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CAS RN: 18107-18-1 | Product Number: T1146

Trimethylsilyldiazomethane (ca. 10% in Hexane, ca. 0.6mol/L)


Purity:
Synonyms:
  • TMS-Diazomethane (ca. 10% in Hexane, ca. 0.6mol/L)
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Product Number T1146
Molecular Formula / Molecular Weight C__4H__1__0N__2Si = 114.22 
Physical State (20 deg.C) Liquid
Storage Temperature 0-10°C
Store Under Inert Gas Store under inert gas
Condition to Avoid Light Sensitive,Moisture Sensitive,Heat Sensitive
CAS RN 18107-18-1
Reaxys Registry Number 956593
PubChem Substance ID 87576934
MDL Number

MFCD00053946

Specifications
Appearance Light yellow to Yellow clear liquid
Concentration(Neutralization titration) 10.0 to 11.0 w/w%
High boiling impurities to pass test
Properties (reference)
GHS
Pictogram Pictogram Pictogram Pictogram Pictogram Pictogram
Signal Word Danger
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.
Related Laws:
Transport Information:
UN Number UN2924
Class 3 / 8
Packing Group II
HS Number 2931900090
Application
TCI Practical Example: Methyl Esterification of Carboxylic Acid Using TMS Diazomethane

TCI反応実例:TMSジアゾメタンを用いたカルボン酸のメチルエステル化

Used Chemicals

Procedure

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.

Experimenter’s Comments

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.

Analytical Data

Boc-D-Ser(Bzl)-OMe

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).

Other References


Application
Safe Methyl Esterification Reagent

Typical Procedure: To a solution of fatty acid (0.10 mmol) in 20% methanolic benzene (1 mL) is added trimethylsilyldiazomethane (ca. 10% in hexane) (0.5 mL) and stirred. The mixture is left for 30 min at room temperature and used for a GC sample.

References


Application
An Application for the Synthesis of Natural Product

References


PubMed Literature


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