(3As,5aR,6aR,6bS)-4-bromo-2,2-dimethyl-3a,5a,6a,6b-tetrahydrooxireno[2,3-g][1,3]benzodioxole

Base Information

• Chemical Name: (3As,5aR,6aR,6bS)-4-bromo-2,2-dimethyl-3a,5a,6a,6b-tetrahydrooxireno[2,3-g][1,3]benzodioxole
• CAS No.: 130669-74-8
• Molecular Formula: C9H11 Br O3
• Molecular Weight: 247.089
• DSSTox Substance ID: DTXSID30455882
• Nikkaji Number: J1.007.731A
• Wikidata: Q82278036
• Mol file: 130669-74-8.mol

Synonyms:130669-74-8;(3As,5aR,6aR,6bS)-4-bromo-2,2-dimethyl-3a,5a,6a,6b-tetrahydrooxireno[2,3-g][1,3]benzodioxole;DTXSID30455882;IJFOOAYHPAECGI-WCTZXXKLSA-N;AKOS015913657;[3aS-(3aalpha,5abeta,6abeta,6balpha)]-4-Bromo-3a,5a,6a,6b-tetrahydro-2,2-dimethyloxireno[e]-1,3-benzodioxole;J-005847;(3AS)-4-BROMO-3A,5A,6A,6B-TETRAHYDRO-2,2;2,2-Dimethyl-7-bromo-4alpha,5alpha-epoxy-3aalpha,4,5,7aalpha-tetrahydro-1,3-benzodioxole;(3aS,5aR,6aR,6bS)-4-Bromo-2,2-dimethyl-3a,5a,6a,6b-tetrahydro-2H-oxireno[e][1,3]benzodioxole;[3aS-(3aalpha,5abeta,6abeta,6balpha)]-4-Bromo-3a,5a,6a,6b-tetrahydro-2,2-dimethyloxireno[e]-1,3-benzodioxole, 98%

Chemical Property of (3As,5aR,6aR,6bS)-4-bromo-2,2-dimethyl-3a,5a,6a,6b-tetrahydrooxireno[2,3-g][1,3]benzodioxole

Chemical Property:

• Vapor Pressure: 0.003mmHg at 25°C
• Melting Point: 76-79 °C(lit.)
• Refractive Index: 1.55
• Boiling Point: 293.785°C at 760 mmHg
• Flash Point: 117.688°C
• PSA: 30.99000
• Density: 1.577g/cm³
• LogP: 1.56630
• Storage Temp.: ?20°C
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 245.98916
• Heavy Atom Count: 13
• Complexity: 287

Purity/Quality:

98%Min ^*data from raw suppliers

[3aS-(3aα,5aβ,6aβ,6bα)]-4-Bromo-3a,5a,6a,6b-tetrahydro-2,2-dimethyloxireno[e]-1,3-benzodioxole 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C3C(O3)C=C(C2O1)Br)C
• Isomeric SMILES: CC1(O[C@H]2[C@H]3[C@H](O3)C=C([C@H]2O1)Br)C

Technology Process of (3As,5aR,6aR,6bS)-4-bromo-2,2-dimethyl-3a,5a,6a,6b-tetrahydrooxireno[2,3-g][1,3]benzodioxole

There total 9 articles about (3As,5aR,6aR,6bS)-4-bromo-2,2-dimethyl-3a,5a,6a,6b-tetrahydrooxireno[2,3-g][1,3]benzodioxole 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: 95.0%

(3aS,7aS)-4-bromo-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole (130669-75-9) → (1S,2S,5R,6R)-3-bromo-5,6-epoxy-1,2-O-isopropylidencyclohex-3-en-1,2-diol (130669-74-8)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In chloroform; for 24h;

DOI:10.1016/S0040-4039(00)60978-4

Reference yield:

cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene (67451-62-1,82683-92-9,132958-32-8,130792-45-9) → (1S,2S,5R,6R)-3-bromo-5,6-epoxy-1,2-O-isopropylidencyclohex-3-en-1,2-diol (130669-74-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / p-TsOH / acetone / 0.5 h / 20 °C

2: 85 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 20 °C

With toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; acetone;

DOI:10.1016/j.tetasy.2006.01.024

Reference yield:

cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene (67451-62-1,82683-92-9,132958-32-8,130792-45-9) + acetone (67-64-1) → (1S,2S,5R,6R)-3-bromo-5,6-epoxy-1,2-O-isopropylidencyclohex-3-en-1,2-diol (130669-74-8)

Guidance literature:

cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene; acetone; With toluene-4-sulfonic acid; at 20 ℃; for 0.5h; Inert atmosphere;

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.2174/15701808113109990036

upstream raw materials:

(3aS,7aS)-4-bromo-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole

bromobenzene

cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene

acetone

Downstream raw materials:

(3aS,4R,5S,7aS)-7-bromo-3a,4,5,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-4,5-diol

(3aR,5aR,6aR,6bR)-2,2-dimethyl-3a,5a,6a,6b-tetrahydrooxireno-[2′,3′:3,4]benzo[1,2-d][1,3]dioxole

C₄₃H₅₂Br₄O₁₃

(3aS,4R,5S,7aS)-5-((3aS,4R,5S,7aS)-5-Benzyloxy-7-bromo-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-4-yloxy)-7-bromo-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-4-ol