Product Name

  • Name

    Bismuththiol

  • EINECS 214-014-1
  • CAS No. 1072-71-5
  • Article Data26
  • CAS DataBase
  • Density 1.8 g/cm3
  • Solubility 20 g/L (20 °C) in water
  • Melting Point 161-165 °C
  • Formula C2H2N2S3
  • Boiling Point 211.3 °C at 760 mmHg
  • Molecular Weight 150.249
  • Flash Point 81.6 °C
  • Transport Information
  • Appearance white to light yellow crystal powder
  • Safety 26-36-37/39
  • Risk Codes 36-36/37/38
  • Molecular Structure Molecular Structure of 1072-71-5 (Bismuththiol)
  • Hazard Symbols IrritantXi
  • Synonyms 2, 5-Dimercapto-1,3,4-thiodiazole;2,5-Dimercapto-thiadiazole;2,5-Dimercapto-1,3,4-thiodiazole;Bismuthiol I;Dimercaptothiadiazole;1,3, 4-Thiadiazolidine-2,5-dithione;2, 5-Dimercapto-thiadiazole;2,5-Dimercaptothiadiazole;1,3,4-Thiadiazole-2,5-dithiol;D 2 (Chinese flotation agent);1,3,4-Thiadiazolidine-2,5-dithione(8CI9CI);2,5-Dimercapto-1,3,4-thiadiazole;1,3,4-thiadiazolidine-2,5-dithione;2,5-Dimercapto-1,3,4-Thiadiazol;2,5-Dimercapto-1,3,4-thiadiazole 98%;2,5-Dimercapto-1,3,4-thiadiazole (DMTD);bismuththiol; 2,5-dimercapto-1,3,4-thiadiazole;
  • PSA 131.62000
  • LogP 1.11550

Synthetic route

carbon disulfide
75-15-0

carbon disulfide

2,5-Dimercapto-1,3,4-thiadiazole
1072-71-5

2,5-Dimercapto-1,3,4-thiadiazole

Conditions
ConditionsYield
With hydrazine hydrate; sodium hydroxide In ethanol; water at 0℃; for 17.5h; Reflux;98%
With hydrazine hydrate In ethanol at 80℃; for 4h; Temperature;93%
With sulfuric acid; hydrazine hydrate; sodium hydroxide87%
malonic acid dihydrazide
3815-86-9

malonic acid dihydrazide

carbon disulfide
75-15-0

carbon disulfide

A

malonic acid
141-82-2

malonic acid

B

2,5-Dimercapto-1,3,4-thiadiazole
1072-71-5

2,5-Dimercapto-1,3,4-thiadiazole

Conditions
ConditionsYield
Stage #1: malonic acid dihydrazide; carbon disulfide With potassium hydroxide In ethanol for 3h; Rearrangement; cyclization; Heating;
Stage #2: With hydrogenchloride In ethanol Hydrolysis; ring cleavage;		A n/a
B 90%
...Expand
carbon disulfide
75-15-0

carbon disulfide

succinic acid dihydrazide
4146-43-4

succinic acid dihydrazide

A

succinic acid
110-15-6

succinic acid

B

2,5-Dimercapto-1,3,4-thiadiazole
1072-71-5

2,5-Dimercapto-1,3,4-thiadiazole

Conditions
ConditionsYield
Stage #1: carbon disulfide; succinic acid dihydrazide With potassium hydroxide In ethanol for 3h; Rearrangement; cyclization; Heating;
Stage #2: With hydrogenchloride In ethanol Hydrolysis; ring cleavage;		A n/a
B 90%
...Expand
5-mercapto-1,3,4-thiadiazole-2(3H)-thione
1072-71-5

5-mercapto-1,3,4-thiadiazole-2(3H)-thione

2,5-Dimercapto-1,3,4-thiadiazole
1072-71-5

2,5-Dimercapto-1,3,4-thiadiazole

Conditions
ConditionsYield
In argon matrix at -263.16℃; for 2h; UV-irradiation;
2,5-dimercapto-1,3,4-thiadiazole mono-sodium salt

2,5-dimercapto-1,3,4-thiadiazole mono-sodium salt

2,5-Dimercapto-1,3,4-thiadiazole
1072-71-5

2,5-Dimercapto-1,3,4-thiadiazole

Conditions
ConditionsYield
Stage #1: 2,5-dimercapto-1,3,4-thiadiazole mono-sodium salt With sulfuric acid In water at 20℃; Inert atmosphere;
Stage #2: Industry scale;
1-acryloyloxymethyl-3,4-epoxycyclohexane
64630-63-3

1-acryloyloxymethyl-3,4-epoxycyclohexane

2,5-Dimercapto-1,3,4-thiadiazole
1072-71-5

2,5-Dimercapto-1,3,4-thiadiazole

C22H30N2O6S3

C22H30N2O6S3

Conditions
ConditionsYield
With 2,5-bis(1,1-dimethylethyl)-1,4-benzenediol at 60℃; for 3h;99.6%
methacrylic acid 7-oxabicyclo[4.1.0]hept-3-ylmethyl ester

methacrylic acid 7-oxabicyclo[4.1.0]hept-3-ylmethyl ester

2,5-Dimercapto-1,3,4-thiadiazole
1072-71-5

2,5-Dimercapto-1,3,4-thiadiazole

C24H34N2O6S3

C24H34N2O6S3

Conditions
ConditionsYield
With 2,5-bis(1,1-dimethylethyl)-1,4-benzenediol at 40℃; for 5h;99.2%
methacrylic acid 7-oxabicyclo[4.1.0]hept-3-ylmethyl ester

methacrylic acid 7-oxabicyclo[4.1.0]hept-3-ylmethyl ester

1-acryloyloxymethyl-3,4-epoxycyclohexane
64630-63-3

1-acryloyloxymethyl-3,4-epoxycyclohexane

2,5-Dimercapto-1,3,4-thiadiazole
1072-71-5

2,5-Dimercapto-1,3,4-thiadiazole

C23H32N2O6S3

C23H32N2O6S3

Conditions
ConditionsYield
With 2,5-bis(1,1-dimethylethyl)-1,4-benzenediol In isopropyl alcohol at 70℃; for 4h;98.9%
...Expand
2,5-Dimercapto-1,3,4-thiadiazole
1072-71-5

2,5-Dimercapto-1,3,4-thiadiazole

1-chloro-2,4-dinitro-benzene
97-00-7

1-chloro-2,4-dinitro-benzene

2,5-bis(2,4-dinitrophenylthio)-1,3,4-thiadiazole

2,5-bis(2,4-dinitrophenylthio)-1,3,4-thiadiazole

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 20℃; for 24h;98%
With potassium hydroxide In water; N,N-dimethyl-formamide Heating;93%
2,5-Dimercapto-1,3,4-thiadiazole
1072-71-5

2,5-Dimercapto-1,3,4-thiadiazole

1,3,4-thiadiazole-2,5-disulfonic acid

1,3,4-thiadiazole-2,5-disulfonic acid

Conditions
ConditionsYield
With potassium permanganate Heating;98%
α-bromoacetophenone
70-11-1

α-bromoacetophenone

2,5-Dimercapto-1,3,4-thiadiazole
1072-71-5

2,5-Dimercapto-1,3,4-thiadiazole

2-({5-[(2-oxo-2-phenylethyl)sulfanyl]-1,3,4-thiadiazol-2-yl}sulfanyl)-1-phenyl-1-ethanone

2-({5-[(2-oxo-2-phenylethyl)sulfanyl]-1,3,4-thiadiazol-2-yl}sulfanyl)-1-phenyl-1-ethanone

Conditions
ConditionsYield
With zinc(II) oxide In neat (no solvent) at 25 - 30℃;98%
Stage #1: 2,5-Dimercapto-1,3,4-thiadiazole With triethylamine In ethanol for 0.25h;
Stage #2: α-bromoacetophenone In ethanol for 3h; Reflux;		87%
2,5-Dimercapto-1,3,4-thiadiazole
1072-71-5

2,5-Dimercapto-1,3,4-thiadiazole

2-Bromo-4'-methoxyacetophenone
2632-13-5

2-Bromo-4'-methoxyacetophenone

1-(4-methoxyphenyl)-2-[(5-{[2-(4-methoxyphenyl)-2-oxoethyl]sulfanyl}-1,3,4-thiadiazol-2-yl)sulfanyl]-1-ethanone

1-(4-methoxyphenyl)-2-[(5-{[2-(4-methoxyphenyl)-2-oxoethyl]sulfanyl}-1,3,4-thiadiazol-2-yl)sulfanyl]-1-ethanone

Conditions
ConditionsYield
With zinc(II) oxide In neat (no solvent) at 25 - 30℃;94%
Stage #1: 2,5-Dimercapto-1,3,4-thiadiazole With triethylamine In ethanol for 0.25h;
Stage #2: 2-Bromo-4'-methoxyacetophenone In ethanol for 3h; Reflux;		87%
2,5-Dimercapto-1,3,4-thiadiazole
1072-71-5

2,5-Dimercapto-1,3,4-thiadiazole

para-bromophenacyl bromide
99-73-0

para-bromophenacyl bromide

1-(4-bromophenyl)-2-[(5-{[2-(4-bromophenyl)-2-oxoethyl]sulfanyl}-1,3,4-thiadiazol-2-yl)sulfanyl]-1-ethanone

1-(4-bromophenyl)-2-[(5-{[2-(4-bromophenyl)-2-oxoethyl]sulfanyl}-1,3,4-thiadiazol-2-yl)sulfanyl]-1-ethanone

Conditions
ConditionsYield
With zinc(II) oxide In neat (no solvent) at 25 - 30℃;94%
Stage #1: 2,5-Dimercapto-1,3,4-thiadiazole With triethylamine In ethanol for 0.25h;
Stage #2: para-bromophenacyl bromide In ethanol for 3h; Reflux;		89%
isooctylthiochloride

isooctylthiochloride

2,5-Dimercapto-1,3,4-thiadiazole
1072-71-5

2,5-Dimercapto-1,3,4-thiadiazole

2,5-bis(isooctyldithio)-1,3,4-thiadiazole

2,5-bis(isooctyldithio)-1,3,4-thiadiazole

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 30℃; for 3h;94%
carbonyldihydridotris(triphenylphosphine)osmium
36179-61-0, 12104-84-6

carbonyldihydridotris(triphenylphosphine)osmium

2,5-Dimercapto-1,3,4-thiadiazole
1072-71-5

2,5-Dimercapto-1,3,4-thiadiazole

carbonylbis(1,3,4-thiadiazole-2,5-dithiolato)bis(triphenylphosphine)osmium(II)

carbonylbis(1,3,4-thiadiazole-2,5-dithiolato)bis(triphenylphosphine)osmium(II)

Conditions
ConditionsYield
In toluene the mixt. of Os complex and ligand was heated under reflux for 4 h; ppt. was filtered off, washed with toluene, ethanol, n-hexane, dried invac., elem. anal.;93%
2,5-Dimercapto-1,3,4-thiadiazole
1072-71-5

2,5-Dimercapto-1,3,4-thiadiazole

4-chlorobenzoylmethyl bromide
536-38-9

4-chlorobenzoylmethyl bromide

1-(4-chlorophenyl)-2-[(5-{[2-(4-chlorophenyl)-2-oxoethyl]sulfanyl}-1,3,4-thiadiazol-2-yl)sulfanyl]-1-ethanone

1-(4-chlorophenyl)-2-[(5-{[2-(4-chlorophenyl)-2-oxoethyl]sulfanyl}-1,3,4-thiadiazol-2-yl)sulfanyl]-1-ethanone

Conditions
ConditionsYield
With zinc(II) oxide In neat (no solvent) at 25 - 30℃;93%
Stage #1: 2,5-Dimercapto-1,3,4-thiadiazole With triethylamine In ethanol for 0.25h;
Stage #2: 4-chlorobenzoylmethyl bromide In ethanol for 3h; Reflux;		87%
2-Isocyanatoethyl methacrylate
30674-80-7

2-Isocyanatoethyl methacrylate

2,5-Dimercapto-1,3,4-thiadiazole
1072-71-5

2,5-Dimercapto-1,3,4-thiadiazole

C16H20N4O6S3

C16H20N4O6S3

Conditions
ConditionsYield
In acetone at 20℃; for 5.5h;92.4%
In acetic acid butyl ester at 50℃;76%
carbon disulfide
75-15-0

carbon disulfide

didecylamine
1120-49-6

didecylamine

2,5-Dimercapto-1,3,4-thiadiazole
1072-71-5

2,5-Dimercapto-1,3,4-thiadiazole

C44H84N4S5

C44H84N4S5

Conditions
ConditionsYield
Stage #1: carbon disulfide; didecylamine; 2,5-Dimercapto-1,3,4-thiadiazole With sodium ethanolate In butan-1-ol at 0℃; for 5h;
Stage #2: With ammonium tetramolybdate In butan-1-ol at 130℃; under 3750.38 Torr; for 5h; Sealed tube; Inert atmosphere;		92.1%
...Expand
triphenylbismuthane
603-33-8

triphenylbismuthane

2,5-Dimercapto-1,3,4-thiadiazole
1072-71-5

2,5-Dimercapto-1,3,4-thiadiazole

2C2HN2S3(1-)*Bi(3+)*C6H5(1-)

2C2HN2S3(1-)*Bi(3+)*C6H5(1-)

Conditions
ConditionsYield
In ethanol; toluene at 112℃; for 0.166667h; Microwave irradiation;92%
4-bromoethylbutanoate
2969-81-5

4-bromoethylbutanoate

2,5-Dimercapto-1,3,4-thiadiazole
1072-71-5

2,5-Dimercapto-1,3,4-thiadiazole

diethyl 4,4′-[(1,3,4-thiadiazol-2,5diyl)bis(sulfanediyl)]dibutanoate

diethyl 4,4′-[(1,3,4-thiadiazol-2,5diyl)bis(sulfanediyl)]dibutanoate

Conditions
ConditionsYield
Stage #1: 2,5-Dimercapto-1,3,4-thiadiazole With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h; Reflux;
Stage #2: Ethyl 4-bromobutyrate In N,N-dimethyl-formamide for 8h; Reflux;		92%
2,5-Dimercapto-1,3,4-thiadiazole
1072-71-5

2,5-Dimercapto-1,3,4-thiadiazole

1,3-dimethyl-5-chloro-pyrazole-4-carbonyl chloride
27006-83-3

1,3-dimethyl-5-chloro-pyrazole-4-carbonyl chloride

C14H12Cl2N6O2S3

C14H12Cl2N6O2S3

Conditions
ConditionsYield
With potassium carbonate In chloroform at 0 - 20℃; for 6h;92%
S-tert-butylsulfinimide
146374-27-8

S-tert-butylsulfinimide

2,5-Dimercapto-1,3,4-thiadiazole
1072-71-5

2,5-Dimercapto-1,3,4-thiadiazole

2,5-bis(2-tert-butyldisulfanyl)-1,3,4-thiadiazole

2,5-bis(2-tert-butyldisulfanyl)-1,3,4-thiadiazole

Conditions
ConditionsYield
With copper(l) iodide; magnesium sulfate In N,N-dimethyl-formamide at 100℃; for 24h; Sealed tube;92%
copper(II) acetate monohydrate
6046-93-1

copper(II) acetate monohydrate

2,5-Dimercapto-1,3,4-thiadiazole
1072-71-5

2,5-Dimercapto-1,3,4-thiadiazole

C2N2S3(2-)*Cu(2+)

C2N2S3(2-)*Cu(2+)

Conditions
ConditionsYield
With potassium hydroxide In water at 60℃; for 2h;92%

Bismuththiol Consensus Reports

Reported in EPA TSCA Inventory.

Bismuththiol Specification

The Bismuththiol , with cas registry number of 1072-71-5, has other registry numbers including 10472-91-0, 10502-35-9, and 66057-67-8. It also called Bismuththiol ; 2,5-Dimercapto-1,3,4-thiadiazole ; DMTD . The IUPAC name is 1,3,4-thiadiazolidine-2,5-dithione . The systematic name is also called 1,3,4-thiadiazolidine-2,5-dithione . It belongs to the categories of (1)API intermediates; (2)Analytical Chemistry; (3)Bipyridyls, etc. (Chelating Reagents); (4)Chelating Reagents.

Physical properties of Bismuththiol are: (1) ACD/LogP: 0.20 ; (2) # of Rule of 5 Violations: 0 ; (3) ACD/LogD (pH 5.5): -0.02 ; (4) ACD/LogD (pH 7.4): -1.36 ; (5) ACD/BCF (pH 5.5): 1 ; (6) ACD/BCF (pH 7.4): 1 ; (7) ACD/KOC (pH 5.5): 18.25 ; (8) ACD/KOC (pH 7.4): 1 ; (9) #H bond acceptors: 2 ; (10) #H bond donors: 2 ; (11) #Freely Rotating Bonds: 0 ; (12) Index of Refraction: 1.902 ; (13) Molar Refractivity: 38.8 cm3 ; (14) Molar Volume: 83.2 cm3 ; (15) Surface Tension: 133 dyne/cm ; (16) Enthalpy of Vaporization: 44.76 kJ/mol ; (17) Vapour Pressure: 0.184 mmHg at 25°C.

Preparation of Bismuththiol : This chemical can be prepared by the carbon disulfide. The reaction occures in the solvent of liquid ammonia and ethanol using the reagent of Hydrazine hydrate for 1 hour. The yield is 62%.

Uses of Bismuththiol : (1) It is used as pharmaceutical intermediates, raw materials
of organic synthesis, analytical reagents, fuel additives, etc. (2) This compound is mainly used to prepare other chemicals. Here will give you a example. Bismuththiol is used to prepare the 3H,3'H-5,5'-disulfanediyl-bis-[1,3,4]thiadiazole-2-thione using solvent of Methanol for 48 hours. This process also needs irradiation. The yield is about 20%.

When you are using this chemical, please be cautious about it as the following:
The Bismuththiol is irritating to eyes, respiratory system and skin. It is poison by intraperitoneal route. When heated to decomposition, it emits very toxic fumes of NOx and SOx. When use it, wear suitable protective clothing, suitable gloves and eye/face protection. If contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES:S=C1SC(=S)NN1 ;
(2) InChI:InChI=1/C2H2N2S3/c5-1-3-4-2(6)7-1/h(H,3,5)(H,4,6) ;
(3) InChIKey:BIGYLAKFCGVRAN-UHFFFAOYAT

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 200mg/kg (200mg/kg)   National Technical Information Service. Vol. AD277-689,
quail LD50 oral > 316mg/kg (316mg/kg)   Ecotoxicology and Environmental Safety. Vol. 6, Pg. 149, 1982.

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