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CAS RN: 524-95-8 | Product Number: D0281

2-Aminoethyl Diphenylborinate


Purity: >98.0%(T)(HPLC)
Synonyms:
  • (2-Aminoethoxy)diphenylborane
  • Diphenylborinic Acid 2-Aminoethyl Ester
Documents:
10G
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25G
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Product Number D0281
Purity / Analysis Method >98.0%(T)(HPLC)
Molecular Formula / Molecular Weight C__1__4H__1__6BNO = 225.10 
Physical State (20 deg.C) Solid
Store Under Inert Gas Store under inert gas
Condition to Avoid Light Sensitive,Moisture Sensitive
CAS RN 524-95-8
Reaxys Registry Number 2942273
PubChem Substance ID 87566979
SDBS (AIST Spectral DB) 7335
MDL Number

MFCD00014823

Specifications
Appearance White to Almost white powder to crystal
Purity(HPLC) min. 98.0 area%
Purity(Nonaqueous Titration) min. 98.0 %
Melting point 189.0 to 194.0 °C
Solubility in Methanol almost transparency
Properties (reference)
Melting Point 190 °C
Solubility (soluble in) Methanol
GHS
Pictogram Pictogram
Signal Word Warning
Hazard Statements H302 : Harmful if swallowed.
H315 : Causes skin irritation.
H319 : Causes serious eye irritation.
Precautionary Statements P501 : Dispose of contents/ container to an approved waste disposal plant.
P270 : Do not eat, drink or smoke when using this product.
P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ eye protection/ face protection.
P337 + P313 : If eye irritation persists: Get medical advice/ attention.
P301 + P312 + P330 : IF SWALLOWED: Call a POISON CENTER/doctor if you feel unwell. Rinse mouth.
Related Laws:
EC Number 208-366-5
RTECS# ED6150000
Transport Information:
HS Number 2931900090
Application
TCI Practical Example: The Regioselective Koenigs-Knorr-Type Glycosylation of Carbohydrates Using a Borinic Acid Ester Catalyst

Used Chemicals

Procedure

To a solution of methyl α-L-fucopyranoside (392 mg, 2.2 mmol, 1.1 equiv), silver(I) oxide (463 mg, 2.0 mmol, 1.0 equiv) and 2-aminoethyl diphenylborinate (45 mg, 0.2 mmol, 10 mol%) in acetonitrile (23 mL) was added 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (822 mg, 2.0 mmol, 1 equiv) at r.t. and the mixture was stirred for 4 hours. The reaction mixture was filtered through celite pad and washed with dichloromethane (30 mL). The solvent was removed under reduced pressure and the residue was purified by column chromatography (ethyl acetate:hexane = 0:1 - 3:1 on silica gel), to give 1 as a white amorphous (914 mg, 90%).

Experimenter’s Comments

The reaction mixture was monitored by TLC (ethyl acetate, Rf = 0.51).
The color of the reaction mixture turned from black to gray as the reaction proceeds.

Analytical Data(Compound 1)

1H NMR (400 MHz, CDCl3); δ 5.23 (t, J = 9.5 Hz, 1H), 5.07 (t, J = 9.5 Hz, 1H), 5.04 (dd, J = 9.5, 7.8 Hz, 1H), 4.83 (d, J = 3.8 Hz, 1H), 4.68 (d, J = 7.8 Hz, 1H), 4.25 (dd, J = 12.2, 2.7 Hz, 1H), 4.17 (dd, J = 12.2, 5.1 Hz, 1H), 3.99 (dd, J = 10.0, 3.8 Hz, 1H), 3.95 (brq, J = 6.8 Hz, 1H), 3.83 (dd, J = 10.0, 3.5 Hz, 1H), 3.76 (ddd, J = 10.0, 5.1, 2.7 Hz, 1H), 3.72 (m, 1H), 3.43 (s, 3H), 3.14 (d, J = 3.8 Hz, 1H), 2.27 (brs, 1H), 2.10 (s, 3H), 2.07 (s, 3H), 2.04 (s, 3H), 2.02 (s, 3H), 1.31 (d, J = 6.8 Hz, 3H).

Lead Reference

Other References


Application
Inositol 1,4,5-trisphosphate (IP3) Receptor Antagonist

References


PubMed Literature


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