2-Methyl-6-nitrobenzoic anhydride

Base Information

• Chemical Name: 2-Methyl-6-nitrobenzoic anhydride
• CAS No.: 434935-69-0
• Molecular Formula: C16H12 N2 O7
• Molecular Weight: 344.28
• Hs Code.: 29163990
• European Community (EC) Number: 628-525-6
• UNII: EC8MK6FE8B
• DSSTox Substance ID: DTXSID60440549
• Nikkaji Number: J1.631.429C
• Wikipedia: 2-Methyl-6-nitrobenzoic_anhydride
• Wikidata: Q11186403
• Mol file: 434935-69-0.mol

Synonyms:2-methyl-6-nitrobenzoic anhydride

Chemical Property of 2-Methyl-6-nitrobenzoic anhydride

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 177 °C
• Refractive Index: 1.623
• Boiling Point: 559.436°C at 760 mmHg
• Flash Point: 246.455°C
• PSA: 135.01000
• Density: 1.417g/cm³
• LogP: 4.16340
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: very faint turbidity in hot Toluene
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 344.06445073
• Heavy Atom Count: 25
• Complexity: 506

Purity/Quality:

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

2-Methyl-6-nitrobenzoic Anhydride >98.0%(T) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C(=CC=C1)[N+](=O)[O-])C(=O)OC(=O)C2=C(C=CC=C2[N+](=O)[O-])C
• Uses: 2-Methyl-6-nitrobenzoic anhydride can be used:As a versatile lactonization reagent applicable in the preparation of varieties of macrolide natural products and lactones.As a reaction promoter in the synthesis of carboxamide derivatives by using corresponding amines and carboxylic acids.In the total synthesis of GRP78 inhibitor prunustatin A, antifungal compound (3R,16E,20E,23R)-(?)-eushearilide and an antiobestic drug tetrahydrolipstatin.

Technology Process of 2-Methyl-6-nitrobenzoic anhydride

There total 6 articles about 2-Methyl-6-nitrobenzoic anhydride 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: 81.0%

2-methyl-6-nitrobenzoic acid (13506-76-8) → 2-methyl-6-nitrobenzoic anhydride (434935-69-0)

Guidance literature:

With thionyl chloride; In dichloromethane; at 20 ℃; for 15h;

2-methyl-6-nitrobenzoic acid; With pyridine; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1016/S0040-4039(02)01819-1

Reference yield: 81.0%

2-methyl-6-nitrobenzoic acid (13506-76-8) + 2-methyl-6-nitrobenzoyl chloride (66232-57-3) → 2-methyl-6-nitrobenzoic anhydride (434935-69-0)

Guidance literature:

With pyridine; at 20 ℃; for 24h;

DOI:10.1021/jo030367x

Reference yield:

Methoxyacetyl chloride (38870-89-2) + 2-methyl-6-nitrobenzoic acid (13506-76-8) → Methoxyacetic anhydride (19500-95-9) + 2-methyl-6-nitrobenzoic anhydride (434935-69-0) + C11H11NO6

Guidance literature:

With triethylamine; In chloroform-d1; at 20 ℃; Title compound not separated from byproducts;

DOI:10.1021/jo030367x

upstream raw materials:

2-methyl-6-nitrobenzoyl chloride

2-methyl-6-nitrobenzoic acid

Methoxyacetyl chloride

2-cyano-3-nitrotoluene

Downstream raw materials:

3-phenylpropyl benzoate

1-methyl-3-phenylpropyl benzoate

3-phenylpropyl (E)-2-butenoate

3-phenylpropyl 3-butenoate

Refernces

• 1、 Shiina, Isamu,Kubota, Mari,Oshiumi, Hiromi,Hashizume, Minako. "An Effective Use of Benzoic Anhydride and Its Derivatives for the Synthesis of Carboxylic Esters and Lactones: A Powerful and Convenient Mixed Anhydride Method Promoted by Basic Catalysts". . p. 1822 - 1830. Retrieved 2007/10/03.