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Sigma-Aldrich

N,N-Diisopropylaniline

97%

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Linear Formula:
C6H5N[CH(CH3)2]2
CAS Number:
4107-98-6
Molecular Weight:
177.29
MDL number:
MFCD00048277
UNSPSC Code:
12352100
PubChem Substance ID:
24867307
NACRES:
NA.22

Quality Level

100

Assay

97%

form

liquid

refractive index

n20/D 1.519 (lit.)

bp

95-96 °C/11 mmHg (lit.)

density

0.91 g/mL at 25 °C (lit.)

SMILES string

CC(C)N(C(C)C)c1ccccc1

InChI

1S/C12H19N/c1-10(2)13(11(3)4)12-8-6-5-7-9-12/h5-11H,1-4H3

InChI key

OVSARSKQWCLSJT-UHFFFAOYSA-N

General description

N,N-Diisopropylaniline is an N,N-dialkylaniline. Its borane adducts have been prepared and reported as hydroborating agents. Thermal dissociation of the borane-N,N-diisopropylaniline adduct has been reported to afford gaseous diborane. N,N-Diisopropylaniline is a diisoproplyamino derivative that can be prepared by reacting bromobenzene with diisopropylamine.

Application

N,N-Diisopropylaniline was used for the synthesis of 4-diisopropylamino benzonitrile. It may be used for the synthesis of 6-(4-bromophenyl)-3-methoxy-5-methyl-8-oxabicyclo[3.2.1]octa-3,6-dien-2-one and N,N,N′,N′-tetraisopropylbenzidine.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

183.2 °F

Flash Point(C)

84 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Dual fluorescence and fast intramolecular charge transfer with 4-(diisopropylamino) benzonitrile in alkane solvents.
Demeter A, et al.
Chemical Physics Letters, 323(3), 351-360 (2000)
Brown et al.
The Journal of organic chemistry, 65(15), 4655-4661 (2000-08-26)
Several N,N-diethyl-tert-alkylamines, such as N,N-diethyl-2-methyl-2-butylamine (1, t-PentNEt2), N,N-diethyl-2,3-dimethyl-2-butylamine (2, t-HexNEt2), N,N-diethyl-2,3,3-trimethyl-2-butylamine (3, t-HeptNEt2), and N,N-diethyl-1,1,3,3-tetramethylbutylamine (4, t-OctNEt2) with varying steric bulk around nitrogen (by changing the tert-alkyl group) have been prepared and examined as borane carriers. The complexing ability of
N-alkylation of hindered secondary aromatic amines with 2-iodobutane.
Katritzky AR, et al.
ORL; Journal for Oto-Rhino-Laryngology and Its Related Specialties, 23(4), 399-402 (1991)
Yvonne D Williams et al.
The Journal of organic chemistry, 78(23), 11707-11713 (2013-11-01)
Methoxytropolones are useful scaffolds for therapeutic development because of their known biological activity and established value in the synthesis of α-hydroxytropolones. Upon treatment with triflic acid, a series of 3-methoxy-8-oxabicyclo[3.2.1]octa-3,6-dien-2-ones rearrange rapidly and cleanly to form methoxytropolones. Interestingly, bicycles that
Synthesis of N,N,N',N'-tetraalkylbenzidines through oxidative coupling of N,N-dialkylarylamines induced by SbCl5.
Vitale P, et al.
ARKIVOC (Gainesville, FL, United States), 3, 36-48 (2013)
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