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140333

Sigma-Aldrich

Benzyl 2,2,2-trichloroacetimidate

≥96%

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Synonym(s):
2,2,2-Trichloroacetimidic acid benzyl ester
Linear Formula:
CCl3C(=NH)OCH2C6H5
CAS Number:
Molecular Weight:
252.52
Beilstein/REAXYS Number:
2525375
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

≥96%

form

liquid

impurities

<1% benzyl alcohol

refractive index

n20/D 1.545 (lit.)

bp

106-114 °C/0.5 mmHg (lit.)

transition temp

solidification point 3-4 °C

density

1.359 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

ClC(Cl)(Cl)C(=N)OCc1ccccc1

InChI

1S/C9H8Cl3NO/c10-9(11,12)8(13)14-6-7-4-2-1-3-5-7/h1-5,13H,6H2

InChI key

HUZCTWYDQIQZPM-UHFFFAOYSA-N

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1 of 4

This Item
295892245631B9550
vibrant-m

140333

Benzyl 2,2,2-trichloroacetimidate

vibrant-m

295892

Benzyl acetoacetate

vibrant-m

245631

Benzyl bromoacetate

vibrant-m

B9550

Benzyl benzoate

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

form

liquid

form

-

form

liquid

form

liquid

storage temp.

2-8°C

storage temp.

-

storage temp.

-

storage temp.

-

density

1.359 g/mL at 25 °C (lit.)

density

1.112 g/mL at 25 °C (lit.)

density

1.446 g/mL at 25 °C (lit.)

density

1.118 g/mL at 20 °C (lit.)

refractive index

n20/D 1.545 (lit.)

refractive index

n20/D 1.512 (lit.)

refractive index

n20/D 1.544 (lit.)

refractive index

n20/D 1.568 (lit.)

Application

Benzyl 2,2,2-trichloroacetimidate was used as reagent during the synthesis of funiculosin dimethyl ether and (S)-3-(benzyloxy)-2-methylpropanal. It was used in the acid-catalyzed benzylation of hydroxy groups.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

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


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The total synthesis of scytophycin C. Part 1: stereocontrolled synthesis of the C1? C32 protected seco acid.
Paterson I, et al.
Tetrahedron, 54(39), 11935-11954 (1998)
Studies of novel cyclitols. A synthesis of 3'O, 4'O -dimethylfuniculosin.
Williams DR, et al.
Tetrahedron Letters, 41(49), 9397-9401 (2000)
Tetrahedron Asymmetry, 3, 1547-1547 (1992)

Articles

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

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