TRIETHYL 3-METHYL-4-PHOSPHONOCROTONATE

Base Information

• Chemical Name: TRIETHYL 3-METHYL-4-PHOSPHONOCROTONATE
• CAS No.: 41891-54-7
• Molecular Formula: C11H21 O5 P
• Molecular Weight: 264.259
• Hs Code.: 2931900090
• Mol file: 41891-54-7.mol

Synonyms:Crotonicacid, 3-methyl-4-phosphono-, triethyl ester (7CI);Diethyl3-ethoxycarbonyl-2-methyl-2-propenyl phosphonate;Triethyl3-methyl-4-phosphono-2-butenoate;Triethyl 3-methyl-4-phosphonocrotonate;Triethyl 4-phosphono-3-methyl-2-butenoate;

Chemical Property of TRIETHYL 3-METHYL-4-PHOSPHONOCROTONATE

Chemical Property:

• Appearance/Colour: Clear Colourless to Pale Yellow Oil
• Vapor Pressure: 6.2E-05mmHg at 25°C
• Refractive Index: n20/D 1.46
• Boiling Point: 345.3°Cat760mmHg
• Flash Point: 176.4°C
• PSA: 71.64000
• Density: 1.083g/cm³
• LogP: 2.76190
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Ethyl Acetate

Purity/Quality:

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

Triethyl3-Methyl-4-phosphono-2-butenoate(~90%) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Triethyl 3-Methyl-4-phosphono-2-butenoate is used in the synthesis of potent insect growth regulators. Also used in the synthesis of retinoic acids. This compound is an E/Z mixture.

Technology Process of TRIETHYL 3-METHYL-4-PHOSPHONOCROTONATE

There total 4 articles about TRIETHYL 3-METHYL-4-PHOSPHONOCROTONATE 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: 100.0%

ethyl (E)-4-bromo-3-methyl-2-butenoate (51318-62-8) + triethyl phosphite (122-52-1) → diethyl 3-(ethoxycarbonyl)-3-methylprop-2-en-yl phosphate (41891-54-7)

Guidance literature:

for 1h; Reflux; Inert atmosphere;

DOI:10.1021/acs.joc.1c00946

Reference yield: 65.0%

ethyl 4-bromo-3-methylcrotonate (51318-62-8,51371-55-2,26918-14-9) + triethyl phosphite (122-52-1) → triethyl 3-methyl-4-phosphonocrotonate (39760-56-0,3917-43-9,41891-54-7)

Guidance literature:

DOI:10.1007/BF00953422

Reference yield:

ethyl 4-bromo-3-methylcrotonate (51318-62-8,51371-55-2,26918-14-9) + triethyl phosphite (122-52-1) → diethyl 3-(ethoxycarbonyl)-3-methylprop-2-en-yl phosphate (41891-54-7) + ethyl (Z)-4-(diethylphosphono)-3-methyl-2-butenoate

Guidance literature:

at 95 - 120 ℃; for 3h;

upstream raw materials:

ethyl (E)-4-bromo-3-methyl-2-butenoate

triethyl phosphite

ethyl 4-bromo-3-methylcrotonate

diethyl trimethylsilyl phosphate

Downstream raw materials:

ethyl (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate

ethyl 3-methyl-4-cyclohexylidenebut-2-enoate

(2Z,4E,6Z)-ethyl 8-(2'-isopropyl-3'-methyl-2'-cyclohexen-1'-ylidene)-3,7-dimethyl-2,4,6-octatrienoate

(2E,4E,6Z)-ethyl 8-(2'-isopropyl-3'-methyl-2'-cyclohexen-1'-ylidene)-3,7-dimethyl-2,4,6-octatrienoate

Refernces

• 1、 Narayanasamy, Sureshbabu,Sun, Jian,Pavlovicz, Ryan E.,Eroglu, Abdulkerim,Rush, Cassandra E.,Sunkel, Benjamin D.,Li, Chenglong,Harrison, Earl H.,Curley, Robert W.. "Synthesis of apo-13- and apo-15-lycopenoids, cleavage products of lycopene that are retinoic acid antagonists". . p. 1021 - 1029. Retrieved 2017/05/17.
• 2、 Atigadda, Venkatram R.,Xia, Gang,Deshpande, Anil,Wu, Lizhi,Kedishvili, Natalia,Smith, Craig D.,Krontiras, Helen,Bland, Kirby I.,Grubbs, Clinton J.,Brouillette, Wayne J.,Muccio, Donald D.. "Conformationally Defined Rexinoids and Their Efficacy in the Prevention of Mammary Cancers". . p. 7763 - 7774. Retrieved 2015/10/20.