1,2,3-Benzothiadiazole-7-carbonyl chloride

Base Information

• Chemical Name: 1,2,3-Benzothiadiazole-7-carbonyl chloride
• CAS No.: 124371-49-9
• Molecular Formula: C7H3 Cl N2 O S
• Molecular Weight: 198.633
• DSSTox Substance ID: DTXSID10593271
• Wikidata: Q82487712
• Mol file: 124371-49-9.mol

Synonyms:124371-49-9;1,2,3-BENZOTHIADIAZOLE-7-CARBONYL CHLORIDE;benzothiadiazole-7-carboxylic acid chloride;1,2,3-Benzothiadiazole-7-carbonyl chloride (9CI);benzo[d][1,2,3]thiadiazole-7-carbonyl chloride;SCHEMBL7555956;DTXSID10593271;FHWNOXLHRUSQMV-UHFFFAOYSA-N;7-benzothiadiazolecarboxylic acid chloride;DB-296999;Benzo-1,2,3-thiadiazole-7-carbonyl Chloride;Benzo-1,2.3-thiadiazole-7-carbonyl chloride;benzo[d][1,2,3]thiadiazole-7-carbonylchloride;benzo-1,2,3-thiadiazole-7-carboxylic acidchloride;benzo-1,2,3-thiadiazole-7-carboxylic acid chloride

Chemical Property of 1,2,3-Benzothiadiazole-7-carbonyl chloride

Chemical Property:

• PSA: 71.09000
• LogP: 2.07030
• XLogP3: 2.4
• 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:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C2C(=C1)N=NS2)C(=O)Cl

Technology Process of 1,2,3-Benzothiadiazole-7-carbonyl chloride

There total 17 articles about 1,2,3-Benzothiadiazole-7-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: 95.0%

benzo[d][1,2,3]thiadiazole-7-carboxylic acid (35272-27-6) → benzothiadiazole-7-carboxylic acid chloride (124371-49-9)

Guidance literature:

benzo[d][1,2,3]thiadiazole-7-carboxylic acid; With oxalyl dichloride; In dichloromethane; at -5 - 0 ℃;

With N,N-dimethyl-formamide; at 20 ℃; for 5h;

DOI:10.1016/j.bmcl.2020.127369

Reference yield:

2-chloro-3-nitrobenzoic acid methyl ester (53553-14-3) → benzothiadiazole-7-carboxylic acid chloride (124371-49-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 99 percent

2: H₂ / Raney nickel / tetrahydrofuran

3: 86 percent / NaNO₂; H(+)

4: 98 percent / NaOH; H₂O

5: SOCl₂

With sodium hydroxide; thionyl chloride; water; hydrogen; hydrogen cation; sodium nitrite; nickel; In tetrahydrofuran; 1: Substitution / 2: Reduction / 3: Diazotization / 4: Hydrolysis / 5: Substitution;

DOI:10.1002/(SICI)1096-9063(199708)50:4<275::AID-PS593>3.0.CO;2-7

Reference yield:

1,2-Dichloro-3-nitrobenzene (3209-22-1) → benzothiadiazole-7-carboxylic acid chloride (124371-49-9)

Guidance literature:

Multi-step reaction with 6 steps

1: K₂CO₃ / N,N-dimethyl-acetamide

2: Na₂S / propan-2-ol; H₂O

3: 76 percent / Ni(PPh₃)4

4: 97 percent / isoamyl nitrite; HCl / butan-1-ol

5: 88 percent / KOH / butan-1-ol

6: SOCl₂

With hydrogenchloride; sodium sulfide; potassium hydroxide; thionyl chloride; potassium carbonate; isopentyl nitrite; tetrakis(triphenylphosphine)nickel⁽⁰⁾; In N,N-dimethyl acetamide; water; isopropyl alcohol; butan-1-ol; 1: Substitution / 2: Reduction / 3: Substitution / 4: Cyclization / 5: Hydrolysis / 6: Substitution;

DOI:10.1002/(SICI)1096-9063(199708)50:4<275::AID-PS593>3.0.CO;2-7

upstream raw materials:

benzo[d][1,2,3]thiadiazole-7-carboxylic acid

Benzo[1,2,3]thiadiazole-7-nitrile

2-chloro-3-nitrobenzoic acid methyl ester

1,2-Dichloro-3-nitrobenzene

Downstream raw materials:

benzo[1,2,3]thiadiazole-7-carboxylic acid methtyl ester

benzo-1,2,3-thiadiazole-7-carboxylic acid 2-(2,4-dichlorophenoxyacetoxy)ethyl ester

3-[benzo-1,2,3-thiadiazole-7-carbonyloxy]-1-phenyl-1-propene

1-[benzo-1,2,3-thiadiazole-7-carbonyloxymethyl]-1-phenylcyclopropane

Refernces

• 1、 -. "Preparation method of benzo [d][1, 2, 3] thiadiazole -7-trifluoroethyl ester". Paragraph 0015; 0035-0064; 0073-0074. . Retrieved 2020/02/29.
• 2、 -. "Benzo [1, 2, 3] thiadiazole -7 - carboxylic acid ester derivatives as activator for plant disease agent application". Paragraph 0098-0099; 0104-0105. . Retrieved 2017/04/29.