1,2,3,4,5,7-Hexachloro-2-(dichloromethyl)-6,6-dimethylbicyclo[3.1.1]heptane

Base Information

• Chemical Name: 1,2,3,4,5,7-Hexachloro-2-(dichloromethyl)-6,6-dimethylbicyclo[3.1.1]heptane
• CAS No.: 84227-47-4
• Molecular Formula: C15H23 N O3
• Molecular Weight: 265.353
• DSSTox Substance ID: DTXSID60274462
• ChEMBL ID: CHEMBL1321008
• Mol file: 84227-47-4.mol

Synonyms:84227-47-4;1,2,3,4,5,7-hexachloro-2-(dichloromethyl)-6,6-dimethylbicyclo[3.1.1]heptane;KBio3_002011;Spectrum_001953;SpecPlus_000592;Spectrum2_001892;Spectrum3_000866;Spectrum4_000706;Spectrum5_002054;BSPBio_002511;KBioGR_001231;KBioSS_002507;SPECTRUM330079;DivK1c_006688;SPBio_001824;CHEMBL1321008;KBio1_001632;KBio2_002499;KBio2_005067;KBio2_007635;DTXSID60274462;CCG-39359;NCGC00094550-01;NCGC00094550-02;NCGC00094550-03

Chemical Property of 1,2,3,4,5,7-Hexachloro-2-(dichloromethyl)-6,6-dimethylbicyclo[3.1.1]heptane

Chemical Property:

• Vapor Pressure: 5.75E-06mmHg at 25°C
• Refractive Index: n20/D 1.524
• Boiling Point: 140 °C0.05 mm Hg(lit.)
• Flash Point: 111°C
• PSA: 30.93000
• Density: 1.085 g/mL at 20 °C(lit.)
• LogP: 1.48990
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 413.823172
• Heavy Atom Count: 18
• Complexity: 384

Purity/Quality:

99% ，98% ^*data from raw suppliers

1-BENZYL-1-AZA-12-CROWN-4 95 ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2(C(C(C(C1(C2Cl)Cl)(C(Cl)Cl)Cl)Cl)Cl)Cl)C

Technology Process of 1,2,3,4,5,7-Hexachloro-2-(dichloromethyl)-6,6-dimethylbicyclo[3.1.1]heptane

There total 3 articles about 1,2,3,4,5,7-Hexachloro-2-(dichloromethyl)-6,6-dimethylbicyclo[3.1.1]heptane 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: 71.0%

N-benzyl-diethanolamine (101-32-6) + diethylene glycol ditosylate (7460-82-4) → 10-benzyl-1,4,7-trioxa-10-azacyclododecane (84227-47-4)

Guidance literature:

With tetrabutylammomium bromide; lithium chloride; sodium hydroxide; In water; benzene; at 70 ℃; for 25h; Reagent/catalyst;

DOI:10.1134/S1070428012100156

Reference yield: 54.0%

1,11-diiodo-3,6-9-trioxaundecane (36839-56-2) + benzylamine (100-46-9) → 10-benzyl-1,4,7-trioxa-10-azacyclododecane (84227-47-4)

Guidance literature:

With sodium carbonate; In acetonitrile; for 18h; Heating;

DOI:10.1021/jo00382a028 DOI:10.1021/jo00259a008

Reference yield:

Tetraethylene glycol (112-60-7) → 10-benzyl-1,4,7-trioxa-10-azacyclododecane (84227-47-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / thionyl chloride / pyridine / Ambient temperature

2: NaI / acetone / 70 h / Heating

3: 54 percent / Na₂CO₃ / acetonitrile / 18 h / Heating

With thionyl chloride; sodium carbonate; sodium iodide; In pyridine; acetone; acetonitrile;

upstream raw materials:

1,11-diiodo-3,6-9-trioxaundecane

benzylamine

Tetraethylene glycol

N-benzyl-diethanolamine

Downstream raw materials:

1,4,7-trioxa-10-azacyclododecane

N-(2-nitrobenzyl)monoaza-12-crown-4

10-methyl-1,4,7-trioxa-10-azacyclododecane

Refernces

• 1、 Arnold, Kristin A.,Mallen, Jesus,Trafton, John E.,White, Banita D.,Fronczek, Frank R.,et al.. "Ring-Side-Arm Cooperativity in Cation Inclusion Complexes of 12-Membered Ring Lariat Ethers: Effect of Side-Arm Chain Length and a Clarification of Long-Side-Arm Binding Strengths". . p. 5652 - 5657. Retrieved 2007/10/02.
• 2、 Sakamoto, Hidefumi,Kimura, Keiichi,Koseki, Yasuaki,Matsuo, Mitsunori,Shono, Toshiyuki. "Lipophilic Bis(monoaza crown ether) Derivatives: Synthesis and Cation-Complexing Properties". . p. 4974 - 4979. Retrieved 2007/10/02.