5-Methyl-2-nitroaniline

Base Information

• Chemical Name: 5-Methyl-2-nitroaniline
• CAS No.: 578-46-1
• Molecular Formula: C7H8 N2 O2
• Molecular Weight: 152.153
• Hs Code.: 2921430090
• European Community (EC) Number: 209-423-7
• NSC Number: 404025,28586
• UN Number: 2660
• UNII: YY17U389O6
• DSSTox Substance ID: DTXSID2025634
• Nikkaji Number: J85.098E
• Wikidata: Q27294773
• ChEMBL ID: CHEMBL278016
• Mol file: 578-46-1.mol

Synonyms:5-Methyl-2-nitroaniline;578-46-1;3-AMINO-4-NITROTOLUENE;6-Nitro-m-toluidine;Benzenamine, 5-methyl-2-nitro-;m-Toluidine, 6-nitro-;5-Methyl-o-nitroaniline;Benzenamine, 3-methyl-6-nitro-;EINECS 209-423-7;NSC 28586;BRN 2691416;5-Methyl-2-nitro-phenylamine;UNII-YY17U389O6;CHEMBL278016;DTXSID2025634;YY17U389O6;NSC-28586;4-12-00-01861 (Beilstein Handbook Reference);NSC28586;6-Nitro-m-toluidin;MFCD00007814;3-Methyl-6-nitro-benzenamin;SCHEMBL138990;DTXCID205634;5-Methyl-2-nitroaniline, 95%;AMY7298;(5-methyl-2-nitro-phenyl)-amine;Tox21_200333;BDBM50065372;NSC404025;AKOS009159261;CCG-302546;CS-W010956;LS-1407;NSC-404025;SB76055;NCGC00091413-01;NCGC00091413-02;NCGC00257887-01;AC-24836;CAS-578-46-1;DS-12741;FT-0620611;EN300-85317;A19647;W-105437;Q27294773;Z1664380848

Chemical Property of 5-Methyl-2-nitroaniline

Chemical Property:

• Vapor Pressure: 0.000529mmHg at 25°C
• Melting Point: 110-111 °C(lit.)
• Boiling Point: 312.4 °C at 760 mmHg
• PKA: 0.03±0.25(Predicted)
• Flash Point: 142.8 °C
• PSA: 71.84000
• Density: 1.269 g/cm³
• LogP: 2.58980
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 152.058577502
• Heavy Atom Count: 11
• Complexity: 155
• Transport DOT Label: Poison

Purity/Quality:

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

5-?Methyl-?2-?nitroaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): TN
• Hazard Codes: T,N
• Statements: 23/24/25-33-51/53
• Safety Statements: 28-36/37-45-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC(=C(C=C1)[N+](=O)[O-])N
• Uses: 5-Methyl-2-nitroaniline has been used in the preparation of N-(5-methyl-2-nitrophenyl)-4-[N-(pyridin-3-ylmethoxy carbonyl)aminomethyl]benzamide.

Technology Process of 5-Methyl-2-nitroaniline

There total 23 articles about 5-Methyl-2-nitroaniline 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: 86.0%

N-(5-methyl-2-nitrophenyl)pyrimidin-2-amine → 5-methyl-2-nitroaniline (578-46-1)

Guidance literature:

N-(5-methyl-2-nitrophenyl)pyrimidin-2-amine; With triethylsilane; trifluoroacetic acid; at 50 ℃; Inert atmosphere;

With acetic acid; hydrazine; In methanol; at 20 ℃; regioselective reaction; Inert atmosphere;

DOI:10.1021/acs.orglett.5b03493

Reference yield: 65.0%

5-methylbenzofuroxan (19164-41-1) → 5-methyl-2-nitroaniline (578-46-1) + 4-methyl-2-nitroaniline (89-62-3)

Guidance literature:

With iron(II) sulfate; In water; dimethyl sulfoxide; Title compound not separated from byproducts; Ambient temperature;

DOI:10.1080/00397919408010585

Reference yield: 55.0%

3,4-Dinitrotoluene (610-39-9) → 5-methyl-2-nitroaniline (578-46-1)

Guidance literature:

With formic acid; triethylamine; palladium on activated charcoal; at 100 ℃; for 1h;

DOI:10.1021/jo01312a039

upstream raw materials:

3-methoxy-4-nitrotoluene

3-Methylacetanilide

3,4-Dinitrotoluene

N-(5-methyl-2-nitrophenyl)acetamide

Downstream raw materials:

5-methyl-2-nitro-N-phenylaniline

5-methyl-2-nitrobenzenesulfonyl chloride

5,5′-dimethyl-[1,1′-biphenyl]-2,2′-diamine

N-ferrocenyl-5-methyl-2-nitrobenzenamine

Refernces

• 1、 Pawar, Govind Goroba,Brahmanandan, Abhilashamole,Kapur, Manmohan. "Palladium(II)-catalyzed, heteroatom-directed, regioselective C-H nitration of anilines using pyrimidine as a removable directing group". supporting information. p. 448 - 451. Retrieved 2016/02/18.
• 2、 Suzuki,Kawakami,Maeda. "Non-reductive conversion of 1-nitro-9,10-anthraquinone to 1-amino-9,10-anthraquinones". . p. 9217 - 9220. Retrieved 2007/10/02.