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654213

Sigma-Aldrich

2-Methylpyridine borane complex

95%

Synonym(s):

2-Picoline borane complex

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About This Item

CAS Number:
3999-38-0
MDL number:
MFCD11042668
UNSPSC Code:
12352005
PubChem Substance ID:
24884021
NACRES:
NA.22

Assay

95%

form

solid

reaction suitability

reagent type: reductant

storage temp.

2-8°C

SMILES string

CC1=NC=CC=C1.B

InChI

1S/C6H7N.B/c1-6-4-2-3-5-7-6;/h2-5H,1H3;

InChI key

QHXLIQMGIGEHJP-UHFFFAOYSA-N

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General description

2-Methylpyridine borane complex is a nontoxic alternate to the reducing agent sodium cyanoborohydride.

Application

2-Methylpyridine borane complex solution (2-Picoline borane complex) was used as reducing agent for the labeling of oligosaccharides by reductive amination. It may be used in the following studies:
  • Synthesis of alkoxyamine derivatives, via reduction of oxime ethers.
  • Reductive amination reactions of C1-C10 aldehyde 2,4-dinitrophenylhydrazones.
  • Synthesis of various trifluoromethylated amino compounds.
  • An alternative reagent for reductive aminations.
Environmentally benign reducing agent

Reactant for:
Reductive amination
N-Benzyl-protection of amino acid derivatives by reductive alkylation
Reductive alkoxyamination

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H261,H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3 - Water-react 2

Target Organs

Respiratory system

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

212.0 °F - closed cup

Flash Point(C)

100 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Sato, S. et al
Tetrahedron, 60, 7899-7899 (2004)
Shigehisa Uchiyama et al.
Analytical chemistry, 81(1), 485-489 (2008-12-06)
A new method for the determination of carbonyls in air using 2,4-dinitrophenylhydrazine (DNPH) has been developed. The traditional method for the measurement of carbonyl compounds, using DNPH to form the corresponding 2,4-dinitrophenylhydrazone (DNPhydrazone) derivatives, is subject to analytical errors because
Trifluoroacetaldehyde: A useful industrial bulk material for the synthesis of trifluoromethylated amino compounds.
Mimura H, et al.
Journal of Fluorine Chemistry, 131(4), 477-486 (2010)
Maaike M Appeldoorn et al.
Carbohydrate research, 381, 33-42 (2013-09-24)
In order to use corn fiber as a source for bioethanol production the enzymatic hydrolysis of the complex glucuronoarabinoxylans present has to be improved. Several oligosaccharides present in the supernatant of mild acid pretreated and enzymatically saccharified corn fiber that
One-pot synthesis of alkoxyamine derivatives by reductive alkoxyamination with a 2-picoline-borane complex.
Kawase Y , et al.
Heterocycles, 78(2), 463-470 (2009)
View All Related Papers

Articles

Reductive amination with 2-picoline-borane complex

2-picoline-borane (pic-BH3) is an excellent alternative reagent for reductive aminations.

Asymmetric Catalysis with Chiral Oxazaborolidinium Ions (COBIs)

Learn about the applications of chiral oxazaborolidinium ions (COBIs) as Lewis acid catalysts in different asymmetric reactions such as cyclopropanation, epoxidation, and radical reactions along with details of their catalytic action.

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