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560146

Sigma-Aldrich

4-Chloro-2-iodobenzoic acid

97%

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About This Item

Linear Formula:
C6H3Cl(I)COOH
CAS Number:
Molecular Weight:
282.46
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

97%

mp

163-167 °C (lit.)

SMILES string

OC(=O)c1ccc(Cl)cc1I

InChI

1S/C7H4ClIO2/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3H,(H,10,11)

InChI key

LRRDANNSUCQNDU-UHFFFAOYSA-N

General description

4-Chloro-2-iodobenzoic acid is an electron-deficient substituted 2-iodobenzoic acid. It reacts with ynamide to provide the 3,4-disubstituted isocoumarin.

Application

4-Chloro-2-iodobenzoic acid may be used to synthesize:
  • 6-chloro-3-(4-methoxyphenyl)-1H-isochromen-1-one
  • (Z)-3-benzylidene-5-chloroisobenzofuran-1(3H)-one
  • 6-chloro-3-pentyl-1H-isochromen-1-one
  • 4-chloro-2-iodobenzophenone

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Veronika Hampl et al.
Scientia pharmaceutica, 79(1), 21-30 (2011-05-28)
New isocoumarins were prepared in an efficient way from 2-iodobenzoic acid derivatives and hept-1-yne in a Sonogashira reaction, followed by spontaneous cyclization. Catalytic hydrogenation gave the corresponding dihydroisocoumarins. A 4-chloroisocoumarin was prepared on an alternative pathway. Some of the new
The synthesis and electronic absorption spectra of 3-phenyl-3 (4-pyrrolidino-2-substituted phenyl)-3H-naphtho [2, 1-b] pyrans: further exploration of the ortho substituent effect.
Gabbutt CD, et al.
Tetrahedron, 62(4), 737-745 (2006)
Regioselective synthesis of 3, 4-disubstituted isocoumarins through the Pd-catalyzed annulation of 2-iodoaromatic acids with ynamides.
Liu H, et al.
Chemical Communications (Cambridge, England), 52(41), 6801-6804 (2016)
Regioselective One-Pot Synthesis of Isocoumarins and Phthalides from 2-Iodobenzoic Acids and Alkynes by Temperature Control.
Kumar MR, et al.
Advanced Synthesis & Catalysis, 355(16), 3221-3230 (2013)

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