cis-1,2-Cyclooctanediol

Base Information

• Chemical Name: cis-1,2-Cyclooctanediol
• CAS No.: 27607-33-6
• Molecular Formula: C8H16 O2
• Molecular Weight: 144.214
• Hs Code.: 2906199090
• European Community (EC) Number: 626-469-7
• DSSTox Substance ID: DTXSID501037225
• Nikkaji Number: J88.506A
• Wikidata: Q76416139
• Mol file: 27607-33-6.mol

Synonyms:cis-1,2-Cyclooctanediol;27607-33-6;Cis-cyclooctane-1,2-diol;1,2-Cyclooctanediol, (1R,2S)-rel-;(1R,2S)-CYCLOOCTANE-1,2-DIOL;cis-1,2-cyclo-octanediol;SCHEMBL371486;Cyclooctane-1alpha,2alpha-diol;cis-1,2-Cyclooctanediol, 99%;(1R,2S)-1,2-Cyclooctanediol;HUSOFJYAGDTKSK-OCAPTIKFSA-N;DTXSID501037225;(1R*,2S*)-1,2-Cyclooctanediol;MFCD00134226;AKOS015915801;AS-76775;CS-0160249;D81840;J-016823

Chemical Property of cis-1,2-Cyclooctanediol

Chemical Property:

• Vapor Pressure: 0.00134mmHg at 25°C
• Melting Point: 78-80 °C(lit.)
• Refractive Index: 1.501
• Boiling Point: 264.6°C at 760 mmHg
• PKA: 14.52±0.40(Predicted)
• Flash Point: 125.5°C
• PSA: 40.46000
• Density: 1.061g/cm³
• LogP: 1.06240
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 144.115029749
• Heavy Atom Count: 10
• Complexity: 81.3

Purity/Quality:

98%,99%, ^*data from raw suppliers

Cis-cyclooctane-1,2-diol 97% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-36/37-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCCC(C(CC1)O)O
• Isomeric SMILES: C1CCC[C@@H]([C@@H](CC1)O)O
• Uses: cis-1,2-Cyclooctanediol may be used in the preparation of suberic acid.

Technology Process of cis-1,2-Cyclooctanediol

There total 51 articles about cis-1,2-Cyclooctanediol 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: 90.0%

(1S,2S)-(Z)-cyclooct-5-ene-1,2-diol (69926-50-7) → (1S,2S)-cyclooctane-1,2-diol (4277-32-1,27607-33-6,42565-22-0,91049-46-6,108268-29-7,20480-40-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1248/cpb.46.17

Reference yield: 85.0%

cis-Cyclooctene (931-88-4,931-87-3,25267-51-0) → 1,8-octanedial (638-54-0) + (1R,2S)-Cyclooctane-1,2-diol (27607-33-6)

Guidance literature:

With cis-[Ru(1,4,7-trimethyl-1,4,7-triazacyclononane)O₂(trifluoroacetate)]ClO₄; In water; tert-butyl alcohol; at 20 ℃; for 14h;

DOI:10.1021/ja0528230

Reference yield: 83.0%

cis-Cyclooctene (931-88-4,931-87-3,25267-51-0) → (1R,2S)-Cyclooctane-1,2-diol (27607-33-6) + trans-1,2-cyclooctanediol (42565-22-0)

Guidance literature:

cis-Cyclooctene; With sodium periodate; acetic acid; lithium bromide; at 95 ℃; for 18h;

With potassium carbonate; In methanol; at 25 ℃; for 24h;

DOI:10.1021/ol052080n

upstream raw materials:

cis-Cyclooctene

1,8-octanedial

(1R*,2S*)-cyclooct-5-ene-1,2-diol

(E)-cyclooctene

Downstream raw materials:

octane-1,8-dioic acid

1,8-octanedial

cyclooctane-1,2-dione

1,2-cyclooctene

Refernces

• 1、 De Boer, Johannes W.,Brinksma, Jelle,Browne, Wesley R.,Meetsma, Auke,Alsters, Paul L.,Hage, Ronald,Feringa, Ben L.. "cis-Dihydroxylation and epoxidation of alkenes by [Mn2O(RCO 2)2(tmtacn)2]: Tailoring the selectivity of a highly H2O2-efficient catalyst". . p. 7990 - 7991. Retrieved 2005.
• 2、 Bjorkman, Kathryn R.,Schoenfeldt, Nicholas J.,Notestein, Justin M.,Broadbelt, Linda J.. "Microkinetic modeling of cis-cyclooctene oxidation on heterogeneous Mn-tmtacn complexes". . p. 17 - 25. Retrieved 2012.
• 3、 Ray, Rahul,Matteson, Donald S.. "OSMIUM TETROXIDE CATALYSED HYDROXYLATION OF HINTERED OLEFINS". . p. 449 - 450. Retrieved 1980.
• 4、 Chen, Kui,Costas, Miquel,Kim, Jinheung,Tipton, Adrianne K.,Que Jr., Lawrence. "Olefin cis-dihydroxylation versus epoxidation by non-heme iron catalysts: Two faces of an FeIII-OOH coin". . p. 3026 - 3035. Retrieved 2002.
• 5、 Bukowski, Michael R.,Comba, Peter,Lienke, Achim,Limberg, Christian,Lopez De Laorden, Carlos,Mas-Balleste, Ruben,Merz, Michael,Que Jr., Lawrence. "Catalytic epoxidation and 1,2-dihydroxylation of olefins with bispidine-iron(II)/H2O2 systems". . p. 3446 - 3449. Retrieved 2006.
• 6、 Makino, Kazuishi,Nojima, Shinya,Shimada, Naoyuki,Urata, Sari. "An Efficient Deprotection of 2,6-Bis(trifluoromethyl)phenylboronic Esters via Catalytic Protodeboronation Using Tetrabutyl ammonium Fluoride". supporting information. p. 2300 - 2304. Retrieved 2019/12/11.
• 7、 Borrell, Margarida,Costas, Miquel. "Mechanistically Driven Development of an Iron Catalyst for Selective Syn-Dihydroxylation of Alkenes with Aqueous Hydrogen Peroxide". supporting information. p. 12821 - 12829. Retrieved 2017/09/25.