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528994

Sigma-Aldrich

Ethyl 3-iodobenzoate

98%

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About This Item

Linear Formula:
IC6H4CO2C2H5
CAS Number:
Molecular Weight:
276.07
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

98%

refractive index

n20/D 1.581 (lit.)

bp

272 °C (lit.)

density

1.64 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)c1cccc(I)c1

InChI

1S/C9H9IO2/c1-2-12-9(11)7-4-3-5-8(10)6-7/h3-6H,2H2,1H3

InChI key

POGCXCWRMMXDAQ-UHFFFAOYSA-N

General description

Ethyl 3-iodobenzoate is a halogenated aromatic ester. It affords arylzinc bromide via reaction with i-PrMgBr in THF, followed by reaction with ZnBr2.

Application

Ethyl 3-iodobenzoate may be used to synthesize:
  • arylzinc bromide
  • functionalized arylmagnesium compound
  • ethyl3-phenylbenzoate
  • ethyl 3-[(12-tert-butyldimethylsilyloxymethyl-1,12-dicarba-closo-dodecaboran)-1-yl]benzoate
  • ethyl 3-(4-methoxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)benzoate
  • ethyl 3-(1-methyl-2-oxo-4-phenyl-1,2-dihydroquinolin-3-yl)benzoate

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

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)

230.0 °F - closed cup

Flash Point(C)

110 °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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Copper catalyzed conjugate addition of highly functionalized arylmagnesium compounds to enones.
Varchi G, et al.
Tetrahedron, 56(18), 2727-2731 (2000)
Ni (II)-catalyzed cross-coupling between polyfunctional arylzinc derivatives and primary alkyl iodides.
Giovannini R and Knochel P.
Journal of the American Chemical Society, 120(43), 11186-11187 (1998)
Shinya Fujii et al.
Bioorganic & medicinal chemistry, 17(1), 344-350 (2008-11-22)
A novel series of androgen receptor (AR) ligands bearing an acidic heterocycle with hydrogen-bonding ability as the terminal polar group was developed. Since most non-steroidal AR ligands so far known are structurally limited to nitro- or cyanobenzanilide as the polar
Nonpeptide Arginine Vasopressin Antagonists for Both V1A and V2 Receptors: Synthesis and Pharmacological Properties of 2-Phenyl-4'-((2, 3, 4, 5-tetrahydro-1H-1-benzazepin-1-yl) carbonyl) benzanilide Derivatives.
Matsuhisa A, et al.
Chemical & Pharmaceutical Bulletin, 45(11), 1870-1874 (1997)
Synthesis of 3, 4-Disubstituted Quinolin-2-(1H)-ones via Palladium-Catalyzed Decarboxylative Arylation Reactions.
Carrer A, et al.
Advanced Synthesis & Catalysis, 355(10), 2044-2054 (2013)

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