tert-Butyl 2-iodoacetate

tert-Butyl 2-iodoacetate Property

Boiling point:

206.4±13.0 °C(Predicted)

Density 

1.614±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

Appearance

Light yellow to brown Liquid

InChI

InChI=1S/C6H11IO2/c1-6(2,3)9-5(8)4-7/h4H2,1-3H3

InChIKey

QYPDJIDQEZDFLS-UHFFFAOYSA-N

SMILES

C(OC(C)(C)C)(=O)CI

Safety

RIDADR 

2810

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

2915907098

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H227Combustible liquid

H301Toxic if swalloed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P370+P378In case of fire: Use … for extinction.

P403+P235Store in a well-ventilated place. Keep cool.

P405Store locked up.

P501Dispose of contents/container to..…

tert-Butyl 2-iodoacetate Chemical Properties,Usage,Production

Uses

tert-Butyl Iodoacetate is used in the synthesis and biological evaluation of water-soluble derivative of potent V-ATPase inhibitor archazolid.

Synthesis

The general procedure for the synthesis of tert-butyl iodoacetate from tert-butyl bromoacetate was as follows: tert-butyl bromoacetate (6) (1.00 g, 5.13 mmol, 1.0 eq.) was slowly added dropwise to a pre-prepared solution of sodium iodide (1.15 g, 7.69 mmol, 1.5 eq.) in anhydrous acetone (30 mL). The reaction mixture was stirred continuously at room temperature for 150 min and the progress of the reaction was monitored by thin layer chromatography (TLC) [unfolding agent: petroleum ether/ethyl acetate = 2:1; Rf value of tert-butyl iodoacetate = 0.73] to confirm the complete conversion of the reaction. Subsequently, the reaction solution was filtered to remove insoluble impurities and the filtrate was concentrated by rotary evaporator. To the concentrated residue, pentane (15 mL) was added for washing and the filtrate was filtered again to remove the precipitate. Finally, the filtrate was concentrated under vacuum to afford the target product tert-butyl iodoacetate (1.01 g, 81% yield) as a light yellow oil.

References

[1] Patent: US5618808, 1997, A
[2] Angewandte Chemie - International Edition, 2010, vol. 49, # 15, p. 2738 - 2742
[3] Journal of Organic Chemistry, 2006, vol. 71, # 19, p. 7307 - 7314
[4] Journal of Labelled Compounds and Radiopharmaceuticals, 1997, vol. 39, # 6, p. 509 - 524
[5] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 24, p. 7735 - 7738