Diazo-4

Base Information

• Chemical Name: Diazo-4
• CAS No.: 123330-72-3
• Molecular Formula: C26H24 N6 O12
• Molecular Weight: 612.50176
• Mol file: 123330-72-3.mol

Synonyms:diazo-4

Chemical Property of Diazo-4

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 276.56000
• Density: g/cm³
• LogP: -0.15484
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 19
• Exact Mass: 612.14522022
• Heavy Atom Count: 44
• Complexity: 1060

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C(=O)C=[N+]=[N-])OCCOC2=C(C=CC(=C2)C(=O)C=[N+]=[N-])N(CC(=O)O)CC(=O)O)N(CC(=O)O)CC(=O)O

Technology Process of Diazo-4

There total 11 articles about Diazo-4 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:

3-hydroxy-4-nitro-benzoic acid (619-14-7) → {[2-{2-[2-(Bis-carboxymethyl-amino)-5-(2-diazo-acetyl)-phenoxy]-ethoxy}-4-(2-diazo-acetyl)-phenyl]-carboxymethyl-amino}-acetic acid (123330-72-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) pyridine; 2.) H₂O / 1.) 100 deg C, 30 min

2: SOCl₂, DMF / 0.25 h / Heating

3: pyridine / CHCl₃ / Heating

4: 45percent aq. KOH / methanol / 0.5 h

5: 1.) K₂CO₃, N-methylpyrrolidone / 1.) 125 deg C; 2.) 50 min

6: 95 percent / H₂ / 5percent Pd/C / ethyl acetate; ethanol / 1 h / Ambient temperature

7: 64 percent / 1,8-bis(dimethylamino)naphthalene / 120 h / 125 °C

8: CF₃COOH / CH₂Cl₂ / Ambient temperature

9: oxalyl chloride, DMF / CH₂Cl₂ / 0.25 h / Heating

10: CH₂Cl₂; diethyl ether / Ambient temperature

11: aq. 1M tetramethylammonium hydroxide / methanol / Ambient temperature

With pyridine; 1-methyl-pyrrolidin-2-one; potassium hydroxide; thionyl chloride; oxalyl dichloride; tetramethyl ammoniumhydroxide; water; hydrogen; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; potassium carbonate; N,N-dimethyl-formamide; trifluoroacetic acid; palladium on activated charcoal; In methanol; diethyl ether; ethanol; dichloromethane; chloroform; ethyl acetate;

DOI:10.1021/ja00202a042

Reference yield:

3-Acetoxy-4-Nitrobenzoic Acid (51257-24-0) → {[2-{2-[2-(Bis-carboxymethyl-amino)-5-(2-diazo-acetyl)-phenoxy]-ethoxy}-4-(2-diazo-acetyl)-phenyl]-carboxymethyl-amino}-acetic acid (123330-72-3)

Guidance literature:

Multi-step reaction with 10 steps

1: SOCl₂, DMF / 0.25 h / Heating

2: pyridine / CHCl₃ / Heating

3: 45percent aq. KOH / methanol / 0.5 h

4: 1.) K₂CO₃, N-methylpyrrolidone / 1.) 125 deg C; 2.) 50 min

5: 95 percent / H₂ / 5percent Pd/C / ethyl acetate; ethanol / 1 h / Ambient temperature

6: 64 percent / 1,8-bis(dimethylamino)naphthalene / 120 h / 125 °C

7: CF₃COOH / CH₂Cl₂ / Ambient temperature

8: oxalyl chloride, DMF / CH₂Cl₂ / 0.25 h / Heating

9: CH₂Cl₂; diethyl ether / Ambient temperature

10: aq. 1M tetramethylammonium hydroxide / methanol / Ambient temperature

With pyridine; 1-methyl-pyrrolidin-2-one; potassium hydroxide; thionyl chloride; oxalyl dichloride; tetramethyl ammoniumhydroxide; hydrogen; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; potassium carbonate; N,N-dimethyl-formamide; trifluoroacetic acid; palladium on activated charcoal; In methanol; diethyl ether; ethanol; dichloromethane; chloroform; ethyl acetate;

DOI:10.1021/ja00202a042

Reference yield:

tert-Butyl 3-hydroxy-4-nitrobenzoate (123330-86-9) → {[2-{2-[2-(Bis-carboxymethyl-amino)-5-(2-diazo-acetyl)-phenoxy]-ethoxy}-4-(2-diazo-acetyl)-phenyl]-carboxymethyl-amino}-acetic acid (123330-72-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) K₂CO₃, N-methylpyrrolidone / 1.) 125 deg C; 2.) 50 min

2: 95 percent / H₂ / 5percent Pd/C / ethyl acetate; ethanol / 1 h / Ambient temperature

3: 64 percent / 1,8-bis(dimethylamino)naphthalene / 120 h / 125 °C

4: CF₃COOH / CH₂Cl₂ / Ambient temperature

5: oxalyl chloride, DMF / CH₂Cl₂ / 0.25 h / Heating

6: CH₂Cl₂; diethyl ether / Ambient temperature

7: aq. 1M tetramethylammonium hydroxide / methanol / Ambient temperature

With 1-methyl-pyrrolidin-2-one; oxalyl dichloride; tetramethyl ammoniumhydroxide; hydrogen; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; potassium carbonate; N,N-dimethyl-formamide; trifluoroacetic acid; palladium on activated charcoal; In methanol; diethyl ether; ethanol; dichloromethane; ethyl acetate;

DOI:10.1021/ja00202a042

upstream raw materials:

1,2-Bis<2-amino>-5-(diazoacetyl)phenoxy>ethane

3-hydroxy-4-nitro-benzoic acid

3-Acetoxy-4-Nitrobenzoic Acid

tert-Butyl 3-hydroxy-4-nitrobenzoate

Refernces