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242934

Sigma-Aldrich

Ethyl iodoacetate

98%

Synonym(s):

Ethyl 2-iodoacetate, Ethyl monoiodoacetate, Iodoacetic acid ethyl ester

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About This Item

Linear Formula:
ICH2COOC2H5
CAS Number:
623-48-3
Molecular Weight:
214.00
Beilstein:
741934
EC Number:
210-796-3
MDL number:
MFCD00001081
UNSPSC Code:
12352100
PubChem Substance ID:
24854592
NACRES:
NA.22

Quality Level

200

Assay

98%

refractive index

n20/D 1.503 (lit.)

bp

179-180 °C (lit.)

density

1.808 g/mL at 25 °C (lit.)

functional group

ester
iodo

storage temp.

2-8°C

SMILES string

CCOC(=O)CI

InChI

1S/C4H7IO2/c1-2-7-4(6)3-5/h2-3H2,1H3

InChI key

MFFXVVHUKRKXCI-UHFFFAOYSA-N

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General description

Ethyl iodoacetate, also known as iodoacetic acid ethyl ester, serves as an alkylating agent and a radical precursor in organic synthesis. It is also commonly used as a lachrymatory agent.

Application

Ethyl iodoacetate was used in the synthesis of trans-2,3-disubstituted indolines by reacting with 1-azido-2-allylbenzene derivatives via a diastereoselective radical cascade.

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H300,H314

Hazard Classifications

Acute Tox. 2 Oral - Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

170.6 °F - closed cup

Flash Point(C)

77 °C - closed cup

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

242934-VAR:
242934-5G:4548173987248
242934-100ML:
242934-25G:4548173987255
242934-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCF4174
BCBV8471
BCBL8657V
BCBG0849V
1451857V

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François Brucelle et al.
The Journal of organic chemistry, 78(12), 6245-6252 (2013-06-01)
The preparation of trans-2,3-disubstituted indolines from 1-azido-2-allylbenzene derivatives via a diastereoselective radical cascade using ethyl iodoacetate and triethylborane is described. Further lactamization afforded substituted benzopyrrolizidinones with excellent diastereomeric ratios. The radical cascade/lactamization sequence was efficiently applied to the synthesis of

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