3,4-Dichloro-1,2,5-thiadiazole supplier

Name
3,4-Dichloro-1,2,5-thiadiazole
EINECS 227-232-7
CAS No. 5728-20-1
Article Data10
CAS DataBase
Density 1.737 g/cm³
Solubility
Melting Point 82-83 °C
Formula C₂Cl₂N₂S
Boiling Point 157.999 °C at 760 mmHg
Molecular Weight 155.007
Flash Point 49.669 °C
Transport Information UN 2810
Appearance liquid
Safety 26-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 1,2,5-Thiadiazole, 3,4-dichloro-;
PSA 54.02000
LogP 1.84490

Synthetic route

: 2038-44-0
dichloroglyoxime

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

Conditions

Conditions	Yield
With pyridine; disulfur dichloride In acetonitrile at -25℃; for 5h; Inert atmosphere; Reflux;	78%
With sulfur dichloride In N,N-dimethyl-formamide

: 460-19-5
ethanedinitrile

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

Conditions

Conditions	Yield
With disulfur dichloride In N,N-dimethyl-formamide
With sulfur dichloride

: 33355-75-8
hexa-P-phenyl-P,P'-ethane-1,2-diyldiamino-bis-phosphonium; dichloride

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

Conditions

Conditions	Yield
With sulfur tetrafluoride; triethylamine In dichloromethane

: 540-61-4
2-aminoacetonitrile

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

Conditions

Conditions	Yield
With disulfur dichloride; chlorine In N,N-dimethyl-formamide

: 333-18-6
1,2-diaminoethane dihydrochloride

A: 5097-45-0
3-Chloro-1,2,5-thiadiazole

B: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

Conditions

Conditions	Yield
With disulfur dichloride; chlorine; iron In N,N-dimethyl-formamide	A 5 g B 115.7 g

: 110-89-4
piperidine

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

: 3-(piperidin-1-yl)-4-chloro-1,2,5-thiadiazole

Conditions

Conditions	Yield
at 110 - 120℃;	100%
at 90 - 100℃; Inert atmosphere;	94%
In neat (no solvent) at 90℃; for 2h;
In neat (no solvent) at 90℃; for 2h;

: 31252-42-3
4-benzylpyperidine

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

: 3-(4-benzylpiperidin-1-yl)-4-chloro-1,2,5-thiadiazole

Conditions

Conditions	Yield
at 110 - 120℃;	100%

: 110-91-8
morpholine

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

: 30165-96-9
3-Morpholino-4-chloro-1,2,5-thiadiazole

Conditions

Conditions	Yield
	98%
at 110℃; for 2.5h; Inert atmosphere;	95%
at 110 - 120℃;	90%

: 111-49-9
hexamethylene imine

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

: 1119451-34-1
3-(1-azepanyl)-4-chloro-1,2,5-thiadiazole

Conditions

Conditions	Yield
at 120℃; for 4h; Inert atmosphere;	98%

: 30315-46-9
(S)-1-tert-butylamino-2,3-dihydroxypropane

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

: 26791-15-1
(S)-(-)-3-(3-tert-butylamnio-2-hydroxypropoxy)-4-chloro-1,2,5-thiadiazole

Conditions

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol for 1h; Heating / reflux;	96.6%

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

: 4,5-dimethyl-2-(trimethylsilyl)phenyl triflate

: 41533-37-3
3-chloro-5,6-dimethyl-1,2-benzoisothiazole

Conditions

Conditions	Yield
With cesium fluoride In tetrahydrofuran Inert atmosphere;	96%

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

: 717903-52-1
6-(trimethylsilyl)benzo[d][1,3]dioxol-5-yl triflate

: 3-chloro-5,6-dioxolo-1,2-benzoisothiazole

Conditions

Conditions	Yield
With cesium fluoride In tetrahydrofuran Inert atmosphere;	96%

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

: 4,5-dimethoxy-2-(trimethylsilyl)phenyl trifluoromethanesulfonate

: 3-chloro-5,6-dimethoxy-1,2-benzoisothiazole

Conditions

Conditions	Yield
With cesium fluoride In tetrahydrofuran Inert atmosphere;	93%

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

A: 82878-41-9
2-(Chlorimino)-N-(difluor-λ4-sulfanyliden)-1,1,2-trifluorethanamin

B: 82878-40-8
2-Chlor-2-(chlorimino)-N-(difluor-λ4-sulfanyliden)-1,1-difluorethanamin

C: 32751-05-6
N,N-Dichlor-N'-(difluor-λ4-sulfanyliden)-1,1,2,2-tetrafluor-1,2-ethandiamin

D: 82878-42-0
Bis<2-<(difluor-λ4-sulfanyliden)amino>-1,1,2,2-tetrafluorethyl>diazen

Conditions

Conditions	Yield
With HgF3 at 140℃; for 1h; further reagent: BrF3;	A n/a B n/a C n/a D 91%
With bromine trifluoride at -15℃; Title compound not separated from byproducts;

...Expand

: 109-01-3
1-methyl-piperazine

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

: 870987-89-6
3-chloro-4-(4-methylpiperazin-1-yl)-1,2,5-thiadiazole

Conditions

Conditions	Yield
In ethanol at 100℃; for 2.5h; Sealed tube; Microwave irradiation;	91%
at 105 - 110℃; for 2.5h;	90.2%
at 105 - 110℃; for 2.5h;	90.2%

: 92-54-6
4-phenyl-1-piperazine

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

: 1048981-72-1
3-chloro-4-(4-phenylpiperazin-1-yl)-1,2,5-thiadiazole

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100 - 110℃;	91%
at 105 - 110℃; for 2.5h;

: 771-99-3
4-phenylpiperidine

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

Conditions

Conditions	Yield
at 110 - 120℃;	91%

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

: 4039-32-1
lithium hexamethyldisilazane

: C8H18ClN3SSi2

Conditions

Conditions	Yield
In n-heptane at -78℃; for 0.5h;	90%

: 7453-26-1
1,3-dimethyl-1,1,3,3-tetraphenyldisilazane

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

: C28H26ClN3SSi2

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -10℃; for 0.5h;	88%

: 123-75-1
pyrrolidine

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

: 173053-55-9
3-(pyrrolidin-1-yl)-4-chloro-1,2,5-thiadiazole

Conditions

Conditions	Yield
at 22℃; Inert atmosphere;	87%

: 7550-45-0
titanium tetrachloride

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

: 80044-97-9
(SN2C2Cl2)2TiCl4

Conditions

Conditions	Yield
In dichloromethane under N2 and exclusion of air, to a soln. of SN2C2Cl2 in dry CH2Cl2 addn. of TiCl4 in CH2Cl2 under stirring at room temp.; removal of solvent, recrystn. (CH2Cl2), sublimation (vac., room temp.), elem. anal.;	82%

: 2744-08-3, 2744-09-4, 6329-61-9
decahydroisoquinoline

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

: 3-chloro-4-(octahydroisoquinolin-2(1H)-yl)-1,2,5-thiadiazole

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100 - 110℃;	81%

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

: C2Cl2N2O3S2

Conditions

Conditions	Yield
With sulfur trioxide In dichloromethane Ambient temperature;	79%

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

: 57260-71-6
1-t-Butoxycarbonylpiperazine

: 291748-19-1
4-(4-chloro-[1,2,5]thiadiazol-3-yl)piperazine-1-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
In N,N-dimethyl-formamide Heating;	77%
With potassium carbonate In acetonitrile	1.54 g (31%)
With diisopropylamine In N,N-dimethyl-formamide at 100℃; for 16h;	2.7 g
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 100℃; for 16h;

: 88284-48-4
2-(trimethylsilyl)phenyl trifluoromethanesulfonate

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

: 7716-66-7
3-chloro-1,2-benzisothiazole

Conditions

Conditions	Yield
With cesium fluoride In tetrahydrofuran Reagent/catalyst; Solvent; Inert atmosphere;	76%

: 3449-26-1
1,1,3,3-tetramethyl-1,3-diphenyldisilazane

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

: C18H22ClN3SSi2

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -10℃; for 0.5h;	75%

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

: C19H26F3IO5SSi3

: 3-chloro-5,6-oxadisilole-1,2-benzoisothiazole

Conditions

Conditions	Yield
Stage #1: C19H26F3IO5SSi3 With cesium fluoride Stage #2: 3,4-dichloro-1,2,5-thiadiazole In tetrahydrofuran at 60℃; for 3h;	75%

: 768-66-1
2,2,6,6-tetramethyl-piperidine

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

: 895167-58-5
2-chloro-2-(2,2,6,6-tetramethyl-1-piperidinylthio)iminoacetonitrile

Conditions

Conditions	Yield
Stage #1: 2,2,6,6-tetramethyl-piperidine With n-butyllithium In tert-butyl methyl ether at -20℃; Stage #2: 3,4-dichloro-1,2,5-thiadiazole In tert-butyl methyl ether at -50℃;	74%

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

KF: KF

A: 82878-37-3
3,4-Difluoro-1,2,5-thiadiazole

B: 82878-38-4
3-chloro-4-fluoro-1,2,5-thiadiazole

Conditions

Conditions	Yield
In sulfolane at 180℃; for 10h;	A 73% B 24%
In sulfolane at 180℃; for 10h; further reagent: 18-Crown<6>, XeF2;	A 48% B 24%

...Expand

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

: 4039-32-1
lithium hexamethyldisilazane

: 895167-57-4
2-chloro-2-(N,N-bis(trimethylsilyl)aminothio)iminoacetonitrile

Conditions

Conditions	Yield
In tetrahydrofuran; diethyl ether; cyclohexane at -78℃; for 1h;	73%

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

: 881009-83-2
2-methoxy-6-(trimethylsilyl)phenyltrifluoromethanesulfonate

: 103486-06-2
3-chloro-4-methoxy-1,2-benzoisothiazole

Conditions

Conditions	Yield
With cesium fluoride In tetrahydrofuran Inert atmosphere; regioselective reaction;	70%

: 4-bromo-2-methoxy-6-(trimethylsilyl)phenyl trifluoromethanesulfonate

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

A: 3-chloro-4-methoxy-6-bromo-1,2-benzoisothiazole

B: 3-chloro-5-bromo-7-methoxy-1,2-benzoisothiazole

Conditions

Conditions	Yield
With cesium fluoride In tetrahydrofuran Inert atmosphere; regioselective reaction;	A 69% B 9%

...Expand

: 88284-48-4
2-(trimethylsilyl)phenyl trifluoromethanesulfonate

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

: 108-59-8
malonic acid dimethyl ester

A: 35212-85-2
3-Amino-benzo[b]thiophene-2-carboxylic acid methyl ester

B: dimethyl 2,1-benzoisothiazole-3-malonate

Conditions

Conditions	Yield
Stage #1: 2-(trimethylsilyl)phenyl trifluoromethanesulfonate; 3,4-dichloro-1,2,5-thiadiazole With cesium fluoride In tetrahydrofuran at 20 - 65℃; Inert atmosphere; Stage #2: malonic acid dimethyl ester With sodium methylate In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;	A 11% B 68%

...Expand

: 5728-20-1
3,4-dichloro-1,2,5-thiadiazole

: 780820-44-2
3,6-dimethyl-2-(trimethylsilyl)phenyl triflate

: 3-chloro-4,7-dimethyl-1,2-benzoisothiazole

Conditions

Conditions	Yield
With cesium fluoride In tetrahydrofuran Inert atmosphere;	67%

3,4-Dichloro-1,2,5-thiadiazole Specification

The 3,4-Dichloro-1,2,5-thiadiazole, with the CAS registry number 5728-20-1, is also known as 1,2,5-Thiadiazole, 3,4-dichloro-. It belongs to the product categories of Xanthones; Building Blocks; Halogenated Heterocycles; Heterocyclic Building Blocks; Thiadiazoles; Thiadiazoles Heterocyclic Building Blocks. Its EINECS registry number is 227-232-7. This chemical's molecular formula is C₂Cl₂N₂S and molecular weight is 155.01. What's more, its IUPAC name is the same with its product name. It should be stored in a cool, dry and well-ventilated place. This chemical can be used as intermediates for Timolol.

Physical properties about 3,4-Dichloro-1,2,5-thiadiazole are: (1)ACD/LogP: 1.595; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.60; (4)ACD/LogD (pH 7.4): 1.60; (5)ACD/BCF (pH 5.5): 9.59; (6)ACD/BCF (pH 7.4): 9.59; (7)ACD/KOC (pH 5.5): 175.57; (8)ACD/KOC (pH 7.4): 175.57; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 54.02 Å²; (13)Index of Refraction: 1.602; (14)Molar Refractivity: 30.61 cm³; (15)Molar Volume: 89.262 cm³; (16)Polarizability: 12.135×10^-24cm³; (17)Surface Tension: 61.9920 dyne/cm; (18)Density: 1.737 g/cm³; (19)Flash Point: 49.669 °C; (20)Enthalpy of Vaporization: 37.842 kJ/mol; (21)Boiling Point: 157.999 °C at 760 mmHg; (22)Vapour Pressure: 3.471 mmHg at 25 °C.

Uses of 3,4-Dichloro-1,2,5-thiadiazole: it is used to produce other chemicals. For example, it can react with 2-amino-ethanol to get 3-chloro-4-[(2-hydroxyethyl)amino]-1,2,5-thiadiazole. The reaction occurs with reagent 2-methyl-propan-2-ol and other condition of heating for 28 days. The yield is 61.6 %.

3,4-Dichloro-1,2,5-thiadiazole can react with 2-amino-ethanol to get 3-chloro-4-[(2-hydroxyethyl)amino]-1,2,5-thiadiazole.

When you are dealing with this chemical, you should be very careful. This chemical is inflammation to the skin, eyes and respiratory system or other mucous membranes. Therefore, you should wear suitable gloves and eye/face protection. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: Clc1nsnc1Cl
(2) InChI: InChI=1S/C2Cl2N2S/c3-1-2(4)6-7-5-1
(3) InChIKey: YNZQOVYRCBAMEU-UHFFFAOYSA-N

Product Name

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

Synthetic route

3,4-Dichloro-1,2,5-thiadiazole Specification

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