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365858

Sigma-Aldrich

4-Iodobenzotrifluoride

97%

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Synonym(s):
4-Iodo-α,α,α-trifluorotoluene
Linear Formula:
IC6H4CF3
CAS Number:
Molecular Weight:
272.01
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

form

liquid

refractive index

n20/D 1.516 (lit.)

bp

185-186 °C/745 mmHg (lit.)

mp

−8.33 °C (lit.)

density

1.851 g/mL at 25 °C (lit.)

SMILES string

FC(F)(F)c1ccc(I)cc1

InChI

1S/C7H4F3I/c8-7(9,10)5-1-3-6(11)4-2-5/h1-4H

InChI key

SKGRFPGOGCHDPC-UHFFFAOYSA-N

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1 of 4

This Item
535990233021249475
4-Iodobenzotrifluoride 97%

365858

4-Iodobenzotrifluoride

4-(Trifluoromethoxy)iodobenzene 97%

535990

4-(Trifluoromethoxy)iodobenzene

bp

185-186 °C/745 mmHg (lit.)

bp

177-179 °C (lit.)

bp

-

bp

188-190 °C (lit.), 78-79 °C/16 mmHg (lit.)

refractive index

n20/D 1.516 (lit.)

refractive index

n20/D 1.504 (lit.)

refractive index

-

refractive index

n20/D 1.476 (lit.)

density

1.851 g/mL at 25 °C (lit.)

density

1.84 g/mL at 25 °C (lit.)

density

-

density

1.404 g/mL at 25 °C (lit.)

mp

−8.33 °C (lit.)

mp

-

mp

82-85 °C (lit.)

mp

-

form

liquid

form

-

form

solid

form

liquid

General description

4-Iodobenzotrifluoride undergoes aminocarbonylation in DMF using phosphoryl chloride to give N,N-dimethyl-(4-trifluoromethyl)benzamide. Mechanism of the copper-free Sonogashira cross-coupling reaction of 4-iodobenzotrifluoride with differently para-substituted phenylacetylenes has been investigated.

Application

4-Iodobenzotrifluoride may be employed as substrate with electron-deficient aromatic ring, during Mizoroki-Heck reaction with acrylic acid, to afford 4-trifluoromethylcinnnamic acid.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

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

156.2 °F - closed cup

flash_point_c

69 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


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Two competing mechanisms for the copper-free Sonogashira cross-coupling reaction.
Ljungdahl T, et al.
Organometallics, 27(11), 2490-2498 (2008)
Kazushi Hosoi et al.
Organic letters, 4(17), 2849-2851 (2002-08-17)
[reaction: see text] Palladium-catalyzed coupling reaction of N,N-dimethylformamide with aryl or alkenyl halides successfully proceeded in the presence of phosphoryl chloride to afford the corresponding tertiary amides in good yields.
Atsushi Ohtaka et al.
Molecules (Basel, Switzerland), 16(11), 9067-9076 (2011-10-29)
Linear polystyrene-stabilized PdO nanoparticles (PS-PdONPs) were prepared by thermal decomposition of Pd(OAc)(2) in the presence of polystyrene. X-ray diffraction (XRD) and transmission electron microscopy (TEM) indicated the production of PdO nanoparticles. The loading of palladium was determined by inductively coupled

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