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176192

Borane tetrahydrofuran complex solution

1.0 M in THF

Synonym(s):

Borane-THF (1:1), Boron hydride (BH3)-THF (1:1), Tetrahydrofuran-trihydroborane complex, Trihydrido(tetrahydrofuran)boron

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About This Item

Linear Formula:
BH3OC4H8
CAS Number:
14044-65-6
Molecular Weight:
85.94
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
24850560
MDL number:
MFCD00012429
Beilstein/REAXYS Number:
3668402
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contains

<0.005 M sodium borohydride as stabilizer

Quality Segment

200

reaction suitability

reagent type: reductant

concentration

1.0 M in THF

density

0.898 g/mL at 25 °C

functional group

ether

storage temp.

2-8°C

SMILES string

B.C1CCOC1

InChI

1S/C4H8O.BH3/c1-2-4-5-3-1;/h1-4H2;1H3

InChI key

RMCYTHFAWCWRFA-UHFFFAOYSA-N

General description

Borane tetrahydrofuran complex (BH3-THF) is widely used as a reducing agent in organic synthesis. It is also used as a reagent in hydroboration reactions.

Application

BH3-THF can be used as a reducing agent for the reduction of various functional groups such as carboxylic acids, aldehydes, ketones, esters, acid chlorides, nitriles, epoxides, amides, lactones, oximes, and imines into corresponding alcohols and amines. Grignard reagents, arylmercury, arylthalium, and allyl and propargyllithium compounds react with BH3−THF to give organoboranes, which can be oxidized to the corresponding alcohols, phenols, and 1,3-diols.
It can also be used:
  • To synthesize the chiral borane catalyst, which is used in the enantioselective halo-aldol reaction.
  • To prepare 9-unsubstituted acridines by reduction of corresponding acridones.
  • To reduce nylon surface amide groups to secondary amines.

New, Safer, NIMBA-Stabilized BH3 THF Solutions

Packaging

The 25 mL Sure/Seal™ bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.

Legal Information

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

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Danger

target_organs

Central nervous system, Respiratory system

supp_hazards

EUH019

Storage Class

4.3 - Hazardous materials which set free flammable gases upon contact with water

flash_point_f

1.4 °F - closed cup

flash_point_c

-17 °C - closed cup

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - STOT SE 3 - Water-react. 1

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