahydrofuran complex, 1M soln. in THF, stab. with 5mmol NaBH4

CAS Number
14044-65-6
Synonyms
BTHF

Size Price ($) Quantity Availability
25ml 26.10
100ml 53.50
500ml 208.00
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Borane-tetrahydrofuran complex, 1M soln. in THF, stab. with 5mmol NaBH4

MDL
MFCD00012429
EINECS
237-881-8

Chemical Properties

Formula
C4H11BO
Formula Weight
85.94
Flash Point
-21°(-8°F)
Density
0.878
Sensitivity
Air & Moisture Sensitive
Solubility
Miscible and reacts violently with water.

Applications

Borane-tetrahydrofuran complex is an important reagent used in the reduction of certain functional groups viz. aldehyde, ketone, carboxylic acid, amide, oxime, imine and nitrile. It is also used as hydro borating agent. It acts as a borane source for oxazaborolidine catalyzed asymmetric reductions. It is utilized to reduce nylon surface amide groups to secondary amines.

Notes

Air and moisture sensitive. Forms explosive peroxides in contact with air. Incompatible with acids, acid chlorides, acid anhydrides, oxidizing agents and alcohols. On hydrolysis, it forms hydrogen and boric acid.

Literature References

Examples of hydroboration reactions:

Hydroboration, followed by reaction of the trialkylborane with a diazoketone to give a homologated ketone: Org. Synth. Coll., 6, 919 (1988). In situ generation of "disiamyl" borane from 2-methyl-2-butene, and use of this reagent in selective hydroboration reactions: Org. Synth. Coll., 7, 258 (1990). Preparation of di-3-pinanylborane from (-)-ɑ-pinene, and its use in asymmetric hydroborations, see: Org. Synth. Coll., 7, 339 (1990).

For use in the reduction of carboxylic acids to alcohols, see: Org. Synth. Coll., 7, 221 (1990).

For other reactions of borane, see Borane-dimethyl­ sulfide complex, L07705.

Wang, X.; Xie, L.; Huang, K. W.; Lai, Z. A rationally designed amino-borane complex in a metal organic framework: a novel reusable hydrogen storage and size-selective reduction material. Chem. Commun. 2015, 51 (36), 7610-7613.

Zhou, Y.; Yen, C. H.; Fu, S.; Yang, G.; Zhu, C.; Du, D.; Wo, P. C.; Cheng, X.; Yang, J.; Wai, C. M.; Lin, Y. One-pot synthesis of B-doped three-dimensional reduced graphene oxide via supercritical fluid for oxygen reduction reaction. Green Chem. 2015, 17 (6), 3552-3560.

GHS Hazard and Precautionary Statements

Hazard Statements: H225-H260-H302-H333-H315-H318-H351-H335

Highly flammable liquid and vapour. In contact with water releases flammable gases which may ignite spontaneously. Harmful if swallowed. May be harmful if inhaled. Causes skin irritation. Causes serious eye damage. Suspected of causing cancer. May cause respiratory irritation.

Precautionary Statements: P223-P210-P303+P361+P353-P305+P351+P338-P405-P501a

Keep away from any possible contact with water, because of violent reaction and possible flash fire. Keep away from heat/sparks/open flames/hot surfaces. - No smoking. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
3668402
Hazard Class
4.3
Packing Group
I
Harmonized Tariff Code
2942.00
TSCA
Yes

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