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2-(Trimethylsilyl)ethoxymethyl chloride

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Name

2-(Trimethylsilyl)ethoxymethyl chloride

EINECS 278-483-4
CAS No. 76513-69-4 Density 0.92 g/cm3
PSA 9.23000 LogP 2.53750
Solubility decomposes in water Melting Point N/A
Formula C6H15ClOSi Boiling Point 182.1 °C at 760 mmHg
Molecular Weight 166.723 Flash Point 46.7 °C
Transport Information UN 2920 8/PG 2 Appearance Colorless to light yellow liquid
Safety 26-28-36/37/39-45-16 Risk Codes 10-34
Molecular Structure Molecular Structure of 76513-69-4 (2-(Trimethylsilyl)ethoxymethyl chloride) Hazard Symbols CorrosiveC
Synonyms

2-(Trimethylsilanyl)ethoxymethylchloride;Chloromethyl2-(trimethylsilyl)ethyl ether;Chloromethyl trimethylsilylethyl ether;SEMchloride;[2-(Chloromethoxy)ethyl]trimethylsilane;[2-[(Chloromethyl)oxy]ethyl]trimethylsilane;[[2-(Trimethylsilyl)ethyl]oxy]methyl chloride;b-(Trimethylsilyl)ethoxymethyl chloride;

Article Data 8

2-(Trimethylsilyl)ethoxymethyl chloride Synthetic route

75-77-4

chloro-trimethyl-silane

1462-35-7

1-bromo-2-(chloromethoxy)ethane

76513-69-4

(2-trimethylethylsilylethoxy)methyl chloride

Conditions
ConditionsYield
Stage #1: 1-bromo-2-(chloromethoxy)ethane With magnesium for 4h; Reflux;
Stage #2: chloro-trimethyl-silane at 20℃; Reagent/catalyst;
99%
Stage #1: 1-bromo-2-(chloromethoxy)ethane With n-butyllithium; methylmagnesium chloride In tetrahydrofuran; hexane at 20 - 30℃; for 0.333333h;
Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at 20 - 30℃; for 0.333333h;
85.8%
Stage #1: 1-bromo-2-(chloromethoxy)ethane With n-butyllithium; butyl magnesium bromide In tetrahydrofuran; hexane at 15 - 30℃; for 0.333333h;
Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at 30℃; for 0.333333h;
80.4%
50-00-0

formaldehyd

2916-68-9

2-(Trimethylsilyl)ethanol

76513-69-4

(2-trimethylethylsilylethoxy)methyl chloride

Conditions
ConditionsYield
With hydrogenchloride for 0.5h;90%
With hydrogenchloride at 0℃;87%
With hydrogenchloride for 0.433333h;85%
288-32-4

1H-imidazole

76513-69-4

(2-trimethylethylsilylethoxy)methyl chloride

101226-33-9

1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole

Conditions
ConditionsYield
Stage #1: 1H-imidazole With sodium hydride In tetrahydrofuran at 0 - 25℃; for 0.5h; Inert atmosphere;
Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In tetrahydrofuran at 0 - 25℃; for 14h; Inert atmosphere;
100%
Stage #1: 1H-imidazole With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.75h;
Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In tetrahydrofuran; mineral oil at 20℃;
93%
Stage #1: 1H-imidazole With potassium tert-butylate In dimethyl sulfoxide at 0℃; for 0.5h; Large scale;
Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In dimethyl sulfoxide at 0 - 15℃; for 16h; Large scale;
90%
63598-38-9

1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enopyranose

76513-69-4

(2-trimethylethylsilylethoxy)methyl chloride

76513-66-1

1,5-anhydro-4,6-O-benzylidene-2-deoxy-3-O-<<2-(trimethylsilyl)ethoxy>methyl>-D-ribo-hex-1-enopyranose

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane100%
With N-ethyl-N,N-diisopropylamine In dichloromethane for 5h; Ambient temperature;100%
76513-69-4

(2-trimethylethylsilylethoxy)methyl chloride

123190-86-3

(1R,7aS)-tetrahydro-1-methyl-1-(hydroxymethyl)-1H,3H-pyrrolo<1,2-c>oxazol-3-one

123190-87-4

(1R,7aS)-tetrahydro-1-methyl-1-<<2-(trimethylsilyl)ethoxy>methoxy>methyl-1H,3H-pyrrolo<1,2-c>oxazol-3-one

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 14h; Ambient temperature;100%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 23℃; Yield given;
76513-69-4

(2-trimethylethylsilylethoxy)methyl chloride

114877-74-6

N-(2-Allyl-phenyl)-4-hydroxy-butyramide

114877-90-6

N-(2-Allyl-phenyl)-4-(2-trimethylsilanyl-ethoxymethoxy)-butyramide

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide100%
76513-69-4

(2-trimethylethylsilylethoxy)methyl chloride

105427-88-1

methyl 3-bromo-5-chloro-2,4-dihydroxy-6-methylbenzoate

105427-90-5

methyl 2,4-bis[2-(trimethylsilyl)ethoxymethoxy]-3-bromo-5-chloro-6-methylbenzoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;100%
With N-ethyl-N,N-diisopropylamine In dichloromethane Yield given;
76513-69-4

(2-trimethylethylsilylethoxy)methyl chloride

144617-49-2

7-(4-tert-Butyldimethylsiloxy-2-hydroxybutyl)-1,4-dioxa-8-thiaspiro<4.5>dec-6-ene

144617-50-5

7-<4-tert-Butyldimethylsilyloxy-2-(2-trimethylsilylethoxy)methoxybutyl>-1,4-dioxa-8-thiaspiro<4.5>dec-6-ene

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 14h; Ambient temperature;100%
76513-69-4

(2-trimethylethylsilylethoxy)methyl chloride

14-acetylpodocarpa-8,11,13-trien-12-ol

154843-48-8

14-acetyl-12-<2'-(trimethylsilyl)ethoxymethoxy>podocarpa-8,11,13-triene

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 5h; Ambient temperature;100%
76513-69-4

(2-trimethylethylsilylethoxy)methyl chloride

173396-52-6

ethyl (1R,2S,3R,4R)-2,3-dihydroxy-4-methoxy-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohex-5-ene-1-carboxylate

173289-89-9

ethyl (1R,2S,3R,4R)-2-hydroxy-4-methoxy-5-methyl-3-(2-trimethylsilylethoxymethoxy)-2-(2-trimethylsilyl-3-furyl)cyclohex-5-ene-1-carboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine100%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h;96%

2-(Trimethylsilyl)ethoxymethyl chloride Specification

The systematic name of 2-(Trimethylsilyl)ethoxymethyl chloride is [2-(chloromethoxy)ethyl](trimethyl)silane. With the CAS registry number 76513-69-4, it is also named as Silane, [2-(chloromethoxy)ethyl]trimethyl-. The product's categories are Aliphatics; Biochemistry; Protection & Derivatization Reagents (for Synthesis); Reagents for Oligosaccharide Synthesis; Si (Classes of Silicon Compounds); Si-(C)4 Compounds; Silicon Compounds (for Synthesis); Synthetic Organic Chemistry. It is colorless to light yellow liquid which is stable under normal temperature and pressure. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.23; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.23; (4)ACD/LogD (pH 7.4): 2.23; (5)ACD/BCF (pH 5.5): 29.25; (6)ACD/BCF (pH 7.4): 29.25; (7)ACD/KOC (pH 5.5): 390.03; (8)ACD/KOC (pH 7.4): 390.03; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 9.23 Å2; (13)Index of Refraction: 1.413; (14)Molar Refractivity: 45.15 cm3; (15)Molar Volume: 181 cm3; (16)Polarizability: 17.9×10-24 cm3; (17)Surface Tension: 21.1 dyne/cm; (18)Density: 0.92 g/cm3; (19)Flash Point: 46.7 °C; (20)Enthalpy of Vaporization: 40.12 kJ/mol; (21)Boiling Point: 182.1 °C at 760 mmHg; (22)Vapour Pressure: 1.12 mmHg at 25°C.

Preparation of 2-(Trimethylsilyl)ethoxymethyl chloride: It can be obtained by formaldehyde and 2-trimethylsilanyl-ethanol. This reaction needs reagent HCl at temperature of 0 °C. The yield is 87%.

Uses of 2-(Trimethylsilyl)ethoxymethyl chloride: It can react with 1H-imidazole to get 1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole. This reaction needs reagent NaH and solvent tetrahydrofuran at temperature of 20 °C. The reaction time is 2.5 hours.

When you are using this chemical, please be cautious about it as the following:
It is flammable and can cause burns, so people should keep it away from sources of ignition. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. After contact with skin, wash immediately with plenty of soap-suds. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure.
1. SMILES:ClCOCC[Si](C)(C)C
2. InChI:InChI=1/C6H15ClOSi/c1-9(2,3)5-4-8-6-7/h4-6H2,1-3H3 
3. InChIKey:BPXKZEMBEZGUAH-UHFFFAOYAW

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