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.
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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/418/501/product-dating-information-06-25-mk.pdf
807796
Cyrene™
BioRenewable, DMF and NMP Substitute
Synonym(s):
Dihydrolevoglucosenone
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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
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
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This Item | 920207 | 911046 | 920193 |
|---|---|---|---|
| assay ≥98.5% (GC) | assay - | assay ≥99.5% | assay - |
| technique(s) : 0.5% using Water (by Karl Fischer) | technique(s) - | technique(s) - | technique(s) - |
| Quality Level 100 | Quality Level - | Quality Level 200 | Quality Level - |
| form liquid | form liquid | form liquid | form liquid |
| density 1.25 g/mL | density 1.141 g/mL | density 1.25 g/mL (lit.) | density 1.153 g/mL |
| bp 227 °C | bp - | bp 182 °C/20 mmHg (lit.) | bp - |
General description
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
1. Dispersive ability for graphene solutions.[1]
2. Alternative to DMF in the synthesis of metal-organic frameworks.[2]
3. Organic synthesis:
- Cacchi-type annulation
- Synthesis of urea
- HATU Amide Coupling - Replacement for DMF in amide and dipeptide coupling reactions[3].
- Suzuki-Miyaura coupling reaction.
- Sonogashira coupling reaction.
- Reductive homocoupling reaction.
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
Signal Word
Warning
Hazard Statements
Precautionary 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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The 4L M-Bottle provides safe handling of solvents due to an innovative solvent bottle design with sealing technology to eliminate leaks and reduce risks in solvent dispensing.
Green chemicals evaluation aligns with the 12 Principles of Green Chemistry, emphasizing resource efficiency and hazard reduction.
Pourquoi devrait-on choisir entre solvants écologiques et solvants fiables ? Nous vous proposons les deux à la fois grâce à nos solutions biorenouvelables et plus écologiques. Le solvant Cyrene™ est une nouvelle alternative aprotique dipolaire aux solvants courants frappés par la restriction REACH, tels que la N-méthyl-2-pyrrolidone (NMP) et le diméthylformamide (DMF).
Acta Interactive Archive Vol 51
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How can I determine the shelf life / expiration / retest date of this product?
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How is shipping temperature determined? And how is it related to the product storage temperature?
1 answer-
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
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Could you provide information on whether Cyrene has any softening or solubilizing effects on ABS and PET-G plastics?
1 answer-
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/S2352554121002187Helpful?
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What is the recommended operating temperature for stripping photoresist on Silicon or GaAs semiconductor wafers when using Cyrene?
1 answer-
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.
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Why should you use BioRenewable solvents?
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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.
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Do BioRenewable solvents have a similar quality to petroleum-based solvents?
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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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What is a BioRenewable solvent?
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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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