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Sigma-Aldrich

Ethyl 3-iodobenzoate

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$57.19

About This Item

Linear Formula:
IC6H4CO2C2H5
CAS Number:
58313-23-8
Molecular Weight:
276.07
MDL number:
MFCD00044769
UNSPSC Code:
12352100
PubChem Substance ID:
24877634
NACRES:
NA.22

$57.19

List Price$60.20Save 5%
Web-Only Promotion

Available to ship onApril 15, 2025Details

Request a Bulk Order

Quality Level

100

assay

98%

refractive index

n20/D 1.581 (lit.)

bp

272 °C (lit.)

density

1.64 g/mL at 25 °C (lit.)

functional group

ester
iodo

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

Related Categories

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.[1]

Application

Ethyl 3-iodobenzoate may be used to synthesize:
  • arylzinc bromide[1]
  • functionalized arylmagnesium compound[2]
  • ethyl3-phenylbenzoate[3]
  • ethyl 3-[(12-tert-butyldimethylsilyloxymethyl-1,12-dicarba-closo-dodecaboran)-1-yl]benzoate[4]
  • ethyl 3-(4-methoxy-1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)benzoate[5]
  • ethyl 3-(1-methyl-2-oxo-4-phenyl-1,2-dihydroquinolin-3-yl)benzoate[5]

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV6021
MKBG7416V
MKBF0094V
MKBB1397
00216EJ

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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
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)
Copper catalyzed conjugate addition of highly functionalized arylmagnesium compounds to enones.
Varchi G, et al.
Tetrahedron, 56(18), 2727-2731 (2000)
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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