M-AMINOPHENYLTRIMETHOXYSILANE

M-AMINOPHENYLTRIMETHOXYSILANE Property

Melting point:

60-62°C

Boiling point:

110-114°C 0,6mm

Density 

1,19 g/cm³

Flash point:

180°C

storage temp. 

Refrigerator, Under Inert Atmosphere

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

4.17±0.10(Predicted)

Specific Gravity

1.19

color 

Pale Yellow to Dark Yellow

Hydrolytic Sensitivity

7: reacts slowly with moisture/water

InChI

InChI=1S/C9H15NO3Si/c1-11-14(12-2,13-3)9-6-4-8(10)5-7-9/h4-7H,10H2,1-3H3

InChIKey

CNODSORTHKVDEM-UHFFFAOYSA-N

SMILES

C1(N)=CC=C([Si](OC)(OC)OC)C=C1

Safety

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36/37/39

TSCA 

No

HS Code 

29319090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H312Harmful in contact with skin

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P322Specific measures (see …on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

M-AMINOPHENYLTRIMETHOXYSILANE Chemical Properties,Usage,Production

Chemical Properties

C lear colorless liquid

Uses

Aminophenyltrimethoxysilane is a useful intermediate for the preparation of aromatic silanes as high thermal stability coupling agents.

Synthesis

Tetrahydrofuran (THF, 700 mL) was added to a 2000 mL round-bottomed flask under nitrogen protection, followed by addition of magnesium particles (11.8 g, 485 mmol) and 1,2-dibromoethane (2 drops) to the mixture and stirred at 45 °C. Maintaining the temperature at 45 °C, pre-prepared 4-bromo-N,N-bis(trimethylsilyl)aniline (70 g, 220 mmol) was slowly added to the reaction solution and stirred at reflux for 3 hours. Upon completion of the reaction, the reaction solution was cooled to 0 °C, followed by slow dropwise addition of tetramethyl orthosilicate (32.6 mL, 220 mmol, dissolved in 60 mL THF) solution at room temperature (25 °C). After the dropwise addition was completed, stirring was continued for 30 minutes at room temperature (25 °C). At the end of the reaction, an excess of saturated aqueous ammonium chloride (NH4Cl) solution was slowly added to the reaction mixture and stirred overnight. The reaction mixture was extracted with ethyl acetate (EA), the organic layer was separated, dried over anhydrous magnesium sulfate (MgSO4) and concentrated under reduced pressure. The resulting concentrate was purified by silica gel column chromatography (eluent ratio: ethyl acetate:hexane = 1:12) to give the final target product 4-(trimethoxysilyl)aniline (13.6 g, three-step overall yield 29%).

References

[1] Patent: KR101810836, 2017, B1. Location in patent: Paragraph 0210-0214