2-(4-BROMOPHENYL)-PROPANEDIOIC ACID, 1,3-MDIETHYL ESTER

Base Information

• Chemical Name: 2-(4-BROMOPHENYL)-PROPANEDIOIC ACID, 1,3-MDIETHYL ESTER
• CAS No.: 149506-35-4
• Molecular Formula: C11H11 Br O4
• Molecular Weight: 287.11
• Mol file: 149506-35-4.mol

Synonyms:Propanedioicacid, (4-bromophenyl)-, dimethyl ester (9CI); 2-(4-Bromophenyl)malonic aciddimethyl ester; Dimethyl (4-bromophenyl)malonate

Chemical Property of 2-(4-BROMOPHENYL)-PROPANEDIOIC ACID, 1,3-MDIETHYL ESTER

Chemical Property:

• Boiling Point: 330.0±27.0 °C(Predicted)
• PKA: 11.03±0.46(Predicted)
• PSA: 52.60000
• Density: 1.467±0.06 g/cm3(Predicted)
• LogP: 1.87870

Purity/Quality:

99%, ^*data from raw suppliers

Dimethyl(4-Bromophenyl)malonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Dimethyl (4-Bromophenyl)malonate is a useful synthetic intermediate in the synthesis of Macitentan (M105005); an orally active, potent dual endothelin receptor antagonist used for pulmonary arterial hypertension.

Technology Process of 2-(4-BROMOPHENYL)-PROPANEDIOIC ACID, 1,3-MDIETHYL ESTER

There total 6 articles about 2-(4-BROMOPHENYL)-PROPANEDIOIC ACID, 1,3-MDIETHYL ESTER 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: 79.0%

(4-bromo-phenyl)-acetic acid methyl ester (41841-16-1) + carbonic acid dimethyl ester (616-38-6) → 2-(4-bromophenyl)-malonic acid dimethyl ester (149506-35-4)

Guidance literature:

(4-bromo-phenyl)-acetic acid methyl ester; With sodium hydride; In tetrahydrofuran; mineral oil; at 40 - 45 ℃; for 5h;

carbonic acid dimethyl ester; In tetrahydrofuran; mineral oil; at 20 - 32 ℃; for 24h;

DOI:10.1021/jm3009103

Reference yield: 40.0%

dimethyl diazomalonate (6773-29-1) + 4-Bromophenylboronic acid (5467-74-3) → C11H10BrFO4 + 2-(4-bromophenyl)-malonic acid dimethyl ester (149506-35-4)

Guidance literature:

With (pentamethylcyclopentadienyl)*Rh(OAc)2; potassium carbonate; N-fluorobis(benzenesulfon)imide; In N,N-dimethyl acetamide; at 40 ℃; for 16h; Reagent/catalyst; Solvent; Temperature;

DOI:10.1039/c8ob02801j

Reference yield:

2-(4-bromophenyl)-acetic acid (1878-68-8) → 2-(4-bromophenyl)-malonic acid dimethyl ester (149506-35-4)

Guidance literature:

Multi-step reaction with 3 steps

1: SOCl₂, DMF / CH₂Cl₂ / Ambient temperature

2: Et₃N / CH₂Cl₂ / 2 h / Ambient temperature

3: 1.) LDA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 deg C, 40 min

With thionyl chloride; triethylamine; N,N-dimethyl-formamide; lithium diisopropyl amide; In dichloromethane;

DOI:10.1002/(SICI)1099-1344(199605)38:5<425::AID-JLCR860>3.0.CO;2-B

upstream raw materials:

(4-bromo-phenyl)-acetic acid methyl ester

methyl chloroformate

2-(4-bromophenyl)acetyl chloride

2-(4-bromophenyl)-acetic acid

Downstream raw materials:

methyl 4-(4'-bromophenyl)-4,4-dimethoxycarbonylbutanoate

2-(4-bromophenyl)propane-1,3-diol

5-(4-bromophenyl)-4,6-dihydroxypyrimidine

2-(4-bromophenyl)propanedioic acid

Refernces

• 1、 Jagtap, Kunal M.,Niphade, Navnath C.,Gaikwad, Chandrashekhar T.,Shinde, Gorakshanath B.,Toche, Raghunath B.,Joshi, Divyesh R.,Mathad, Vijayavitthal T.. "Improved and single-pot process for the synthesis of macitentan, an endothelin receptor antagonist, via lithium amide-mediated nucleophilic substitution". . p. 653 - 661. Retrieved 2018/03/09.
• 2、 -. "Preparation method of 5-(4-bromophenyl)-4,6-dichloropyrimidine". . . Retrieved 2019/01/08.