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179752

Sigma-Aldrich

Borane pyridine complex

~8 M BH3

Synonym(s):

NSC 10219, NSC 53324, Pyridine borane, Trihydro(pyridine)boron

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About This Item

Empirical Formula (Hill Notation):
C5H8BN
CAS Number:
110-51-0
Molecular Weight:
92.93
MDL number:
MFCD00012435
UNSPSC Code:
12352005
eCl@ss:
39151701
PubChem Substance ID:
24850651
NACRES:
NA.22

form

liquid

Quality Level

200

reaction suitability

reagent type: reductant

concentration

~8 M BH3

refractive index

n20/D 1.532 (lit.)

mp

10-11 °C (lit.)

density

0.92 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

[BH3-][n+]1ccccc1

InChI

1S/C5H8BN/c6-7-4-2-1-3-5-7/h1-5H,6H3

InChI key

LPGWNCNRGQANGC-UHFFFAOYSA-N

Application

Borane pyridine complex is commonly used as a reducing reagent for the reductive amination of aldehydes and ketones. It is the precursor to synthesize carbon-based material, BC4N. Along with iodine, it can be used as a reagent for hydroboration of alkenes and alkynes.
Used for:
  • Investigations of site energy distribution functions from Toth isotherm for adsorption of gases on heterogeneous surfaces
  • Preparation of α−alkyl-β-hydroxy esters
  • Regioselective immobilization of short oligonucleotides to acrylic copolymer gels
  • Preparation of Igs conjugated with viral peptide epitopes
  • Sintering of silicon carbide

Reducing agent for high performance liquid chromatography analysis of oligosaccharides

Modifier in decant oil affecting its carbonization to mesophase pitch

Caution

May darken in storage.

Other Notes

may contain excess pyridine

pictograms

FlameSkull and crossbones
GHS02,GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 3 Dermal - Acute Tox. 3 Oral - Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

69.8 °F

flash_point_c

21 °C

Certificates of Analysis (COA)

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A novel carbon material derived from pyridine-borane.
Riedel, Ralf et al.
Advanced Materials, 3(11), 551-552 (1991)
Reductive aminations of ketones and aldehydes using borane-pyridine.
Pelter, Andrew et al.
Journal of the Chemical Society, 717-720 (1984)
Matthew A Zajac
The Journal of organic chemistry, 73(17), 6899-6901 (2008-08-06)
Efforts to couple 4 with 12 employing base mediation are problematic due to the formation of 6. To circumvent this issue, 12 was converted to the pyridine borane complex (13). Alkylation of 4 with 13 provided 3 after removal of
T Miron et al.
Analytical biochemistry, 440(1), 12-14 (2013-05-28)
In this note, we describe a method devised to detect, by means of mass spectrometry (MS), tryptophan-containing peptides and proteins using pyridine-borane. This reagent selectively reduces tryptophan residues, converting them to 2,3-dihydro-tryptophan, thereby enabling quantitation of tryptophans.
Journal of the Chemical Society. Perkin Transactions 1, 717-717 (1984)
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