benzo[d][1,3]dioxole-5-carbonyl azide

Base Information

• Chemical Name: benzo[d][1,3]dioxole-5-carbonyl azide
• CAS No.: 54022-34-3
• Molecular Formula: C₈H₅N₃O₃
• Molecular Weight: 191.146
• Mol file: 54022-34-3.mol

Synonyms:benzo[d][1,3]dioxole-5-carbonyl azide

Chemical Property of benzo[d][1,3]dioxole-5-carbonyl azide

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

2H-1,3-benzodioxole-5-carbonylazide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of benzo[d][1,3]dioxole-5-carbonyl azide

There total 7 articles about benzo[d][1,3]dioxole-5-carbonyl azide 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: 68.0%

3,4-(methylenedioxy)benzoyl chloride (25054-53-9) → benzo[d][1,3]dioxole-5-carbonyl azide (54022-34-3)

Guidance literature:

With sodium azide; In water; acetone;

Reference yield:

Piperonylic acid (94-53-1) → benzo[d][1,3]dioxole-5-carbonyl azide (54022-34-3)

Guidance literature:

With diphenyl phosphoryl azide; triethylamine; In benzene; for 0.666667h;

DOI:10.1016/S0040-4039(99)01392-1

Reference yield:

1,2-(methylenedioxy)-4-bromobenzene (2635-13-4) → benzo[d][1,3]dioxole-5-carbonyl azide (54022-34-3)

Guidance literature:

Multi-step reaction with 2 steps

1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; N-ethyl-N,N-diisopropylamine / toluene / 16 h / 100 °C / Sealed tube; Inert atmosphere

2: sodium azide / toluene / 16 h / 20 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium azide; N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In toluene;

DOI:10.1002/anie.202005891

upstream raw materials:

benzo[d][1,3]dioxole-5-carbohydrazide

3,4-(methylenedioxy)benzoyl chloride

Piperonylic acid

methyl 3,4-methylenedioxybenzoate

Downstream raw materials:

1-(benzo[d][1,3]dioxol-5-yl)urea

N-methyl-3,4-(methylenedioxy)aniline

N-(phenylcarbamoyl)benzo[d][1,3]dioxole-5-carboxamide

piperonylonitrile

Refernces

• 1、 Chakrabarti, Kaushik,Dutta, Kuheli,Kundu, Sabuj. "Synthesis of: N -methylated amines from acyl azides using methanol". supporting information. p. 5891 - 5896. Retrieved 2020/08/21.
• 2、 Kumar, Ravi,Arigela, Rajesh K.,Kundu, Bijoy. "Unprecedented Transformation of a Directing Group Generated in Situ and Its Application in the One-Pot Synthesis of 2-Alkenyl Benzonitriles". . p. 11807 - 11812. Retrieved 2015/08/11.