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471232

Sigma-Aldrich

Dibutylamine

≥99.5%

Synonym(s):

N,N-Di-n-butylamine, N-Butyl-1-butanamine, n-Dibutylamine, Di-n-butylamine

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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:
24870706
NACRES:
NA.22
Assay:
≥99.5%
bp:
159 °C (lit.)
vapor pressure:
1.9 mmHg ( 20 °C)

vapor density

4.46 (vs air)

Quality Level

200

vapor pressure

1.9 mmHg ( 20 °C)

Assay

≥99.5%

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.)

solubility

water: soluble 3.8 g/L at 20 °C

density

0.767 g/mL at 25 °C (lit.)

functional group

amine

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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General description

Dibutylamine is a highly reactive catalyst, commonly used as a reagent in the derivatization of isocyanates.

Application

Dibutylamine can be used as a reactant to synthesize:,·      
  • N, N




  • -Dibutyl-4-methylaniline by Pd-catalyzed Buchwald-Hartwig amination reaction with aryl chlorides and bromides.     
  • N,N-Dibutylacetamide by acetylation reaction with isopropenyl acetate.

It can also be used as:      
  • A strong hindered base in the different elimination reactions.
  • An organocatalyst to synthesize annulated pyrano[2,3-d]pyrimidine derivatives via multicomponent condensation reaction of aromatic aldehydes, malononitrile, and barbituric acid.

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

104.9 °F - closed cup

Flash Point(C)

40.5 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 2 petroleums
Hazardous rank III
Water insoluble liquid

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

471232-500ML:
471232-1L:
471232-VAR:
471232-18L:
471232-100ML:
471232-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW2111
MKCW6683
MKCT7978
MKCS8158
MKCS8156

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Determination of complex mixtures of airborne isocyanates and amines. Part 1. Liquid chromatography with ultraviolet detection of monomeric and polymeric isocyanates as their dibutylamine derivatives.
Spanne M, et al.
Analyst, 121(8), 1095-1099 (1996)
Chemistry of blocked isocyanates. II. Kinetics and mechanism of the reaction of dibutylamine with phenyl and 2-methylphenyl oxime carbamates.
Levine AW and Fech Jr J.
The Journal of Organic Chemistry, 37(15), 2455-2460 (1972)
Determination of complex mixtures of airborne isocyanates and amines. Part 3. Methylenediphenyl diisocyanate, methylenediphenylamino isocyanate and methylenediphenyldiamine and structural analogues after thermal degradation of polyurethane
Haakan T et al.
Analyst, 122, 275-278 (1997)
Dibutylamine (DBA): A highly efficient catalyst for the synthesis of pyrano [2, 3-d] pyrimidine derivatives in aqueous media
Ajmal R B et al.
Journal of Taibah University for Science , 10, 9-18 (2016)
Reddi Mohan Naidu Kalla et al.
European journal of medicinal chemistry, 76, 61-66 (2014-02-27)
A series of 2-amino-3-cyano-4H-chromen-4-ylphosphonates have been synthesized by reacting substituted salicylaldehydes, malononitrile, and dialkylphosphites using a catalytic amount of dibutylamine as an organocatalyst employing Knoevenagel, Pinner, and phospha-Michael reactions simultaneously in ethanol. This protocol is an environmentally friendly procedure and
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