2-ISOPROPYLANILINE Chemical Properties

Melting point:

-6.87°C (estimate)

Boiling point:

112-113 °C/18 mmHg (lit.)

Density 

0.955 g/mL at 25 °C (lit.)

vapor pressure 

0.05 mm Hg ( 20 °C)

refractive index 

n20/D 1.548(lit.)

Flash point:

204 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

4.42±0.10(Predicted)

form 

Liquid

color 

Clear pale yellow to orange or brown

Specific Gravity

0.966

Water Solubility 

Insoluble in water.

Sensitive 

Light Sensitive

BRN 

636283

CAS DataBase Reference

643-28-7(CAS DataBase Reference)

EPA Substance Registry System

o-Isopropylaniline (643-28-7)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

RTECS 

BY4200000

TSCA 

TSCA listed

HS Code 

29214990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-ISOPROPYLANILINE Usage And Synthesis

Chemical Properties

Clear pale yellow liquid

Uses

Reagent in determination of tungsten.

Uses

2-Isopropylaniline is used in the synthesis of a colorless amine-coordinated zinc complex. The reactions of 1,1?-bis(hydroxymethyl)ferrocene with 2-isopropylaniline, in the presence of a catalyst [RuCl2(PPh3)3], was studied

Definition

ChEBI: 2-Isopropylaniline is an alkylbenzene.

Synthesis Reference(s)

[1] Dr. Huaibo Zhao,  Prof. Daniele Leonori.“Minimization of Back-Electron Transfer Enables the Elusive sp3 C−H Functionalization of Secondary Anilines.” Angewandte Chemie International Edition 60 14 (2021): 7669–7674.

General Description

The reactions of 1,1′-bis(hydroxymethyl)ferrocene with 2-isopropylaniline, in the presence of a catalyst [RuCl₂(PPh₃)₃], was studied.

Synthesis

Charge a dry tube equipped with a stirring bar with Ir(dtbbpy)(ppy)2PF6 (4 mg, 4 μmol, 2 mol%), Co(dmgH)(dmgH2)Cl2 (11 mg, 0.03 mmol, 15 mol%), and 2-isopropyl-N-methylaniline (30 mg, 0.20 mmol, 1.0 equiv.); Cap the tube with a Supelco aluminium crimp seal with septum (PTFE/butyl); Evacuate the reaction mixture under high vacuum and backfill with N2 (x 3); Add degassed CH3CN (2.0 mL, 0.1 M), 2-isopropyl-N-methylaniline (30 mg, 0.20 mmol) and Et3N (28 μL, 0.20 mmol, 1.0 equiv.) sequentially to the reaction mixture; Cool the reaction mixture to -78°C and degas by three cycles of freeze, pump (5 min), backfill (with N2), and thaw;
Degas the reaction mixture thoroughly; Seal the vial with parafilm and place approximately 4 cm from blue LEDs; Switch on the blue LEDs and stir the reaction mixture under irradiation without fan for 24 hours; Open the tube and dilute the reaction mixture with H2O (10 mL) and EtOAc (10 mL); Separate the layers and extract the aqueous layer with EtOAc (2 x 10 mL); Wash the combined organic layers with brine (10 mL); Dry the mixture over Na2SO4; Filter the residue and evaporate; Purify the crude product by flash column chromatography on silica gel with hexane-EtOAc to obtain 2-isopropylaniline.^[1] 

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