Dimethyl isopropylidenemalonate

Base Information

• Chemical Name: Dimethyl isopropylidenemalonate
• CAS No.: 22035-53-6
• Molecular Formula: C8H12O4
• Molecular Weight: 172.181
• Hs Code.: 2917190090
• European Community (EC) Number: 820-678-9
• DSSTox Substance ID: DTXSID70409041
• Nikkaji Number: J1.017.550J
• Wikidata: Q72470732
• Mol file: 22035-53-6.mol

Synonyms:dimethyl isopropylidenemalonate;22035-53-6;Dimethyl 2-(propan-2-ylidene)malonate;Dimethyl 2-propan-2-ylidenepropanedioate;1,3-dimethyl 2-(propan-2-ylidene)propanedioate;MFCD00517665;2-propan-2-ylidenepropanedioic acid dimethyl ester;dimethylisopropylidenemalonate;dimethyl isopropylidenemalonate;Propanedioic acid, (1-methylethylidene)-, dimethyl ester;SCHEMBL4824220;DTXSID70409041;QJASGQYZCPDCJR-UHFFFAOYSA-N;AC7750;AKOS001632546;Dimethyl (propan-2-ylidene)propanedioate;AS-60869;SY024179;CS-0155169;FT-0654357;EN300-185743;A815855

Chemical Property of Dimethyl isopropylidenemalonate

Chemical Property:

• Boiling Point: 178.9 °C at 760 mmHg
• Flash Point: 75.8 °C
• PSA: 52.60000
• Density: 1.07 g/cm³
• LogP: 0.66880
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: Acetone, Chloroform, Dichloroemethane, Ethyl Acetate
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 172.07355886
• Heavy Atom Count: 12
• Complexity: 205

Purity/Quality:

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

DimethylIsopropylidenemalonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=C(C(=O)OC)C(=O)OC)C
• Uses: Dimethyl Isopropylidenemalonate can be prepared to use as inhibitors of indoleamine 2,?3-?dioxygenase to treat cancer.

Technology Process of Dimethyl isopropylidenemalonate

There total 7 articles about Dimethyl isopropylidenemalonate 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: 65.0%

acetone (67-64-1) + malonic acid dimethyl ester (108-59-8) → dimethyl isopropylidenemalonate (22035-53-6)

Guidance literature:

With acetic anhydride; zinc(II) chloride; for 25h; Heating;

Reference yield: 25.0%

methanol (67-56-1) + 3-diazo-5,5-dimethyl-[3H,5H]furan-2,4-dione → dimethyl isopropylidenemalonate (22035-53-6) + (±)-3-carbomethoxy-4,4-dimethyloxetan-2-one (129249-51-0)

Guidance literature:

In dichloromethane; at 0 ℃; for 12h; Irradiation;

DOI:10.1055/s-0032-1316860

Reference yield:

malonic acid dimethyl ester (108-59-8) → dimethyl isopropylidenemalonate (22035-53-6)

Guidance literature:

Zinc chloride; In acetic anhydride; acetone;

upstream raw materials:

acetone

malonic acid dimethyl ester

propene

dimethyl malonate sodium salt

Downstream raw materials:

2,6,6-Trimethyl-cyclohex-3-ene-1,1-dicarboxylic acid dimethyl ester

(2R,5S)-2,5,6,6-Tetramethyl-cyclohex-3-ene-1,1-dicarboxylic acid dimethyl ester

2-[(2E,4E,6E)-1,5-Dimethyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-2,4,6-trien-(E)-ylidene]-malonic acid monomethyl ester

2-(Isopropylidene)-1,3-propanediol

Refernces

• 1、 Gao, Min,Gong, Xiangnan,Hu, Lin,Luo, Yanshu,Xia, Yuanzhi,Xu, Qianlan,Zhao, Yukun. "A Unified Catalytic Asymmetric (4+1) and (5+1) Annulation Strategy to Access Chiral Spirooxindole-Fused Oxacycles". supporting information. p. 19813 - 19820. Retrieved 2021/08/03.
• 2、 Couladouros, Elias A.,Dakanali, Marianna,Demadis, Konstantinos D.,Vidali, Veroniki P.. "A short biomimetic approach to the fully functionalized bicyclic framework of type A acylphloroglucinols". supporting information; experimental part. p. 4430 - 4433. Retrieved 2009/12/24.