5057-99-8

Basic information

• Product Name: (+/-)-TRANS-1,2-CYCLOPENTANEDIOL
• Synonyms: (+/-)-TRANS-1,2-CYCLOPENTANEDIOL;TRANS-1,2-CYCLOPENTANEDIOL;1,2-Cyclopentanediol;trans-cyclopentane-1,2-diol;Cyclopentane-1,2-diol;trans-Cyclopentanediol-1,2;rel-(1R*,2R*)-1,2-Cyclopentanediol;rel-(1S*,2S*)-Cyclopentane-1,2-diol
• CAS NO: 5057-99-8
• Molecular Formula: C₅H₁₀O₂
• Molecular Weight: 102.13
• EINECS: 225-757-6
• Product Categories: Organic Building Blocks;Oxygen Compounds;Polyols
• Mol File: 5057-99-8.mol
• Article Data: 22

Chemical Properties

• Melting Point: 54-56 °C(lit.)
• Boiling Point: 136 °C21.5 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: off-white crystalline powder
• Density: 1.235
• Vapor Pressure: 0.0304mmHg at 25°C
• Refractive Index: 1.
• Storage Temp.: 2-8°C
• PKA: 14.48±0.40(Predicted)
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: (+/-)-TRANS-1,2-CYCLOPENTANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-TRANS-1,2-CYCLOPENTANEDIOL(5057-99-8)
• EPA Substance Registry System: (+/-)-TRANS-1,2-CYCLOPENTANEDIOL(5057-99-8)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 3-4.3-10
• Hazardous Substances Data: 5057-99-8(Hazardous Substances Data)

Usage

Chemical Properties

off-white crystalline powder

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

InChI:InChI=1/C5H10O2/c6-4-2-1-3-5(4)7/h4-7H,1-3H2

Upstream product

• 3008-40-0 cyclopentane-1,2-dione 
• 285-67-6 Cyclopentene oxide 
• 99440-98-9 2-hydroxycyclopentanone 
• 67-56-1 methanol 
• 120640-00-8 (+/-)-(trans-2-hydroxy-cyclopentyl)-trimethyl-ammonium; iodide 
• 96-41-3 Cyclopentanol 
• 5057-98-7 cis-1,2-cyclopentanediol 
• 287-92-3 Cyclopentane 
• 542-92-7 cyclopenta-1,3-diene 
• 142-29-0 cyclopentene 
• 75-65-0 tert-butyl alcohol 
• 111-30-8 Glutaraldehyde 
• 7722-84-1 dihydrogen peroxide 
• 67-64-1 acetone 

Downstream Products

• 930-46-1 (1R,2R)-cyclopentane-1,2-diol 
• 63261-45-0 (S,S)-cyclopentane-1,2-diol 
• 99493-88-6 (R)-2-hydroxycyclopentanone 
• 7462-36-4 trans-1,2-cyclopentanediol phenylboronic ester 
• 1365970-45-1 (S)-2-(((((1R,2R)-2-(allyloxy)cyclopentyloxy)carbonyl)amino)-3,3-dimethylbutyric acid) 
• 20520-67-6 trans-2-acetoxycyclopentanol 
• 147333-12-8 (2S)-2-hydroxycyclopentan-1-one 
• 2206-54-4 trans-1,2-(diphenylcarbonyloxy)cyclopentane 
• 110-94-1 1,5-pentanedioic acid 
• 110-15-6 succinic acid 
• 124-38-9 carbon dioxide 

Relevant articles and documents

Photo-Induced Dihydroxylation of Alkenes with Diacetyl, Oxygen, and Water

Herein reported is a photo-induced production of vicinal diols from alkenes under mild reaction conditions. The present dihydroxylation method using diacetyl (= butane-2,3-dione), oxygen, and water dispenses with toxic reagents and intractable waste generation.

Selective transition-metal-free vicinal cis-dihydroxylation of saturated hydrocarbons

A transition-metal-free cis-dihydroxylation of saturated hydrocarbons under ambient reaction conditions has been developed. The described approach allows a direct and selective synthesis of vicinal diols. The new reaction thereby proceeds via radical iodination and a sequence of oxidation steps. A broad scope of one-pot dual C(sp3)-H bond functionalization for the selective synthesis of vicinal syn-diols was demonstrated.

Hot water-promoted ring-opening of epoxides and aziridines by water and other nucleopliles

Effective hydrolysis of epoxides and aziridines was conducted by heating them in water at 60 or 100 °C. Other types of nucleophile such as amines, sodium azide, and thiophenol could also efficiently open epoxides and aziridines in hot water. It was proposed that hot water acted as a modest acid catalyst, reactant, and solvent in the hydrolysis reactions.