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Merck
CN

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

Key Documents

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Product Name

Borane tetrahydrofuran complex solution, 1.0 M in THF

InChI

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

SMILES string

B.C1CCOC1

InChI key

RMCYTHFAWCWRFA-UHFFFAOYSA-N

contains

<0.005 M sodium borohydride as stabilizer

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

Quality Level

200

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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.

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.

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

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

supp_hazards

EUH019

Storage Class

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

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
SHBS7627
SHBS7625
SHBS7626
SHBS7628
SHBS7624

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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)
Polymer, 47, 4916-4916 (2006)
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)
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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