Published TCIMAIL newest issue No.199
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CAS RN: 157141-27-0 | Product Number: C1500
Cyanomethylenetributylphosphorane
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Purity: >97.0%(T)
Synonyms:
- Tsunoda Reagent
Product Documents:
| Size | Unit Price | Belgium | Japan* | Quantity |
|---|---|---|---|---|
| 1G |
€90.00
|
Contact Us | ≥100 |
|
| 5G |
€287.00
|
Contact Us | ≥100 |
|
| 25G |
€919.00
|
Contact Us | ≥80 |
|
*Stock available in Belgium will be delivered in 1 to 3 days
*Stock available in Japan will be delivered in 1 to 2 weeks (excludes regulated items and dry ice shipments).
| Product Number | C1500 |
Purity / Analysis Method 
|
>97.0%(T) |
| Molecular Formula / Molecular Weight | C__1__4H__2__8NP = 241.36 |
| Physical State (20 deg.C) | Liquid |
| Storage Temperature
|
Refrigerated (0-10°C) |
| Store Under Inert Gas | Store under inert gas |
| Condition to Avoid | Air Sensitive,Moisture Sensitive,Heat Sensitive |
| CAS RN | 157141-27-0 |
| Reaxys Registry Number | 6919233 |
| PubChem Substance ID | 87566497 |
| MDL Number | MFCD01321151 |
Specifications
| Appearance | Yellow to Amber to Dark purple clear liquid |
| Purity(Nonaqueous Titration) | min. 97.0 % |
Properties (reference)
| Specific Gravity (20/20) | 0.92 |
| Refractive Index | 1.50 |
GHS
| 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:
Transport Information:
| HS Number | 2931498090 |
Application
TCI Practical Example: Mitsunobu Reaction Using Tsunoda Reagent
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Used Chemicals
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Procedure
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To a solution of 3,4-dihydro-7-hydroxy-2(1H)-quinolinone (500 mg, 3.06 mmol), 4-(2-hydroxyethyl)morpholine (0.45 mL, 3.7 mmol, 1.2 eq.) in toluene (15 mL) was added Tsunoda reagent (1.0 mL, 3.8 mmol, 1.25 eq.) at r.t. and the mixture was stirred at 100 °C for 3 hours. The solvent was removed under reduced pressure and the residue was purified by column chromatography (dichloromethane:methanol = 1:0 - 10:1 on silica gel) to give 1 as a white solid (790 mg, 93%).
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Experimenter’s Comments
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The reaction mixture was monitored by UPLC.
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Analytical Data
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Compound 1
1H NMR (270 MHz, DMSO-d6); δ 9.97 (s, 1H), 7.41 (d, 1H, J = 7.8 Hz), 6.49 (d, 1H, J = 8.1 Hz), 6.43 (d, 1H, J = 1.9 Hz), 4.00 (t, 2H, J = 5.7 Hz), 3.59-3.55 (m, 4H), 2.78 (t, 2H, J = 7.3 Hz), 2.65 (t, 2H, J = 5.7 Hz), 2.46-2.33 (m, 6H).
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Lead Reference
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- Acetylcholinesterase Inhibition of Diversely Functionalized Quinolinones for Alzheimer’s Disease Therapy
Application
New Mitsunobu Reaction (Tsunoda Reagent)
References
- Carbon-carbon bond formation with new Mitsunobu reagents
- Formation of heterocycles by the Mitsunobu reaction. Stereoselective synthesis of (+)-α-skytanthine
PubMed Literature
Documents
Product Articles
[TCIMAIL No.156] Mitsunobu Reaction Using Acetone Cyanohydrin[TCI Practical Example] Mitsunobu Reaction Using Tsunoda 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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