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CAS RN: 927384-44-9 | Product Number: B3655

2-(4-Bromophenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborine


Purity: >98.0%(GC)(N)
Synonyms:
  • 4-Bromo-1-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)benzene
  • 2-(4-Bromophenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine
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Product Number B3655
Purity / Analysis Method >98.0%(GC)(N)
Molecular Formula / Molecular Weight C__1__6H__1__2BBrN__2 = 323.00 
Physical State (20 deg.C) Solid
Storage Temperature Refrigerated (0-10°C)
Store Under Inert Gas Store under inert gas
Condition to Avoid Light Sensitive,Air Sensitive,Heat Sensitive
CAS RN 927384-44-9
Reaxys Registry Number 10686860
PubChem Substance ID 125307608
MDL Number

MFCD16038141

Specifications
Appearance White to Orange to Green powder to crystal
Purity(GC) min. 98.0 %
Purity(with Total Nitrogen) min. 98.0 %
Properties (reference)
GHS
Related Laws:
Transport Information:
HS Number 2934999090
Application
TCI Practical Example: Suzuki-Miyaura Coupling of Diaminonaphthalene (dan)-Protected Bromophenylboronic Acid

Suzuki-Miyaura Coupling of Diaminonaphthalene (dan)-Protected Bromophenylboronic Acid

Used Chemicals

Procedure

To a reaction vessel, 2-(4-bromophenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborine (3.0 g, 9.3 mmol), 4-(ethoxycarbonyl)phenylboronic acid (2.7 g, 4.0 mmol), Pd(PPh3)4 (0.54 g, 0.47 mmol), potassium carbonate (3.9 g, 28.0 mmol), toluene (30 mL), ion-exchange water (15 mL) were subsequently added and heated at 90 °C. After the consumption of the starting material, the reaction mixture was cooled to room temperature. Dichloromethane was added and aqueous layer was removed. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated to obtain crude product. The crude was dissolved in dichloromethane and passed through a pad of silica gel and concentrated. The residue was washed with hexane to give 1 (2.5 g, yield. 69%) as a pale yellow powder.

Experimenter’s Comments

The reaction mixture was monitored by TLC (hexane:ethyl acetate = 4:1, Rf = 0.5).

Analytical Data

1H NMR (400 MHz, CDCl3); δ 8.17-8.10 (m, 2H), 7.80-7.65 (m, 6H), 7.16 (dd, 2H, J = 7.3, 8.2 Hz), 7.8 (dd, 2H, J = 7.3, 8.2 Hz), 6.45 (dd, 2H, J = 0.8, 7.3 Hz), 6.08 (brs, 2H), 4.42 (q, 2H, J = 7.2 Hz), 1.43 (t, 3H, J = 7.2 Hz).

Lead Reference

Other Reference


PubMed Literature


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