Ethyl iodoacetate

Base Information

• Chemical Name: Ethyl iodoacetate
• CAS No.: 623-48-3
• Molecular Formula: C4H7 I O2
• Molecular Weight: 214.003
• Hs Code.: 2915900090
• European Community (EC) Number: 210-796-3
• NSC Number: 58809
• UNII: X9ZR7PV2QF
• DSSTox Substance ID: DTXSID5060770
• Nikkaji Number: J54.938J
• Wikipedia: Ethyl_iodoacetate
• Wikidata: Q1821085
• Mol file: 623-48-3.mol

Synonyms:ETHYL IODOACETATE;623-48-3;ethyl 2-iodoacetate;Ethyl monoiodoacetate;Acetic acid, iodo-, ethyl ester;Iodoacetic acid, ethyl ester;EINECS 210-796-3;NSC 58809;X9ZR7PV2QF;Ethylester kyseliny jodoctove [Czech];Iodoacetic acid ethyl ester;BRN 0741934;Ethylester kyseliny jodoctove;iodo-acetic acid ethyl ester;S 9;Acetic acid, 2-iodo-, ethyl ester;MFCD00001081;NSC-58809;4-02-00-00535 (Beilstein Handbook Reference);C4H7IO2;ethyliodoacetate;Iodoacetic acid ethyl;Ethyl iodoacetate, 98%;iodoacetic acid ethylester;UNII-X9ZR7PV2QF;ethoxycarbonylmethyl iodide;WLN: I1VO2;SCHEMBL145800;DTXSID5060770;C4-H7-I-O2;NSC58809;AKOS005068284;Ethyl 2-iodoacetate - stabilized over Cu;Ethyl iodoacetate, purum, >=98.0% (GC);Q1821085

Chemical Property of Ethyl iodoacetate

Chemical Property:

• Appearance/Colour: clear light yellow to orange liquid
• Vapor Pressure: 0.925mmHg at 25°C
• Melting Point: <25 °C
• Refractive Index: n20/D 1.503(lit.)
• Boiling Point: 179-180 °C(lit.)
• Flash Point: 77 ºC
• PSA: 26.30000
• Density: 1.808
• LogP: 0.98450
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Water Solubility.: Insoluble in water.
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 213.94908
• Heavy Atom Count: 7
• Complexity: 62.7

Purity/Quality:

98% ^*data from raw suppliers

Ethyl iodoacetate 98% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 25-34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Halogenated Esters
• Canonical SMILES: CCOC(=O)CI
• Uses: 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.

Technology Process of Ethyl iodoacetate

There total 34 articles about Ethyl iodoacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

ethyl bromoacetate (105-36-2) → ethyl iodoacetae (623-48-3)

Guidance literature:

With sodium iodide; In acetone; at 20 ℃; Darkness;

DOI:10.1002/anie.201703340

Reference yield: 99.0%

trimethylsilanyl-acetic acid ethyl ester (4071-88-9) → chloro-trimethyl-silane (75-77-4) + ethyl iodoacetae (623-48-3)

Guidance literature:

With Iodine monochloride; In tetrachloromethane; for 0.5h; Ambient temperature;

Reference yield: 71.0%

hydrogen ethyl malonate (1071-46-1) → α,α-diiodoethylacetate (82665-91-6) + ethyl iodoacetae (623-48-3)

Guidance literature:

With N-iodo-succinimide; sodium acetate; In acetonitrile; at 100 ℃; for 10h; Inert atmosphere;

DOI:10.1002/adsc.201600506

upstream raw materials:

diazoacetic acid ethyl ester

ethyl-(1,1-difluoro-2-iodo-ethyl)-ether

thiocyanato-acetic acid ethyl ester

ethyl iodide

Downstream raw materials:

(3-hydroxy-p-menth-4⁽⁸⁾-en-3-yl)-acetic acid ethyl ester

methylthioacetic acid ethyl ester

ethyl 2,6,6-trimethylcyclohex-2-ene-1-carboxylate

3-hydroxy-5-methyl-3-phenyl-hexanoic acid

Refernces

• 1、 Cozzi, Pier Giorgio. "A catalytic, Me2Zn-mediated, enantioselective reformatsky reaction with ketones". . p. 2951 - 2954. Retrieved 2006.
• 2、 Tsuboi,Wada,Muranaka,Takeda. "A new method for the synthesis of 3,5-disubstituted 2(5H)-furanones. Synthesis of (±)-acarenoic acid". . p. 2917 - 2921. Retrieved 1987.
• 3、 Tappin, Nicholas D. C.,Renaud, Philippe. "Methyl Radical Initiated Kharasch and Related Reactions". supporting information. p. 275 - 282. Retrieved 2020/12/07.
• 4、 Meyer, Daniel,Renaud, Philippe. "Enantioselective Hydroazidation of Trisubstituted Non-Activated Alkenes". supporting information. p. 10858 - 10861. Retrieved 2017/08/30.