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532851

Sigma-Aldrich

Methyl 2-iodobenzoate

97%

Synonym(s):

Methyl o-iodobenzoate

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About This Item

Linear Formula:
IC6H4CO2CH3
CAS Number:
610-97-9
Molecular Weight:
262.04
EC Number:
210-243-6
MDL number:
MFCD00016351
UNSPSC Code:
12352100
PubChem Substance ID:
24877921
NACRES:
NA.22

Quality Level

200

Assay

97%

refractive index

n20/D 1.604 (lit.)

bp

149-150 °C/10 mmHg (lit.)

density

1.784 g/mL at 25 °C (lit.)

functional group

ester
iodo

SMILES string

COC(=O)c1ccccc1I

InChI

1S/C8H7IO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,1H3

InChI key

BXXLTVBTDZXPTN-UHFFFAOYSA-N

General description

Methyl 2-iodobenzoate can be prepared from 2-iodobenzoic acid via esterification. It undergoes cobalt-catalyzed cyclization with aldehydes to form phthalide derivatives. The microbial dihydroxylation of methyl 2-iodobenzoate forms a nonracemic iodocyclohexene carboxylate intermediate. This intermediate forms the precursor for preparing kibdelone C.

Application

Methyl 2-iodobenzoate may be used in the preparation of:
  • N-substituted 4-methylene-3,4-dihydro-1(2H)-isoquinolin-1-ones
  • methyl diphenylacetylene-2-carboxylate
  • methyl 2-heptynylphenylbenzoate
  • (E)-2-[3-[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-oxopropyl]benzoic acid methyl ester
  • 4-(2-carbomethoxyphenyl)-3-(1-methylethoxy)cyclobut-3-ene-1,2-dione
  • 3-(2-carbomethoxyphenyl)-4-methylcyclobuten-3-ene-1,2-dione 2-(ethylene acetal)

Storage Class Code

10 - Combustible liquids

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.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

532851-50G:4548173989303
532851-VAR:
532851-250G:4548173989310
532851-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG5628
BCCB1928
BCBK3405V
BCBH9341V
BCBC7626V

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A short synthesis of nonracemic iodocyclohexene carboxylate fragment for kibdelone and congeners.
Endoma-Arias MAA and Hudlicky T.
Tetrahedron Letters, 52(49), 6632-6634 (2011)
An efficient synthesis of LTD4 antagonist L-699,392.
The Journal of Organic Chemistry, 58(14), 3731-3735 (1993)
Synthesis of Polyimides via the Palladium-Catalyzed Carbonylation of Bis (o-iodo esters) and Diamines.
Perry RJ, et al.
Macromolecules, 28(10), 3509-3515 (1995)
Synthesis of N-substituted 4-methylene-3, 4-dihydro-1 (2H)-isoquinolin-1-ones via a palladium-catalysed three-component process.
Grigg R, et al.
Tetrahedron, 43(14), 2601-2603 (2002)
Palladium homogeneous and supported catalysis: synthesis of functional acetylenics and cyclisation to heterocycles.
Villemin D and Goussu D.
Heterocycles, 29(7), 1255-1261 (1989)
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