2,2-Dibromocyclopropanecarboxylic acid

Base Information

• Chemical Name: 2,2-Dibromocyclopropanecarboxylic acid
• CAS No.: 5365-17-3
• Molecular Formula: C4H4 Br2 O2
• Molecular Weight: 243.883
• NSC Number: 143379
• DSSTox Substance ID: DTXSID90301437,DTXSID70900967
• Nikkaji Number: J1.246.730C
• Mol file: 5365-17-3.mol

Synonyms:2,2-dibromocyclopropanecarboxylic acid;5365-17-3;2,2-dibromocyclopropane-1-carboxylic acid;NSC143379;NoName_12;SCHEMBL11817472;DTXSID70900967;DTXSID90301437;NSC-143379;2,2-dibromocyclopropane carboxylic acid;EN300-50411;Z600508418

Chemical Property of 2,2-Dibromocyclopropanecarboxylic acid

Chemical Property:

• Vapor Pressure: 0.000226mmHg at 25°C
• Boiling Point: 302.7°Cat760mmHg
• Flash Point: 136.9°C
• Density: 2.632g/cm³
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 243.85576
• Heavy Atom Count: 8
• Complexity: 132

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C1(Br)Br)C(=O)O

Technology Process of 2,2-Dibromocyclopropanecarboxylic acid

There total 6 articles about 2,2-Dibromocyclopropanecarboxylic 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: 91.0%

2,2-dibromocyclopropane-1-methanol (22084-99-7) → 2,2-dibromocyclopropane-1-carboxylic acid (5365-17-3)

Guidance literature:

With potassium permanganate; tetrabutylammomium bromide; In water; benzene; at 0 ℃; for 16h;

DOI:10.1002/(SICI)1522-2675(20000315)83:3<571::AID-HLCA571>3.0.CO;2-M

Reference yield: 49.0%

1,1-dibromo-2-vinylcyclopropane (5398-65-2) → 2,2-dibromocyclopropane-1-carboxylic acid (5365-17-3)

Guidance literature:

With potassium permanganate; sulfuric acid; water; cetyltrimethylammonim bromide; acetic acid; In dichloromethane; at 5 ℃; for 4h; Inert atmosphere;

Reference yield: 26.0%

1,1-dibromo-2-butylcyclopropane (5398-70-9) → 2,2-dibromocyclopropane-1-carboxylic acid (5365-17-3) + (2,2-dibromocyclopropyl)acetic acid + 1-(2,2-dibromocyclopropyl)-butan-1-one

Guidance literature:

With chromium(VI) oxide; acetic acid; at 30 - 31 ℃; for 1h;

DOI:10.1016/j.tet.2004.02.024

upstream raw materials:

1,1-dibromo-2-vinylcyclopropane

2,2-dibromocyclopropane-1-methanol

1,1-dibromo-2-butylcyclopropane

Downstream raw materials:

(1SR,2RS)-2-bromocyclopropanecarboxylic acid

Refernces

• 1、 Al-Dulayymi, Ahmad,Li, Xiaoming,Neuenschwander, Markus. "Synthesis of novel precursors of calicene and 7-methylcalicene". . p. 571 - 582. Retrieved 2000.
• 2、 Nizovtsev, Alexey V.,Baird, Mark S.,Bolesov, Ivan G.. "Unusual selectivity in the oxidative functionalization of gem-dibromocyclopropanes". . p. 3717 - 3729. Retrieved 2007/10/03.