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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:
53716-82-8
Molecular Weight:
128.13
UNSPSC Code:
12191600
NACRES:
NA.21

Quality Level

100

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

, 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

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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.
2. Alternative to DMF in the synthesis of metal-organic frameworks.
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

Other Notes

To see other BioRenewable or Greener Solvents

Legal Information

CYRENE is a trademark of Circa Group Pvt Ltd

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

807796-2.5L:
807796-4L:
807796-200L:
807796-100ML:
807796-18L:
807796-VAR:
807796-1L:
807796-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT5129
MKCW5129
MKCV9484
MKCT3563
MKCS4896

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Dihydrolevoglucosenone (Cyrene) as a bio-based alternative for dipolar aprotic solvents
Sherwood, J., et al.
Chemical Communications (Cambridge, England), 50, 9650-9652 (2014)
Kirsty L Wilson et al.
Beilstein journal of organic chemistry, 12, 2005-2011 (2016-11-11)
Pd-catalysed C-C bond formation is an essential tool within the pharmaceutical and agrochemical industries. Many of these reactions rely heavily on polar aprotic solvents; however, despite their utility, these solvents are incompatible with the drive towards more sustainable chemical synthesis.
Kirsty L Wilson et al.
Organic & biomolecular chemistry, 16(16), 2851-2854 (2018-04-10)
Amide bonds are one of the underpinning linkages in all living systems and are fundamental within drug discovery. Current methods towards their synthesis frequently rely on the use of dipolar aprotic solvents; however, due to increasingly stringent regulations and growing
Improved 2-pyridyl reductive homocoupling reaction using biorenewable solvent Cyrene?(dihydrolevoglucosenone)
Webb DA. et al.
RSC Sustainability, 1, 1522-1529 (2023)
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
View All Related Papers

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Greener Alternatives Evaluation Matrix

Green chemicals evaluation aligns with the 12 Principles of Green Chemistry, emphasizing resource efficiency and hazard reduction.

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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