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807796

Sigma-Aldrich

Cyrene

greener alternative

BioRenewable, DMF and NMP Substitute

Synonym(s):

Dihydrolevoglucosenone

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About This Item

Empirical Formula (Hill Notation):
C6H8O3
CAS Number:
Molecular Weight:
128.13
UNSPSC Code:
12191600
NACRES:
NA.21

Quality Level

Assay

≥98.5% (GC)

form

liquid

greener alternative product characteristics

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

sustainability

Greener Alternative Product

technique(s)

: 0.5% using Water (by Karl Fischer)

bp

227 °C

mp

-18 °C

density

1.25 g/mL

greener alternative category

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 "Designing Safer Chemicals", ″Safer Solvents and Auxiliaries″ and ″Use of Renewable Feedstocks″. Click here 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.[1]
2. Alternative to DMF in the synthesis of metal-organic frameworks.[2]
3. Organic synthesis:

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


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    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
    Kewen Pan et al.
    Nature communications, 9(1), 5197-5197 (2018-12-07)
    Printed electronics offer a breakthrough in the penetration of information technology into everyday life. The possibility of printing electronic circuits will further promote the spread of the Internet of Things applications. Inks based on graphene have a chance to dominate
    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
    Cyrene? blends: a greener solvent system for organic syntheses
    Sullivan C, et al.
    Green Chemistry, 24, 7184-7193 (2022)
    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

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