Iodomethyl pivalate

Base Information

• Chemical Name: Iodomethyl pivalate
• CAS No.: 53064-79-2
• Molecular Formula: C6H11IO2
• Molecular Weight: 242.057
• European Community (EC) Number: 258-339-7
• DSSTox Substance ID: DTXSID70201128
• Nikkaji Number: J138.324H
• Wikidata: Q72484020
• Mol file: 53064-79-2.mol

Synonyms:Iodomethyl pivalate;53064-79-2;iodomethyl 2,2-dimethylpropanoate;pivalic acid iodomethyl ester;2,2-Dimethylpropionic Acid Iodomethyl Ester;pivaloyloxymethyl iodide;Iodomethyl 2,2-Dimethylpropionate;Propanoic acid, 2,2-dimethyl-, iodomethyl ester;EINECS 258-339-7;MFCD02179270;C6H11IO2;(Pivaloyloxy)methyl Iodide;POMI;pivaloyloxymethyliodide;iodomethyl trimethylacetate;2,2-Dimethyl-propanoic Acid Iodomethyl Ester;SCHEMBL248949;DTXSID70201128;AMY13386;C6-H11-I-O2;Trimethylacetic Acid Iodomethyl Ester;AKOS015892725;BS-13181;SY039192;2,2-dimethyl-propionic acid iodomethyl ester;2,2-Dimethylpropanoic acid, iodomethyl ester;2,2-dimethylpropionic acid, iodomethyl ester;CS-0066217;FT-0640126;I0912;2,2-dimethyl-propionic acid iodo-methyl ester;EN300-123433;F11433;A829379;Iodomethyl Pivalate (stabilized with Copper chip)

Chemical Property of Iodomethyl pivalate

Chemical Property:

• Appearance/Colour: Sight yellow or colorless
• Vapor Pressure: 0.383mmHg at 25°C
• Melting Point: 33-35 °C(lit.)
• Refractive Index: 1.506
• Boiling Point: 197.2 °C at 760 mmHg
• Flash Point: 73.1 °C
• PSA: 26.30000
• Density: 1.614 g/cm³
• LogP: 1.96820
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 241.98038
• Heavy Atom Count: 9
• Complexity: 104

Purity/Quality:

98.0%min ^*data from raw suppliers

IodomethylPivalate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C(=O)OCI
• Uses: Iodomethyl pivalate can be used as reagent used for the addition of pivaloyl group.

Technology Process of Iodomethyl pivalate

There total 6 articles about Iodomethyl pivalate 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: 94.0%

Chloromethyl pivalate (18997-19-8) → iodomethyl pivaloate (53064-79-2)

Guidance literature:

With sodium iodide; calcium chloride; In ethyl acetate; at 78 ℃; for 6h;

Reference yield: 93.0%

→ iodomethyl pivaloate (53064-79-2)

Guidance literature:

Reference yield: 78.0%

chloromethyl hexanoate (66542-51-6) → iodomethyl hexanoate (63379-66-8) + iodomethyl pivaloate (53064-79-2)

Guidance literature:

With sodium iodide; In acetone;

upstream raw materials:

Chloromethyl pivalate

chloromethyl hexanoate

trioxane

pivaloyl chloride

Downstream raw materials:

2,2-Dimethyl-propionic acid 3-trimethylsilanyloxy-cyclohex-2-enylmethyl ester

1-<(Pivalyloxy)methoxy>-2,4-dinitrobenzene

2,2-dimethylpropionic acid (4-nitrophenoxy)methyl ester

(3-oxocyclohex-1-en-1-yl)methyl pivalate

Refernces

Preparation and reactivity of polyfunctional zinc and copper organometallics bearing sulfur functionalities

10.1016/S0040-4020(01)88872-4

The research explores the development and reactivity of novel zinc and copper organometallic compounds that incorporate sulfur functionalities. The study builds on the foundation laid by the applications of sulfur-stabilized lithium organometallics in organic chemistry. The researchers successfully prepared the first polyfunctional zinc and copper organometallic compounds with sulfur functionalities positioned in the alpha or gamma location relative to the carbon-metal bond. Key chemicals involved in this research include iodomethyl pivalate, iodomethylthiobenzoate, and various a-chloroalkyl phenyl sulfides, which facilitated the formation of these organometallics. The presence of sulfur functionalities, such as phenylthio and thioester groups, significantly enhanced the reactivity of these compounds towards typical organic electrophiles like allylic halides, acyl chlorides, and aldehydes. The study also highlights the role of copper salts, specifically CuCN*2LiCl, in transmetallation processes that further enhanced the reactivity of these organometallics. The findings demonstrate the potential of these compounds for synthesizing highly functionalized molecules with applications in organic chemistry.