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CAS RN: 1660-93-1 | Product Number: T0847
3,4,7,8-Tetramethyl-1,10-phenanthroline
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Purity: >98.0%(T)(HPLC)
Synonyms:
Product Documents:
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| Product Number | T0847 |
| Purity / Analysis Method | >98.0%(T)(HPLC) |
| Molecular Formula / Molecular Weight | C__1__6H__1__6N__2 = 236.32 |
| Physical State (20 deg.C) | Solid |
| Storage Temperature | Room Temperature (Recommended in a cool and dark place, <15°C) |
| Store Under Inert Gas | Store under inert gas |
| Condition to Avoid | Light Sensitive,Air Sensitive |
| Packaging and Container | 1G-Glass Bottle with Plastic Insert (View image) |
| CAS RN | 1660-93-1 |
| Reaxys Registry Number | 171279 |
| PubChem Substance ID | 87576680 |
| SDBS (AIST Spectral DB) | 8013 |
| MDL Number | MFCD00004974 |
Specifications
| Appearance | White to Light yellow powder to crystal |
| Purity(HPLC) | min. 98.0 area% |
| Purity(Nonaqueous Titration) | min. 98.0 % |
| Solubility in hot Methanol | almost transparency |
| NMR | confirm to structure |
Properties (reference)
GHS
Related Laws:
Transport Information:
| H.S.code* | 2933.99-000 |
Application
TCI Practical Example: Nickel(II)-Catalyzed One Pot Synthesis of Sulfones from Aryl Boronic Acid and DABSO
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Used Chemicals
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- 4-Biphenylboronic Acid (contains varying amounts of Anhydride) [B2294]
- Nickel(II) Bromide Ethylene Glycol Dimethyl Ether Complex (=NiBr2(glyme)) [N1050]
- 3,4,7,8-Tetramethyl-1,10-phenanthroline (= tmphen) [T0847]
- Bis(sulfur Dioxide)-1,4-diazabicyclo[2.2.2]octane Adduct (= DABSO) [B3960]
- Lithium tert-Butoxide (= LiOtBu)
- tert-Butyl Bromoacetate [B1473]
- 1,3-Dimethyl-2-imidazolidinone (= DMI) [D1477]
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Procedure
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Under nitrogen atmosphere, a degassed DMI (20 mL) solution of 4-biphenylboronic acid (792 mg, 4.00 mmol), DABSO (577 mg, 2.40 mmol), tmphen (95 mg, 0.40 mmol), lithium tert-butoxide (320 mg, 4.00 mmol) and NiBr2(glyme) (123 mg, 0.40 mmol) was stirred at 100 °C for 14 hours. The mixture was cooled to room temperature and tert-butyl bromoacetate (1.17 mL, 8.00 mmol) was added and the reaction mixture stirred for 1 hour. Water (20 mL) was poured into the reaction mixture and the mixture was extracted with diethyl ether (50 mL x 3). The combined organic phase was washed with water (50 mL) and brine (40 mL), dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by medium pressure preparative chromatography (ethyl acetate:hexane = 5:95 - 15:85 on silica gel) to give compound 1 as a white solid (1.01 g, 76%).
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Experimenter’s Comments
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NiBr2(glyme) and LiOtBu were weighed into a sample tube in a glove box because these reagents are moisture sensitive. If these were used in air, it should be weighted quickly and used up the reagents as soon as possible after opening.
Since the ligand of NiBr2(glyme) may be desorbed under reduced pressure, depressurization operations is desirable to be finished as soon as possible.
The reaction mixture was monitored by TLC (ethyl acetate:hexane = 2:1, Rf = 0.38) and UPLC-MS.
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Analytical Data
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Compound 1
1H NMR (400 MHz, CDCl3); δ 8.00 (d, 2H, J = 8.9 Hz), 7.78 (m, 2H), 7.58–7.66 (m, 2H), 7.42-7.54 (m, 3H), 4.08 (s, 2H), 1.58 (s, 2H), 1.39 (s, 9H).
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Lead Reference
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- Nickel(II)-Catalyzed Synthesis of Sulfinates from Aryl and Heteroaryl Boronic Acids and the Sulfur Dioxide Surrogate DABSO
PubMed Literature
Articles/Brochures
TCIMAIL
[Research Articles] Ruthenium Complex Acting as a Light Switch for DNA Mismatches[Research Articles] Catalytic Decarboxylative Cross-Coupling of Aryl Chlorides and Benzoates
[Research Articles] Catalytic Functionalization of Un-activated Primary C-H Bonds
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Safety Data Sheet (SDS)
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Specifications
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