CAS RN: 18107-18-1 | Product Number: T1146
Trimethylsilyldiazomethane (ca. 10% in Hexane, ca. 0.6mol/L)
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|Molecular Formula / Molecular Weight||C__4H__1__0N__2Si = 114.22|
|Physical State (20 deg.C)||Liquid|
|Store Under Inert Gas||Store under inert gas|
|Condition to Avoid||Light Sensitive,Moisture Sensitive,Heat Sensitive|
|Reaxys Registry Number||956593|
|PubChem Substance ID||87576934|
|Appearance||Light yellow to Yellow clear liquid|
|Concentration(Neutralization titration)||10.0 to 11.0 w/w%|
|High boiling impurities||to pass test|
|Hazard Statements||H314 : Causes severe skin burns and eye damage.
H372 : Causes damage to organs through prolonged or repeated exposure.
H335 : May cause respiratory irritation.
H361f : Suspected of damaging fertility.
H336 : May cause drowsiness or dizziness.
H304 : May be fatal if swallowed and enters airways.
H411 : Toxic to aquatic life with long lasting effects.
H225 : Highly flammable liquid and vapour.
|Precautionary Statements||P273 : Avoid release to the environment.
P260 : Do not breathe dust/ fume/ gas/ mist/ vapours/ spray.
P210 : Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.
P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection.
P370 + P378 : In case of fire: Use dry sand, dry chemical or alcohol-resistant foam to extinguish.
P391 : Collect spillage.
P303 + P361 + P353 : IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water.
P301 + P310 : IF SWALLOWED: Immediately call a POISON CENTER/doctor.
P301 + P330 + P331 : IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P304 + P340 + P310 : IF INHALED: Remove person to fresh air and keep comfortable for breathing. Immediately call a POISON CENTER/doctor.
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.
|Class||3 / 8|
- Boc-D-Ser(Bzl)-OH [B1863]
- Trimethylsilyldiazomethane (ca. 10% in Hexane, ca. 0.6mol/L) [T1146]
- Diethyl ether
To a stirred solution of Boc-D-Ser(Bzl)-OH (596 mg, 2.02 mmol) in Et2O/MeOH (7:2, 18 mL) was added TMS-diazomethane (0.6 mol/L hexane solution, 4.0 mL, 2.4 mmol) dropwise for 5 min at 0 °C and the mixture was stirred at the same temperature. After 2 h, TMS-diazomethane (0.4 mL, 0.24 mmol) was added and stirred for further 3 h. The reaction mixture was allowed to warm to room temperature and concentrated in vacuo to give Boc-D-Ser(Bzl)-OMe (625 mg, 100%) as a pale brown oil.
The reaction mixture was monitored by TLC (ethyl acetate:hexane = 3:1, Rf = 0.52).
Nitrogen gas evolution was observed when TMS-diazomethane was added dropwise.
1H NMR (400 MHz, CDCl3); δ 7.36-7.26 (m, 5H), 5.40 (brd, J = 8.8 Hz, 1 H), 4.55 (d, J = 12.0 Hz, 1H), 4.48 (d, J = 12.0 Hz, 1H), 4.42 (td, J = 3.4, 9.2 Hz, 1H), 3.87 (dd, J = 3.2, 9.6 Hz, 1H), 3.74 (s, 3H), 3.68 (dd, J = 3.2, 9.2 Hz, 1H), 1.45 (s, 9H).
13C NMR (101 MHz, CDCl3); δ 171.13, 155.43, 137.49, 128.35 (2C), 127.76, 127.52 (2C), 79.92, 73.14, 69.88, 53.91, 52.39, 28.25 (3C).
- New Methods and Reagents in Organic Synthesis. 14. A Simple Efficient Preparation of Methyl Esters with Trimethylsilyldiazomethane (TMSCHN2) and Its Application to Gas Chromatographic Analysis of Fatty Acids
- N. Hashimoto, T. Aoyama, T. Shioiri, Chem. Pharm. Bull. 1981, 29, 1475.
- A. Presser, A. Hufner, Monatsh. Chem. 2004, 135, 1015.
- 1)Total Synthesis of Norzoanthamine
- 2)Synthetic Studies of the Zoanthamine Alkaloids: The Total Syntheses of Norzoanthamine and Zoanthamine
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