Product Name

  • Name

    Dithiooxamide

  • EINECS 201-203-9
  • CAS No. 79-40-3
  • Article Data16
  • CAS DataBase
  • Density 1.523 g/cm3
  • Solubility Soluble in alcohols. Slightly soluble in water. Insoluble in ether
  • Melting Point ≥300 °C(lit.)
  • Formula C2H4N2S2
  • Boiling Point 252.1 °C at 760 mmHg
  • Molecular Weight 120.199
  • Flash Point 106.2 °C
  • Transport Information
  • Appearance orange to brown crystalline powder
  • Safety 36/37
  • Risk Codes 22-36/37/38
  • Molecular Structure Molecular Structure of 79-40-3 (Dithiooxamide)
  • Hazard Symbols HarmfulXn
  • Synonyms Oxamide,dithio- (8CI);Dithiooxalic acid diamide;Ethanedithioamide;Hydrorubeanic acid;NSC 1893;Rubean;Rubeane;Rubeanic acid;
  • PSA 116.22000
  • LogP 0.95920

Synthetic route

Oxalamide
471-46-5

Oxalamide

dithiooxamide
79-40-3

dithiooxamide

Conditions
ConditionsYield
With Lawessons reagent In acetonitrile Heating;67.36%
2-nitroacetamide
14011-21-3

2-nitroacetamide

A

thiooxalamide
16475-48-2

thiooxalamide

B

dithiooxamide
79-40-3

dithiooxamide

Conditions
ConditionsYield
With Lawessons reagent In toluene at 80℃; for 0.5h; Other reagent;A 32%
B 14%
With tetraphosphorus decasulfide In 1,4-dioxane at 80℃; for 0.2h; other reagent;A 21%
B 14%
ethanedinitrile
460-19-5

ethanedinitrile

dithiooxamide
79-40-3

dithiooxamide

Conditions
ConditionsYield
With hydrogen sulfide in alkoh.Loesung;
With sodium hydrogensulfide das Natriumsalz entsteht, in alkoholischer Loesung;
With cyclohexane-1,1-dithiol In ethanol
With hydrogen sulfide in alkoh.Loesung;
With hydrogenchloride; sodium hydrogensulfide; water
ethanol
64-17-5

ethanol

phenylhydrazine
100-63-0

phenylhydrazine

thiooxalamic acid nitrile

thiooxalamic acid nitrile

A

amino-(N'-phenyl-hydrazono)-acetonitrile
178168-62-2

amino-(N'-phenyl-hydrazono)-acetonitrile

B

hydrogen sulfide
7783-06-4

hydrogen sulfide

C

dithiooxamide
79-40-3

dithiooxamide

dimethyl thiooxalimidate
79844-63-6

dimethyl thiooxalimidate

hydrogen sulfide
7783-06-4

hydrogen sulfide

dithiooxamide
79-40-3

dithiooxamide

ethanedinitrile
460-19-5

ethanedinitrile

H2S (2 mol)

H2S (2 mol)

dithiooxamide
79-40-3

dithiooxamide

ethanedinitrile
460-19-5

ethanedinitrile

hydrogen sulfide
7783-06-4

hydrogen sulfide

A

Flaveanwasserstoff
471-24-9

Flaveanwasserstoff

B

dithiooxamide
79-40-3

dithiooxamide

A

dithiooxamide
79-40-3

dithiooxamide

B

cadmium(II) bromide

cadmium(II) bromide

Conditions
ConditionsYield
Kinetics; decomposition in a N2 gas flow;
2-Bromoacetylpyridine
40086-66-6

2-Bromoacetylpyridine

dithiooxamide
79-40-3

dithiooxamide

4,4'-di(pyrid-2-yl)-2,2'-bithiazole

4,4'-di(pyrid-2-yl)-2,2'-bithiazole

Conditions
ConditionsYield
In ethanol at 78℃;100%
Trimethylenediamine
109-76-2

Trimethylenediamine

dithiooxamide
79-40-3

dithiooxamide

1,1',4,4',5,5',6,6'-octahydro-2,2'-bipyrimidine
21786-88-9

1,1',4,4',5,5',6,6'-octahydro-2,2'-bipyrimidine

Conditions
ConditionsYield
Stage #1: dithiooxamide With ethyl bromide In ethanol at 60℃; for 4h; Inert atmosphere; Schlenk technique;
Stage #2: Trimethylenediamine In ethanol at 60 - 80℃; for 1.33333h; Inert atmosphere; Schlenk technique;
100%
2,2-diethoxy-ethanamine
645-36-3

2,2-diethoxy-ethanamine

dithiooxamide
79-40-3

dithiooxamide

N,N'-(2,2-diethoxyethyl)dithiooxamide

N,N'-(2,2-diethoxyethyl)dithiooxamide

Conditions
ConditionsYield
In ethanol99%
dithiooxamide
79-40-3

dithiooxamide

Oxalamide
471-46-5

Oxalamide

Conditions
ConditionsYield
With bismuth(III) nitrate In acetonitrile for 0.25h; Heating;99%
With Oxone In acetonitrile for 1h; Heating;97%
With 12-tungstosilic acid In acetonitrile for 1.5h; Reflux;97%
dithiooxamide
79-40-3

dithiooxamide

dimethyl acetylenedicarboxylate
762-42-5

dimethyl acetylenedicarboxylate

triphenylphosphine
603-35-0

triphenylphosphine

dimethyl 2-[(2-amino-2-thioxoethanthioyl)amino]-3-(1,1,1-triphenyl-λ5-phosphanylidene)succinate
1204685-94-8

dimethyl 2-[(2-amino-2-thioxoethanthioyl)amino]-3-(1,1,1-triphenyl-λ5-phosphanylidene)succinate

Conditions
ConditionsYield
In hexane; ethyl acetate at 20℃; for 1h;95%
N-(2-benzene-2,2-dichloroethylidene)-4-chlorobenzenesulfonamide
98416-35-4

N-(2-benzene-2,2-dichloroethylidene)-4-chlorobenzenesulfonamide

dithiooxamide
79-40-3

dithiooxamide

N-[2,2-dichloro-1-(4-chlorophenylsulfonylamino)-2-phenylethyl]ethanedithioamide
1377583-54-4

N-[2,2-dichloro-1-(4-chlorophenylsulfonylamino)-2-phenylethyl]ethanedithioamide

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 100℃; for 15h;95%
dithiooxamide
79-40-3

dithiooxamide

thiooxalamide
16475-48-2

thiooxalamide

Conditions
ConditionsYield
With 2,2'-bipyridinium chlorochromate In acetonitrile for 0.0833333h; Product distribution; Further Variations:; Reagents; Temperatures; without microwave irradiation; solvent-free; microwave irradiation;94%
1-(3-bromophenyl)-2-phenylethan-1-one
40396-53-0

1-(3-bromophenyl)-2-phenylethan-1-one

dithiooxamide
79-40-3

dithiooxamide

5-amino-2-benzyl-2-(3-bromophenyl)-2H-imidazole-4-thiol
1260214-92-3

5-amino-2-benzyl-2-(3-bromophenyl)-2H-imidazole-4-thiol

Conditions
ConditionsYield
With ammonia In methanol at 150℃; for 1h; Microwave irradiation;94%
dithiooxamide
79-40-3

dithiooxamide

2-bromo-7-methyl-5-oxo-5H-1,3,4-thiadiazolo<3,2-a>pyrimidine

2-bromo-7-methyl-5-oxo-5H-1,3,4-thiadiazolo<3,2-a>pyrimidine

C8H7N5S3O*HBr

C8H7N5S3O*HBr

Conditions
ConditionsYield
In ethanol for 2h; Heating;93%
bis(acetylacetonato)dioxidomolybdenum(VI)

bis(acetylacetonato)dioxidomolybdenum(VI)

dithiooxamide
79-40-3

dithiooxamide

bis(dithiooxamidate)dioxomolybdenum(VI)
1414938-99-0

bis(dithiooxamidate)dioxomolybdenum(VI)

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 15h;92%
2-Bromo-1-(5-hexylthiophen-2-yl)ethanone
1117953-26-0

2-Bromo-1-(5-hexylthiophen-2-yl)ethanone

dithiooxamide
79-40-3

dithiooxamide

4,4'-Bis(5-hexylthiophen-2-yl)-2,2'-bithiazole

4,4'-Bis(5-hexylthiophen-2-yl)-2,2'-bithiazole

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 90℃; for 12h; Inert atmosphere;91.6%
trimethyl indium
3385-78-2

trimethyl indium

dithiooxamide
79-40-3

dithiooxamide

((CH3)2In)2(NHCS)2
86356-19-6

((CH3)2In)2(NHCS)2

Conditions
ConditionsYield
In toluene byproducts: CH4; under N2, to dithiooxamide dissolved or suspended in toluene added dropwise alkyl component (pure or dild. with toluene); elem. anal.;90%
oxopentachlororhenic acid

oxopentachlororhenic acid

dithiooxamide
79-40-3

dithiooxamide

dithiooxamide ReOCl3 complex
104067-54-1, 88784-48-9

dithiooxamide ReOCl3 complex

Conditions
ConditionsYield
With HCl In acetic acid under N2 soln. of ligand in AcOH/HCl was added to soln. of Re compd. inthe same solvent; filtration, washing with AcOH/HCl followed by petrolem ether; drying invac. over NaOH; elem. anal.;90%
dithiooxamide
79-40-3

dithiooxamide

triphenylphosphine
603-35-0

triphenylphosphine

acetylenedicarboxylic acid diethyl ester
762-21-0

acetylenedicarboxylic acid diethyl ester

diethyl 2-[(2-amino-2-thioxoethanthioyl)amino]-3-(1,1,1-triphenyl-λ5-phosphanylidene)succinate
1204685-95-9

diethyl 2-[(2-amino-2-thioxoethanthioyl)amino]-3-(1,1,1-triphenyl-λ5-phosphanylidene)succinate

Conditions
ConditionsYield
In hexane; ethyl acetate at 20℃; for 1h;90%
1-bromo-undecan-2-one
73121-60-5

1-bromo-undecan-2-one

dithiooxamide
79-40-3

dithiooxamide

4,4'-dinonyl-2,2'-bithiazole
180729-91-3

4,4'-dinonyl-2,2'-bithiazole

Conditions
ConditionsYield
In ethanol for 6h; Heating;89%
In ethanol Hantzsch Thiazole Synthesis; Inert atmosphere; Schlenk technique;
3-(α-bromoacetyl)-4-hydroxy-6-methyl-2H-pyran-2-one
23754-53-2

3-(α-bromoacetyl)-4-hydroxy-6-methyl-2H-pyran-2-one

dithiooxamide
79-40-3

dithiooxamide

4-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)thiazole-2-carbothioamide
1295500-84-3

4-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)thiazole-2-carbothioamide

Conditions
ConditionsYield
In ethanol for 0.166667h; Hantzsch reaction; Reflux; Microwave irradiation;88%
dithiooxamide
79-40-3

dithiooxamide

N-(2-benzene-2,2-dichloroethylidene)-4-methylbenzenesulfonamide
236404-04-9

N-(2-benzene-2,2-dichloroethylidene)-4-methylbenzenesulfonamide

N-[2,2-dichloro-1-(4-methylphenylsulfonylamino)-2-phenylethyl]ethanedithioamide
1377583-52-2

N-[2,2-dichloro-1-(4-methylphenylsulfonylamino)-2-phenylethyl]ethanedithioamide

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 100℃; for 15h;88%
2,3-Dichloro-1,4-naphthoquinone
117-80-6

2,3-Dichloro-1,4-naphthoquinone

dithiooxamide
79-40-3

dithiooxamide

dibenzo[b,i]thianthrene-5,7,12,14-tetraone
21634-42-4

dibenzo[b,i]thianthrene-5,7,12,14-tetraone

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 50℃; for 10h;88%
2,3-Dichloro-1,4-naphthoquinone
117-80-6

2,3-Dichloro-1,4-naphthoquinone

dithiooxamide
79-40-3

dithiooxamide

2,2'-bis(naphtho<2,3-d>thiazole-4,9-dione)
96354-84-6

2,2'-bis(naphtho<2,3-d>thiazole-4,9-dione)

Conditions
ConditionsYield
With sodium hydrogencarbonate In ethanol for 2h; Heating;86%
With triethylamine In N,N-dimethyl-formamide at 50℃; for 10h;57%
tert-butylamine
75-64-9

tert-butylamine

dithiooxamide
79-40-3

dithiooxamide

N,N'-Bis(tert-butyl)dithioxamid
26818-54-2

N,N'-Bis(tert-butyl)dithioxamid

Conditions
ConditionsYield
In ethanol 1.) 40 deg C, 2.) 5 h, RT;85%
nickel(II) chloride hexahydrate

nickel(II) chloride hexahydrate

dithiooxamide
79-40-3

dithiooxamide

((NH2)2(CS)2)2NiCl2*2H2O

((NH2)2(CS)2)2NiCl2*2H2O

Conditions
ConditionsYield
In ethanol refluxed 1-2.5 h, 1:1 mol. ratio, concd.; washed (ethanol), dried in vac. over P2O5; elem.anal.;85%
Mo2(N,N'-di-p-anisyl-formamidinato)3(O2CCH3)

Mo2(N,N'-di-p-anisyl-formamidinato)3(O2CCH3)

sodium methylate
124-41-4

sodium methylate

dithiooxamide
79-40-3

dithiooxamide

[Mo2(N,N'-di-p-anisylformamidinato)3]2(dithiooxamidato)

[Mo2(N,N'-di-p-anisylformamidinato)3]2(dithiooxamidato)

Conditions
ConditionsYield
In tetrahydrofuran; methanol byproducts: NaCH3COO, CH3OH; (N2); NaOCH3 in MeOH added to a soln. of Mo complex and ligand in THF, stirred at ambient temp. for 2 h; evapd. (vac.), extd. (CH2Cl2), filtered, concd. (vac.), pptd. (EtOH), washed (EtOH and hexanes), dried (vac.), dissolved in CH2Cl2, layered withhexanes, crystd. for 3 d; elem. anal.;85%
N-(2-benzene-2,2-dichloroethylidene)-4-chlorobenzenesulfonamide
98416-35-4

N-(2-benzene-2,2-dichloroethylidene)-4-chlorobenzenesulfonamide

dithiooxamide
79-40-3

dithiooxamide

N,N'-bis[2,2-dichloro-1-(4-chlorophenylsulfonylamino)-2-phenylethyl]ethanebis(thioamide)
1377583-60-2

N,N'-bis[2,2-dichloro-1-(4-chlorophenylsulfonylamino)-2-phenylethyl]ethanebis(thioamide)

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 100℃; for 15h;85%
dithiooxamide
79-40-3

dithiooxamide

1-acetyl-1,2,3,4-tetrahydro-9H-carbazole
335330-07-9

1-acetyl-1,2,3,4-tetrahydro-9H-carbazole

(Z)-N1-[1-(2,3,4,9-tetrahydro-1H-carbazol-1-yl)ethylidene]ethanebis(thioamide)

(Z)-N1-[1-(2,3,4,9-tetrahydro-1H-carbazol-1-yl)ethylidene]ethanebis(thioamide)

Conditions
ConditionsYield
With acetic acid for 0.0166667h; Microwave irradiation; Green chemistry;85%
bromomethyl 2-methoxyphenyl ketone
31949-21-0

bromomethyl 2-methoxyphenyl ketone

dithiooxamide
79-40-3

dithiooxamide

C20H16N2O2S2
1242469-34-6

C20H16N2O2S2

Conditions
ConditionsYield
In ethanol at 20℃; for 5h; Reflux;84%
In ethanol
4-(N,N-dibutylamino)benzaldehyde
90134-10-4

4-(N,N-dibutylamino)benzaldehyde

dithiooxamide
79-40-3

dithiooxamide

C32H44N4S2
1442657-00-2

C32H44N4S2

Conditions
ConditionsYield
In propan-1-ol at 120℃; Schlenk technique; Inert atmosphere;83%
1-(2,3,4,5,6-pentafluorophenyl)-2-bromo-1-ethanone
5122-16-7

1-(2,3,4,5,6-pentafluorophenyl)-2-bromo-1-ethanone

dithiooxamide
79-40-3

dithiooxamide

4,4'-bis(perfluorophenyl)-2,2'-bithiazole
1422972-57-3

4,4'-bis(perfluorophenyl)-2,2'-bithiazole

Conditions
ConditionsYield
In ethanol Hantzsch Thiazole Synthesis; Reflux;83%
1-bromooctan-2-one
26818-08-6

1-bromooctan-2-one

dithiooxamide
79-40-3

dithiooxamide

4,4'-dihexyl 2,2'-bithiazole
180729-92-4

4,4'-dihexyl 2,2'-bithiazole

Conditions
ConditionsYield
In ethanol for 4h; Reflux;81%
In ethanol for 4h; Reflux; Inert atmosphere;80.8%
In ethanol for 4h; Reflux;
In ethanol
In ethanol
N-(2,2,2-trichloroethylidene)benzenesulfonamide
55596-11-7

N-(2,2,2-trichloroethylidene)benzenesulfonamide

dithiooxamide
79-40-3

dithiooxamide

N-[2,2,2-trichloro-1-(phenylsulfonylamino)ethyl]ethanedithioamide
1257096-40-4

N-[2,2,2-trichloro-1-(phenylsulfonylamino)ethyl]ethanedithioamide

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 90 - 100℃; for 12h;81%
dithiooxamide
79-40-3

dithiooxamide

3,4-ethylenedioxythiophene-2-carboxaldehyde
204905-77-1

3,4-ethylenedioxythiophene-2-carboxaldehyde

2,5-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)thiazolo[5,4-d]thiazole
1544476-48-3

2,5-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)thiazolo[5,4-d]thiazole

Conditions
ConditionsYield
Stage #1: dithiooxamide; 3,4-ethylenedioxythiophene-2-carboxaldehyde In nitrobenzene at 150℃; for 0.5h; Inert atmosphere; Microwave irradiation;
Stage #2: With chloranil In tetrahydrofuran; nitrobenzene for 0.166667h; Reflux; Inert atmosphere;
81%

DITHIOOXAMIDE Chemical Properties

Molecular Formula:C2H4N2S2
Molecular Weight:120.20
EINECS:201-203-9
Density:1.523 g/cm3
Melting Point:>300 °C
Boiling Point:252.1 °C at 760 mmHg
Flash Point:106.2 °C
Solubility:negligible
Stability:Stable.

Dithiooxamide's Synonyms: DITHIOOXALAMIDE;DITHIOOXALIC DIAMIDE;DITHIOOXAMIDE;ETHANEDITHIOAMIDE;RUBEANE;RUBEAN-HYDROGEN;RUBEANIC ACID;dithiono-oxalicacidiamide

DITHIOOXAMIDE Uses

Insecticide.Reagent for the spectrophotometric determination of palladium in the presence of piperidine, quinoline, a-picoline and collidine.

DITHIOOXAMIDE Toxicity Data With Reference

1.   

orl-rat LDLo:500 mg/kg

   NCNSA6    National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. 5 (1953),43.
2.   

orl-mus LD50:350 mg/kg

   FATOAO    Farmakologiya i Toksikologiya (Moscow). 28 (1965),230.
3.   

ipr-mus LD50:100 mg/kg

   NTIS**    National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD277-689 .
4.   

ivn-mus LD50:56 mg/kg

   CSLNX*    U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#04475 .

DITHIOOXAMIDE Consensus Reports

Reported in EPA TSCA Inventory.

DITHIOOXAMIDE Safety Profile

Poison by ingestion, intraperitoneal, and intravenous routes. When heated to decomposition it emits very toxic fumes of NOx and SOx.

Dithiooxamide's Safety Information
Hazard Codes  Xn
Risk Statements  22-36/37/38
Safety Statements  36/37
WGK Germany  3
RTECS  RP1575000
HS Code  29309070

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