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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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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)

156.2 °F - closed cup

Flash Point(C)

69 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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.
Two competing mechanisms for the copper-free Sonogashira cross-coupling reaction.
Ljungdahl T, et al.
Organometallics, 27(11), 2490-2498 (2008)
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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