4-Azidobenzoyl chloride

Base Information

• Chemical Name: 4-Azidobenzoyl chloride
• CAS No.: 14848-01-2
• Molecular Formula: C7H4 Cl N3 O
• Molecular Weight: 181.581
• Hs Code.: 2929909090
• European Community (EC) Number: 238-910-7
• DSSTox Substance ID: DTXSID30163995
• Nikkaji Number: J227.210E
• Wikidata: Q83033017
• Mol file: 14848-01-2.mol

Synonyms:4-azidobenzoyl chloride;p-azidobenzoyl chloride

Chemical Property of 4-Azidobenzoyl chloride

Chemical Property:

• Melting Point: 58 °C
• Refractive Index: 1.5618 (estimate)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 66.82000
• Density: g/cm³
• LogP: 2.46016
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 181.0042895
• Heavy Atom Count: 12
• Complexity: 217

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(=O)Cl)N=[N+]=[N-]

Technology Process of 4-Azidobenzoyl chloride

There total 5 articles about 4-Azidobenzoyl 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: 100.0%

4-azidobenzoic acid (6427-66-3) → 4-azidobenzoyl chloride (14848-01-2)

Guidance literature:

With oxalyl dichloride; N,N-dimethyl-formamide; In benzene; at 20 ℃; for 6h;

DOI:10.24820/ark.5550190.p010.321

Reference yield:

4-amino-benzoic acid (150-13-0,159246-81-8,8014-65-1) → 4-azidobenzoyl chloride (14848-01-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NaNO₂; 2.) NaN₃ / 1.) TFA, 0 deg C, 0.5 h; 2.) Et₂O, 1 h

2: 90 percent / PCl₅ / diethyl ether / 0.33 h

With sodium azide; phosphorus pentachloride; sodium nitrite; In diethyl ether;

DOI:10.1021/jo00009a037

Reference yield:

4-nitro-benzoic acid (62-23-7) → 4-azidobenzoyl chloride (14848-01-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: palladium 10% on activated carbon; hydrogen / methanol / 5 h / 20 °C

2.1: water; hydrogenchloride; potassium nitrite / 1 h / 0 °C

2.2: 3 h / 0 °C

3.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / Inert atmosphere; Darkness

With hydrogenchloride; potassium nitrite; oxalyl dichloride; palladium 10% on activated carbon; water; hydrogen; N,N-dimethyl-formamide; In methanol; dichloromethane;

DOI:10.1016/j.tet.2016.03.096

upstream raw materials:

4-azidobenzoic acid

4-amino-benzoic acid

4-nitro-benzoic acid

Downstream raw materials:

3-(4-azidobenzoyl)-1,3-thiazolidine-2-thione

6-<(4-Azidobenzoyl)amino>-1-hexanol

3-(4-Azidobenzoyl)-6-methoxy-2-(4-methoxyphenyl)benzothiophene

4-<(dimethylamino)carbonyl>phenyl azide

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