[2-(Bromomethyl)-2-methyl-3-methylidenecyclopentyl]acetic acid

Base Information

• Chemical Name: [2-(Bromomethyl)-2-methyl-3-methylidenecyclopentyl]acetic acid
• CAS No.: 98049-45-7
• Molecular Formula: C₁₀H₁₅BrO₂
• Molecular Weight: 247.132
• DSSTox Substance ID: DTXSID60406069
• Mol file: 98049-45-7.mol

Synonyms:98049-45-7;SCHEMBL6053900;DTXSID60406069;2(BROMOMETHYL)-2-METHYL-3-METHYLENECYCLOPENTANEACETIC ACID;AKOS002735551;[2-(Bromomethyl)-2-methyl-3-methylidenecyclopentyl]acetic acid

Chemical Property of [2-(Bromomethyl)-2-methyl-3-methylidenecyclopentyl]acetic acid

Chemical Property:

• Vapor Pressure: 2.41E-05mmHg at 25°C
• Refractive Index: 1.527
• Boiling Point: 334.6°C at 760 mmHg
• Flash Point: 156.1°C
• PSA: 37.30000
• Density: 1.37g/cm³
• LogP: 2.82850
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 246.02554
• Heavy Atom Count: 13
• Complexity: 237

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(CCC1=C)CC(=O)O)CBr

Technology Process of [2-(Bromomethyl)-2-methyl-3-methylidenecyclopentyl]acetic acid

There total 5 articles about [2-(Bromomethyl)-2-methyl-3-methylidenecyclopentyl]acetic acid 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: 98.0%

(+)-endo-9,10-dibromocamphor (85706-53-2,85719-17-1,91928-01-7) → (1'R,2'R)-2-(2'-bromomethyl-2'-methyl-3'-methylenecyclopentyl)ethanoic acid (98049-45-7)

Guidance literature:

With potassium hydroxide; In water; dimethyl sulfoxide; for 1h; KOH/THF;

Reference yield: 94.0%

(1S)-9,10-dibromocamphor (85706-53-2) → (1'R,2'R)-2-(2'-bromomethyl-2'-methyl-3'-methylenecyclopentyl)ethanoic acid (98049-45-7)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; for 4.5h; Ambient temperature;

Reference yield:

(1R)-3-endo-bromocamphor (10293-06-8) → (1'R,2'R)-2-(2'-bromomethyl-2'-methyl-3'-methylenecyclopentyl)ethanoic acid (98049-45-7)

Guidance literature:

Multi-step reaction with 4 steps

1: bromine / chlorosulfonic acid / 1 h / first in an ice bath then without it

2: bromine / chlorosulfonic acid / 144 h / in the dark; the reagents were added in three portions

3: 55 percent Chromat_. / zinc / diethyl ether; acetic acid / 0.75 h / 0 °C / addition of zinc over 20 min at 0 deg C (care!)

4: 94 percent / 0.5 N KOH / tetrahydrofuran / 4.5 h / Ambient temperature

With potassium hydroxide; bromine; zinc; In tetrahydrofuran; chlorosulfonic acid; diethyl ether; acetic acid;

upstream raw materials:

(+)-endo-9,10-dibromocamphor

(1S)-9,10-dibromocamphor

(1R)-3-endo-bromocamphor

3-endo-9-dibromo-1,7,7-trimethylbicyclo<2.2.1>heptan-2-one

Downstream raw materials:

4-Bromo-benzoic acid 2-((1R,2R,4R)-1-methyl-5-oxo-bicyclo[2.1.1]hex-2-yl)-ethyl ester

Refernces

• 1、 Hutchinson, John H.,Money, Thomas. "A formal enantiospecific synthesis of California red scale pheromone". . p. 3182 - 3185. Retrieved 2007/10/02.