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24544-04-5

Basic Information
CAS No.: 24544-04-5
Name: 2,6-Diisopropylaniline
Article Data: 37
Cas Database
Molecular Structure:
Molecular Structure of 24544-04-5 (2,6-Diisopropylaniline)
Formula: C12 H19 N
Molecular Weight: 177.29
Synonyms: Aniline,2,6-diisopropyl- (6CI,8CI);2,6-Bis(1-methylethyl)aniline;2,6-Bis(1-methylethyl)benzenamine;2,6-Diisopropylphenylamine;N-(2,6-Diisopropylphenyl)amine;
EINECS: 246-305-4
Density: 1.2 g/cm3
Melting Point: -45 °C(lit.)
Boiling Point: 420.7 °C at 760 mmHg
Flash Point: 208.2 °C
Solubility: <0.20 g/L inwater
Appearance: Clear liquid
Hazard Symbols: IrritantXi
Risk Codes: R36/37/38
Safety: S26;S37/39
Transport Information: 180kgs
PSA: 26.02000
LogP: 4.09680
Synthetic route

2-oxo-2-phenylethyl (2,6-diisopropylphenyl)carbamate

24544-04-5

2,6-diisopropylbenzenamine

Conditions
ConditionsYield
With potassium phosphate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ascorbic acid In water; acetonitrile at 20℃; for 2h; Sealed tube; Irradiation; Inert atmosphere;99%
91563-76-7

1,3-diisopropyl-2-nitrobenzene

24544-04-5

2,6-diisopropylbenzenamine

Conditions
ConditionsYield
With borane-ammonia complex; copper(II) oxide In methanol at 50℃; for 0.333333h;96%
With sodium tetrahydroborate In tetrahydrofuran; water at 20℃; for 16h; Inert atmosphere; Green chemistry; chemoselective reaction;88%
With sodium tetrahydroborate; iron; water at 20℃; for 16h;88%
With hydrogen; C27H27ClIrNO In methanol at 60℃; under 4560.31 Torr; for 6h; Autoclave;78%
With C22H25ClF3NORu; hydrogen In methanol; water at 80℃; under 2280.15 Torr; Autoclave;67%

N,N-dibenzyl-2,6-diisopropylaniline

24544-04-5

2,6-diisopropylbenzenamine

Conditions
ConditionsYield
With formic acid; potassium hydroxide In ethanol at 70℃; for 1h;94%
71757-58-9

2,6-diisopropylcyclohexylamine

7440-05-3

palladium

24544-04-5

2,6-diisopropylbenzenamine

Conditions
ConditionsYield
93%
440084-13-9

N-(3-(2,6-diisopropylphenylamino)-3-methylbutan-2-ylidene)-2,6-diisopropylbenzenamine

A

440084-14-0

3-[[2,6-bis(1-methylethyl)phenyl]amino]-3-methyl-2-butanone

B

24544-04-5

2,6-diisopropylbenzenamine

Conditions
ConditionsYield
With sulfuric acid In ethanol; water at 40 - 65℃; for 3 - 4.5h; Inert atmosphere;A 91%
B 91%
136551-45-6

2,6-diisopropyl-1-azidobenzene

24544-04-5

2,6-diisopropylbenzenamine

Conditions
ConditionsYield
With 1,3-diadamantane-4,5-dihydroimidazole chloride; potassium tert-butylate; bis(pinacol)diborane; copper(l) chloride In toluene at 25℃; for 4h; Schlenk technique; Inert atmosphere;91%
627-37-2

N-methyl-N-allylamine

153998-83-5

N-(2,6-diisopropylphenyl)benzimidamide

A

24544-04-5

2,6-diisopropylbenzenamine

B

1,4-dimethyl-2-phenyl-4,5-dihydro-1H-imidazole

Conditions
ConditionsYield
With bis(trimethylsilyl)amide yttrium(III) In neat (no solvent) at 100℃; for 120h; Inert atmosphere;A n/a
B 85%
60090-48-4

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

A

24544-04-5

2,6-diisopropylbenzenamine

B

2909-77-5

N,N-dimethyl-2,6-di(isopropyl)aniline

C

103110-98-1

N-methyl-2,6-di(isopropyl)aniline

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether Heating;A 4%
B 9%
C 79%
With sodium tetrahydroborate
129161-76-8

2,4,6-tri-t-butylphenyldifluoroborane

lithium (2,6-diisopropylphenyl)amide

A

152240-94-3

2,4,6-tri(t-butyl)phenyl-2,6-di(isopropyl)phenyliminoborane

B

24544-04-5

2,6-diisopropylbenzenamine

Conditions
ConditionsYield
In hexane byproducts: LiF; dropping a soln. of 2,4,6-tri-t-butylphenyl-difluoroborane in n-hexane to a suspension of freshly lithiated 2,6-di(isopropyl)phenylamine in n-hexane cooled with ice (under N2) followed by refluxing for 3 h; removal of the solvent under reduced pressure and subliming the iminoborane from the residue in anoil pump vacuum, elem. anal.;A 79%
B n/a

(2,6-diisopropylphenyl)carbamic acid tert-butyl ester

24544-04-5

2,6-diisopropylbenzenamine

Conditions
ConditionsYield
With methanol; oxalyl dichloride at 20℃; for 2h;78%
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

1. Introduction of 2,6-Diisopropylaniline
2,6-Diisopropylaniline, with CAS number of 24544-04-5, can be called 2,6-Bis(1-methylethyl)aniline; 2,6-Bis(1-methylethyl)benzenamine; 2,6-Diisopropylphenylamine ; N-(2,6-Diisopropylphenyl)amine. 2,6-Diisopropylaniline is stable under normal temperatures and pressures, but incompatible with strong oxidizing agents, acids, acid chlorides, acid anhydrides, chloroformates. The colorless to pale orange liquid slightly soluble in water and the solubility is less than 0.20g/L.

2. Properties of 2,6-Diisopropylaniline
H bond acceptors: 1
H bond donors: 2
Freely Rotating Bonds: 3
Polar Surface Area: 26.02 Å2
Index of Refraction: 1.525
Molar Refractivity: 58.85 cm3
Molar Volume: 191.8 cm3
Surface Tension: 33.9 dyne/cm
Enthalpy of Vaporization: 49.49 kJ/mol
Vapour Pressure: 0.0147 mmHg at 25°C
Density: 1.2 g/cm3
Melting Point: -45 °C(lit.)
Flash Point: 208.2 °C
Boiling Point: 420.7 °C at 760 mmHg
Water solubility:  <0.20 g/L
Product Categories: Amines; C11 to C38; Nitrogen Compounds; Aniline Derivatives; o-alkylated Anilines

3. Toxicity of 2,6-Diisopropylaniline

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 oral 3204mg/kg (3204mg/kg) LIVER: OTHER CHANGES

BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE

BLOOD: CHANGES IN SPLEEN
Fundamental and Applied Toxicology. Vol. 3, Pg. 285, 1983.

4. Safety Information of 2,6-Diisopropylaniline
Moderately toxic by ingestion. When heated to decomposition it emits toxic vapors of NOx.
Hazard Codes: IrritantXi
Risk Statements:
R36/37/38: Irritating to eyes, respiratory system and skin.
R52/53: Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic
Safety Statements:
S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S61 Avoid release to the environment. Refer to special instructions / safety data sheets.
S37/39: Wear suitable gloves and eye/face protection.
WGK Germany: 2
RTECS: BX4025000
HS Code: 29214980

5. Use of 2,6-Diisopropylaniline
2,6-Diisopropylaniline is an important intermediates for the manufacture of carbodiimides stabilizers, RIM-PUR, synthetic resins, pesticides, antioxidants, pharmaceuticals and other products and it is a key intermediate for synthesis of new insecticides Diafenthiuron on pesticides synthetic.

6. Preparation of 2,6-Diisopropylaniline
2,6 diisopropylaniline was made by the high pressure liquid alkylation of aniline and propene under the aluminum catalysis. The conversion of aniline and the selectivity of 2,6 diisopropylaniline was respectively more than 80% and 50% under the conditions of the molar ratio of aniline to propene being 1:2 at 280~290 °C for 4~5 hrs.