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Merck
CN

8.03646

Diisopropylamine

for synthesis

Synonym(s):

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

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About This Item

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

Key Documents

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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

grade

synthesis grade

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

Quality Level

200

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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.

signalword

Danger

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

flash_point_f

7.8 °F - closed cup

flash_point_c

-13.45 °C - closed cup

Hazard Classifications

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

Regulatory Information

危险化学品
This item has

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)
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)
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)
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

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