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496219

Sigma-Aldrich

N,N-Diisopropylethylamine

99.5%, biotech. grade

Synonym(s):

N-Ethyldiisopropylamine, DIPEA, Ethyldiisopropylamine, ‘Hünig’s base’

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About This Item

Linear Formula:
[(CH3)2CH]2NC2H5
CAS Number:
7087-68-5
Molecular Weight:
129.24
EC Number:
230-392-0
MDL number:
MFCD00008868
UNSPSC Code:
12352116
PubChem Substance ID:
329757490
NACRES:
NA.21
grade:
biotech. grade
application(s):
peptide synthesis
bp:
127 °C (lit.)
vapor pressure:
31 mmHg ( 37.7 °C)
Pricing and availability is not currently available.

grade

biotech. grade

Quality Level

200

vapor pressure

31 mmHg ( 37.7 °C)

Assay

99.5%

form

liquid

impurities

<0.050% water

color

APHA: <20

refractive index

n20/D 1.414 (lit.)

pH

12.3 (20 °C)

bp

127 °C (lit.)

mp

<−50 °C (lit.)

solubility

water: soluble 4.01 g/L at 20 °C

density

0.742 g/mL at 25 °C (lit.)

application(s)

peptide synthesis

SMILES string

CCN(C(C)C)C(C)C

InChI

1S/C8H19N/c1-6-9(7(2)3)8(4)5/h7-8H,6H2,1-5H3

InChI key

JGFZNNIVVJXRND-UHFFFAOYSA-N

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General description

N, N-Diisopropylethylamine is a hindered non-nucleophilic amine base used in alkylation, aldol-like reactions, eliminations, and selective generation of enolates. It is widely used as a proton scavenger in organic synthesis. Due to its less nucleophilic nature, it produces less byproducts.
N, N-Diisopropylethylamine is a hindered non-nucleophilic amine base used in alkylation, aldol-like reactions, eliminations, and selective generation of enolates. It is widely used as a proton scavenger in organic synthesis. Due to its less nucleophilic nature, it produces less byproducts.

Application

N, N-Diisopropylethylamine can be used as a base:
  • In the palladium (0)-catalyzed alkoxy carbonylation of allyl phosphates and acetate.
  • In the selective enolate formation along with boryl triflates.
  • In the C–N coupling of aryl halides with nitroarenes in the presence of nickel catalyst.

N,N-Diisopropylethylamine may be used in the synthesis of mannosylated ovalbumin peptides.[1]

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Dam. 1 - Flam. Liq. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

49.1 °F

Flash Point(C)

9.5 °C

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Certificates of Analysis (COA)

Lot/Batch Number
STBL3356
SHBR4804
SHBQ4239
SHBQ2974
SHBR0490

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Asymmetric Hydrogenation of α,β-Unsaturated Nitriles with Base-Activated Iridium N, P Ligand Complexes
Muller MA and Pfaltz A.
Angewandte Chemie (International Edition in English), 126(33), 8812-8815 (2014)
Lipase-catalysed synthesis of olvanil in organic solvents.
Reyes-Duarte D, et al.
Biotechnology Letters, 24(24), 2057-2061 (2002)
Alexandre Yersin et al.
Biophysical journal, 94(1), 230-240 (2007-09-18)
Interaction between the iron transporter protein transferrin (Tf) and its receptor at the cell surface is fundamental for most living organisms. Tf receptor (TfR) binds iron-loaded Tf (holo-Tf) and transports it to endosomes, where acidic pH favors iron release. Iron-free
Facile and Gram-scale Synthesis of Metal-free Catalysts: Toward Realistic Applications for Fuel Cells.
Kim OH, et al.
Scientific Reports, 5 (2015)
Jonathan F Lovell et al.
Biomacromolecules, 12(9), 3115-3118 (2011-07-23)
We demonstrate that porphyrins can be used as efficient cross-linkers to generate a new class of hydrogels with enabling optical properties. Tetracarboxylic acid porphyrins reacted with PEG diamines to form a condensation polyamide in a range of appropriate conditions, with
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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    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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  2. 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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