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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
bp:
159 °C (lit.)
vapor pressure:
1.9 mmHg ( 20 °C)
Pricing and availability is not currently available.

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. [1] [2]

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX4882
MKCW2111
MKCW6683
MKCT7978
MKCS8158

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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)
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)
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)
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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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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