trans-1,2-Cyclopentanediol

Base Information

• Chemical Name: trans-1,2-Cyclopentanediol
• CAS No.: 5057-99-8
• Molecular Formula: C5H10O2
• Molecular Weight: 102.133
• Hs Code.: 2906190090
• European Community (EC) Number: 225-757-6,829-081-8
• NSC Number: 15389
• DSSTox Substance ID: DTXSID80923980,DTXSID501311584
• Nikkaji Number: J384.067K
• Wikidata: Q76085860
• Mol file: 5057-99-8.mol

Synonyms:5057-99-8;trans-1,2-Cyclopentanediol;trans-Cyclopentane-1,2-diol;(1r,2r)-cyclopentane-1,2-diol;930-46-1;(1R)-TRANS-1,2-CYCLOPENTANEDIOL;(+/-)-trans-1,2-Cyclopentanediol;(1R,2R)-trans-1,2-Cyclopentanediol;(1R,2R)-1,2-Cyclopentanediol;1,2-Cyclopentanediol, (1R,2R)-rel-;1,2-Cyclopentanediol, trans-;(1R,2R)-rel-Cyclopentane-1,2-diol;86703-52-8;(1~{r},2~{r})-Cyclopentane-1,2-Diol;1,2-Cyclopentanediol #;1,2-trans-cyclopentanediol;EINECS 225-757-6;MFCD00082582;(trans)-cyclopentane-1,2-diol;NSC15389;AI3-26281;SCHEMBL594229;Cyclopentane-1beta,2alpha-diol;DTXSID80923980;DTXSID501311584;AMY19937;AC7934;MFCD00082580;NSC-15389;AKOS015913325;rac-(1R,2R)-cyclopentane-1,2-diol;CS-W005508;AS-48726;(+/-)-trans-1,2-Cyclopentanediol, 97%;EN300-254263;EN300-254982;F52991;6VV

Chemical Property of trans-1,2-Cyclopentanediol

Chemical Property:

• Appearance/Colour: off-white crystalline powder
• Vapor Pressure: 0.0304mmHg at 25°C
• Melting Point: 54-56 °C(lit.)
• Refractive Index: 1.
• Boiling Point: 216.4 °C at 760 mmHg
• PKA: 14.48±0.40(Predicted)
• Flash Point: 112.7 °C
• PSA: 40.46000
• Density: 1.235 g/cm³
• LogP: -0.10790
• Storage Temp.: 2-8°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:

97% ^*data from raw suppliers

(1R,2R)-rel-trans-1,2-Cyclopentanediol ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Alcohols and Polyols, Other
• Canonical SMILES: C1CC(C(C1)O)O
• Isomeric SMILES: C1C[C@H]([C@@H](C1)O)O
• Uses: (1R,2R)-rel-trans-1,2-Cyclopentanediol is a building block for the synthesis of chiral phosphine ligands. It can also be used to prepare benzoquinolines and benzoindoles via heterocyclization of naphthylamines with diols catalyzed by iridium chloride/BINAP

Technology Process of trans-1,2-Cyclopentanediol

There total 25 articles about trans-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: 98.0%

Cyclopentene oxide (285-67-6) → trans-cyclopentane-1,2-diol (5057-99-8,86703-52-8)

Guidance literature:

With water; tetra(n-butyl)ammonium hydrogensulfate; at 20 - 45 ℃;

DOI:10.1039/b301081c

Reference yield: 95.7%

cyclopentene (142-29-0) → trans-cyclopentane-1,2-diol (5057-99-8,86703-52-8)

Guidance literature:

With dihydrogen peroxide; toluene-4-sulfonic acid; In water; at 50 ℃; for 21h; Sealed flask;

DOI:10.1002/adsc.201100187

Reference yield: 60.0%

cyclopentene (142-29-0) + tert-butyl alcohol (75-65-0) → trans-cyclopentane-1,2-diol (5057-99-8,86703-52-8) + Glutaraldehyde (111-30-8,29257-65-6,79215-57-9) + trans-2-tert-butoxycyclopentanol

Guidance literature:

With dihydrogen peroxide; tungsten(VI) oxide; silica gel; In tert-butyl alcohol; at 34.85 ℃; for 24h; Further Variations:; Catalysts; Solvents; Product distribution;

DOI:10.1006/jcat.2001.3319

upstream raw materials:

cyclopentane-1,2-dione

1,2-dibromo-cyclopentane

(+/-)-trans-cyclopentene-⁽¹⁾-diol-(3.4)

trans-1,2-dibromocyclopentane

Downstream raw materials:

(1R,2R)-cyclopentane-1,2-diol

(S,S)-cyclopentane-1,2-diol

(R)-2-hydroxycyclopentanone

trans-1,2-cyclopentanediol phenylboronic ester

Refernces

• 1、 Wang, Tianmiao,Tamura, Masazumi,Nakagawa, Yoshinao,Tomishige, Keiichi. "Preparation of Highly Active Monometallic Rhenium Catalysts for Selective Synthesis of 1,4-Butanediol from 1,4-Anhydroerythritol". . p. 3615 - 3626. Retrieved 2019/07/15.
• 2、 Rosatella, Andreia A.,Afonso, Carlos A.M.. "Bronsted acid-catalyzed dihydroxylation of olefins in aqueous medium". supporting information; experimental part. p. 2920 - 2926. Retrieved 2012/01/03.