2,6-Diisopropylaniline

Base Information

• Chemical Name: 2,6-Diisopropylaniline
• CAS No.: 24544-04-5
• Molecular Formula: C12 H19 N
• Molecular Weight: 177.29
• Hs Code.: 29214980
• European Community (EC) Number: 246-305-4
• UNII: 190BG0089I
• DSSTox Substance ID: DTXSID5022279
• Nikkaji Number: J33.769B
• Wikipedia: 2,6-Diisopropylaniline
• Wikidata: Q27252049
• ChEMBL ID: CHEMBL3183764
• Mol file: 24544-04-5.mol

Synonyms:2,6-DIISOPROPYLANILINE;24544-04-5;Benzenamine, 2,6-bis(1-methylethyl)-;diisopropylaniline;2,6-di(propan-2-yl)aniline;Aniline, 2,6-diisopropyl-;2,6-Diisopropyl aniline;2,6-Diisopropylphenylamine;2,6-Dilsopropylaniline;BRN 2208763;2,6-bis(propan-2-yl)aniline;2,6-bis(1-methylethyl)aniline;EINECS 246-305-4;MFCD00008887;DTXSID5022279;UNII-190BG0089I;190BG0089I;EC 246-305-4;3-12-00-02764 (Beilstein Handbook Reference);2,6-diisopropyaniline;2,6-diisoproylaniline;2,6 diisopropylaniline;2, 6-diisopropylaniline;2,6-diisopropyl-aniline;2,6-di-iso-propylaniline;Diisopropylaniline, 2,6-;2,6-diisopropyl-phenylamine;2,6-diisopropylphenyl-amine;(2,6-diisopropylphenyl)amine;2,6-diisopropyl-phenyl amine;SCHEMBL104314;2,6-Diisopropylaniline, 97%;DTXCID302279;CHEMBL3183764;AMY25623;BCP25856;Tox21_302145;BBL011276;STK940261;AKOS000118849;AC-4779;AT11199;CS-W017358;NCGC00255131-01;BP-21134;DS-12418;LS-19720;SY001946;CAS-24544-04-5;D1755;FT-0610671;EN300-19395;2,6-Diisopropylaniline, technical grade, 90%;2,6-Diisopropylaniline, technical, ~90% (GC);A817358;W-107307;Q27252049;F8881-7788;Z104473708;DIPA 2,6-DIISOPROPYLANILINE 2,6-bis(1-methylethyl)-benzenamin

Chemical Property of 2,6-Diisopropylaniline

Chemical Property:

• Appearance/Colour: Clear liquid
• Vapor Pressure: <0.01 mm Hg ( 20 °C)
• Melting Point: -45 °C(lit.)
• Refractive Index: 1.5332
• Boiling Point: 420.7 °C at 760 mmHg
• PKA: 4.25±0.10(Predicted)
• Flash Point: 208.2 °C
• PSA: 26.02000
• Density: 1.2 g/cm³
• LogP: 4.09680
• Storage Temp.: Store below +30°C.
• Solubility.: <0.2g/l
• Water Solubility.: <0.20 g/L
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 177.151749610
• Heavy Atom Count: 13
• Complexity: 135

Purity/Quality:

99% ^*data from raw suppliers

2,6-Diisopropylaniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 52/53-36/37/38
• Safety Statements: 61-37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Aromatic
• Canonical SMILES: CC(C)C1=C(C(=CC=C1)C(C)C)N
• Description: 2,6-Diisopropylaniline is an organic compound with the formula H2NC6H3(CHMe2)2 (Me = CH3). It is a colorless liquid although, like many anilines, samples can appear yellow or brown.
• Uses: 2,6-Diisopropylaniline is used as intermediate for the manufacture of carbodiimides stabilizers, RIM-PUR, synthetic resins, pesticides, antioxidants, pharmaceuticals and other products. 2,6-Diisopropylaniline may be used in the preparation of multitopic Schiff-base ligand precursors.It may be used in the preparation of NSN-donor proligand, 4,5-bis(2,6-diisopropylanilino)-2,7-di-tert-butyl-9,9-dimethylthioxanthene. It may be used to prepare N-heterocyclic carbene complexes for α-arylation of acyclic ketones, amination of haloarenes, and aqueous Suzuki coupling. 2,6-Diisopropylaniline may be used in the preparation of organocatalyst based on naphthalene diimides (NDIs). 2,6-Diisopropylaniline acts as an intermediate used in the production of carbodiimides stabilizers, synthetic resins, antioxidants and active pharmaceutical ingredients. It is also used in the preparation of multitopic Schiff-base ligand precursors and 4,5-bis(2,6-diisopropylanilino)-2,7-di-tert-butyl-9,9-dimethylthioxanthene. It also undergoes condensation reaction with triacetylmethane to get -[1-(2,6-diisopropylphenylamino)ethylidene]pentane-2,4-dione. Further, it is used to prepare N-heterocyclic carbene complexes for alfa-arylation of acyclic ketones, amination of haloarenes and aqueous Suzuki coupling. In addition to this, it is used in the prepartion of organocatalyst based on naphthalene diimides. 2,6-Diisopropylaniline was used in the preparation of multitopic Schiff-base ligand precursors. It was also used in the preparation of NSN-donor proligand, 4,5-bis(2,6-diisopropylanilino)-2,7-di-tert-butyl-9,9-dimethylthioxanthene.

Technology Process of 2,6-Diisopropylaniline

There total 49 articles about 2,6-Diisopropylaniline 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: 99.0%

2-oxo-2-phenylethyl (2,6-diisopropylphenyl)carbamate → 2,6-diisopropylbenzenamine (24544-04-5)

Guidance literature:

With potassium phosphate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ascorbic acid; In water; acetonitrile; at 20 ℃; for 2h; Sealed tube; Irradiation; Inert atmosphere;

DOI:10.1021/acs.joc.8b00096

Reference yield: 96.0%

1,3-diisopropyl-2-nitrobenzene (91563-76-7) → 2,6-diisopropylbenzenamine (24544-04-5)

Guidance literature:

With borane-ammonia complex; copper(II) oxide; In methanol; at 50 ℃; for 0.333333h;

DOI:10.1002/cctc.201902391

Reference yield: 94.0%

N,N-dibenzyl-2,6-diisopropylaniline → 2,6-diisopropylbenzenamine (24544-04-5)

Guidance literature:

With formic acid; potassium hydroxide; In ethanol; at 70 ℃; for 1h;

DOI:10.1002/adsc.201900686

upstream raw materials:

propene

aniline

2,6-di(isopropyl)-N-methyleneaniline

3-Methoxy-pyridine-2-carboxylic acid (2,6-diisopropyl-phenyl)-amide

Downstream raw materials:

N-(2,6-diisopropylphenyl) acetamide

methyl 2-((2,6-diisopropylphenyl)amino)-2-oxoacetate

1-(2,6-Diisopropyl-cyclohexyl)-3-propyl-thiourea

2-bromo-1,3-diisopropylbenzene

Refernces

• 1、 Xu, Mengyin,Wang, Yang,Zhou, Yifeng,Yao, Zi-Jian. "N,N-Chelate nickel(II) complexes bearing Schiff base ligands as efficient hydrogenation catalysts for amine synthesis". . . Retrieved 2021/12/09.
• 2、 Lv, Wen-Rui,Li, Rong-Jian,Liu, Zhen-Jiang,Jin, Yan,Yao, Zi-Jian. "Synthesis, Structure, and Catalytic Hydrogenation Activity of [NO]-Chelate Half-Sandwich Iridium Complexes with Schiff Base Ligands". . p. 8181 - 8188. Retrieved 2021/05/26.