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Sigma-Aldrich

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
Beilstein:
3668402
MDL number:
MFCD00012429
UNSPSC Code:
12352005
PubChem Substance ID:
24850560
NACRES:
NA.22

contains

<0.005 M sodium borohydride as stabilizer

Quality Level

200

reaction suitability

reagent type: reductant

concentration

1.0 M in THF

density

0.898 g/mL at 25 °C

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

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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

New, Safer, NIMBA-Stabilized BH3 THF Solutions
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.

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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Signal Word

Danger

Hazard Classifications

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

Target Organs

Central nervous system, Respiratory system

Supplementary Hazards

EUH019

Storage Class Code

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

WGK

WGK 2

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °C - closed cup

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Borane-Tetrahydrofuran
Zaidlewicz M, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2001)
Simple and convenient conversion of acridones into 9-unsubstituted acridines via acridanes using borane tetrahydrofuran complex
Desbois N, et al.
Tetrahedron Letters, 50(49), 6894-6896 (2009)
Nylon surface modification. Part 1. Targeting the amide groups for selective introduction of reactive functionalities
Jia X, et al.
Polymer, 47(14), 4916-4924 (2006)
Polymer, 47, 4916-4916 (2006)
Jung Seok Lee et al.
Macromolecular bioscience, 15(9), 1314-1322 (2015-06-04)
We designed poly(β-amino esters) (PBAEs) bearing both UV light- and pH-sensitive groups and used PBAEs to prepare nanoparticles (NPs) that can be utilized for on-demand burst release of guest molecules in response to multiple triggers. Due to the presence of

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