7-bromobenzo[c][1,2,5]thiadiazole-4-carbonitrile

Base Information

• Chemical Name: 7-bromobenzo[c][1,2,5]thiadiazole-4-carbonitrile
• CAS No.: 1331742-86-9
• Molecular Formula: C7H2BrN3S
• Molecular Weight: 240.083
• Mol file: 1331742-86-9.mol

Synonyms:7-bromobenzo[c][1,2,5]thiadiazole-4-carbonitrile;4-bromo-7-cyano-2,1,3-benzothiadiazole

Chemical Property of 7-bromobenzo[c][1,2,5]thiadiazole-4-carbonitrile

Chemical Property:

• Melting Point: 258.0 to 262.0 °C
• Boiling Point: 347.6±22.0 °C(Predicted)
• PKA: -4.23±0.50(Predicted)
• PSA: 77.81000
• Density: 1.94±0.1 g/cm3(Predicted)
• LogP: 2.32548
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature

Purity/Quality:

98%,99%, ^*data from raw suppliers

7-Bromo-2,1,3-benzothiadiazole-4-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 7-bromobenzo[c][1,2,5]thiadiazole-4-carbonitrile

There total 8 articles about 7-bromobenzo[c][1,2,5]thiadiazole-4-carbonitrile 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: 84.0%

7-bromobenzo[c][1,2,5]thiadiazole-4-carboxaldehyde (1071224-34-4) → 7-bromobenzo[c][1,2,5]thiadiazole-4-carbonitrile (1331742-86-9)

Guidance literature:

With hydroxylamine hydrochloride; at 100 ℃; for 2h;

DOI:10.1039/c4tc01558d

Reference yield:

3-methyl-2-nitroaniline (601-87-6) → 7-bromobenzo[c][1,2,5]thiadiazole-4-carbonitrile (1331742-86-9)

Guidance literature:

Multi-step reaction with 6 steps

1: palladium 10% on activated carbon; ammonium formate / methanol / 3 h / 70 °C

2: triethylamine; thionyl chloride / dichloromethane / 16 h / 0 - 40 °C

3: bromine; hydrogen bromide / water / 16 h / Reflux

4: hydrogen bromide; N-Bromosuccinimide; dibenzoyl peroxide; acetic acid / tetrachloromethane / 3 h / Reflux

5: sodium periodate / N,N-dimethyl-formamide / 5 h / 150 °C

6: hydroxylamine hydrochloride / 2 h / 100 °C

With sodium periodate; N-Bromosuccinimide; thionyl chloride; palladium 10% on activated carbon; hydroxylamine hydrochloride; hydrogen bromide; bromine; ammonium formate; acetic acid; triethylamine; dibenzoyl peroxide; In methanol; tetrachloromethane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1039/c4tc01558d

Reference yield:

3-methyl-1,2-benzenediamine (2687-25-4) → 7-bromobenzo[c][1,2,5]thiadiazole-4-carbonitrile (1331742-86-9)

Guidance literature:

Multi-step reaction with 5 steps

1: triethylamine; thionyl chloride / dichloromethane / 16 h / 0 - 40 °C

2: bromine; hydrogen bromide / water / 16 h / Reflux

3: hydrogen bromide; N-Bromosuccinimide; dibenzoyl peroxide; acetic acid / tetrachloromethane / 3 h / Reflux

4: sodium periodate / N,N-dimethyl-formamide / 5 h / 150 °C

5: hydroxylamine hydrochloride / 2 h / 100 °C

With sodium periodate; N-Bromosuccinimide; thionyl chloride; hydroxylamine hydrochloride; hydrogen bromide; bromine; acetic acid; triethylamine; dibenzoyl peroxide; In tetrachloromethane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1039/c4tc01558d

upstream raw materials:

7-bromobenzo[c][1,2,5]thiadiazole-4-carboxaldehyde

3-methyl-2-nitroaniline

3-methyl-1,2-benzenediamine

4-Methyl-2,1,3-benzothiadiazol

Refernces

• 1、 Lin, Li-Yen,Lu, Chih-Wei,Huang, Wei-Ching,Chen, Yi-Hong,Lin, Hao-Wu,Wong, Ken-Tsung. "New A-A-D-A-A-type electron donors for small molecule organic solar cells". . p. 4962 - 4965. Retrieved 2011.