Dimethyl chloromalonate

Base Information

• Chemical Name: Dimethyl chloromalonate
• CAS No.: 28868-76-0
• Molecular Formula: C5H7ClO4
• Molecular Weight: 166.561
• Hs Code.: 2917198090
• European Community (EC) Number: 249-275-0
• UNII: QH3S4XL5PI
• DSSTox Substance ID: DTXSID6049018
• Nikkaji Number: J286.469J
• Wikidata: Q27287259
• ChEMBL ID: CHEMBL3185914
• Mol file: 28868-76-0.mol

Synonyms:Dimethyl chloromalonate;28868-76-0;Dimethyl 2-chloromalonate;dimethyl 2-chloropropanedioate;Propanedioic acid, chloro-, dimethyl ester;1,3-dimethyl 2-chloropropanedioate;UNII-QH3S4XL5PI;2-Chloro-malonic acid dimethyl ester;C5H7ClO4;QH3S4XL5PI;DTXSID6049018;Chloromalonic acid dimethyl ester;EINECS 249-275-0;NCGC00249607-01;dimethyl chloropropanedioate;Propanedioic acid, 2-chloro-, 1,3-dimethyl ester;DTXCID1028944;dimethylchloromalonate;CAS-28868-76-0;Dimethyl?chloromalonate;Dimethyl2-chloromalonate;Dimethyl chloromalonate, 94%;SCHEMBL453120;C5-H7-Cl-O4;CHEMBL3185914;dimethyl 2-chloranylpropanedioate;Tox21_113538;BBL011526;MFCD00042837;STL146642;AKOS005720777;Tox21_113538_1;CS-W010804;DIMETHYL .ALPHA.-CHLOROMALONATE;DS-2785;2-chloropropanedioic acid dimethyl ester;NCGC00249607-02;BP-20371;CHLOROPROPANEDIOIC ACID DIMETHYL ESTER;D5467;FT-0625073;EN300-86385;MALONIC ACID, CHLORO-, DIMETHYL ESTER;F20957;A819643;SR-01000944774;J-017304;SR-01000944774-1;Q27287259

Chemical Property of Dimethyl chloromalonate

Chemical Property:

• Appearance/Colour: COLORLESS TO LIGHT YELLOW LIQUID
• Vapor Pressure: 0.148mmHg at 25°C
• Refractive Index: n20/D 1.437(lit.)
• Boiling Point: 215.441 °C at 760 mmHg
• PKA: 9.02±0.46(Predicted)
• Flash Point: 106.667 °C
• PSA: 52.60000
• Density: 1.283 g/cm³
• LogP: -0.06020
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 166.0032864
• Heavy Atom Count: 10
• Complexity: 129

Purity/Quality:

98%,99%, ^*data from raw suppliers

Dimethyl Chloromalonate >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C(C(=O)OC)Cl
• Uses: Dimethyl chloromalonate is suitable for use in the synthesis of 4,5,6-trichloropyrimidine. It may be used in the stereoselective synthesis of highly functionalized nitrocyclopropanes. It may be used in one-pot synthesis of tetra-alkoxycarbonylallylidenetriphenylphosphoranes.

Technology Process of Dimethyl chloromalonate

There total 5 articles about Dimethyl chloromalonate 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: 82.0%

malonic acid dimethyl ester (108-59-8) → 2-chlorodimethylmalonate (28868-76-0)

Guidance literature:

With sulfuryl dichloride; In dichloromethane; for 72h; Reflux;

DOI:10.3987/COM-08-S(N)100

Reference yield: 28.0%

2,3-Dimethyl-2-butene (563-79-1) + dimethyl acetylenedicarboxylate (762-42-5) → dimethyl-3,3,4-trimethyl-1,4-pentadiene-1,2-dicarboxylate (72163-16-7) + (E)-dihydro-3-carbomethoxymethylene-4,5,5-trimethyl-2(3H)-furanone (72163-25-8) + dimethyl chlorofumarate (5331-33-9) + 2-chlorodimethylmalonate (28868-76-0)

Guidance literature:

With aluminium trichloride; In dichloromethane; for 1.5h; Ambient temperature;

Reference yield: 17.0%

2,3-Dimethyl-2-butene (563-79-1) + dimethyl acetylenedicarboxylate (762-42-5) → dimethyl-3,3,4-trimethyl-1,4-pentadiene-1,2-dicarboxylate (72163-16-7) + (E)-dihydro-3-carbomethoxymethylene-4,4,5,5-tetramethyl-2(3H)-furanone (72163-26-9) + (Z)-dihydro-3-carbomethoxymethylene-4,4,5,5-tetramethyl-2(3H)-furanone (72163-23-6) + 2-chlorodimethylmalonate (28868-76-0)

Guidance literature:

With aluminium trichloride; In dichloromethane; for 1.5h; Further byproducts given; Ambient temperature;

upstream raw materials:

malonic acid dimethyl ester

2-Chlor-3,3-dimethoxy-acrylsaeure-methylester

2,3-Dimethyl-2-butene

dimethyl acetylenedicarboxylate

Downstream raw materials:

(toluene-4-sulfonyl)-malonic acid dimethyl ester

dimethyl 2-fluoromalonate

2-(4-Hydroxy-3-methoxycarbonyl-phenoxy)-malonic acid dimethyl ester

2-(3-Carboxy-4-hydroxy-phenoxy)-malonic acid dimethyl ester

Refernces

• 1、 Nokami, Junzo,Mae, Masayuki,Fukutake, Satoshi,Ubuka, Tomoyuki,Yamada, Mitsuhiro. "Synthesis of 2'-deoxy-4'-C-hydroxymethyl-4'-thioribonucleosides and their 2',3'-dideoxy and 2',3'didehydro-2',3'-dideoxy analogues". body text. p. 1337 - 1360. Retrieved 2009/07/05.
• 2、 Hanson, Alfred W.,McCulloch, Archibald W.,McInnes, A. Gavin. "APPLICATIONS OF THE ENE REACTION. SYNTHESIS AND PROPPERTIES OF SUBSTITUTED &α-METHYLENE-&γ-LACTONES". . p. 288 - 301. Retrieved 2007/10/02.