Chloromethyl pivalate

Base Information

• Chemical Name: Chloromethyl pivalate
• CAS No.: 18997-19-8
• Molecular Formula: C6H11ClO2
• Molecular Weight: 150.605
• Hs Code.: 29159000
• European Community (EC) Number: 242-735-1
• UNII: ZQU16YZ6MF
• DSSTox Substance ID: DTXSID1066445
• Nikkaji Number: J26.281A
• Wikidata: Q63393271
• Mol file: 18997-19-8.mol

Synonyms:Chloromethyl pivalate;18997-19-8;chloromethyl 2,2-dimethylpropanoate;Pivaloyloxymethyl chloride;Propanoic acid, 2,2-dimethyl-, chloromethyl ester;Pivalic acid chloromethyl ester;Chloromethyl Trimethylacetate;18797-19-8;POM-Cl;ZQU16YZ6MF;2,2-Dimethylpropionic Acid Chloromethyl Ester;Magnesium,isopropylmethoxy- (8CI);chloromethyl 2,2-dimethylpropionate;EINECS 242-735-1;Chloromethyl 2,2-dimethylpropanoate;Chloromethyl 2,2-dimethylpropionate;Chloromethyl trimethylacetate;chioromethyl pivalate;MFCD00000884;Chloromethyl pivaloate;chloro-methyl pivalate;pivaloxymethyl chloride;pivaloyloxymethylchloride;pivalyloxymethyl chloride;ClCH2OC(O)CMe3;Pivalic acid chloromethyl;UNII-ZQU16YZ6MF;SCHEMBL300;Chloromethyl pivalate, 97%;DTXSID1066445;GGRHYQCXXYLUTL-UHFFFAOYSA-;Chloromethyl2,2-dimethylpropionate;AKOS006223678;CS-W018522;Trimethylacetic Acid Chloromethyl Ester;AS-19276;FT-0623677;P1012;EN300-78938;2,2-dimethyl-propionic acid chloromethyl ester;2,2-dimethylpropanoic acid, chloromethyl ester;D77849;((TERT-BUTYLCARBONYL)OXY)METHYL CHLORIDE;2-DIMETHYLPROPIONIC ACID CHLOROMETHYL ESTER;SR-01000944704;(2,2-DIMETHYL-1-OXOPROPOXY)METHYL CHLORIDE;SR-01000944704-1;Q63393271;F0001-0685;.ALPHA.,.ALPHA.-DIMETHYLPROPIONYLOXYMETHYL CHLORIDE

Chemical Property of Chloromethyl pivalate

Chemical Property:

• Appearance/Colour: clear colorless to very faint yellow clear liquid
• Vapor Pressure: 5.45mmHg at 25°C
• Melting Point: <-40 °C
• Refractive Index: n20/D 1.417(lit.)
• Boiling Point: 143 °C at 760 mmHg
• Flash Point: 42.9 °C
• PSA: 26.30000
• Density: 1.056 g/cm³
• LogP: 1.77200
• Storage Temp.: Flammables area
• Water Solubility.: Miscible with most organic solvents. Immiscible with water.
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 150.0447573
• Heavy Atom Count: 9
• Complexity: 104

Purity/Quality:

98.0%min ^*data from raw suppliers

Chloromethyl Pivalate [Amino-Protecting Agent] >99.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 10-20/21/22-36/37/38
• Safety Statements: 16-26-36-41-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Other Toxic Gases & Vapors
• Canonical SMILES: CC(C)(C)C(=O)OCCl
• Uses: Chloromethyl pivalate was used in the synthesis of pivaloyloxy methyl ester of ofloxacin as prodrug. It was used as the reagent during the synthesis of an isoindoline-annulated, tricyclic sultam library via microwave-assisted, continuous-flow organic synthesis.

Technology Process of Chloromethyl pivalate

There total 8 articles about Chloromethyl 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: 70.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + pivaloyl chloride (3282-30-2) → Chloromethyl pivalate (18997-19-8)

Guidance literature:

With zinc(II) chloride; at 50 - 55 ℃; for 10h;

DOI:10.1080/00397919508011821

Reference yield: 64.0%

chlorosulfuric acid chloromethyl ester (49715-04-0) + Trimethylacetic acid (75-98-9) → Chloromethyl pivalate (18997-19-8)

Guidance literature:

With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; In dichloromethane; 1.) 20-22 deg C, 2.) 30 min;

Reference yield: 55.0%

chlorobromomethane (74-97-5) + sodium pivalate (1184-88-9) → Chloromethyl pivalate (18997-19-8)

Guidance literature:

In N,N-dimethyl-formamide;

upstream raw materials:

Methyl pivalate

formaldehyd

pivaloyl chloride

chlorosulfuric acid chloromethyl ester

Downstream raw materials:

6-aminopenicillanic acid pivaloyloxymethyl ester

2-<<3-(trifluormetil)fenil>amino>benzoato de pivaloiloximetilo

1-(2,2-dimethyl-1-oxopropoxy)methyl L-N-(phenylmethoxycarbonyl) tyrosinate

2-<(2,3-dimetilfenil)amino>benzoato de pivaloiloximetilo

Refernces

• 1、 Waranis,Sloan. "Effects of vehicles and prodrug properties and their interactions on the delivery of 6-mercaptopurine through skin: Bisacyloxymethyl-6-mercaptopurine prodrugs". . p. 587 - 595. Retrieved 1987.
• 2、 -. "Substituted pyrazole compound, preparation method, pharmaceutical composition and applications thereof". Paragraph 0152-0155; 0158. . Retrieved 2020/03/12.
• 3、 Rennison, David,Laita, Olivia,Bova, Sergio,Cavalli, Maurizio,Hopkins, Brian,Linthicum, Darwin S.,Brimble, Margaret A.. "Design and synthesis of prodrugs of the rat selective toxicant norbormide". supporting information; experimental part. p. 3997 - 4011. Retrieved 2012/09/08.