(1,4,5,6,7,7-Hexachlorobicyclo[2.2.1]hept-5-en-2-yl)methyl acetate

Base Information

• Chemical Name: (1,4,5,6,7,7-Hexachlorobicyclo[2.2.1]hept-5-en-2-yl)methyl acetate
• CAS No.: 1085-62-7
• Molecular Formula: C₁₀H₈Cl₆O₂
• Molecular Weight: 372.89
• NSC Number: 80509
• DSSTox Substance ID: DTXSID80292143
• Mol file: 1085-62-7.mol

Synonyms:1085-62-7;(1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hept-5-en-2-yl)methyl acetate;NSC80509;DTXSID80292143;NSC-80509

Chemical Property of (1,4,5,6,7,7-Hexachlorobicyclo[2.2.1]hept-5-en-2-yl)methyl acetate

Chemical Property:

• Vapor Pressure: 9.67E-06mmHg at 25°C
• Boiling Point: 372.4°Cat760mmHg
• Flash Point: 142.2°C
• Density: 1.66g/cm³
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 371.862596
• Heavy Atom Count: 18
• Complexity: 448

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1CC2(C(=C(C1(C2(Cl)Cl)Cl)Cl)Cl)Cl

Technology Process of (1,4,5,6,7,7-Hexachlorobicyclo[2.2.1]hept-5-en-2-yl)methyl acetate

There total 6 articles about (1,4,5,6,7,7-Hexachlorobicyclo[2.2.1]hept-5-en-2-yl)methyl acetate 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: 81.0%

rac-((1R,2S,4S)-1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hept-5-en-2-yl)methanol (1080-25-7,17280-40-9,64577-08-8) + acetyl chloride (75-36-5) → (+/-)-2-endo-acetoxymethyl-1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hept-5-ene (1085-62-7,57413-45-3)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 17h;

DOI:10.1016/j.tetasy.2005.06.014

Reference yield:

rac-((1R,2S,4S)-1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hept-5-en-2-yl)methanol (1080-25-7,17280-40-9,64577-08-8) + acetic anhydride (108-24-7) → (+/-)-2-endo-acetoxymethyl-1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hept-5-ene (1085-62-7,57413-45-3)

Guidance literature:

With benzene;

DOI:10.1021/ja01621a082

Reference yield:

hexachlorocyclopentadiene (77-47-4) → (+/-)-2-endo-acetoxymethyl-1,4,5,6,7,7-hexachlorobicyclo[2.2.1]hept-5-ene (1085-62-7,57413-45-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / hydroquinone / 4 h / 145 °C

2: 81 percent / pyridine / CH₂Cl₂ / 17 h / 20 °C

With pyridine; hydroquinone; In dichloromethane; 1: Diels-Alder reaction;

DOI:10.1016/j.tetasy.2005.06.014

upstream raw materials:

5-hydroxymethyl-1,2,3,4,7,7-hexachlorobicyclo<2.2.1>hept-2-ene

acetic acid

Allyl acetate

hexachlorocyclopentadiene

Downstream raw materials:

(-)-(1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl methanol