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8.03646

Sigma-Aldrich

Diisopropylamine

for synthesis

Synonym(s):

Diisopropylamine, N,N-Diisopropylamine, Bis(1-methylethyl)amine

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10 ML
$23.80
100 ML
$36.30
1 L
$73.00
2.5 L
$144.00
20 KG
$802.00

$23.80

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10 ML
$23.80
100 ML
$36.30
1 L
$73.00
2.5 L
$144.00
20 KG
$802.00

About This Item

Linear Formula:
(CH3)2CHNHCH(CH3)2
CAS Number:
108-18-9
Molecular Weight:
101.19
MDL number:
MFCD00008862
UNSPSC Code:
12352116
EC Index Number:
203-558-5
NACRES:
NA.22
grade:
for synthesis
synthesis grade
assay:
≥99% (GC)
bp:
83-84 °C/1013 hPa
vapor pressure:
93.33 hPa ( 20 °C)

$23.80

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grade

for synthesis
synthesis grade

Quality Level

200

vapor pressure

93.33 hPa ( 20 °C)

assay

≥99% (GC)

form

liquid

autoignition temp.

295 °C

potency

420 mg/kg LD50, oral (Rat)
2900 mg/kg LD50, skin (Rabbit)

expl. lim.

1.1-7.1 % (v/v)

dilution

(for synthesis)

pH

11.8 (20 °C, 6 g/L in H2O)

bp

83-84 °C/1013 hPa

mp

-70 °C

transition temp

flash point -13.45 °C (DIN 51755 Part 1)

density

0.72 g/cm3 at 20 °C

storage temp.

2-30°C

SMILES string

N(C(C)C)C(C)C

InChI

1S/C6H15N/c1-5(2)7-6(3)4/h5-7H,1-4H3

InChI key

UAOMVDZJSHZZME-UHFFFAOYSA-N

General description

Diisopropylamine (DIPA) is an aliphatic secondary amine commonly used as an organic base in chemical synthesis.

Application

Diisopropylamine can be used as:

  • A reagent to synthesize furan, dihydrofuran, or butanolide derivatives by reacting with γ-ketothioesters.[1]
  • A catalyst to prepare aryl disulfides via oxidative coupling of aryl thiols in the presence of air as an oxidant.[2]
  • A base in Pd-catalyzed cross-coupling reactions such as Heck and Sonogashira reaction.[3][4]

It can also be used as a starting material to prepare lithium diisopropylamide (LDA), a strong non-nucleophilic base widely used in organic synthesis for deprotonation reactions.[5]

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

7.8 °F - closed cup

flash_point_c

-13.45 °C - closed cup

Certificates of Analysis (COA)

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Diisopropylamine as a single catalyst in the synthesis of aryl disulfides
Kucinski, K and Hreczycho G
Green Processing and Synthesis, 7(1), 12-15 (2018)
Synthesis of new trifluoromethylated furans, dihydrofurans and butenolides starting from γ-ketothioesters and diisopropylamine
Bouillon J-P, et al.
Synthesis, 2006(06), 1050-1056 (2006)
Controlled mono and double Heck reactions in water catalyzed by an oxime-derived palladacycle
Botella Luis and Najera C
Tetrahedron Letters, 45(9), 1833-1836 (2004)
Design and synthesis of a novel banana-shaped functional molecule via double cross-coupling
Yang Bingchuan, et al.
Molecules (Basel), 24(4), 698-698 (2019)
Alexander C Hoepker et al.
Journal of the American Chemical Society, 133(18), 7135-7151 (2011-04-20)
Ortholithiation of 1-chloro-3-(trifluoromethyl)benzene with lithium diisopropylamide (LDA) in tetrahydrofuran at -78 °C displays characteristics of reactions in which aggregation events are rate limiting. Metalation with lithium-chloride-free LDA involves a rate-limiting deaggregation via dimer-based transition structures. The post-rate-limiting proton transfers are

Questions

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  1. 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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  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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