4-Iodo-2-methylaniline

Base Information

• Chemical Name: 4-Iodo-2-methylaniline
• CAS No.: 13194-68-8
• Molecular Formula: C7H8IN
• Molecular Weight: 233.052
• Hs Code.: 29214300
• European Community (EC) Number: 236-154-2
• NSC Number: 60731
• DSSTox Substance ID: DTXSID50157270
• Nikkaji Number: J213.740B
• Wikidata: Q72438454
• Mol file: 13194-68-8.mol

Synonyms:4-Iodo-2-methylaniline;13194-68-8;2-Amino-5-iodotoluene;4-iodo-2-methylbenzenamine;4-Iodo-o-toluidine;Benzenamine, 4-iodo-2-methyl-;2-methyl-4-iodoaniline;4-Iodo-2-methyl-phenylamine;(4-iodo-2-methylphenyl)amine;MFCD00025299;EINECS 236-154-2;4-iodo-2-methylphenylamine;4-iodo-2-methyl-aniline;Aniline, 4-iodo-2-methyl-;NSC60731;4-iodo-2-methyl aniline;SCHEMBL218997;4-Iodo-2-methylaniline, 97%;DTXSID50157270;HMS1760A15;BCP27395;CK1165;NSC 60731;NSC-60731;STL089346;AKOS000111238;DS-0817;PS-3168;AC-24896;SY018977;AM20060294;BB 0245922;CS-0005831;FT-0618798;I0690;EN300-17571;AE-641/01196008;J-507955;Z56960244

Chemical Property of 4-Iodo-2-methylaniline

Chemical Property:

• Appearance/Colour: Grey to purple crystals
• Vapor Pressure: 0.00428mmHg at 25°C
• Melting Point: 86-89 °C(lit.)
• Refractive Index: 1.663
• Boiling Point: 278.4 °C at 760 mmHg
• PKA: 3.66±0.10(Predicted)
• Flash Point: 122.1 °C
• PSA: 26.02000
• Density: 1.791 g/cm³
• LogP: 2.76300
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Light Sensitive
• Solubility.: soluble in Methanol
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 232.97015
• Heavy Atom Count: 9
• Complexity: 94.9

Purity/Quality:

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

4-Iodo-2-methylaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36-26,36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=CC(=C1)I)N

Technology Process of 4-Iodo-2-methylaniline

There total 11 articles about 4-Iodo-2-methylaniline 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: 95.0%

o-toluidine (95-53-4) → 4-iodo-2-methylaniline (13194-68-8)

Guidance literature:

With N-chloro-N-(benzenesulfonyl)benzenesulfonamide; potassium iodide; In N,N-dimethyl-formamide; at 25 - 30 ℃;

DOI:10.1021/acs.joc.1c01642

Reference yield: 90.0%

4-Bromo-2-methylaniline (583-75-5) → 4-iodo-2-methylaniline (13194-68-8)

Guidance literature:

With copper(l) iodide; sodium iodide; N,N`-dimethylethylenediamine; In 1,4-dioxane; at 110 ℃; for 18h; Inert atmosphere; Schlenk technique;

DOI:10.1055/s-0033-1338598

Reference yield:

o-toluidine (95-53-4) → 2-iodo-6-methylbenzenamine (832133-11-6) + 4-iodo-2-methylaniline (13194-68-8)

Guidance literature:

With ammonium iodide; dihydrogen peroxide; In acetic acid; at 20 ℃; for 8h;

DOI:10.1016/j.tetlet.2007.06.138

upstream raw materials:

N-(2-methylphenyl)acetamide

4-iodo-2-methyl-1-nitro-benzene

2-iodo-5,5-dimethyl-2-nitro-cyclohexane-1,3-dione

o-toluidine

Downstream raw materials:

N-benzylidene-4-iodo-2-methyl-aniline

N,N'-bis-(4-iodo-2-methyl-phenyl)-formamidine

iodine

2-amino-5-iodobenzoic acid

Refernces

• 1、 Militzer,Smith,Evans. "-". . p. 436. Retrieved 1941.
• 2、 Hosseini, Abolfazl,Khalilzadeh, Mohammad A.,Keipour, Hoda,Tajbakhsh, Mahmood. "Iodination of activated aromatic compounds using nanostructure solid acid catalyst". . p. 2407 - 2414. Retrieved 2012.
• 3、 Misal, Balu,Palav, Amey,Ganwir, Prerna,Chaturbhuj, Ganesh. "Sulfated polyborate-H2O assisted tunable activation of N-iodosuccinimide for expeditious mono and diiodination of arenes". supporting information. . Retrieved 2021/05/26.
• 4、 Bovonsombat, Pakorn,Lorpaiboon, Wanutcha,Laoboonchai, Sarocha,Sriprachaya-anunt, Prima,Yimkosol, Warangkana,Siriphatcharachaikul, Natthapatch,Siricharoensang, Pornpawit,Kangwannarakul, Terawee,Maeda, Jin,Losuwanakul, Satreerat,Mahesh Abhyankar, Maitraye. "A novel DMSO-assisted regioselective iodination of aniline analogues". . . Retrieved 2020/10/05.