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CAS RN: | Product Number: R0273

Reagents for Metallophotoredox Cross-Coupling Reactions [NiBr2(dme), [Ir[dF(CF3)ppy]2(dtbbpy)]PF6, DABCO] (HPMC encapsulated)

× Reagents for Metallophotoredox Cross-Coupling Reactions [NiBr2(dme), [Ir[dF(CF3)ppy]2(dtbbpy)]PF6, DABCO] (HPMC encapsulated)

Purity:
Synonyms:
  • NiBr2(dme) ca. 0.03 mmol/capsule, [Ir[dF(CF3)ppy]2(dtbbpy)]PF6 ca. 0.12 μmol/capsule, DABCO ca. 1.1 mmol/capsule (HPMC encapsulated)
Product Documents:
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Supplemental Product Information

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Supplemental Product Information:

Contents (per one capsule)

  • NiBr2(dme) : ca. 0.03 mmol
  • [Ir[dF(CF3)ppy]2(dtbbpy)]PF6 : ca. 0.12 μmol
  • DABCO : ca. 1.1 mmol

Directions for Use

  • Each capsule contains all reagents for a single use on 0.60 mmol scale metallophotoredox C-N coupling reaction. Typical condition: 0.60 mmol of aryl bromide and 1.5 equiv of amine in DMAc (0.1 M) at 60 °C with blue LEDs.
    (Reference: J. Org. Chem. 2021, 86, 1357.)

Related Products

  • N1298 NiBr2(dme)
  • D5817 [Ir[dF(CF3)ppy]2(dtbbpy)]PF6
  • D0134 DABCO

Product Number R0273
Physical State (20 deg.C) Solid
Storage Temperature Refrigerated (0-10°C)
Store Under Inert Gas Store under inert gas
Condition to Avoid Air Sensitive
Specifications
Appearance White to Almost white capsule
Functionality test (conversion ratio) min. 90.0 %
Properties (reference)
GHS
Pictogram Pictogram Pictogram Pictogram Pictogram
Signal Word Danger
Hazard Statements H302 : Harmful if swallowed.
H315 : Causes skin irritation.
H318 : Causes serious eye damage.
H372 : Causes damage to organs through prolonged or repeated exposure.
H317 : May cause an allergic skin reaction.
H334 : May cause allergy or asthma symptoms or breathing difficulties if inhaled.
H350 : May cause cancer.
H412 : Harmful to aquatic life with long lasting effects.
H228 : Flammable solid.
Precautionary Statements P501 : Dispose of contents/ container to an approved waste disposal plant.
P273 : Avoid release to the environment.
P260 : Do not breathe dust/ fume/ gas/ mist/ vapors/ spray.
P270 : Do not eat, drink or smoke when using this product.
P202 : Do not handle until all safety precautions have been read and understood.
P240 : Ground/bond container and receiving equipment.
P285 : In case of inadequate ventilation wear respiratory protection.
P210 : Keep away from heat/sparks/open flames/hot surfaces. No smoking.
P201 : Obtain special instructions before use.
P241 : Use explosion-proof electrical/ ventilating/ lighting/ equipment.
P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection.
P272 : Contaminated work clothing must not be allowed out of the workplace.
P370 + P378 : In case of fire: Use dry sand, dry chemical or alcohol-resistant foam to extinguish.
P308 + P313 : IF exposed or concerned: Get medical advice/ attention.
P302 + P352 : IF ON SKIN: Wash with plenty of soap and water.
P333 + P313 : If skin irritation or rash occurs: Get medical advice/ attention.
P362 : Take off contaminated clothing and wash before reuse.
P301 + P312 + P330 : IF SWALLOWED: Call a POISON CENTER/doctor if you feel unwell. Rinse mouth.
P305 + P351 + P338 + P310 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER/doctor.
P304 + P341: IF INHALED: If breathing is difficult, remove person to fresh air and keep comfortable for breathing.
P405 : Store locked up.
Related Laws:
Transport Information:
UN Number (DOT-AIR) UN1325
Class (DOT-AIR) 4.1
Packing Group (TCI-A) II
HS Number 3822.19.0080
Application
TCI Practical Example: The Metallophotoredox Reaction Using a Capsule Reagent

The Metallophotoredox Reaction Using a Capsule Reagent

Used Chemicals

Procedure

Reagents for metallophotoredox cross-coupling reactions (HPMC encapsulated) (one capsule) was added to a solution of 5-bromopyrimidine (95 mg, 0.60 mmol) and morpholine (78 μL, 0.90 mmol, 1.5 eq.) in DMAc (6 mL) at r.t. The solution was placed at a distance of 3-5 cm from Blue LED lamp and stirred for 24 hours at 60 °C. The reaction mixture was then filtered through Celite. The filtrate was diluted with sat. Na2SO4 aq. (15 mL) and extracted with ethyl acetate (15 mL x 5). The organic layer was dried over sodium sulfate, concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (dichloromethane:methanol = 10:1) to afford 4-(pyrimidin-5-yl)morpholine (84 mg, 85% yield) as a pale brown solid.

Experimenter’s Comments

The reaction mixture was monitored by GC.
Irradiation of visible light was performed with Kessil A160WE Tuna Blue 40W x 2.
DMAc was degassed with nitrogen for 30 minutes before use.
The shape of the capsule is like below image and each capsule includes NiBr2(dme) (ca. 0.03 mmol), [Ir[dF(CF3)ppy]2(dtbbpy)]PF6 (ca. 0.12 μmol), and DABCO (ca. 1.1 mmol).
The material of the capsule is water-soluble HPMC (hydroxypropyl methylcellulose).

Capsule

Analytical Data

4-(Pyrimidin-5-yl)morpholine

1H NMR (400 MHz, CDCl3); δ 8.74 (s, 1H), 8.37 (s, 2H), 3.91-3.88 (m, 4H), 3.25-3.22 (m, 4H).

Lead Reference

Other Reference


Documents

Product Articles
[Featured Products] HPMC Encapsulated Reagents
[TCI Practical Example] The Metallophotoredox Reaction Using a Capsule Reagent
Product Documents (Note: Some products will not have analytical charts available.)
Safety Data Sheet (SDS)
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Specifications
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