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Sigma-Aldrich

Cyrene™

greener alternative
Cyrene™

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
MDL number:
MFCD23105760
UNSPSC Code:
12191600
NACRES:
NA.21
Assay:
≥98.5% (GC)
technique(s):
: 0.5% using Water (by Karl Fischer)
bp:
227 °C
Pricing and availability is not currently available.

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

SMILES string

O1[C@H]2OC[C@@H]1CCC2=O

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

Related Categories

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

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX0521
MKCW5129
MKCT5129
MKCV9484
MKCT3563

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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
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2 Reviews This action will navigate to reviews.

Questions

1–7 of 7 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

      Helpful?

  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

      Helpful?

  3. Could you provide information on whether Cyrene has any softening or solubilizing effects on ABS and PET-G plastics?

    1 answer

    1. Unfortunately, the compatibility of Cyrene (Dihydrolevoglucosenone) with materials such as ABS and PET-G has not been investigated. This compound is known to dissolve a number of polymeric materials. Please see the link below to review a publication that may be helpful:
      https://www.sciencedirect.com/science/article/pii/S2352554121002187

      Helpful?

  4. What is the recommended operating temperature for stripping photoresist on Silicon or GaAs semiconductor wafers when using Cyrene?

    1 answer

    1. It is known that research is currently underway in this area and Cyrene™ has shown promise. However, due to the confidential nature of these processes, a specific recommended operating temperature cannot be provided. Nevertheless, it's worth noting that the safe operating temperature of neat Cyrene™ is below 140 °C. It is advisable for the user to conduct additional safety checks and tests for their specific application.

      Helpful?

  5. What is a BioRenewable solvent?

    1 answer

    1. 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.

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  6. Why should you use BioRenewable solvents?

    1 answer

    1. 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.

      Helpful?

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

    1 answer

    1. 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.

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Reviews

Active Filters

  1. Oslo
    • Review 1
    • Votes 30
    5 out of 5 stars.

    Cyrene as a polar solvent

    We have used Cyrene as a replacement solvent to DMSO and it has worked very good. It dissolves all of the reagents very well, and the resulting product is very similar. There is some odor to it, but as long as you work in a fume hood it is not a problem.

    Helpful?

  2. 1 Ratings-Only Review

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