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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

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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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

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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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