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365858

Sigma-Aldrich

4-Iodobenzotrifluoride

97%

Synonym(s):

4-Iodo-α,α,α-trifluorotoluene

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About This Item

Linear Formula:
IC6H4CF3
CAS Number:
455-13-0
Molecular Weight:
272.01
EC Number:
207-234-4
MDL number:
MFCD00039398
UNSPSC Code:
12352100
PubChem Substance ID:
24862587
NACRES:
NA.22

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

Related Categories

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
GHS07

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

Certificates of Analysis (COA)

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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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