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679585

Sigma-Aldrich

4-Methoxybenzyl-2,2,2-trichloroacetimidate

Synonym(s):

p-Methoxybenzyl trichloroacetimidate

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About This Item

Empirical Formula (Hill Notation):
C10H10Cl3NO2
CAS Number:
Molecular Weight:
282.55
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22

impurities

Major impurity is Trichloroacetamide by GCMS.

refractive index

n20/D 1.5488

bp

135-137 °C/0.7 mmHg

density

1.361 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

COc1ccc(COC(=N)C(Cl)(Cl)Cl)cc1

InChI

1S/C10H10Cl3NO2/c1-15-8-4-2-7(3-5-8)6-16-9(14)10(11,12)13/h2-5,14H,6H2,1H3

InChI key

TYHGKLBJBHACOI-UHFFFAOYSA-N

Application

4-Methoxybenzyl-2,2,2-trichloroacetimidate can be used as a reagent for the protection of alcohols as the p-methoxybenzyl ether. 1o, 2o, and 3o alcohols can be easily protected using this reagent with equal efficiency in the presence of a variety of different protective groups. This reagent is commonly used under acidic conditions therefore it offers an alternative method to the Williamson ether synthesis, which is typically used basic conditions to protect base-sensitive alcohols.

Pictograms

Exclamation markEnvironment

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

>230.0 °F

Flash Point(C)

> 110 °C


Certificates of Analysis (COA)

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4-Methoxybenzyl 2, 2, 2-Trichloro acetimidate
Wuts, Peter GM
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2001)
The Journal of Organic Chemistry, 54, 3738-3738 (1989)
Tetrahedron Letters, 29, 4139-4139 (1988)
Tetrahedron, 46, 5975-5975 (1990)
Tetrahedron, 63, 3682-3682 (2007)

Articles

Trichloroacetimidates are also commonly employed as alcohol alkylation reagents, particularly when existing functionality is not acid sensitive.

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