176192

Sigma-Aldrich

Borane tetrahydrofuran complex solution

1.0 M in THF

Linear Formula:
BH3OC4H8
CAS Number:
Molecular Weight:
85.94
Beilstein/REAXYS Number:
3668402
MDL number:
PubChem Substance ID:
NACRES:
NA.22

contains

<0.005 M sodium borohydride as stabilizer

Quality Level

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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.

Packaging

4×25, 100, 800 mL in Sure/Seal™
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

Signal Word

Danger

Target Organs

Respiratory system

Supp Hazards

EUH018 - EUH019

RIDADR

UN 3399A 4.3(3) / PGI

WGK Germany

WGK 3

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °C - closed cup

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...

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service

Social Media

LinkedIn icon
Twitter icon
Facebook Icon
Instagram Icon

MilliporeSigma

Research. Development. Production.

We are a leading supplier to the global Life Science industry with solutions and services for research, biotechnology development and production, and pharmaceutical drug therapy development and production.

© 2021 Merck KGaA, Darmstadt, Germany and/or its affiliates. All Rights Reserved.

Reproduction of any materials from the site is strictly forbidden without permission.