| Identification | More | [Name]
Ethyldiisopropylamine | [CAS]
7087-68-5 | [Synonyms]
3-METHYL-1-BUTINE-3-OL
DIEA
DIISOPROPYLETHYLAMINE
DIPEA
edia
ETHYLDIISOPROPYLAMINE
HUENIGS BASE
HUENIG'S BASE
HUNIGS BASE
'HUNIG'S BASE'
HUNIG'S BASE
N-ETHYLDIISOPROPYLAMINE
N-ETHYLDISSOPROPLYAMINE
N,N'-DIISOPROPYLETHYLAMINE
N,N-DIISOPROPYLETHYLAMINE
(CH3)2CHN(C2H5)CH(CH3)2
1,1’-Dimethyltriethylamine
1,1'-Dimethyltriethylamine
2-Propanamine, N-ethyl-N-(1-methylethyl)-
2-Propanamine,N-ethyl-N-(1-methylethyl)- | [EINECS(EC#)]
230-392-0 | [Molecular Formula]
C8H19N | [MDL Number]
MFCD00008868 | [Molecular Weight]
129.24 | [MOL File]
7087-68-5.mol |
| Chemical Properties | Back Directory | [Appearance]
Clear, colorless to light yellow liquid | [mp ]
-46 °C
| [Melting point ]
<-50 °C (lit.) | [bp ]
127 °C | [Boiling point ]
127 °C (lit.) | [density ]
0.782 | [vapor pressure ]
31 mmHg ( 37.7 °C) | [refractive index ]
n20/D 1.457
| [Fp ]
6 °C
| [storage temp. ]
Store in dark! | [solubility ]
miscible | [form ]
Liquid | [pka]
10.98±0.28(Predicted) | [Specific Gravity]
0.755 (20/4℃) | [color ]
APHA: <20 | [PH]
12.3 (H2O, 20℃)(as an emulsion) | [explosive limit]
0.7-6.3%(V) | [Water Solubility ]
miscible | [Detection Methods]
GC | [Detection Methods]
GC,NMR | [BRN ]
605301 | [InChIKey]
JGFZNNIVVJXRND-UHFFFAOYSA-N | [CAS DataBase Reference]
7087-68-5(CAS DataBase Reference) | [NIST Chemistry Reference]
(i-C3H7)2(C2H5)N(7087-68-5) | [EPA Substance Registry System]
7087-68-5(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
C,F | [Risk Statements ]
R11:Highly Flammable.
R22:Harmful if swallowed.
R34:Causes burns.
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R10:Flammable. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S16:Keep away from sources of ignition-No smoking .
S27:Take off immediately all contaminated clothing .
S60:This material and/or its container must be disposed of as hazardous waste .
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) . | [RIDADR ]
UN 2734 8/PG 2
| [WGK Germany ]
2
| [F ]
9-34 | [Autoignition Temperature]
240 °C | [Hazard Note ]
Highly Flammable/Corrosive/Harmful | [TSCA ]
Yes | [HazardClass ]
3 | [PackingGroup ]
II | [HS Code ]
29211980 | [Toxicity]
LD50 orally in Rabbit: > 200 - 500 mg/kg |
| Raw materials And Preparation Products | Back Directory | [Preparation Products]
(11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-DIMETHYLAMINE-->3-HYDROXYMETHYL-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER-->N-Boc-5,6,7,8-tetrahydro-3-methoxy-[1,2,4]triazolo[4,3-A]pyrazine ,98%-->2-Ethylpiperazine-->3-(5-METHYL-1,2,4-OXADIAZOL-3-YL)BENZALDEHYDE-->1-Boc-azetidine-3-ylmethanol-->BAPTA, TETRASODIUM SALT-->BAPTA-->3-Azetidinecarboxylic acid-->2-(TRIFLUOROMETHYL)THIAZOLE-5-CARBALDEHYDE-->4,5-Diaminopyrimidine-->3-(N-Boc-aminomethyl)azetidine-->1-Boc-3-(Aminomethyl)azetidine-->2-(PIPERAZIN-1-YL)-ACETIC ACID N-(2-PHENYLETHYL)-AMIDE-->1-Boc-3-Cyanoazetidine-->TERT-BUTYL N-(BENZYLOXY)CARBAMATE-->METHYL 2-((PIPERIDIN-4-YL)METHYL)BENZOATE-->2-((1-(TERT-BUTOXYCARBONYL)PIPERIDIN-4-YL)METHYL)BENZOIC ACID-->3-[(4-METHYLPIPERAZIN-1-YL)METHYL]BENZALDEHYDE-->(R)-4-Boc-Piperazine-3-carboxylic acid-->5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4(3H)-one-->6-CHLORO-5-NITROPYRIMIDIN-4-AMINE-->N-(4-FORMYL-PYRIDIN-3-YL)-2,2-DIMETHYL-PROPIONAMIDE-->3-((1-(TERT-BUTOXYCARBONYL)PIPERIDIN-4-YL)METHYL)BENZOIC ACID-->4-((1-(TERT-BUTOXYCARBONYL)PIPERIDIN-4-YL)METHYL)BENZOIC ACID-->METHYL 4-((PIPERIDIN-4-YL)METHYL)BENZOATE-->METHYL 3-((PIPERIDIN-4-YL)METHYL)BENZOATE-->METHYL 5-NITRO-2-FUROATE-->5-Amino-4,6-dichloropyrimidine-->4,6-Dichloro-5-nitropyrimidine-->4-(3-BROMOPHENYL)MORPHOLINE-->Faropenem sodium hemipentahydrate-->5-AMINO-6-CHLORO-PYRIMIDIN-4-OL-->4-AMINO-6-CHLOROPYRIMIDIN-5-YLAMINE-->4-CHLORO-6-HYDRAZINO-PYRIMIDIN-5-YLAMINE-->4-ETHYNYLANILINE-->3-Bromo-2-methoxy-propene-->PIPERAZINE-1,4-DICARBOXYLIC ACID TERT-BUTYL ESTER METHYL ESTER |
| Questions And Answer | Back Directory | [Description]
Also known as Hunig’s base and abbreviated as DIPEA or DIEA, N,N-Diisopropylethylamine is a sterically hindered amine and an organic compound. The colourless liquid was named as Hung’s base after Siegfried Hunig, a German chemist. It is noteworthy that the compound is commercially available.
In organic chemistry, the compound is used as a base. Since the nitrogen centre is isolated by an ethyl group and the two isopropyl groups, N,N-Diisopropylethylamine can bind to protons. The compound is, therefore, a base similar to 2,2,6,6-tetramethylpiperidine, but a poor nucleophile, a blend of properties that makes it valuable as an organic reagent.
Traditionally, DIPEA is prepared by the alkylation of diisopropylamine with diethyl sulphate. DIPEA can then be purified through distillation from potassium hydroxide if necessary.
| [Stability and Reactivity]
DIPEA exhibits violent reaction as well as flammability with nitrates, oxidizing agents, and peroxides.
It can also react very exothermically and possibility of spitting with halogens and strong acids. In an alkaline environment, the compound is likely to react violently. In addition, the compound can form toxic products such as n-nitrosamines when combined with nitrous acid as well as oxygen, nitrosating agents, and nitrates.
Under normal conditions (temperature and pressure), DIPEA is very stable. However, it is soluble in most organic solvents.
| [Applications]
N,N-Diisopropylethylamine is utilized as a base in the palladium(0)catalysed alkoxycarbonylation of both allyl acetates and phosphates . When treated with triphenyphosphine in the presence of DIPEA in ethanol under carbon monoxide pressure, diethyl-2-hexenyl phosphate produces mixtures of cisand trans--ethyl heptenoates in a ratio of 84:16. DIPEA is used as a neutralizer of the produced phosphoric acid. Notably, the alkyl ester cannot be produced without DIPEA.
When combined with boryl triflates, N,N-Diisopropylethylamine is hugely used in the enolate synthesis of ketones for application in directed cross-adol reactions . When reacted with Di-n-butylboryl Trifluoromethanesulfonate and DIPEA in ether, 4-methyl-2-pentanone generates unisolated baron enolate.
DIPEA is applied as a proton scavenger in organic synthesis. Since the compound is a sterically hindered amine, it lacks quaternization; therefore, making it a perfect choice of a base for use with extremely reactive alkylating agents. DIPEA is specifically useful as a base in the protection of alcohols as substituted ethers in the field of protecting group chemistry.
In the synthesis of peptides, the compound is also used in the coupling of amino acids. The steric nature and basicity of DIPEA during the coupling reaction affects the degree of racemization.
|
| Hazard Information | Back Directory | [Chemical Properties]
Clear, colorless to light yellow liquid | [Uses]
It is used as a base in organic synthesis. Because the nitrogen atom | [General Description]
N-Ethyldiisopropylamine (EDIA) reacts with monoactivated Michael acceptors to afford symmetrical sulfones. | [Purification Methods]
Distil the amine from ninhydrin, then from KOH [Dryland & Sheppard, J Chem Soc, Faraday Trans 1 125 1986]. It is a strong base and should be stored in the absence of carbon dioxide. [Hünig & Kiessel Chem Ber 91 380, 387 1958, Wotiz et al. J Org Chem 24 1202 1959, Beilstein 4 IV 551.] |
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