Dimethadione supplier | CasNO.695-53-4

Name
5,5-Dimethyloxazolidine-2,4-dione
EINECS 211-781-4
CAS No. 695-53-4
Article Data20
CAS DataBase
Density 1.204 g/cm³
Solubility
Melting Point 77-80 °C(lit.)
Formula C₅H₇NO₃
Boiling Point 137 °C / 6mmHg
Molecular Weight 129.115
Flash Point 44.2oC
Transport Information
Appearance white crystalline powder
Safety 22-36-24/25-23-36/37-26
Risk Codes 20/21/22-40-33-36/37/38
Molecular Structure
Hazard Symbols Xn, Xi
Synonyms AC 1198;5,5-Dimethyloxazolidinedione;5,5-Dimethyl-2,4-oxazolidinedione;5,5-Dimethyl-1,3-oxazolidine-2,4-dione;Nortrimethadione;NSC 30152;Dimethadion;DMO;BAY 1400Z;BAX1400Z;Eupractone;
PSA 55.40000
LogP 0.36020

Synthetic route

: 80-55-7
ethyl 2-hydroxy-2,2-dimethylethanoate

: 3019-71-4
Trichloroacetyl isocyanate

: 695-53-4
dimethadione

Conditions

Conditions	Yield
Stage #1: ethyl 2-hydroxy-2,2-dimethylethanoate; Trichloroacetyl isocyanate In dichloromethane at 0 - 20℃; Stage #2: With triethylamine In ethanol Reflux;	72%

: 6453-39-0
5,5-dimethyl-2-thioxo-4-oxazolidinone

: 623-81-4
diethyl sulphite

A: 695-53-4
dimethadione

B: 17994-46-6
3-ethyl-5,5-dimethyl-2-thioxo-oxazolidin-4-one

Conditions

Conditions	Yield
With potassium carbonate; acetone

...Expand

: 6453-39-0
5,5-dimethyl-2-thioxo-4-oxazolidinone

: 695-53-4
dimethadione

Conditions

Conditions	Yield
With water; lead acetate
With water; bromine; potassium bromide

: 141-52-6
sodium ethanolate

: 57-13-6
urea

: 80-55-7
ethyl 2-hydroxy-2,2-dimethylethanoate

: 695-53-4
dimethadione

...Expand

: 57-13-6
urea

: 80-55-7
ethyl 2-hydroxy-2,2-dimethylethanoate

: 695-53-4
dimethadione

Conditions

Conditions	Yield
With sodium ethanolate

: 26212-62-4
5,5-dimethyl-4-p-tolylimino-oxazolidin-2-one

: 695-53-4
dimethadione

Conditions

Conditions	Yield
With hydrogenchloride In ethanol for 10h; Heating;

: 127-48-0
trimethadione

: 695-53-4
dimethadione

Conditions

Conditions	Yield
metabolism study in epileptic fowl;
With human liver microsomes In various solvent(s) at 37℃; for 0.333333h; Enzyme kinetics; N-demethylation; Enzymatic reaction;

: 77626-29-0
4-(tert-Butylimino)-5,5-dimethyloxazolidin-2-on

: 695-53-4
dimethadione

Conditions

Conditions	Yield
With oxonium

: 1189-71-5
isocyanate de chlorosulfonyle

: 75-86-5
2-hydroxy-2-methylpropanenitrile

: 695-53-4
dimethadione

Conditions

Conditions	Yield
With hydrogenchloride; triethylamine 1a) benzene, r.t., 1 h, 1b) reflux, 3 h, 2) EtOH, reflux, 6 h; Yield given. Multistep reaction;
Product distribution; multistep reaction; other cyanohydrins;

acetonylsulfocarbaminate: acetonylsulfocarbaminate

: 695-53-4
dimethadione

Conditions

Conditions	Yield
With silver nitrate
With lead(IV) tetraacetate

: 77609-28-0
(α-bromo-isobutyryl)-carbamic acid ethyl ester

: 695-53-4
dimethadione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) PCl5 2: petroleum ether; CHCl3 / Heating 3: H3O(1+) View Scheme

: 77609-26-8
[2-Bromo-1-tert-butylamino-2-methyl-prop-(E)-ylidene]-carbamic acid ethyl ester

: 695-53-4
dimethadione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: petroleum ether; CHCl3 / Heating 2: H3O(1+) View Scheme

: 26212-60-2
(2-ethoxy-5,5-dimethyl-oxazol-4-ylidene)-p-tolyl-amine

: 695-53-4
dimethadione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: AcOH / acetone / 3 h / Ambient temperature 2: aq. HCl / ethanol / 10 h / Heating View Scheme

: 2110-78-3
methyl 2-hydroxy-2-methylpropionate

: 57-13-6
urea

: 695-53-4
dimethadione

Conditions

Conditions	Yield
With sodium methylate In methanol

: 695-53-4
dimethadione

: 2495-35-4
benzylacrylate

: 1076230-05-1
benzyl 3-(5,5-dimethyl-2,4-dioxo-1,3-oxazolidin-3-yl)propanoate

Conditions

Conditions	Yield
With pyridine In water at 20℃; for 22h; Heating / reflux;	100%

: 695-53-4
dimethadione

: 7417-21-2
2-(3,4-dimethoxyphenyl)ethyl alcohol

: 86970-73-2
3-<2-(3,4-dimethoxyphenyl)ethyl>-5,5-dimethyloxazolidine-2,4-dione

Conditions

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃;	99%
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran for 14h; Ambient temperature;	70%

: 695-53-4
dimethadione

: 612-23-7
2-nitrobenzyl chloride

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 907994-44-9
5,5-dimethyl-3-(2-nitrobenzyl)oxazolidine-2,4-dione

Conditions

Conditions	Yield
With potassium carbonate In hexane; water	93%

...Expand

: 695-53-4
dimethadione

: 612-23-7
2-nitrobenzyl chloride

: 907994-44-9
5,5-dimethyl-3-(2-nitrobenzyl)oxazolidine-2,4-dione

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 2h;	93%

: 695-53-4
dimethadione

: 108805-12-5
3'-(Dimethylamino)spiroazirin>

: 131842-37-0
4-(Dimethylamino)-1-(2-hydroxy-2-methylpropanoyl)-1,3-diazaspiro<4.4>non-3-en-2-on

Conditions

Conditions	Yield
In acetonitrile for 120h; Ambient temperature;	88%

: 695-53-4
dimethadione

: 54856-83-6
3-dimethylamino-2,2-dimethyl-2H-azirine

: 117460-19-2
5-(Dimethylamino)-3,4-dihydro-3-(2'-hydroxy-2'-methylpropionyl)-4,4-dimethyl-2H-imidazol-2-on

Conditions

Conditions	Yield
In acetonitrile for 120h; Mechanism; Ambient temperature; 15N labelling experiments;	83%
In acetonitrile for 120h; Ambient temperature;	83%

: 695-53-4
dimethadione

: 98-88-4
benzoyl chloride

: 74529-69-4
3-Benzoyl-5,5-dimethyl-oxazolidine-2,4-dione

Conditions

Conditions	Yield
With pyridine; aluminium trichloride In acetonitrile for 3h; Ambient temperature;	73%

: 695-53-4
dimethadione

: 98-59-9
p-toluenesulfonyl chloride

: 74529-55-8
5,5-dimethyl-N-[(4-methylphenyl)sulfonyl]oxazolidine-2,4-dione

Conditions

Conditions	Yield
With pyridine; aluminium trichloride In acetonitrile for 3h; Ambient temperature;	73%
With sodium In tetrahydrofuran for 3h; Reflux;	22%

: 695-53-4
dimethadione

: 107267-45-8
3-(Dimethylamino)-2-methyl-2-(1-methylethyl)-2H-azirin

: 131842-36-9
5-(Dimethylamino)-3,4-dihydro-4-isopropyl-4-methyl-3-(2-hydroxy-2-methylpropanoyl)-2H-imidazol-2-on

Conditions

Conditions	Yield
In acetonitrile for 120h; Mechanism; Ambient temperature;	72%
In acetonitrile for 120h; Ambient temperature;	72%

: 5402-55-1
2-thiophenethanol

: 695-53-4
dimethadione

: 86970-75-4
5,5-Dimethyl-3-(2-thiophen-2-yl-ethyl)-oxazolidine-2,4-dione

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran for 14h; Ambient temperature;	68%

: 89500-82-3
2-(2-methyl-[3]thienyl)-ethanol

: 695-53-4
dimethadione

: 89500-85-6
5,5-Dimethyl-3-[2-(2-methyl-thiophen-3-yl)-ethyl]-oxazolidine-2,4-dione

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran for 14h; Ambient temperature;	68%

: 695-53-4
dimethadione

: 4725-34-2
2-(3,4-dihydronaphthalen-1-yl)ethan-1-ol

: N-<2-(3,4-dihydro-1-naphtyl)ethyl>-5,5-dimethyl-2,4-oxazolidinedione

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran for 14h; Ambient temperature;	65%

: 695-53-4
dimethadione

: 86970-96-9
2-(2-hydroxypropyl)-5-methylthiophene

: 86970-77-6
5,5-Dimethyl-3-[1-methyl-2-(5-methyl-thiophen-2-yl)-ethyl]-oxazolidine-2,4-dione

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran for 14h; Ambient temperature;	65%

: 695-53-4
dimethadione

: 1-cyclohexyl-N-(2-hydroxyethyl)-3-methyl-1H-thieno[2,3-c]pyrazole-5-carboxamide

: 1-Cyclohexyl-N-[2-(5,5-dimethyl-2,4-dioxo-1,3-oxazolidin-3-yl)-ethyl]-3-methyl-1H-thieno[2,3-c]pyrazole-5-carboxamide

Conditions

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 2h;	65%

: 695-53-4
dimethadione

: 100-07-2
4-methoxy-benzoyl chloride

: 1381863-04-2
5,5-dimethyl-N-(4-methoxybenzoyl)oxazolidine-2,4-dione

Conditions

Conditions	Yield
Stage #1: 4-methoxy-benzoyl chloride With triethylamine In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: dimethadione In tetrahydrofuran Reflux;	41%

: methyl 3,4,5,7-tetra-O-benzoyl-α-D-gluco-hept-2-ulopyranosonate

: 695-53-4
dimethadione

: 5,5-dimethyl-3-[methyl (3,4,5,7-tetra-O-benzoyl-β-D-gluco-hept-2-ulopyranosyl)onate]oxazolidin-2,4-dione

Conditions

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 24h; Mitsunobu Displacement; stereoselective reaction;	33%

: 695-53-4
dimethadione

: 4-fluoro-3-(trifluoromethyl)phenylboronic acid

: 3-[4-fluoro-3-(trifluoromethyl)phenyl]-5,5-dimethyloxazolidine-2,4-dione

Conditions

Conditions	Yield
With oxygen; copper diacetate In methanol at 70℃; for 12h;	29%

: 695-53-4
dimethadione

: 19291-76-0
1,2-dicyanonaphthalene

: 2,2-dimethyl-3-oxa-tri(1,2-naphtho)tetraazachlorin, nickel complex

Conditions

Conditions	Yield
With ammonium molybdate; urea; nickel dichloride In quinoline at 250℃; for 0.5h; Inert atmosphere;	8%

: 695-53-4
dimethadione

: 716-39-2
2,3-Naphthalenedicarboxylic anhydride

: 1310681-92-5
2,2-dimethyl-3-oxa-tri(2,3-naphtho)tetraazachlorin, nickel complex

Conditions

Conditions	Yield
With ammonium molybdate; urea; nickel dichloride In sulfolane for 1h; Inert atmosphere; Reflux;	6.4%

: 695-53-4
dimethadione

: 136918-14-4
phthalimide

: 1310681-91-4
2,2-dimethyl-3-oxa-tribenzo-tetraazachlorin, nickel complex

Conditions

Conditions	Yield
With ammonium molybdate; urea; nickel dichloride In quinoline at 250℃; for 0.166667h; Inert atmosphere;	5.6%

: 695-53-4
dimethadione

: 91-15-6
phthalonitrile

: 1310681-91-4
2,2-dimethyl-3-oxa-tribenzo-tetraazachlorin, nickel complex

Conditions

Conditions	Yield
With ammonium molybdate; urea; nickel dichloride In quinoline at 250℃; for 0.5h; Inert atmosphere;	4.2%

: 186581-53-3, 908094-01-9
diazomethane

: 695-53-4
dimethadione

: 127-48-0
trimethadione

: 100-69-6
2-vinylpyridine

: 695-53-4
dimethadione

: 104509-14-0
5,5-dimethyl-3-(2-pyridin-2-yl-ethyl)-oxazolidine-2,4-dione

: 109-65-9
1-bromo-butane

: 695-53-4
dimethadione

: 99063-24-8
3-butyl-5,5-dimethyl-oxazolidine-2,4-dione

Conditions

Conditions	Yield
With potassium carbonate; acetone

: 695-53-4
dimethadione

: 64-67-5
diethyl sulfate

: 520-77-4
3-ethyl-5,5-dimethyl-oxazolidine-2,4-dione

Conditions

Conditions	Yield
With potassium carbonate; acetone
With potassium ethoxide
With potassium carbonate; acetone

: 695-53-4
dimethadione

: 75-64-9
tert-butylamine

: 118979-45-6
α-(N'-tert-butyl-ureido)-isobutyric acid

: 695-53-4
dimethadione

: 100-35-6
2-(diethylamino)ethyl chloride

: 3-(2-diethylamino-ethyl)-5,5-dimethyl-oxazolidine-2,4-dione

Conditions

Conditions	Yield
With sodium ethanolate

: 695-53-4
dimethadione

: 77-78-1
dimethyl sulfate

: 127-48-0
trimethadione

: 695-53-4
dimethadione

: 74-88-4
methyl iodide

: 127-48-0
trimethadione

Conditions

Conditions	Yield
With methanol; potassium hydroxide

Dimethadione Chemical Properties

Propazone(695-53-4) is also named as 2,4-Oxazolidinedione, 5,5-dimethyl-;5,5-Dimethyl-1,3-oxazolidine-2,4-dione;5,5-Dimethyloxazolidine-2,4-dione;BAX-1400Z;Dimethadione;Dimethyloxazolidinedione,and so on.Propazone(695-53-4) is usually colorless solid.

CAS: 695-53-4
Molecular Formula: C₅H₇NO₃
Molecular Weight: 129.11
Molecular structure:
EINECS: 211-781-4
Melting point: 77-80 °C(lit.)
Boiling point: 137 °C / 6mmHg
Storage temp.: 2-8°C
Merck: 14,3213
BRN: 113541

Dimethadione Uses

Propazone(695-53-4) is commonly used in vivo measurement of intracellular ph.
Propazone(695-53-4) is also used as an anticonvulsant.

Dimethadione Toxicity Data With Reference

1.		ipr-mus LD₅₀:850 mg/kg		DIPHAH Dissertationes Pharmaceuticae. 18 (1966),337.
2.		ivn-mus LD₅₀:450 mg/kg		MEIEDD Merck Index. 10 (1983),468.

RTECS: RP9100000

Dimethadione Consensus Reports

Reported in EPA TSCA Inventory.

Dimethadione Safety Profile

Moderately toxic by intraperitoneal and intravenous routes. Experimental teratogenic and reproductive effects. When heated to decomposition it emits toxic fumes of NO_x.

Hazard Codes: Xn,Xi
Risk Statements: 20/21/22-40-33-36/37/38(20/21/22: Harmful by inhalation, in contact with skin and if swallowed 40: Limited evidence of a carcinogenic effect 33: Danger of cumulative effects 36/37/38: Irritating to eyes, respiratory system and skin)
Safety Statements: 22-36-24/25-23-36/37-26(22: Do not breathe dust 36: Wear suitable protective clothing 24/25: Avoid contact with skin and eyes 23: Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) 36/37: Wear suitable protective clothing and gloves 26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice)
WGK Germany: 3

Product Name

5,5-Dimethyloxazolidine-2,4-dione

Synthetic route

Dimethadione Chemical Properties

Dimethadione Uses

Dimethadione Toxicity Data With Reference

Dimethadione Consensus Reports

Dimethadione Safety Profile

Related Products

Hot Products