MilliporeSigma
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807796

Sigma-Aldrich

Cyrene

greener alternative

BioRenewable

Synonym(s):
Dihydrolevoglucosenone
Empirical Formula (Hill Notation):
C6H8O3
CAS Number:
Molecular Weight:
128.13
NACRES:
NA.21

Quality Level

assay

≥98.5% (GC)

form

liquid

greener alternative product characteristics

Safer Solvents and Auxiliaries
Use of Renewable Feedstocks
Learn more about the Principles of Green Chemistry.

technique(s)

: 0.5% using Water (by Karl Fischer)

bp

227 °C

mp

-18 °C

density

1.25 g/mL

greener alternative category

Aligned

InChI

1S/C6H8O3/c7-5-2-1-4-3-8-6(5)9-4/h4,6H,1-3H2/t4-,6+/m0/s1

InChI key

WHIRALQRTSITMI-UJURSFKZSA-N

General description

We are committed to bringing you greener alternative products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product is biorenewable and thus aligns with ″Safer Solvents and Auxiliaries″ and ″Use of Renewable Feedstocks″. Click Dihydrolevoglucosenone (Cyrene) as a bio-based alternative for dipolar aprotic solvents for more information.

Cyrene is a biobased dipolar, safe for end-of-life disposal, decomposing into CO2 and H2O. It is an aprotic alternative to common solvents that are of environmental concern. Cyrene is an alternative for many solvents classified by REACH as Substances of Very High Concern (SVHC), such as N-Methylpyrrolidone (NMP) and N,N-Dimethylformamide (DMF).

Application

Cyrene has been applied in replacement of NMP and/or DMF in some applications, such as demonstrating to exceed NMP′s dispersive ability for graphene solutions due to its optimum polarity and high viscosity, creating larger and less defective graphene flakes. Find below more uses for Cyrene.

1. Dispersive ability for graphene solutions.
2. Alternative to DMF in synthesis of metal-organic frameworks.
3. Organic synthesis:
  • Cacchi-type annulation
  • Synthesis of urea
  • HATU Amide Coupling - Replacement for DMF in amide and dipeptide coupling reactions.
  • Suzuki-Miyaura coupling reaction.
  • Sonogashira coupling reaction.

Packaging

1, 2.5 L in glass bottle
100 mL in glass bottle

Features and Benefits

  • 99% biodegradation in 28 days
  • Stable during incineration
  • Not mutagenic or genotoxic
  • ASTM D6866 - Standard Test Methods for Determining the Biobased Content
  • Made from Renewable Resource − Cellulose

Legal Information

CYRENE is a trademark of Circa Group Pvt Ltd

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

226.4 °F - closed cup

Flash Point(C)

108 °C - closed cup

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

  1. What is a BioRenewable solvent?

    BioRenewable solvents are sourced from renewable and sustainable biobased materials, such as soy/palm oil, wood waste, hay or corn byproducts, etc. It is important to highlight that our BioRenewable products do not compete with food production.

  2. Why should you use BioRenewable solvents?

    You will contribute to create a sustainable world, significantly lowering environmental impact. Biorenewable solvents also decrease petroleum sources dependency, have higher recovery rates, and/or are safer for handling and disposal.

  3. Do BioRenewable solvents have a similar quality to petroleum-based solvents?

    BioRenewable solvents can have the same or higher purity level compared to traditional solvents. These solvents are free of the many byproducts of petroleum manufacturing, such as benzene, aldehydes, and ethers.

Jason E Camp
ChemSusChem, 11(18), 3048-3055 (2018-07-26)
The development of green solvents is one of the key tenets of Green Chemistry as solvents account for the majority of waste stemming from the production of the chemicals on which we have all come to rely. An important class
Christian Grune et al.
Journal of pharmaceutical sciences, 110(2), 959-964 (2020-12-05)
Toxic and environmental harmful organic solvents are widely applied to prepare poly(lactic-co-glycolic acid) (PLGA)-based nanoparticles (NP) in standard preparation methods. Alternative non-toxic solvents suffer from disadvantages like high viscosity and plasticizing effects. To overcome these hurdles, Cyrene™ as a new
James Sherwood et al.
Chemical communications (Cambridge, England), 50(68), 9650-9652 (2014-07-10)
Dihydrolevoglucosenone (Cyrene) is a bio-based molecule, derived in two simple steps from cellulose, which demonstrates significant promise as a dipolar aprotic solvent. The dipolarity of dihydrolevoglucosenone is similar to NMP, DMF and sulpholane. Dihydrolevoglucosenone demonstrates similar performance to NMP in
Scope and limitations of a DMF bio-alternative within Sonogashira cross-coupling and Cacchi-type annulation
Wilson, K.L., et al.
Beilstein Journal of Organic Chemistry, 12, 2005-2011 (2016)
Amani Alhifthi et al.
Organic & biomolecular chemistry, 15(47), 10105-10115 (2017-11-25)
A structural, spectroscopic and computational study of a series of oximes was undertaken to investigate how geometric and structural changes relevant to the reaction coordinate for the Beckmann reaction (normal Beckmann) and Beckmann fragmentation (abnormal Beckmann) manifest in the ground

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Biorenewable Solvents

Why should you have to choose between solvents that are ecological and those that are reliable? Enjoy both at once with our biorenewable and greener solutions. Cyrene™ solvent is a new dipolar aprotic alternative to common REACH restricted solvents, such as N methyl-2-pyrrolidone (NMP) and Dimethylformamide (DMF).

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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