2-(Trimethylsilyl)ethoxymethyl chloride
- Product Name
- 2-(Trimethylsilyl)ethoxymethyl chloride
- CAS No.
- 76513-69-4
- Chemical Name
- 2-(Trimethylsilyl)ethoxymethyl chloride
- Synonyms
- SEM-CL;(2-trimethylethylsilylethoxy)methyl chloride;SEM-CI;2-(CHLOROMETHOXY)ETHYLTRIMETHYLSILANE;(Trimethylsilyl)ethoxymethyl chloride;DK891;2-(Trime;SEM-CHLORIDE;2-(triMethylsilyl)ethoxyMethyl chl;2-ChloroethoxyMethyltrimethylsilane
- CBNumber
- CB1275117
- Molecular Formula
- C6H15ClOSi
- Formula Weight
- 166.72
- MOL File
- 76513-69-4.mol
2-(Trimethylsilyl)ethoxymethyl chloride Property
- Boiling point:
- 170-172 °C (lit.) 57-59 °C/8 mmHg (lit.)
- Density
- 0.942 g/mL at 25 °C (lit.)
- refractive index
- n20/D 1.435(lit.)
- Flash point:
- 116 °F
- storage temp.
- 2-8°C
- solubility
- Sol most organic solvents (pentane, CH2Cl2, Et2O, THF, DMF, DMPU, HMPA)
- form
- Liquid
- color
- Clear colorless
- Specific Gravity
- 0.95
- Water Solubility
- decomposes
- Sensitive
- Moisture Sensitive
- Hydrolytic Sensitivity
- 7: reacts slowly with moisture/water
- BRN
- 3587289
- Stability:
- Unstable in Solution
- InChIKey
- BPXKZEMBEZGUAH-UHFFFAOYSA-N
- CAS DataBase Reference
- 76513-69-4(CAS DataBase Reference)
Safety
- Hazard Codes
- C
- Risk Statements
- 10-34
- Safety Statements
- 26-28-36/37/39-45-16
- RIDADR
- UN 2920 8/PG 2
- WGK Germany
- 3
- F
- 8-10-21
- TSCA
- No
- HazardClass
- 3.2
- PackingGroup
- III
- HS Code
- 29319090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H226Flammable liquid and vapour
H314Causes severe skin burns and eye damage
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P310Immediately call a POISON CENTER or doctor/physician.
N-Bromosuccinimide Price
- Product number
- 238902
- Product name
- 2-(Trimethylsilyl)ethoxymethyl chloride
- Purity
- technical grade
- Packaging
- 1g
- Price
- $41.37
- Updated
- 2025/07/31
- Product number
- 238902
- Product name
- 2-(Trimethylsilyl)ethoxymethyl chloride
- Purity
- technical grade
- Packaging
- 5g
- Price
- $151.05
- Updated
- 2025/07/31
- Product number
- C1339
- Product name
- 2-(Chloromethoxy)ethyltrimethylsilane (stabilized with Diisopropylethylamine)
- Purity
- >95.0%(GC)
- Packaging
- 5mL
- Price
- $134
- Updated
- 2025/07/31
- Product number
- C1339
- Product name
- 2-(Chloromethoxy)ethyltrimethylsilane (stabilized with Diisopropylethylamine)
- Purity
- >95.0%(GC)
- Packaging
- 25mL
- Price
- $457
- Updated
- 2025/07/31
- Product number
- 92749
- Product name
- 2-(Trimethylsilyl)ethoxymethyl chloride
- Purity
- ≥95.0% (GC)
- Packaging
- 5ml
- Price
- $199
- Updated
- 2025/07/31
2-(Trimethylsilyl)ethoxymethyl chloride Chemical Properties,Usage,Production
Chemical Properties
Colorless to light yellow liqui
Physical properties
bp 57–59 °C/8 mmHg; d 0.942 g cm?3.
Uses
2-(Chloromethoxy)ethyltrimethylsilane is used in the preparation of SEM [2-(trimethylsilyl)ethoxy]methyl]-ethers. It serves as a phenol protecting group in the synthesis of laterifluorones. Further, it reacts with 1H-imidazole to prepare 1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole.
Uses
2-(Trimethylsilyl)ethoxymethyl Chloride is a reagent used in the protection of alcohols, secondary aryl amines, and imidazole, indole, and pyrrole nitrogens;electrophilic formaldehyde equivalent; acyl anion equivalent,used in One-carbon Homologations, Cyclizations etc.
General Description
2-(Trimethylsilyl)ethoxymethyl chloride (SEM-Cl) is a widely used reagent for the preparation protection groups for amines, alcohols, phenols, and carboxy groups. The nitrogen of amides and sulfonamides groups are also protected by using SEM-Cl reagent.
Synthesis
75-77-4
1462-35-7
76513-69-4
Step 4: Take a small amount of intermediate reagent and place it in the reactor, heat to reflux and maintain reflux for 4 hours. After completion of the reaction, cool to 20°C and slowly add trimethylchlorosilane dropwise. During the dropwise addition, the temperature of the solution was gradually increased. Step 5: At the end of the reaction, desorption operation was carried out, controlling the temperature of the depressurized reactor not to exceed 40°C. The residual system residue was dissolved to form a viscous substance, and ethanol was added slowly until no bubbles were generated, and the waste was disposed of. Finally, the solution obtained by desolventization is distilled to collect 2-(trimethylsilyl)ethoxymethyl chloride with a purity of more than 99%.
Purification Methods
Dissolve SEMCl in pentane, dry it (MgSO4), evaporate and distil the residual oil in a vacuum. Stabilise it with 10ppm of diisopropylamine. Store it under N2 in a sealed container in a refrigerator. [Lipshutz & Pegram Tetrahedron Lett 21 3343 1980.]
References
[1] Patent: CN103408576, 2016, B. Location in patent: Paragraph 0020; 0021; 0025
[2] Patent: CN108409776, 2018, A. Location in patent: Page/Page column 5-7
2-(Trimethylsilyl)ethoxymethyl chloride Preparation Products And Raw materials
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View Lastest Price from 2-(Trimethylsilyl)ethoxymethyl chloride manufacturers
- Product
- 2-(Trimethylsilyl)ethoxymethyl chloride 76513-69-4
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 95.0%
- Supply Ability
- 10000KGS
- Release date
- 2025-07-07
- Product
- 2-(Trimethylsilyl)ethoxymethyl chloride 76513-69-4
- Price
- US $10.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 10 mt
- Release date
- 2024-11-15
- Product
- 2-(Trimethylsilyl)ethoxymethyl chloride 76513-69-4
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 98%
- Supply Ability
- 1ton
- Release date
- 2022-09-30