Basic information
- CAS
5394-63-8- Standard SMILES
CC1=CC(=O)OC(C)(C)O1- InChIKey
XFRBXZCBOYNMJP-UHFFFAOYSA-N- Molecular formula
- C7H10O3
- Average molar mass
- 142.15 g/mol
- Monoisotopic mass
- 142.06299418
Names & identifiers
- Preferred name
- 2,2,6-Trimethyl-4H-1,3-dioxin-4-one
- IUPAC
- 2,2,6-trimethyl-1,3-dioxin-4-one
- English name
- 2,2,6-Trimethyl-4H-1,3-dioxin-4-one
- Molecular formula
- C7H10O3
- Molecular weight
- 142.15
Names & synonyms
Show more names
Database identifiers
- CAS
5394-63-8- PubChem CID
- 79368
- DTXSID
DTXSID10202230- UNII
- PET49NW99A
- EC Number
- 226-403-3
- Nikkaji
- J209.020A
Properties
Computed structural properties
- XLogP
- 1.2
- Topological polar surface area
- 35.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 191
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 12 · 12-13 °C(lit.)
- Boiling point
- 275 °C · ~275 °C(lit.)
- Density
- 1.07 g/mL · 1.07 g/mL at 25 °C(lit.)
- refractive index
- 20 · n20/D 1.460(lit.)
- Flash point
- 67 °F · 67 °F
- storage temp.
- 2 · 2-8°C
- solubility
- water: insoluble
- form
- Liquid
- color
- Dark brown
- Water Solubility
- practically insoluble
- BRN
- 2408 · 2408
- Exposure limits
- 250 ppm; · ACGIH: TWA 250 ppm; STEL 500 ppmOSHA: TWA 1000 ppm(2400 mg/m3)NIOSH: IDLH 2500 ppm; TWA 250 ppm(590 mg/m3)
- InChI
- InChI=1S/C7H10O3/c1-5-4-6(8)10-7(2,3)9-5/h4H,1-3H3
- InChIKey
- XFRBXZCBOYNMJP-UHFFFAOYSA-N
- SMILES
- O1C(C)=CC(=O)OC1(C)C
- CAS DataBase Reference
- 5394 · 5394-63-8(CAS DataBase Reference)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02,GHS07
- Signal word
- Danger
- Hazard statements
- 225 · H225-H319
- Precautionary statements
- 210 · P210-P305+P351+P338
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- F,Xi
- Risk Statements
- 11 · 11-36/37/38-36
- Safety Statements
- 16 · 16-26-27-36/37/39-9-33
- RIDADR
- 1993 · UN 1993 3/PG 2
- WGK Germany
- 3 · 3
- HazardClass
- 3 · 3
- PackingGroup
- II
- HS Code
- 29329995 · 29329995
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 2 Flam · Eye Irrit. 2Flam. Liq. 2
- REACH Registrations
- Active
- Limited Quantities
- 1 L · 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
Danger
H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids];H319 (98.4%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
P210, P233, P240, P241, P242, P243, P264+P265, P280, P303+P361+P353, P305+P351+P338, P337+P317, P370+P378, P403+P235, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 62 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Regulatory Information
Chemical: 4H-1,3-Dioxin-4-one, 2,2,6-trimethyl-
Status: Active Update: 04-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/16365
Regulatory information
Regulatory Information
Chemical: 4H-1,3-Dioxin-4-one, 2,2,6-trimethyl-
Status: Active Update: 04-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/16365
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- ridadr
- UN 1993 3/PG 2
- hs_code
- 29329995
- risk_code
- 11-36/37/38-36
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07
- hazard_code
- F,Xi
- safety_code
- 16-26-27-36/37/39-9-33
- hazard_class
- 3
- Storage Class
- 3 - Flammable liquids
- packing_group
- II
- Hazard statements
- H225-H319
- Limited Quantities
- 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- REACH Registrations
- Active
- Hazard Classifications
- Eye Irrit. 2Flam. Liq. 2
- Precautionary statements
- P210-P305+P351+P338
Chemistry & industry
Applications
DescriptionIt is usually used as intermediate or raw material in the chemistry synthesis. For example, 2,2,6-Trimethyl-4H-1,3-dioxin-4-one can act as the starting material to produce N-alkenyl acetoacetamides through reaction with imines.1 This substance can also be involved in the preparation of acetoacetamide derivatives, which result in the formation of the pyrrole amides via oxime of the acetoacetamides.2 Moreover, this chemical may be introduced to promote the acetoacetylation of O-(hydroxypropyl)cellulose for generating O-(acetoxypropyl)cellulose.3 In addition, this chemical may be used to yield β-keto esters and β-ketoamides through the reaction with secondary or tertiary alcohols (including chiral ones) or primary or secondary amines.4
UsesDiketene-Acetone Adduct can be used in place of diketene in many reactions. As a transportable form of diketene, it is especially important in those countries, where the transportation of diketene is not allowed or at least not desired.
Uses2,2,6-Trimethyl-1,3-dioxin-4-one is used in the synthesis of dihydropyrimininones as picomolar sodium iodide symporter inhibitors. It is also used in the synthesis of resorcinol amide Hsp90 Inhibitor AT13387. It is used in the synthesis of acetylketene by flash pyrolysis.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
Related reactions
Compound notes
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