(1R,2R)-rel-1,2-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexane

Base Information

• Chemical Name: (1R,2R)-rel-1,2-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexane
• CAS No.: 1218790-09-0
• Molecular Formula: C₁₈H₃₄B₂O₄
• Molecular Weight: 336.088
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID50682259
• Wikidata: Q82606572
• Mol file: 1218790-09-0.mol

Synonyms:1218790-09-0;(1R,2R)-rel-1,2-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexane;trans-Cyclohexane-1,2-diboronic acid, pinacol ester;4,4,5,5-tetramethyl-2-[(1R,2R)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexyl]-1,3,2-dioxaborolane;(1r,2r)-1,2-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexane;trans-Cyclohexane-1,2-diboronic acid,pinacol ester;DTXSID50682259;SFKOPBKHPOIHAU-ZIAGYGMSSA-N;MFCD13195762;AKOS016001175;BS-21146;CS-0175492;2,2'-[(1R,2R)-Cyclohexane-1,2-diyl]bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Chemical Property of (1R,2R)-rel-1,2-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexane

Chemical Property:

• PSA: 36.92000
• LogP: 4.48520
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 336.2643199
• Heavy Atom Count: 24
• Complexity: 413

Purity/Quality:

98%min ^*data from raw suppliers

trans-Cyclohexane-1,2-diboronicAcidPinacolEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2CCCCC2B3OC(C(O3)(C)C)(C)C
• Isomeric SMILES: B1(OC(C(O1)(C)C)(C)C)[C@@H]2CCCC[C@H]2B3OC(C(O3)(C)C)(C)C

Technology Process of (1R,2R)-rel-1,2-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexane

There total 20 articles about (1R,2R)-rel-1,2-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexane 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: 84.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 2,2'-bis(1,3,2-benzodioxaborole) (13826-27-2) + trans-1,2-dibromocyclohexane (7429-37-0) → (1R,2S)-1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexane (1416899-54-1,1218790-09-0)

Guidance literature:

2,2'-bis(1,3,2-benzodioxaborole); trans-1,2-dibromocyclohexane; With tetrabutylammonium tetrafluoroborate; In N,N-dimethyl acetamide; at 25 ℃; for 0.316667h; Electrolysis; Inert atmosphere;

2,3-dimethyl-2,3-butane diol; With triethylamine; In N,N-dimethyl acetamide; at 25 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jacs.1c06473

Reference yield: 65.0%

bis(pinacol)diborane (73183-34-3) + cyclohexene (110-83-8) → 1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexane (1325218-41-4,1218790-09-0)

Guidance literature:

With methanol; sodium t-butanolate; In tetrahydrofuran; at 70 ℃; for 16h; Inert atmosphere;

DOI:10.1002/anie.201101941

Reference yield: 65.0%

bis(pinacol)diborane (73183-34-3) + cyclohexene (110-83-8) → (1R,2S)-1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexane (1416899-54-1,1218790-09-0)

Guidance literature:

With chloro(1,5-cyclooctadiene)rhodium(I) dimer; In cyclohexane; at 70 ℃; for 16h; chemoselective reaction; Inert atmosphere;

DOI:10.1039/c2dt31659e

upstream raw materials:

bis(pinacol)diborane

cyclohexene

2,3-dimethyl-2,3-butane diol

1-bromocyclohexane

Downstream raw materials:

cis-1,2-cyclohexane

(1S,2S)-trans-1,2-Cyclohexanediol

(1R,2R)-trans-1,2-cyclohexanediol

anti-cyclohexane-1,2-diyldimethanol

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