cis-1,2-Cyclopentanediol

Base Information

• Chemical Name: cis-1,2-Cyclopentanediol
• CAS No.: 5057-98-7
• Molecular Formula: C5H10O2
• Molecular Weight: 102.133
• Hs Code.: 29061900
• DSSTox Substance ID: DTXSID80964792
• Nikkaji Number: J80.946B
• Wikidata: Q27451766
• ChEMBL ID: CHEMBL399324
• Mol file: 5057-98-7.mol

Synonyms:cis-1,2-Cyclopentanediol;5057-98-7;(1r,2s)-Cyclopentane-1,2-Diol;cis-Cyclopentane-1,2-diol;(1S,2R)-cyclopentane-1,2-diol;1,2-Cyclopentanediol, cis-;cis-1,2-cyclopentandiol;1,2-cis-cyclopentanediol;cis-1,2-cyclopen-tanediol;Cis-Cyclopenten-1,2-diol;SCHEMBL359648;1alpha,2alpha-Cyclopentanediol;CHEMBL399324;(1R,2S)-1,2-cyclopentanediol;DTXSID80964792;cis-1,2-Cyclopentanediol, 98%;1,2-Cyclopentanediol, (1R,2S)-;MFCD00134192;rel-(1R,2S)-1,2-Cyclopentanediol;AKOS015855422;AS-82910;CS-0132323;E81580;EN300-7237727;Q27451766;17Y

Chemical Property of cis-1,2-Cyclopentanediol

Chemical Property:

• Appearance/Colour: colourless liquid or white solid
• Vapor Pressure: 0.0304mmHg at 25°C
• Melting Point: 24-28 °C(lit.)
• Refractive Index: 1.477-1.479
• Boiling Point: 216.4 °C at 760 mmHg
• PKA: 14.48±0.40(Predicted)
• Flash Point: 112.8 °C
• PSA: 40.46000
• Density: 1.235g/cm³
• LogP: -0.10790
• Storage Temp.: 0-6°C
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 102.068079557
• Heavy Atom Count: 7
• Complexity: 55.1

Purity/Quality:

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

cis-1,2-Dihydroxycyclopentane ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(C(C1)O)O
• Isomeric SMILES: C1C[C@H]([C@H](C1)O)O

Technology Process of cis-1,2-Cyclopentanediol

There total 62 articles about cis-1,2-Cyclopentanediol 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: 92.0%

(3aR,6aS)-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-2-one (87057-82-7) → cis-1,2-cyclopentanediol (5057-98-7,86703-52-8)

Guidance literature:

With water; sodium hydroxide; In methanol; at 20 ℃;

DOI:10.1002/anie.201406645

Reference yield: 90.0%

2-(2,6-bis(trifluoromethyl)phenyl)tetrahydro-4H-cyclopenta[d][1,3,2]dioxaborole → cis-1,2-cyclopentanediol (5057-98-7,86703-52-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.5h; Reflux;

DOI:10.1055/s-0039-1690236

Reference yield: 85.0%

Triisopropyl-[(3aR,6aS)-1-(tetrahydro-cyclopenta[1,3]dioxol-2-yl)methyl]-silane (908586-10-7) → cis-1,2-cyclopentanediol (5057-98-7,86703-52-8)

Guidance literature:

With lithium tetrafluoroborate; In acetonitrile; at 70 ℃; for 19h;

DOI:10.1016/j.tetlet.2006.05.121

upstream raw materials:

(+/-)-cis-Cyclopent-3-ene-1,2-diol

(+/-)-cis-1-acetoxy-2-hydroxycyclopentane

trans-1,2-dibromocyclopentane

silver(I) acetate

Downstream raw materials:

2ξ-phenoxy-(3ar,6ac)-tetrahydro-cyclopenta[1,3,2]dioxaphosphole

(2S)-2-hydroxycyclopentan-1-one

cis-2-hydroxycyclopentyl 4-toluenesulfonate

Glutaraldehyde

Refernces

• 1、 Macmillan, David W. C.,Oswood, Christian J.. "Selective Isomerization via Transient Thermodynamic Control: Dynamic Epimerization of trans to cis Diols". supporting information. p. 93 - 98. Retrieved 2022/01/03.
• 2、 Zhang, Yan,Yao, Peiyuan,Cui, Yunfeng,Wu, Qiaqing,Zhu, Dunming. "One-Pot Enzymatic Synthesis of Cyclic Vicinal Diols from Aliphatic Dialdehydes via Intramolecular C?C Bond Formation and Carbonyl Reduction Using Pyruvate Decarboxylases and Alcohol Dehydrogenases". supporting information. p. 4191 - 4196. Retrieved 2018/09/25.