1,2,4-Thiadiazole,3-bromo-5-chloro- supplier

Name
3-BROMO-5-CHLORO-1,2,4-THIADIAZOLE
EINECS
CAS No. 37159-60-7
Article Data2
CAS DataBase
Density 2.133 g/cm³
Solubility
Melting Point 24-25 °C
Formula C₂BrClN₂S
Boiling Point 270.128 °C at 760 mmHg
Molecular Weight 199.458
Flash Point 117.17 °C
Transport Information
Appearance clear colorless to yellow liquid
Safety 36/37/39-26
Risk Codes 36/37/38-20/21/22
Molecular Structure
Hazard Symbols Xn
Synonyms 3-Bromo-5-chloro-1,2,4-thiadiazole;3-bromo-5-chloro-1,2,4-thiadiazole;3-bromo-5-chloro-1,2,4-thiadiazole;
PSA 54.02000
LogP 1.95400

Synthetic route

: 26542-78-9
3,3'-dibromo-5,5'-disulfanediyl-bis-[1,2,4]thiadiazole

: 37159-60-7
3-bromo-5-chloro-[1,2,4]thiadiazole

Conditions

Conditions	Yield
With chlorine In acetic acid

: 37159-60-7
3-bromo-5-chloro-[1,2,4]thiadiazole

: N-(2,4-dimethoxybenzyl)-1-isopropyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazolo[4,3-c]pyridin-4-amine

: 3-(3-bromo-1,2,4-thiadiazol-5-yl)-N-(2.4-dimethoxybenzyl)-1-isopropyl-1H-pyrazolo[4,3-c]pyridin-4-amine

Conditions

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 90℃; for 3h; Sealed tube;	97%

: 37159-60-7
3-bromo-5-chloro-[1,2,4]thiadiazole

: (4-benzyl-6-methyl-pyrimidin-2-yl)-piperidin-4-yl-amine hydrochloride

: 1329669-67-1
(4-Benzyl-6-methyl-pyrimidin-2-yl)-[1-(3-bromo-[1,2,4]thiadiazol-5-yl)-piperidin-4-yl]-amine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 95℃; for 4.5h;	96%

: 37159-60-7
3-bromo-5-chloro-[1,2,4]thiadiazole

: 1329673-47-3
(4-benzyl-6-methyl-pyrimidin-2-yl)-piperidin-4-yl-amine hydrochloride

: 1329669-67-1
(4-Benzyl-6-methyl-pyrimidin-2-yl)-[1-(3-bromo-[1,2,4]thiadiazol-5-yl)-piperidin-4-yl]-amine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 95℃; for 4.5h;	96%

: 37159-60-7
3-bromo-5-chloro-[1,2,4]thiadiazole

: 1373522-74-7
1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)phenyl)piperidine

: 1373522-75-8
3-bromo-5-(4-(piperidin-1-yl)-3-(trifluoromethyl)phenyl)-1,2,4-thiadiazole

Conditions

Conditions	Yield
With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In water; N,N-dimethyl-formamide at 80℃; for 1h; Suzuki coupling;	94%

: 37159-60-7
3-bromo-5-chloro-[1,2,4]thiadiazole

: 4-(3-(phenylsulfonyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)morpholine

: 4-(3-(3-bromo-1,2,4-thiadiazol-5-yl)-5-(phenylsulfonyl)phenyl)morpholine

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; cesium fluoride In 1,4-dioxane; water at 80℃;	91%

: 37159-60-7
3-bromo-5-chloro-[1,2,4]thiadiazole

: 1189047-28-6
(2-(9H-carbazol-9-yl)phenyl)boronic acid

: 1567346-70-6
3,5-bis(2-(9H-carbazol-9-yl)phenyl)-1,2,4-thiadiazole

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 100℃; for 24h; Suzuki Coupling;	89%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran for 12h; Inert atmosphere; Sonication;	89%

: 37159-60-7
3-bromo-5-chloro-[1,2,4]thiadiazole

: 856167-68-5
2-(2-methylpropyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

: 1344997-62-1
5-(3-bromo-1,2,4-thiadiazol-5-yl)-2-isobutylbenzonitrile

Conditions

Conditions	Yield
With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In water; N,N-dimethyl-formamide at 80℃; for 1h; Suzuki coupling;	88%
With potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In water; N,N-dimethyl-formamide at 80℃; for 1h; Suzuki Coupling; Inert atmosphere; Microwave irradiation; Sealed vessel;
With potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In water; N,N-dimethyl-formamide at 80℃; for 1h; Inert atmosphere; Sealed; microwave irradiation;

: 37159-60-7
3-bromo-5-chloro-[1,2,4]thiadiazole

: 952514-86-2
1-phenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-benzo[d]imidazole

: 3,5-bis(3-(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl)-1,2,4-thiadiazole

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 100℃; for 12h; Suzuki Coupling; Inert atmosphere;	88%

: 37159-60-7
3-bromo-5-chloro-[1,2,4]thiadiazole

: 1373522-76-9
4,4,5,5-tetramethyl-2-(2-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)-1,3,2-dioxaborolane

: 1373522-77-0
3-bromo-5-(2-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)-1,2,4-thiadiazole

Conditions

Conditions	Yield
With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In water; N,N-dimethyl-formamide at 80℃; for 1h; Suzuki coupling;	86%

: 37159-60-7
3-bromo-5-chloro-[1,2,4]thiadiazole

: 1-(4-methoxyphenethyl)piperazine dihydrochloride

: 1417825-20-7
1-(3-bromo-[1,2,4]thiadiazol-5-yl)-4-[2-(4-methoxy-phenyl)-ethyl]-piperazine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol at 20℃;	85%

: 37159-60-7
3-bromo-5-chloro-[1,2,4]thiadiazole

: (5,10-diphenyl-5,10-dihydrophenazine-2-yl)boronic acid

: C50H34N6S

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 85℃; for 28h; Inert atmosphere;	85%

: 37159-60-7
3-bromo-5-chloro-[1,2,4]thiadiazole

: (3-(9,9-dimethylacridin-10(9H)-yl)phenyl)boronic acid

: C44H36N4S

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 50 - 100℃; Inert atmosphere;	85%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 50 - 100℃; Inert atmosphere;	85%

: 37159-60-7
3-bromo-5-chloro-[1,2,4]thiadiazole

: 1188094-46-3
phenanthrene-3-ylboronic acid

: C30H18N2S

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 85℃; for 28h; Inert atmosphere;	85%

: 37159-60-7
3-bromo-5-chloro-[1,2,4]thiadiazole

: 98-80-6
phenylboronic acid

: 101495-43-6
3-bromo-5-phenyl-1,2,4-thiadiazole

Conditions

Conditions	Yield
With bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); cesium fluoride In 1,4-dioxane; water at 80℃; for 16h; Inert atmosphere;	84%
With bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); cesium fluoride In 1,4-dioxane; water at 80℃; for 16h; Suzuki-Miyaura coupling; Inert atmosphere;	71%

: 37159-60-7
3-bromo-5-chloro-[1,2,4]thiadiazole

: 864377-33-3
3-(9H-carbazol-9-yl)phenylboronic acid

: 1567346-71-7
3,5-bis(3-(9H-carbazol-9-yl)phenyl)-1,2,4-thiadiazole

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 100℃; for 24h; Suzuki Coupling;	84%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran for 12h; Inert atmosphere; Sonication;	84%

: 37159-60-7
3-bromo-5-chloro-[1,2,4]thiadiazole

: C22H22BNO2S

: C46H40N4S3

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 85℃; for 28h; Inert atmosphere;	84%

: 37159-60-7
3-bromo-5-chloro-[1,2,4]thiadiazole

: (9-(dibenzo[b,d]thiophen-3-yl)-9H-carbazol-3-yl)boronic acid

: C50H28N4S3

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 85℃; for 28h; Inert atmosphere;	82%

: 37159-60-7
3-bromo-5-chloro-[1,2,4]thiadiazole

: C25H22BNO2

: C52H40N4S

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 85℃; for 28h; Inert atmosphere;	81%

: 37159-60-7
3-bromo-5-chloro-[1,2,4]thiadiazole

: (4-(3-phenyl-9H-carbazol-9-yl)phenyl)boronic acid

: C50H32N4S

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; (2)H8-toluene; water at 50 - 100℃; Inert atmosphere;	81%

: 419536-33-7
4-(carbazol-9-yl)phenylboronic acid

: 37159-60-7
3-bromo-5-chloro-[1,2,4]thiadiazole

: 1567346-72-8
3,5-bis(4-(9H-carbazol-9-yl)phenyl)-1,2,4-thiadiazole

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene at 100℃; for 24h; Suzuki Coupling;	80%

: 37159-60-7
3-bromo-5-chloro-[1,2,4]thiadiazole

: (3-(dibenzothiophen-2-yl(phenyl)amine)phenyl)boronic acid

: C50H32N4S3

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 50 - 100℃; Inert atmosphere;	80%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 50 - 100℃; Inert atmosphere;	80%

: 37159-60-7
3-bromo-5-chloro-[1,2,4]thiadiazole

: 123324-71-0
4-tert-butylphenylboronic acid

: 3-bromo-5-(4-(tert-butyl)phenyl)-1,2,4-thiadiazole

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In toluene at 100℃; for 12h; Reflux; Inert atmosphere;	78%

: 37159-60-7
3-bromo-5-chloro-[1,2,4]thiadiazole

: (E)-4-(2-(3-azabicyclo[3.1.0]hexan-6-yl)vinyl)-5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)isoxazole

: (E)-4-(2-(3-(3-bromo-1,2,4-thiadiazol-5-yl)-3-azabicyclo[3.1.0]hexan-6-yl)vinyl)-5-cyclopropyl-3-(3,5-dichloropyridin-4-yl)isoxazole

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 2h;	78%

: 37159-60-7
3-bromo-5-chloro-[1,2,4]thiadiazole

: (4-(3-(naphthalen-2-yl)-9H-carbazol-9-yl)phenyl)boronic acid

: 3-bromo-5-(4-(3-(naphthalen-2-yl)-9H-carbazol-9-yl)phenyl)-1,2,4-thiadiazole

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In toluene at 90℃; for 24h; Inert atmosphere;	77%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In toluene at 90℃; for 24h; Inert atmosphere;	77%

: 37159-60-7
3-bromo-5-chloro-[1,2,4]thiadiazole

: 122775-35-3
3,4-Dimethoxyphenylboronic acid

: 3-bromo-5-(3,4-dimethoxyphenyl)-1,2,4-thiadiazole

Conditions

Conditions	Yield
With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In water; N,N-dimethyl-formamide at 80℃; for 2h; Microwave irradiation;	77%

: 37159-60-7
3-bromo-5-chloro-[1,2,4]thiadiazole

: 98546-51-1
(4-thiomethoxyphenyl)boronic acid

: 1198321-26-4
C9H7BrN2S2

Conditions

Conditions	Yield
With bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); cesium fluoride In 1,4-dioxane; water at 80℃; for 16h; Suzuki-Miyaura coupling; Inert atmosphere;	72%

: 37159-60-7
3-bromo-5-chloro-[1,2,4]thiadiazole

: 201802-67-7
4-(diphenylamino)phenyl boronic acid

: 4-(3-bromo-1,2,4-thiadiazol-5-yl)-N,N-diphenylaniline

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In toluene at 50 - 100℃; Inert atmosphere;	72%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In toluene at 50 - 100℃; Inert atmosphere;	72%

: 37159-60-7
3-bromo-5-chloro-[1,2,4]thiadiazole

: 1189047-28-6
(2-(9H-carbazol-9-yl)phenyl)boronic acid

: 5-(2-(9H-carbazol-9-yl)phenyl)-3-bromo-1,2,4-thiadiazole

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In toluene at 100℃; for 12h; Inert atmosphere;	71%

: 37159-60-7
3-bromo-5-chloro-[1,2,4]thiadiazole

: 339529-96-3
2-(3-{3-[5-benzyloxy-2-ethyl-4-(4,4,5,5-tetramethyl-[1,3,2]diaxabarolan-2-yl)phenoxy]propoxy}-2-propylphenoxy)benzoic acid methyl ester

: 339529-97-4
2-(3-{3-[5-benzyloxy-4-(3-bromo-[1,2,4]thiadiazol-5-yl)-2-ethyl-phenoxy]propoxy}-2-propylphenoxy)benzoic acid methyl ester

Conditions

Conditions	Yield
With caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In toluene at 100℃; for 15h;	70%

: 37159-60-7
3-bromo-5-chloro-[1,2,4]thiadiazole

: 1373522-71-4
4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)phenyl)morpholine

: 1373522-72-5
4-(4-(3-bromo-1,2,4-thiadiazol-5-yl)-2-(trifluoromethyl)phenyl)morpholine

Conditions

Conditions	Yield
With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In water; N,N-dimethyl-formamide at 80℃; for 1h; Suzuki coupling;	69%

1,2,4-Thiadiazole,3-bromo-5-chloro- Specification

The 1,2,4-Thiadiazole,3-bromo-5-chloro-, with the CAS registry number 37159-60-7, has the systematic name and IUPAC name of 3-bromo-5-chloro-1,2,4-thiadiazole. It is a kind of clear colorless to yellow liquid, and the molecular formula of the chemical is C₂BrClN₂S.

The characteristics of 1,2,4-Thiadiazole,3-bromo-5-chloro- are as followings: (1)ACD/LogP: 2.33; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.326; (4)ACD/LogD (pH 7.4): 2.326; (5)ACD/BCF (pH 5.5): 34.519; (6)ACD/BCF (pH 7.4): 34.519; (7)ACD/KOC (pH 5.5): 439.098; (8)ACD/KOC (pH 7.4): 439.098; (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: 1.633; (14)Molar Refractivity: 33.405 cm³; (15)Molar Volume: 93.496 cm³; (16)Polarizability: 13.243×10^-24cm³; (17)Surface Tension: 64.629 dyne/cm; (18)Density: 2.133 g/cm³; (19)Flash Point: 117.17 °C; (20)Enthalpy of Vaporization: 48.782 kJ/mol; (21)Boiling Point: 270.128 °C at 760 mmHg; (22)Vapour Pressure: 0.012 mmHg at 25°C.

You should be cautious while dealing with this chemical. It irritates to eyes, respiratory system and skin, and it is also harmful by inhalation, in contact with skin and if swallowed. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection, and if in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: c1(nc(sn1)Cl)Br
(2)InChI: InChI=1/C2BrClN2S/c3-1-5-2(4)7-6-1
(3)InChIKey: CXUWGEWQRCXJDC-UHFFFAOYAK

Product Name

3-BROMO-5-CHLORO-1,2,4-THIADIAZOLE

Synthetic route

1,2,4-Thiadiazole,3-bromo-5-chloro- Specification

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