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D44952

Sigma-Aldrich

Dibutylamine

≥98%

Synonym(s):

N-butylbutan-1-amine

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About This Item

Linear Formula:
(CH3CH2CH2CH2)2NH
CAS Number:
111-92-2
Molecular Weight:
129.24
Beilstein:
506001
EC Number:
203-921-8
MDL number:
MFCD00009429
UNSPSC Code:
12352100
PubChem Substance ID:
24893877
NACRES:
NA.22

vapor density

4.46 (vs air)

Quality Level

200

vapor pressure

1.9 mmHg ( 20 °C)

Assay

≥98%

form

liquid

autoignition temp.

594 °F

expl. lim.

10 %

refractive index

n20/D 1.417 (lit.)

pH

11.1 (20 °C, 1 g/L)

bp

159 °C (lit.)

mp

−62 °C (lit.)

density

0.767 g/mL at 25 °C (lit.)

SMILES string

CCCCNCCCC

InChI

1S/C8H19N/c1-3-5-7-9-8-6-4-2/h9H,3-8H2,1-2H3

InChI key

JQVDAXLFBXTEQA-UHFFFAOYSA-N

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Application

  • Dibutylamine is extensively used in palladium-catalyzed cross-coupling with aryl halides to synthesize arylamines, popularly known as Buchwald–Hartwig amination.
  • It can be used in the oxone-mediated annulation of 2-aminobenzamides and 1,2-diaminobenzenes to synthesize 2,3-dihydroquinazolin-4(1H)-ones and 1H-benzimidazoles, respectively.
  • It can also be used in the one-pot multicomponent reactions to synthesize tetra- and penta-substituted polyfunctional dihydropyrroles.

Signal Word

Danger

Hazard Statements

H226,H302,H311,H314,H330

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1A

WGK

WGK 1

Flash Point(F)

104.9 °F

Flash Point(C)

40.5 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Oxone-mediated annulation of 2-aminobenzamides and 1, 2-diaminobenzenes with sec-amines via imine-N-oxides: new syntheses of 2, 3-dihydroquinazolin-4 (1 H)-ones and 1 H-benzimidazoles.
Sriramoju V, et al.
New. J. Chem., 42(5), 3188-3191 (2018)
Concise and versatile multicomponent synthesis of multisubstituted polyfunctional dihydropyrroles.
Zhu Q, et al.
Journal of Combinatorial Chemistry, 11(4), 685-696 (2009)
Aqueous hydroxide as a base for palladium-catalyzed amination of aryl chlorides and bromides.
Kuwano R, et al.
The Journal of Organic Chemistry, 67(18), 6479-6486 (2002)
Simple, efficient catalyst system for the palladium-catalyzed amination of aryl chlorides, bromides, and triflates.
Wolfe J P, et al.
The Journal of Organic Chemistry, 65(4), 1158-1174 (2000)
Baiyi Xue et al.
Journal of mass spectrometry : JMS, 46(7), 689-695 (2011-07-12)
Characterization of glycosaminoglycans poses a challenge for current analytical techniques, as they are highly acidic, polydisperse and heterogeneous compounds. The purpose of this study is the separation and analysis of a partially depolymerized heparin-like glycosaminoglycan by on-line ion-pairing reversed-phase high-performance
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