2,2,6-Trimethyl-4H-1,3-dioxin-4-one

HCID 79368

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

2,2,6-Trimethyl-4H-1,3-dioxin-4-one5394-63-82,2,6-Trimethyl-1,3-dioxin-4-oneMFCD000404682,2,6-trimethyl-2,4-dihydro-1,3-dioxin-4-one4H-1,3-Dioxin-4-one, 2,2,6-trimethyl-NSC-23912,2,6-Trimethyl-1,3-dioxen-4-one2,2,6-trimethyl-[1,3]dioxin-4-oneDiketene Acetone Adduct;Benidipine Impurity 16NSC2391
Show more names
TKDDiketton Acetone AdductDIKETENE ACETONE ADDUCT2,2,6-TrimethyL-4H-1,3-dioxin-4-oneDIKETE ACETONE ADDUCT2,2,6-Trimethyl-4H-1,3-dioxin-Trimethyl-(4H)-1,3-dioxin-4-one
EINECS 226-403-3EC 226-403-3PET49NW99ASCHEMBL218538DTXSID10202230NSC 2391AKOS000120979CS-W016430

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

Experimental & physicochemical properties

Physical DescriptionClear dark brown liquid; mp = 12-13 deg C; [Sigma-Aldrich MSDS]

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

Safety & regulation

GHS classification

GHS Classification · 5 items

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 · 2 items

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

Hazards SummaryContains 5-10% acetone (CAS# 67-64-1); Causes no skin and moderate eye irritation in rabbits; Targets the liver and kidney; [Sigma-Aldrich MSDS] See delta-Undecalactone and Dimethoxane.
Hazard Classes and CategoriesFlam. Liq. 2 (100%);Eye Irrit. 2A (98.4%)

Regulatory information

Regulatory Information · 2 items

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

Chemistry & industry

Applications · 3 items

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.

Suppliers100 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
湖北永阔科技有限公司027-59223108 15972152991 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]

Related reactions

63 records

Compound notes

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