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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:
13421-13-1
Molecular Weight:
282.46
MDL number:
MFCD00060676
UNSPSC Code:
12352100
PubChem Substance ID:
24879847
NACRES:
NA.22

Quality Level

100

Assay

97%

mp

163-167 °C (lit.)

functional group

carboxylic acid
chloro
iodo

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

Related Categories

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

560146-VAR:
560146-BULK:
560146-1G:4548173994949
560146-5G:4548173994956

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT2634
MKCN0649
MKBV5755V
MKBT4604V
MKBL6916V

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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)
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
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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