N,O-Bis(trimethylsilyl)acetamide
Synonym(s):BSA;N,O-Bis(trimethylsilyl)acetamide
- CAS NO.:10416-59-8
- Empirical Formula: C8H21NOSi2
- Molecular Weight: 203.43
- MDL number: MFCD00008270
- EINECS: 233-892-7
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-10-30 18:52:02
What is N,O-Bis(trimethylsilyl)acetamide?
Physical properties
bp 71–73°C/35 mmHg.
The Uses of N,O-Bis(trimethylsilyl)acetamide
N,O-Bis(trimethylsilyl)acetamide is a powerful silylating agent; reacts with a wide range of functional
groups.
BSA was used to
trimethylsilylate the hydroxyl group of 12 selectively to form
in almost quantitative yield (eq 32).The presence of catalytic
amounts (~0.02 equiv) of tetrabutylammonium fluoride (TBAF)
significantly promoted the silylation of alcohols under mild conditions
with high chemoselectivity, i.e., TBAF plays a role as a
smooth silyl transfer catalyst from nitrogen to the hydroxyl group.
The Uses of N,O-Bis(trimethylsilyl)acetamide
Powerful silylation reagent for a wide range of functional groups under mild conditions
The Uses of N,O-Bis(trimethylsilyl)acetamide
N,O-bis(trimethylsilyl)-acetamide (BSA) is frequently used with TMCS as a catalyst to modify a variety of functional groups including carboxyl groups. In one novel application, BSA was used to measure carboxypeptidase activity by forming derivatives which could be determined by gas chromatography.BSA has been used to prepare derivatives of steroids and glucocorticoids.
Preparation
made by the reaction of acetamide with a large excess of chlorotrimethylsilane in the presence of triethylamine.
General Description
N,O-Bis(trimethylsilyl)acetamide is an excellent silylation reagent. For some sterically hindered primary or secondary nitro compounds, N,O-bis(trimethylsilyl)acetamide and BSTFA achieve better results than normal silylation conditions.
Purification Methods
Fractionate it through a spinning band column and collect liquid b 71-73o/35mm, and not higher because the main impurity MeCONHSiMe3 distils at b 105-107o/35mm. It is used for derivatising alcohols and sugars [Klebe et al. J Am Chem Soc 88 3390 1966, see Matsuo et al. Carbohydr Res 241 209 1993, Johnson Carbohydr Res 237 313 1992]. Itis FLAMMABLE and TOXIC.
Properties of N,O-Bis(trimethylsilyl)acetamide
Melting point: | 24 °C |
Boiling point: | 71-73 °C35 mm Hg(lit.) |
Density | 0.832 g/mL at 20 °C(lit.) |
vapor pressure | 10 hPa (50 °C) |
refractive index | n |
Flash point: | 53 °F |
storage temp. | Store below +30°C. |
solubility | Miscible with many nonpolar and polar aprotic solvents. |
form | Crystalline Powder, Crystals and/or Chunks |
pka | 5.82±0.50(Predicted) |
Specific Gravity | 0.832 |
color | Light yellow or beige to brown |
Hydrolytic Sensitivity | 7: reacts slowly with moisture/water |
Sensitive | Moisture Sensitive |
BRN | 1306669 |
CAS DataBase Reference | 10416-59-8(CAS DataBase Reference) |
NIST Chemistry Reference | Ethanimidic acid, N-(trimethylsilyl)-, trimethylsilyl ester(10416-59-8) |
EPA Substance Registry System | Ethanimidic acid, N-(trimethylsilyl)-, trimethylsilyl ester (10416-59-8) |
Safety information for N,O-Bis(trimethylsilyl)acetamide
Signal word | Danger |
Pictogram(s) |
Flame Flammables GHS02 Corrosion Corrosives GHS05 Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H226:Flammable liquids H302:Acute toxicity,oral H314:Skin corrosion/irritation |
Precautionary Statement Codes |
P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking. P233:Keep container tightly closed. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for N,O-Bis(trimethylsilyl)acetamide
Abamectin manufacturer
JSK Chemicals
Lanya Chem Industries Pvt Ltd
Anand Agencies
ASM Organics
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