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13274-43-6

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13274-43-6 Usage

Uses

4-METHYL-1,2,4-TRIAZOLINE-3,5-DIONE is a dienophile used in the partial elucidation of Trichogramma putative sex pheromone at trace levels.

Synthesis Reference(s)

The Journal of Organic Chemistry, 31, p. 3444, 1966 DOI: 10.1021/jo01348a532Synthetic Communications, 17, p. 409, 1987 DOI: 10.1080/00397918708063918

Purification Methods

MTAD is obtained as pink needles by sublimation at 40-50o/0.1mm (see 4-phenyl-1,2,4-triazoline-3,5-dione, PTAD below). [Cookson et al. Org Synth 51 121 1971, Cheng et al. J Org Chem 49 2910 1984, Beilstein 26 III/IV 538.]

Check Digit Verification of cas no

The CAS Registry Mumber 13274-43-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,2,7 and 4 respectively; the second part has 2 digits, 4 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 13274-43:
(7*1)+(6*3)+(5*2)+(4*7)+(3*4)+(2*4)+(1*3)=86
86 % 10 = 6
So 13274-43-6 is a valid CAS Registry Number.
InChI:InChI=1/C3H3N3O2/c1-6-2(7)4-5-3(6)8/h1H3

13274-43-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-methyl-1,2,4-triazole-3,5-dione

1.2 Other means of identification

Product number -
Other names 4-Methyl-1,2,4-triazoline-3,5-dione

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:13274-43-6 SDS

13274-43-6Synthetic route

4-methylurazole
16312-79-1

4-methylurazole

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

Conditions
ConditionsYield
With silica gel; periodic acid; sodium nitrite In dichloromethane at 20℃; for 1.5h;100%
With trichloroisocyanuric acid In dichloromethane at 20℃; for 0.5h;100%
With tert-butylhypochlorite In dichloromethane at 0℃; for 1h;99%
ethyl 2-(methylcarbamoyl)hydrazine-1-carboxylate
13482-66-1

ethyl 2-(methylcarbamoyl)hydrazine-1-carboxylate

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

Conditions
ConditionsYield
Stage #1: ethyl 2-(methylcarbamoyl)hydrazine-1-carboxylate With methanol; potassium carbonate at 65℃; for 2h; Inert atmosphere;
Stage #2: With water at 65℃; for 12h;
Stage #3: With tert-butylhypochlorite In ethyl acetate Darkness; Inert atmosphere;
73%
4-methylurazole

4-methylurazole

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

Conditions
ConditionsYield
With tert-butylhypochlorite In ethyl acetate for 0.666667h; Ambient temperature;
C23H31N3O2
97877-81-1

C23H31N3O2

A

adamantylidene-adamantane
30541-56-1

adamantylidene-adamantane

B

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

Conditions
ConditionsYield
In chloroform-d1 at -20.1 - 19.9℃; Equilibrium constant;
8,9-benzo-4-methyl-2,4,6-triazatricyclo<5.2.2.02.6>undeca-8,10-diene-3,5-dione
91550-27-5

8,9-benzo-4-methyl-2,4,6-triazatricyclo<5.2.2.02.6>undeca-8,10-diene-3,5-dione

A

naphthalene
91-20-3

naphthalene

B

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

Conditions
ConditionsYield
With 2,3-Dimethyl-2-butene; 1,1-dichloroethane In chloroform-d1 at 29℃; Kinetics; Thermodynamic data; Further Variations:; Solvents; Temperatures; Decomposition; cycloreversion;
C14H13N3O2

C14H13N3O2

A

1-Methylnaphthalene
90-12-0

1-Methylnaphthalene

B

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

Conditions
ConditionsYield
With 2,3-Dimethyl-2-butene; 1,1-dichloroethane In chloroform-d1 at 29℃; Kinetics; Decomposition; cycloreversion;
C14H13N3O2

C14H13N3O2

A

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

B

2-Methylnaphthalene
91-57-6

2-Methylnaphthalene

Conditions
ConditionsYield
With 2,3-Dimethyl-2-butene; 1,1-dichloroethane In chloroform-d1 at 29℃; Kinetics; Decomposition; cycloreversion;
C14H13N3O2
280774-84-7

C14H13N3O2

A

1-Methylnaphthalene
90-12-0

1-Methylnaphthalene

B

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

Conditions
ConditionsYield
With 2,3-Dimethyl-2-butene; 1,1-dichloroethane In chloroform-d1 at 29℃; Kinetics; Decomposition; cycloreversion;
C14H13N3O2

C14H13N3O2

A

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

B

2-Methylnaphthalene
91-57-6

2-Methylnaphthalene

Conditions
ConditionsYield
With 2,3-Dimethyl-2-butene; 1,1-dichloroethane In chloroform-d1 at 29℃; Kinetics; Decomposition; cycloreversion;
C15H15N3O2

C15H15N3O2

A

1,5-dimethylnaphthalene
571-61-9

1,5-dimethylnaphthalene

B

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

Conditions
ConditionsYield
With 2,3-Dimethyl-2-butene; 1,1-dichloroethane In chloroform-d1 at 29℃; Kinetics; Decomposition; cycloreversion;
C15H15N3O2

C15H15N3O2

A

1,4-dimethylnaphthalene
571-58-4

1,4-dimethylnaphthalene

B

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

Conditions
ConditionsYield
With 2,3-Dimethyl-2-butene; 1,1-dichloroethane In chloroform-d1 at 29℃; Kinetics; Decomposition; cycloreversion;
C15H15N3O2

C15H15N3O2

A

2,3-dimethylnaphthalene
581-40-8

2,3-dimethylnaphthalene

B

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

Conditions
ConditionsYield
With 2,3-Dimethyl-2-butene; 1,1-dichloroethane In chloroform-d1 at 29℃; Kinetics; Decomposition; cycloreversion;
C15H15N3O2
280774-89-2

C15H15N3O2

A

2,3-dimethylnaphthalene
581-40-8

2,3-dimethylnaphthalene

B

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

Conditions
ConditionsYield
With 2,3-Dimethyl-2-butene; 1,1-dichloroethane In chloroform-d1 at 29℃; Kinetics; Decomposition; cycloreversion;
C15H15N3O2

C15H15N3O2

A

2.6-dimethylnaphthalene
581-42-0

2.6-dimethylnaphthalene

B

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

Conditions
ConditionsYield
With 2,3-Dimethyl-2-butene; 1,1-dichloroethane In chloroform-d1 at 29℃; Kinetics; Decomposition; cycloreversion;
C17H19N3O2

C17H19N3O2

A

2,3,6,7-tetramethylnaphthalene
1134-40-3

2,3,6,7-tetramethylnaphthalene

B

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

Conditions
ConditionsYield
With 2,3-Dimethyl-2-butene; 1,1-dichloroethane In chloroform-d1 at 29℃; Kinetics; Decomposition; cycloreversion;
1-(trimethylsilyl)benzene 1,2-oxide
69616-44-0

1-(trimethylsilyl)benzene 1,2-oxide

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

1-(trimethylsilyl)benzene oxide oxepin-4-methyl-1,2,4-triazoline-3,5-dione addukt
69616-47-3

1-(trimethylsilyl)benzene oxide oxepin-4-methyl-1,2,4-triazoline-3,5-dione addukt

Conditions
ConditionsYield
100%
1-(trimethylsilyl)-4-methylbenzene oxide-oxepin
69616-46-2

1-(trimethylsilyl)-4-methylbenzene oxide-oxepin

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

10,11-epoxy-2,6-dimethyl-10-trimethylsilanyl-5,8-dihydro-5,8-ethano-[1,2,4]triazolo[1,2-a]pyridazine-1,3-dione
69616-48-4

10,11-epoxy-2,6-dimethyl-10-trimethylsilanyl-5,8-dihydro-5,8-ethano-[1,2,4]triazolo[1,2-a]pyridazine-1,3-dione

Conditions
ConditionsYield
100%
1-(trimethylsilyl)-2-methylbenzene oxide-oxepin
69616-45-1

1-(trimethylsilyl)-2-methylbenzene oxide-oxepin

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

C13H19N3O3Si

C13H19N3O3Si

Conditions
ConditionsYield
100%
4a,9,9a,10-tetrahydro-9,10-etheno-4a,9-methanoanthracene
106727-04-2

4a,9,9a,10-tetrahydro-9,10-etheno-4a,9-methanoanthracene

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

C20H17N3O2
106745-05-5

C20H17N3O2

Conditions
ConditionsYield
100%
(1α,2β,3α,6α,7β,8α)-4,5:9,10-Dibenzotetracyclo<6.2.1.13,6.02,7>dodeca-4,9-diene
65879-09-6

(1α,2β,3α,6α,7β,8α)-4,5:9,10-Dibenzotetracyclo<6.2.1.13,6.02,7>dodeca-4,9-diene

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

N-methyl-4,5-diazaundecacyclo<11.9.0.01,6.02,14.02,20.03,8.07,12.09,14.013,17.015,19.018,22>docos-10-ene-4,5-dicarboximide

N-methyl-4,5-diazaundecacyclo<11.9.0.01,6.02,14.02,20.03,8.07,12.09,14.013,17.015,19.018,22>docos-10-ene-4,5-dicarboximide

Conditions
ConditionsYield
In diethyl ether for 3h; Ambient temperature; Irradiation;100%
C19H18O2
106727-05-3

C19H18O2

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

C22H21N3O4
106727-06-4

C22H21N3O4

Conditions
ConditionsYield
100%
diisopropylidenethiirane oxide
81355-46-6

diisopropylidenethiirane oxide

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

2,2,4,6,6-Pentamethyl-1-oxo-2,6-dihydro-1H-1λ4-thia-2a,4,5a-triaza-cyclopropa[f]indene-3,5-dione
82613-75-0

2,2,4,6,6-Pentamethyl-1-oxo-2,6-dihydro-1H-1λ4-thia-2a,4,5a-triaza-cyclopropa[f]indene-3,5-dione

Conditions
ConditionsYield
In dichloromethane Ambient temperature;100%
4,5,6,7-tetrahydro-2,2-dimethyl-4,7-methano-2H-indene
85268-28-6

4,5,6,7-tetrahydro-2,2-dimethyl-4,7-methano-2H-indene

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

anti-1,4,5,6,7,8-hexahydro-N,10,10-trimethyl-1,4:5,8-dimethanophthalazine-2,3-dicarboximide
85268-41-3

anti-1,4,5,6,7,8-hexahydro-N,10,10-trimethyl-1,4:5,8-dimethanophthalazine-2,3-dicarboximide

Conditions
ConditionsYield
In ethyl acetate at -78℃; for 0.5h;100%
heptacyclo<8.6.1.02,7.02,14.07,17.08,13.011,16>heptadeca-3,5-dien-12-one ethylene acetal
149576-98-7

heptacyclo<8.6.1.02,7.02,14.07,17.08,13.011,16>heptadeca-3,5-dien-12-one ethylene acetal

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

17-methyl-15,17,19-triazanonacyclo<12.5.2.13,7.02,8.02,13.04,12.06,10.09,13.015,19>docos-20-ene-5,16,18-trione 5-ethyleneacetal

17-methyl-15,17,19-triazanonacyclo<12.5.2.13,7.02,8.02,13.04,12.06,10.09,13.015,19>docos-20-ene-5,16,18-trione 5-ethyleneacetal

Conditions
ConditionsYield
In dichloromethane for 0.5h; Ambient temperature;100%
4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

(5R,6S)-1-Oxa-7-thia-dispiro[4.0.4.4]tetradeca-11,13-diene

(5R,6S)-1-Oxa-7-thia-dispiro[4.0.4.4]tetradeca-11,13-diene

(1'R,2R,4'S,6'S)-4,4'',5,5''-tetrahydro-N-methyldispirodiazabicyclo<2.2.2>oct<7>ene-6',2''(3''H)-thiophene>-2',3'-dicarboximide

(1'R,2R,4'S,6'S)-4,4'',5,5''-tetrahydro-N-methyldispirodiazabicyclo<2.2.2>oct<7>ene-6',2''(3''H)-thiophene>-2',3'-dicarboximide

Conditions
ConditionsYield
In dichloromethane for 0.5h; Ambient temperature;100%
1-Methyl-5,6-di-p-tolyl-1H-pyrazin-2-one
90407-31-1

1-Methyl-5,6-di-p-tolyl-1H-pyrazin-2-one

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

4,8-Dimethyl-7,11-di-p-tolyl-2,4,6,8,10-pentaaza-tricyclo[5.2.2.02,6]undec-10-ene-3,5,9-trione

4,8-Dimethyl-7,11-di-p-tolyl-2,4,6,8,10-pentaaza-tricyclo[5.2.2.02,6]undec-10-ene-3,5,9-trione

Conditions
ConditionsYield
In dichloromethane for 0.5h; Ambient temperature;100%
4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

1-methyl-5,6-diphenylpyrazine-2(1H)-one
62251-28-9

1-methyl-5,6-diphenylpyrazine-2(1H)-one

4,8-Dimethyl-7,11-diphenyl-2,4,6,8,10-pentaaza-tricyclo[5.2.2.02,6]undec-10-ene-3,5,9-trione

4,8-Dimethyl-7,11-diphenyl-2,4,6,8,10-pentaaza-tricyclo[5.2.2.02,6]undec-10-ene-3,5,9-trione

Conditions
ConditionsYield
In dichloromethane for 0.5h; Ambient temperature;100%
4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

1,3-dimethyl-5-phenylpyrazin-2(1H)-one

1,3-dimethyl-5-phenylpyrazin-2(1H)-one

1,4,8-Trimethyl-11-phenyl-2,4,6,8,10-pentaaza-tricyclo[5.2.2.02,6]undec-10-ene-3,5,9-trione

1,4,8-Trimethyl-11-phenyl-2,4,6,8,10-pentaaza-tricyclo[5.2.2.02,6]undec-10-ene-3,5,9-trione

Conditions
ConditionsYield
In dichloromethane for 0.5h; Ambient temperature;100%
(+/-)-(1R*,2R*)-12-oxa-3-azatetracyclo[4.4.3.22,5.01,6]pentadeca-3,7,9-triene
103993-68-6, 106760-64-9

(+/-)-(1R*,2R*)-12-oxa-3-azatetracyclo[4.4.3.22,5.01,6]pentadeca-3,7,9-triene

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

(DL-1R,2S,7R)-N-methyl-12-oxa-3,4,8-triazapentacyclo<4.4.3.22,5.27,10.01,6>heptadeca-8,16-dien-3,4-dicarboximide
106727-16-6

(DL-1R,2S,7R)-N-methyl-12-oxa-3,4,8-triazapentacyclo<4.4.3.22,5.27,10.01,6>heptadeca-8,16-dien-3,4-dicarboximide

Conditions
ConditionsYield
In dichloromethane at 25℃; for 0.5h; Cycloaddition;100%
(+/-)-(1R*,2R*)-12-oxa-3-azatetracyclo[4.4.3.22,5.01,6]pentadeca-3,7,9-triene 3-oxide
106727-19-9

(+/-)-(1R*,2R*)-12-oxa-3-azatetracyclo[4.4.3.22,5.01,6]pentadeca-3,7,9-triene 3-oxide

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

(+/-)-4,13-dioxa-8,9,14-triazaheptacyclo[9.6.1.02,6.02,10.06,15.07,12.014,18]octadecan-8,9-methyldicarboximide

(+/-)-4,13-dioxa-8,9,14-triazaheptacyclo[9.6.1.02,6.02,10.06,15.07,12.014,18]octadecan-8,9-methyldicarboximide

Conditions
ConditionsYield
In dichloromethane at 25℃; for 0.166667h; Cycloaddition;100%
(1R*,2R*)-12-oxa-3,4-diazatetracyclo[4.4.3.22,5.01,6]pentadeca-3,7,9-triene
51372-62-4

(1R*,2R*)-12-oxa-3,4-diazatetracyclo[4.4.3.22,5.01,6]pentadeca-3,7,9-triene

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

(1R*,2S*,7R*)-12-oxa-3,4,8,9-tetraazapentacyclo[4.4.3.22,5.27,10.01,6]heptadeca-3,14-diene-8,9-methyldicarboximide
92674-31-2

(1R*,2S*,7R*)-12-oxa-3,4,8,9-tetraazapentacyclo[4.4.3.22,5.27,10.01,6]heptadeca-3,14-diene-8,9-methyldicarboximide

Conditions
ConditionsYield
In dichloromethane for 0.5h; Cycloaddition;100%
4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

9,10-Ethano-9,10-dihydronaphthalin

9,10-Ethano-9,10-dihydronaphthalin

(1R*,2R*)-3,4-diazatetracyclo[4.4.2.22,5.01,6]tetradeca-7,9,13-triene-3,4-methyldicarboximide
268219-51-8

(1R*,2R*)-3,4-diazatetracyclo[4.4.2.22,5.01,6]tetradeca-7,9,13-triene-3,4-methyldicarboximide

Conditions
ConditionsYield
In dichloromethane at 0℃; for 0.5h; Cycloaddition;100%
4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

(1R*,2R*)-3,4-diazatetracyclo[4.4.2.22,5.01,6]tetradeca-3,7,9-triene
268219-53-0

(1R*,2R*)-3,4-diazatetracyclo[4.4.2.22,5.01,6]tetradeca-3,7,9-triene

(1R*,2R*,7S)-3,4,8,9-tetraazapentacyclo[4.4.2.22,5.27,10.01,6]hexadeca-3,13-diene-8,9-methyldicarboximide
268219-54-1

(1R*,2R*,7S)-3,4,8,9-tetraazapentacyclo[4.4.2.22,5.27,10.01,6]hexadeca-3,13-diene-8,9-methyldicarboximide

Conditions
ConditionsYield
In dichloromethane Cycloaddition;100%
4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

(+/-)-(1R*,2S*)-3,4-diazatetracyclo[4.4.2.22,5.01,6]tetradeca-3,7,9-triene 3-oxide

(+/-)-(1R*,2S*)-3,4-diazatetracyclo[4.4.2.22,5.01,6]tetradeca-3,7,9-triene 3-oxide

(+/-)-(1R*,2S*,7S*)-3,4,8,9-tetraazapentacyclo[4.4.2.22,5.27,10.01,6]hexadeca-3,13-diene-8,9-methyldicarboximide 3-oxide

(+/-)-(1R*,2S*,7S*)-3,4,8,9-tetraazapentacyclo[4.4.2.22,5.27,10.01,6]hexadeca-3,13-diene-8,9-methyldicarboximide 3-oxide

Conditions
ConditionsYield
In dichloromethane at -10℃; for 0.166667h; Cycloaddition;100%
4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

(+/-)-(1R*,2R*)-12-oxa-3,4-diazatetracyclo[4.4.3.22,5.01,6]pentadeca-3,7,9-triene 3-oxide

(+/-)-(1R*,2R*)-12-oxa-3,4-diazatetracyclo[4.4.3.22,5.01,6]pentadeca-3,7,9-triene 3-oxide

(+/-)-(1R*,2S*,7R*)-12-oxa-3,4,8,9-tetraazapentacyclo[4.4.3.22,5.27,10.01,6]heptadeca-3,14-diene-8,9-methyldicarboximide 3-oxide
92707-89-6

(+/-)-(1R*,2S*,7R*)-12-oxa-3,4,8,9-tetraazapentacyclo[4.4.3.22,5.27,10.01,6]heptadeca-3,14-diene-8,9-methyldicarboximide 3-oxide

Conditions
ConditionsYield
In dichloromethane at -10℃; for 0.333333h; Cycloaddition;100%
1,2,3,4-tetrahydrocarbazole
942-01-8

1,2,3,4-tetrahydrocarbazole

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

4-methyl-1-(1,2,3,4-tetrahydro-carbazol-4a-yl)-[1,2,4]triazolidine-3,5-dione

4-methyl-1-(1,2,3,4-tetrahydro-carbazol-4a-yl)-[1,2,4]triazolidine-3,5-dione

Conditions
ConditionsYield
In dichloromethane at 0℃; for 0.0166667h;100%
4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

3-acetyl-6,6-dimethyl-2,3,6,7-tetrahydro-1H-azocino[5,4-b]indole-2-carboxylic acid methyl ester

3-acetyl-6,6-dimethyl-2,3,6,7-tetrahydro-1H-azocino[5,4-b]indole-2-carboxylic acid methyl ester

3-acetyl-6,6-dimethyl-11b-(4-methyl-3,5-dioxo-[1,2,4]triazolidin-1-yl)-2,3,6,11b-tetrahydro-1H-azocino[5,4-b]indole-2-carboxylic acid methyl ester

3-acetyl-6,6-dimethyl-11b-(4-methyl-3,5-dioxo-[1,2,4]triazolidin-1-yl)-2,3,6,11b-tetrahydro-1H-azocino[5,4-b]indole-2-carboxylic acid methyl ester

Conditions
ConditionsYield
100%
Trimethyl-((Z)-1-methyl-hex-1-enyl)-silane
77113-46-3

Trimethyl-((Z)-1-methyl-hex-1-enyl)-silane

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

1-<1-butyl-2-(trimethylsilyl)-2-propenyl>-4-methyl-1,2,4-triazolidine-3,5-dione
137041-34-0

1-<1-butyl-2-(trimethylsilyl)-2-propenyl>-4-methyl-1,2,4-triazolidine-3,5-dione

Conditions
ConditionsYield
In dichloromethane at 20℃; for 24h;99%
(E/Z)-dimethyl(1-methyl-1-propenyl)phenylsilane
156518-26-2

(E/Z)-dimethyl(1-methyl-1-propenyl)phenylsilane

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

1-<2-(dimethylphenylsilyl)-1-methyl-2-propenyl>-4-methyl-1,2,4-triazolidine-3,5-dione
137041-33-9

1-<2-(dimethylphenylsilyl)-1-methyl-2-propenyl>-4-methyl-1,2,4-triazolidine-3,5-dione

Conditions
ConditionsYield
In dichloromethane at 20℃; for 18h; Product distribution; Mechanism; other vinylsilanes;99%
In dichloromethane at 20℃; for 18h;99%
4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

C18H14O

C18H14O

C21H17N3O3

C21H17N3O3

Conditions
ConditionsYield
In dichloromethane at -47℃; for 0.333333h;99%
4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

1,3,5-trimethyl-benzene
108-67-8

1,3,5-trimethyl-benzene

1-(2,4,6-trimethylbenzene)-4-methyl-1,2,4-triazoline-3,5-dione
907968-98-3

1-(2,4,6-trimethylbenzene)-4-methyl-1,2,4-triazoline-3,5-dione

Conditions
ConditionsYield
With trifluoroacetic acid In chloroform at 62℃; for 7h;99%
4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

1-methoxy-3-methyl-benzene
100-84-5

1-methoxy-3-methyl-benzene

1-(4-methoxy-2-methylbenzene)-4-methyl-1,2,4-triazoline-3,5-dione
1268396-59-3

1-(4-methoxy-2-methylbenzene)-4-methyl-1,2,4-triazoline-3,5-dione

Conditions
ConditionsYield
With trifluoroacetic acid In chloroform at 62℃; for 0.166667h; regioselective reaction;99%
cyclohex-1-enyl-trimethyl-silane
17874-17-8

cyclohex-1-enyl-trimethyl-silane

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

4-methyl-1-<2-(trimethylsilyl)-2-cyclohexen-1-yl>-1,2,4-triazolidine-3,5-dione
137041-36-2

4-methyl-1-<2-(trimethylsilyl)-2-cyclohexen-1-yl>-1,2,4-triazolidine-3,5-dione

Conditions
ConditionsYield
In dichloromethane at 20℃; for 48h;98%
5-Benzyl-3,6-dihydro-6-oxo-1,3-diphenyl-1-pyrimidinium-4-olat
101530-90-9

5-Benzyl-3,6-dihydro-6-oxo-1,3-diphenyl-1-pyrimidinium-4-olat

4-methyl-1,2,4-triazoline-3,5-dione
13274-43-6

4-methyl-1,2,4-triazoline-3,5-dione

1-Benzyl-4-methyl-8,11-diphenyl-2,4,6,8,11-pentaazatricyclo<5.2.2.02,6>undecan-3,5,9,10-tetron

1-Benzyl-4-methyl-8,11-diphenyl-2,4,6,8,11-pentaazatricyclo<5.2.2.02,6>undecan-3,5,9,10-tetron

Conditions
ConditionsYield
In ethyl acetate Ambient temperature;98%

13274-43-6Relevant articles and documents

Oxidized Phenyl-Substituted Sesquibicyclic Hydrazines

Nelsen, Stephen F.,Wang, Yichun,Hiyashi, Randy K.,Powell, Douglas R.,Neugebauer, Franz A.

, p. 2981 - 2988 (1995)

The effect of α- and β-phenyl substituents on the neutral, +1, and +2 oxidation states of bis-N,N'-bicyclic hydrazines 1 and 2 is discussed.An α-phenyl substituent on 2 makes first electron removal 1.8 kcal/mol more difficult, but second electron removal

Probing the Dynamic Covalent Chemistry Behavior of Nitrogen-Centered Di- And Triurazole Radicals

Breton, Gary W.,Martin, Kenneth L.

, p. 10865 - 10871 (2020)

Dynamic covalent chemistry (DCvC) describes systems in which readily reversible bond formation allows for control of product distributions by straightforward manipulation of reaction conditions (e.g., changes in temperature, solvent, concentration, etc).

Silica chloride/NaNO2 as a novel heterogeneous system for the oxidation of urazoles under mild conditions

Zolfigol, Mohammad Ali,Torabi, Mehdi,Mallakpour, Shadpour E

, p. 8381 - 8384 (2001)

Urazoles and bis-urazoles can be converted in excellent yields to their corresponding triazolinediones, with a combination of silica chloride (I), wet SiO2 and sodium nitrite in dichloromethane at room temperature.

Diels-Alder Reactions of Protoporphyrin IX Dimethyl Ester

Morgan, Alan R.,Kohli, Dilmeet H.

, p. 7603 - 7606 (1995)

The reaction of a divinyl porphyrin (protoporphyrin IX dimethyl ester) with a number of azo dienophiles was studied.In all cases where reaction occurred and the product could be isolated, the expected addition product was observed.In most cases, / adducts were also identified.

Oxidation of urazoles to their corresponding triazolinediones under mild and heterogeneous conditions via in situ generation of NO+IOx-

Zolfigol,Chehardoli,Shirini,Mallakpour,Nasr-Isfahani

, p. 1965 - 1970 (2001)

A combination of periodic or iodic acids and sodium nitrite in the presence of wet SiO2 was used as an effective oxidizing agent for the oxidation of urazoles and bis-urazoles to their corresponding triazolinediones under mild and heterogeneous conditions with good yields.

-

Stickler,J.C.,Pirkle,W.H.

, p. 3444 - 3445 (1966)

-

Calcium hypochlorite as an efficient reagent for oxidation of urazoles under mild heterogeneous conditions

Zolfigol,Mallakpour,Khazaiae,Vaghaie,Torabi

, p. 914 - 916 (2004)

-

Oxidation of urazoles under mild and heterogeneous conditions with KHSO5 and NaNO2

Zolfigol,Bagherzadeh,Chehardoli,Mallakpour

, p. 1149 - 1154 (2001)

A combination of potassium monopersulfate and sodium nitrite in the presence of wet SiO2 was used as an effective oxidizing agent for the oxidation of urazoles and bis-urazoles to their corresponding triazolinediones under mild and heterogeneous conditions with excellent yields.

Photolysis of matrix-isolated 4-R-1,2,4-triazoline-3,5-diones: Identification of aziridine-2,3-dione transients

Risi, Florence,Pizzala, Louis,Carles, Micheline,Verlaque, Patrick,Aycard, Jean-Pierre

, p. 666 - 670 (1996)

Matrix-isolated 4-methyl-1,2,4-triazolinedione la and 4-phenyl-1,2,4-triazolinedione 1b were photolyzed at λ335 nm and λ≥310 nm, respectively. The reactions induced by photolysis were monitored by FT-IR spectroscopy. The isocyanates 2a and 2b are always the more abundant products with carbon monoxide. Methyl- and phenylaziridine-2,3-diones (3a and 3b) were detected as minor, but well-identified reaction products. The IR experimental absorption bands were assigned by comparison with literature data and with simulated infrared spectra obtained by ab initio calculation at the 6-31G* level. Stable at the matrix temperature (10 K), 3a and 3b photolyzed to isocyanates and CO when irradiated at λ≥230 nm. Irradiation of 2b at this wavelength induces its decomposition. The kinetic data show that the rate constant process 1a→2a is faster than the 1a→3a process (3.29×10-3 and 2.35×10-4 min-1 respectively).

METHOD FOR PRODUCING SOLID TRIAZOLINEDIONE COMPOUND, SOLID TRIAZOLINEDIONE COMPOUND, AND METHOD FOR PRODUCING TRIAZOLINEDIONE COMPOUND

-

Paragraph 0164-0167, (2020/12/25)

Provided are a method for separating a DAPTAD-containing triazolinedione compound in solid form from a reaction solution, a separated solid triazolinedione compound, and a novel method for producing a triazolinedione compound. A triazolinedione solution in which a DAPTAD-containing triazolinedione compound is dissolved is brought into contact with a C5-15 hydrocarbon-based poor solvent to obtain a solid triazolinedione compound. Also, a triazolinedione compound is oxidized using an oxidizing agent that does not produce acid as a byproduct to obtain a triazolinedione compound.

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