Product Name

  • Name

    2,1,3-Benzothiadiazole-5-carboxylic acid

  • EINECS
  • CAS No. 16405-98-4
  • Article Data6
  • CAS DataBase
  • Density 1.609 g/cm3
  • Solubility
  • Melting Point 229 °C
  • Formula C7H4N2O2S
  • Boiling Point 368.748 °C at 760 mmHg
  • Molecular Weight 180.187
  • Flash Point 176.813 °C
  • Transport Information
  • Appearance
  • Safety 26-36/37/39-24/25
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 16405-98-4 (2,1,3-Benzothiadiazole-5-carboxylic acid)
  • Hazard Symbols IrritantXi
  • Synonyms Benzo[c][1,2,5]thiadiazole-5-carboxylicacid;
  • PSA 91.32000
  • LogP 1.38950

Synthetic route

methyl benzo-2,1,3-thiadiazole-5-carboxylate

methyl benzo-2,1,3-thiadiazole-5-carboxylate

benzo[1,2,5]thiadiazole-5-carboxylic acid
16405-98-4

benzo[1,2,5]thiadiazole-5-carboxylic acid

Conditions
ConditionsYield
Stage #1: methyl benzo-2,1,3-thiadiazole-5-carboxylate With sodium hydroxide; ethanol; water at 20℃; for 3h;
Stage #2: With hydrogenchloride In water pH=2;		92%
With pyridine; lithium iodide Heating;
benzo[c][1,2,5]thiadiazole-5-carbaldehyde
71605-72-6

benzo[c][1,2,5]thiadiazole-5-carbaldehyde

benzo[1,2,5]thiadiazole-5-carboxylic acid
16405-98-4

benzo[1,2,5]thiadiazole-5-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide; silver nitrate
N-phenylsulfinylamine
222851-56-1

N-phenylsulfinylamine

3,4-diaminobenzoic acid
619-05-6

3,4-diaminobenzoic acid

benzo[1,2,5]thiadiazole-5-carboxylic acid
16405-98-4

benzo[1,2,5]thiadiazole-5-carboxylic acid

Conditions
ConditionsYield
With xylene
5-methylbenzo[c][1,2,5]thiadiazole
1457-93-8

5-methylbenzo[c][1,2,5]thiadiazole

benzo[1,2,5]thiadiazole-5-carboxylic acid
16405-98-4

benzo[1,2,5]thiadiazole-5-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-bromo-succinimide
3: aqueous acetic acid; hexamethylenetetramine
4: AgNO3; aqueous NaOH
View Scheme
5-bromomethyl-benzo[1,2,5]thiadiazole
65858-50-6

5-bromomethyl-benzo[1,2,5]thiadiazole

benzo[1,2,5]thiadiazole-5-carboxylic acid
16405-98-4

benzo[1,2,5]thiadiazole-5-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
2: aqueous acetic acid; hexamethylenetetramine
3: AgNO3; aqueous NaOH
View Scheme
1-benzo[1,2,5]thiadiazol-5-ylmethyl-1,3,5,7-tetraaza-adamantanium; bromide

1-benzo[1,2,5]thiadiazol-5-ylmethyl-1,3,5,7-tetraaza-adamantanium; bromide

benzo[1,2,5]thiadiazole-5-carboxylic acid
16405-98-4

benzo[1,2,5]thiadiazole-5-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aqueous acetic acid; hexamethylenetetramine
2: AgNO3; aqueous NaOH
View Scheme
benzo[1,2,5]thiadiazole-5-carboxylic acid
16405-98-4

benzo[1,2,5]thiadiazole-5-carboxylic acid

N,0-dimethylhydroxylamine
1117-97-1

N,0-dimethylhydroxylamine

benzo[1,2,5]thiadiazole-5-carboxylic acid methoxy-methyl-amide
937279-22-6

benzo[1,2,5]thiadiazole-5-carboxylic acid methoxy-methyl-amide

Conditions
ConditionsYield
With triethylamine; HATU In dichloromethane at 20℃; for 3h; Inert atmosphere;95%
benzo[1,2,5]thiadiazole-5-carboxylic acid
16405-98-4

benzo[1,2,5]thiadiazole-5-carboxylic acid

4-(4-methoxybenzyl)-6-piperidin-4-ylpyrimidin-2-amine
198554-72-2

4-(4-methoxybenzyl)-6-piperidin-4-ylpyrimidin-2-amine

4-[1-(2,1,3-benzothiadiazol-5-ylcarbonyl)piperidin-4-yl]-6-(4-methoxybenzyl)pyrimidin-2-amine
1085916-69-3

4-[1-(2,1,3-benzothiadiazol-5-ylcarbonyl)piperidin-4-yl]-6-(4-methoxybenzyl)pyrimidin-2-amine

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 20℃;84%
benzo[1,2,5]thiadiazole-5-carboxylic acid
16405-98-4

benzo[1,2,5]thiadiazole-5-carboxylic acid

2,1,3-benzothiadiazol-5-ylmethanol
89795-51-7

2,1,3-benzothiadiazol-5-ylmethanol

Conditions
ConditionsYield
Stage #1: benzo[1,2,5]thiadiazole-5-carboxylic acid With triethylamine; isobutyl chloroformate In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: With sodium tetrahydroborate; water In tetrahydrofuran at 0℃; for 0.5h;		81%
Multi-step reaction with 2 steps
1: DIPEA / tetrahydrofuran / 1.5 h / 0 °C
2: 1.45 g / aq. NaBH4 / tetrahydrofuran / 2 h / 20 °C
View Scheme
benzo[1,2,5]thiadiazole-5-carboxylic acid
16405-98-4

benzo[1,2,5]thiadiazole-5-carboxylic acid

tert-Butyl 2,2,2-trichloroacetimidate
98946-18-0

tert-Butyl 2,2,2-trichloroacetimidate

tert-butyl 2,1,3-benzothiadiazole-5-carboxylate

tert-butyl 2,1,3-benzothiadiazole-5-carboxylate

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In tetrahydrofuran; cyclohexane at 20℃; for 0.5h;76%
6,6-difluoro-5-methyl-5-hexenyl methanesulfonate
509101-25-1

6,6-difluoro-5-methyl-5-hexenyl methanesulfonate

benzo[1,2,5]thiadiazole-5-carboxylic acid
16405-98-4

benzo[1,2,5]thiadiazole-5-carboxylic acid

6,6-difluoro-5-methyl-5-hexenyl benzo[1,2,5]thiadiazole-5-carboxylate

6,6-difluoro-5-methyl-5-hexenyl benzo[1,2,5]thiadiazole-5-carboxylate

Conditions
ConditionsYield
With sodium hydrogencarbonate In DMF (N,N-dimethyl-formamide) at 100℃; for 3h;64%
benzo[1,2,5]thiadiazole-5-carboxylic acid
16405-98-4

benzo[1,2,5]thiadiazole-5-carboxylic acid

benzo[1,2,5]thiadiazole-5-carboxylic acid amide
99620-31-2

benzo[1,2,5]thiadiazole-5-carboxylic acid amide

Conditions
ConditionsYield
With thionyl chloride anschliessend Umsetzen mit NH3;
benzo[1,2,5]thiadiazole-5-carboxylic acid
16405-98-4

benzo[1,2,5]thiadiazole-5-carboxylic acid

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

C10H8N2O4S

C10H8N2O4S

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0℃; for 1.5h;
benzo[1,2,5]thiadiazole-5-carboxylic acid
16405-98-4

benzo[1,2,5]thiadiazole-5-carboxylic acid

4-{2-[1-methyl-4-(1-methyl-4-(4-amino-2-pyrrolecarboxamido)-2-pyrrolecarboxamido)-2-pyrrolecarboxamido]ethyl}morpholine dihydrochloride

4-{2-[1-methyl-4-(1-methyl-4-(4-amino-2-pyrrolecarboxamido)-2-pyrrolecarboxamido)-2-pyrrolecarboxamido]ethyl}morpholine dihydrochloride

4-{2-[1-methyl-4-(1-methyl-4-(1-methyl-4-(benzo[1,2,5]thiadiazole-5-carboxamido)-2-pyrrolecarboxamido)-2-pyrrolecarboxamido)-2-pyrrolecarboxamido]ethyl}morpholine

4-{2-[1-methyl-4-(1-methyl-4-(1-methyl-4-(benzo[1,2,5]thiadiazole-5-carboxamido)-2-pyrrolecarboxamido)-2-pyrrolecarboxamido)-2-pyrrolecarboxamido]ethyl}morpholine

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25 - 37℃; for 16h;
benzo[1,2,5]thiadiazole-5-carboxylic acid
16405-98-4

benzo[1,2,5]thiadiazole-5-carboxylic acid

8-benzo[1,2,5]thiadiazol-5-ylmethyl-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one

8-benzo[1,2,5]thiadiazol-5-ylmethyl-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: DIPEA / tetrahydrofuran / 1.5 h / 0 °C
2.1: 1.45 g / aq. NaBH4 / tetrahydrofuran / 2 h / 20 °C
3.1: MeSO2Cl; DIPEA / CH2Cl2 / 0.5 h / 20 °C
3.2: tetrahydrofuran / 1 h / 20 °C
View Scheme
benzo[1,2,5]thiadiazole-5-carboxylic acid
16405-98-4

benzo[1,2,5]thiadiazole-5-carboxylic acid

4-oxo-1-phenyl-1,3,8-triaza-spiro[4.5]decane-8-carboxylic acid benzo[1,2,5]thiadiazol-5-ylmethyl ester

4-oxo-1-phenyl-1,3,8-triaza-spiro[4.5]decane-8-carboxylic acid benzo[1,2,5]thiadiazol-5-ylmethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: DIPEA / tetrahydrofuran / 1.5 h / 0 °C
2.1: 1.45 g / aq. NaBH4 / tetrahydrofuran / 2 h / 20 °C
3.1: dimethylformamide; tetrahydrofuran / 2 h / 20 °C
3.2: 16.5 percent / dimethylformamide; tetrahydrofuran
View Scheme
benzo[1,2,5]thiadiazole-5-carboxylic acid
16405-98-4

benzo[1,2,5]thiadiazole-5-carboxylic acid

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

benzo[1,2,5]thiadiazole-5-carboxylic acid methoxy-methyl-amide
937279-22-6

benzo[1,2,5]thiadiazole-5-carboxylic acid methoxy-methyl-amide

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 42h; Inert atmosphere;
benzo[1,2,5]thiadiazole-5-carboxylic acid
16405-98-4

benzo[1,2,5]thiadiazole-5-carboxylic acid

5-(benzo[c][1,2,5]thiadiazol-5-yl)-2,2-dimethylfuran-3(2H)-one
1202376-82-6

5-(benzo[c][1,2,5]thiadiazol-5-yl)-2,2-dimethylfuran-3(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: triethylamine; HATU / dichloromethane / 3 h / 20 °C / Inert atmosphere
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 °C / Inert atmosphere
2.2: 3 h / -78 °C
3.1: toluene-4-sulfonic acid / dichloromethane / 2 h / 20 °C
4.1: diethylamine / ethanol / 20 °C
View Scheme
benzo[1,2,5]thiadiazole-5-carboxylic acid
16405-98-4

benzo[1,2,5]thiadiazole-5-carboxylic acid

5-(benzo[c][1,2,5]thiadiazol-5-yl)-4-bromo-2,2-dimethylfuran-3(2H)-one
1202376-83-7

5-(benzo[c][1,2,5]thiadiazol-5-yl)-4-bromo-2,2-dimethylfuran-3(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: triethylamine; HATU / dichloromethane / 3 h / 20 °C / Inert atmosphere
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 °C / Inert atmosphere
2.2: 3 h / -78 °C
3.1: toluene-4-sulfonic acid / dichloromethane / 2 h / 20 °C
4.1: diethylamine / ethanol / 20 °C
5.1: N-Bromosuccinimide / chloroform / 2 h / 20 °C
View Scheme
benzo[1,2,5]thiadiazole-5-carboxylic acid
16405-98-4

benzo[1,2,5]thiadiazole-5-carboxylic acid

1-(benzo[c][1,2,5]thiadiazol-5-yl)-4-hydroxy-4-methylpent-2-yn-1-one
1202376-81-5

1-(benzo[c][1,2,5]thiadiazol-5-yl)-4-hydroxy-4-methylpent-2-yn-1-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: triethylamine; HATU / dichloromethane / 3 h / 20 °C / Inert atmosphere
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 °C / Inert atmosphere
2.2: 3 h / -78 °C
3.1: toluene-4-sulfonic acid / dichloromethane / 2 h / 20 °C
View Scheme
benzo[1,2,5]thiadiazole-5-carboxylic acid
16405-98-4

benzo[1,2,5]thiadiazole-5-carboxylic acid

1-(benzo[c][1,2,5]thiadiazol-5-yl)-4-methyl-4-(trimethylsilyloxy)pent-2-yn-1-one
1202376-80-4

1-(benzo[c][1,2,5]thiadiazol-5-yl)-4-methyl-4-(trimethylsilyloxy)pent-2-yn-1-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine; HATU / dichloromethane / 3 h / 20 °C / Inert atmosphere
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 °C / Inert atmosphere
2.2: 3 h / -78 °C
View Scheme
benzo[1,2,5]thiadiazole-5-carboxylic acid
16405-98-4

benzo[1,2,5]thiadiazole-5-carboxylic acid

5-(benzo[c][1,2,5]thiadiazol-5-yl)-2,2-dimethyl-4-(4-(quinolin-2-ylmethoxy)phenyl)furan-3(2H)-one
1202368-77-1

5-(benzo[c][1,2,5]thiadiazol-5-yl)-2,2-dimethyl-4-(4-(quinolin-2-ylmethoxy)phenyl)furan-3(2H)-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: triethylamine; HATU / dichloromethane / 3 h / 20 °C / Inert atmosphere
2.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 °C / Inert atmosphere
2.2: 3 h / -78 °C
3.1: toluene-4-sulfonic acid / dichloromethane / 2 h / 20 °C
4.1: diethylamine / ethanol / 20 °C
5.1: N-Bromosuccinimide / chloroform / 2 h / 20 °C
6.1: caesium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; toluene / 12 h / Inert atmosphere; Reflux
View Scheme

2,1,3-Benzothiadiazole-5-carboxylic acid Chemical Properties

Molecular Structure of 2,1,3-Benzothiadiazole-5-carboxylic acid (CAS No.16405-98-4):
 
Molecular Formula: C7H4N2O2S   
Molecular Weight: 180.1839
CAS No: 16405-98-4
H bond acceptors: 4
H bond donors: 1
Freely Rotating Bonds: 1
Polar Surface Area: 80.32 Å2
Index of Refraction: 1.749
Molar Refractivity: 45.59 cm3
Molar Volume: 112 cm3
Surface Tension: 89.6 dyne/cm
Density: 1.608 g/cm3
Flash Point: 176.8 °C
Enthalpy of Vaporization: 64.93 kJ/mol
Boiling Point: 368.7 °C at 760 mmHg
Vapour Pressure: 4.35E-06 mmHg at 25°C
InChI: InChI=1/C7H4N2O2S/c10-7(11)4-1-2-5-6(3-4)9-12-8-5/h1-3H,(H,10,11)
InChIKey: YHMXJZVGBCACMT-UHFFFAOYAM
Std. InChI: InChI=1S/C7H4N2O2S/c10-7(11)4-1-2-5-6(3-4)9-12-8-5/h1-3H,(H,10,11)
Std. InChIKey: YHMXJZVGBCACMT-UHFFFAOYSA-N 
Product Categories: Heterocycles series;API intermediates

2,1,3-Benzothiadiazole-5-carboxylic acid Safety Profile

Hazard Codes:IrritantXi
Risk Statements:36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements:26-36/37/39-24/25
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S24/25:Avoid contact with skin and eyes.
Hazard Note:Irritant
HazardClass:IRRITANT

2,1,3-Benzothiadiazole-5-carboxylic acid Specification

   2,1,3-Benzothiadiazole-5-carboxylic acid (CAS No.16405-98-4), its synonyms are Timtec-bb sbb007390 ; Rarechem al be 1094 ; 1,2,3-Benzothiadiazole-5-carboxylic acid ; Benzo-2,1,3-thiadiazole-5-carboxylic acid ; Benzo-1,2,3-thiadiazole-5-carboxylic acid ; Benzo[1,2,5]thiadiazole-5-carboxylic acid  

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