2,1,3-Benzothiadiazole-5-carbonyl chloride

Base Information

• Chemical Name: 2,1,3-Benzothiadiazole-5-carbonyl chloride
• CAS No.: 321309-31-3
• Molecular Formula: C7H3ClN2OS
• Molecular Weight: 198.633
• Hs Code.: 2934999090
• European Community (EC) Number: 672-957-8
• DSSTox Substance ID: DTXSID70379957
• Wikidata: Q82169981
• Mol file: 321309-31-3.mol

Synonyms:2,1,3-benzothiadiazole-5-carbonyl chloride;321309-31-3;benzo[c][1,2,5]thiadiazole-5-carbonyl chloride;SCHEMBL1020666;DTXSID70379957;STVKFABXTFREFG-UHFFFAOYSA-N;MFCD02681992;AKOS005217044;BP-10319;BB 0246860;FT-0609000;Benzo[1,2,5]thiadiazole-5-carbonyl chloride;benzo[c][1,2,5]thiadiazole-5-carbonylchloride;EN300-236402;A821149;2,1,3-Benzothiadiazole-5-carbonyl chloride, AldrichCPR;F2190-0167

Chemical Property of 2,1,3-Benzothiadiazole-5-carbonyl chloride

Chemical Property:

• Vapor Pressure: 0.00133mmHg at 25°C
• Melting Point: 111ºC
• Refractive Index: 1.704
• Boiling Point: 297.6 °C at 760 mmHg
• PKA: -1.13±0.36(Predicted)
• Flash Point: 133.8 °C
• PSA: 71.09000
• Density: 1.577 g/cm³
• LogP: 2.07030
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 197.9654616
• Heavy Atom Count: 12
• Complexity: 202

Purity/Quality:

98%min ^*data from raw suppliers

2,1,3-Benzothiadiazole-5-carbonyl chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 34
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=NSN=C2C=C1C(=O)Cl
• Uses: 2,1,3-Benzothiadiazole-5-carbonyl chloride is used as a reactant in the preparation of phthalazinones as PARP inhibitors for use in the treatment of cancer which is deficient in HR dependent DNA DSB repair pathway.

Technology Process of 2,1,3-Benzothiadiazole-5-carbonyl chloride

There total 4 articles about 2,1,3-Benzothiadiazole-5-carbonyl chloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

Methyl 3,4-diaminobenzoate (36692-49-6) → benzo[c][1,2,5]thiadiazole-5-carbonyl chloride (321309-31-3)

Guidance literature:

Multi-step reaction with 3 steps

1: thionyl chloride; triethylamine; sodium hydrogencarbonate / dichloromethane / 6 h / 0 - 80 °C / Inert atmosphere; Schlenk technique

2: sodium hydroxide / water; 1,4-dioxane / 16 h / 25 °C / Inert atmosphere; Schlenk technique

3: thionyl chloride / 3 h / 80 °C / Inert atmosphere; Schlenk technique

With thionyl chloride; sodium hydrogencarbonate; triethylamine; sodium hydroxide; In 1,4-dioxane; dichloromethane; water;

DOI:10.1021/acs.joc.1c00846

Reference yield:

methyl benzo-2,1,3-thiadiazole-5-carboxylate (175204-21-4) → benzo[c][1,2,5]thiadiazole-5-carbonyl chloride (321309-31-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / water; 1,4-dioxane / 16 h / 25 °C / Inert atmosphere; Schlenk technique

2: thionyl chloride / 3 h / 80 °C / Inert atmosphere; Schlenk technique

With thionyl chloride; sodium hydroxide; In 1,4-dioxane; water;

DOI:10.1021/acs.joc.1c00846

Reference yield:

benzo[c][1,2,5]thiadiazole-5-carboxylic acid (16405-98-4) → benzo[c][1,2,5]thiadiazole-5-carbonyl chloride (321309-31-3)

Guidance literature:

With thionyl chloride; at 80 ℃; for 3h; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.joc.1c00846

upstream raw materials:

Methyl 3,4-diaminobenzoate

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

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

3,4-diaminobenzoic acid

Refernces