Skip to Content
Merck
All Photos(1)

Key Documents

8.03646

Sigma-Aldrich

Diisopropylamine

for synthesis

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

vapor pressure

93.33 hPa ( 20 °C)

Quality Level

200

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)

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

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.
  • A catalyst to prepare aryl disulfides via oxidative coupling of aryl thiols in the presence of air as an oxidant.
  • A base in Pd-catalyzed cross-coupling reactions such as Heck and Sonogashira reaction.

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.

Signal Word

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 Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

7.8 °F - closed cup

Flash Point(C)

-13.45 °C - closed cup

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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)
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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service