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238902

Sigma-Aldrich

2-(Trimethylsilyl)ethoxymethyl chloride

technical grade

Synonym(s):

(2-Chloromethoxyethyl)trimethylsilane, Chloromethyl 2-trimethylsilylethyl ether, SEM-Cl, SEM-chloride

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About This Item

Linear Formula:
(CH3)3SiCH2CH2OCH2Cl
CAS Number:
76513-69-4
Molecular Weight:
166.72
Beilstein/REAXYS Number:
3587289
EC Number:
278-483-4
MDL number:
MFCD00009919
UNSPSC Code:
12352101
PubChem Substance ID:
24854351
NACRES:
NA.22

grade

technical grade

Quality Level

100

form

liquid

refractive index

n20/D 1.435 (lit.)

bp

170-172 °C (lit.)
57-59 °C/8 mmHg (lit.)

density

0.942 g/mL at 25 °C (lit.)

storage temp.

−20°C

SMILES string

C[Si](C)(C)CCOCCl

InChI

1S/C6H15ClOSi/c1-9(2,3)5-4-8-6-7/h4-6H2,1-3H3

InChI key

BPXKZEMBEZGUAH-UHFFFAOYSA-N

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General description

Learn More at the Professor and Product Portal of Professor Bruce Lipshutz.

Application

Phenol protecting group in the synthesis of laterifluorones.
Used to prepare a SEM-ether which was, in turn, removed with BBr3 and cyclized to a benzo-oxapane.

Features and Benefits

Convenient hydroxyl-protecting reagent. SEM-ethers are stable over a wide pH range, and can be selectively cleaved with fluoride ion under mild aprotic conditions.

pictograms

FlameCorrosion
GHS02,GHS05

signalword

Danger

hcodes

H226,H314

Hazard Classifications

Flam. Liq. 3 - Skin Corr. 1B

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

114.8 °F - closed cup

flash_point_c

46 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tetrahedron Letters, 36, 1683-1683 (1995)
The Journal of Organic Chemistry, 55, 5180-5180 (1990)
K C Nicolaou et al.
Journal of the American Chemical Society, 126(17), 5493-5501 (2004-04-29)
The total synthesis of 1-O-methyllateriflorone (2) is described. The construction of the cage-like domain of the molecule involved a biomimetic Claisen/Diels-Alder cascade, whereas the novel spiroxalactone framework was generated by an intramolecular Michael reaction within precursor 16a involving the carboxylate
Tetrahedron Letters, 47, 5909-5909 (2006)

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