807796
Cyrene™
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
, 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 "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).
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:
1. Dispersive ability for graphene solutions.
2. Alternative to DMF in the 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.
- 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
CYRENE is a trademark of Circa Group Pvt Ltd
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Product No.
Description
Pricing
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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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
Structure-reactivity correlations of the abnormal Beckmann reaction of dihydrolevoglucosenone oxime.
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
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
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