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Sigma-Aldrich

4-Methoxybenzyl-2,2,2-trichloroacetimidate

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Synonym(s):
p-Methoxybenzyl trichloroacetimidate
Empirical Formula (Hill Notation):
C10H10Cl3NO2
CAS Number:
89238-99-3
Molecular Weight:
282.55
MDL number:
MFCD00134547
UNSPSC Code:
12352101
PubChem Substance ID:
24885502
NACRES:
NA.22

impurities

Major impurity is Trichloroacetamide by GCMS.

Quality Level

100

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

Related Categories

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
GHS07,GHS09

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

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)
Tetrahedron, 46, 5975-5975 (1990)
Tetrahedron Letters, 37, 1482-1482 (1996)
Tetrahedron Letters, 29, 4139-4139 (1988)
Journal of the American Chemical Society, 112, 7021-7021 (1990)
View All Related Papers

Articles

Trichloroacetimidate Reagents

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

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