Product Name

  • Name

    1-Diethylamino-2-propyne

  • EINECS 223-804-5
  • CAS No. 4079-68-9
  • Article Data47
  • CAS DataBase
  • Density 0.822 g/cm3
  • Solubility Soluble in acid. Insoluble in water.
  • Melting Point 157-161°C
  • Formula C7H13N
  • Boiling Point 135.4 °C at 760 mmHg
  • Molecular Weight 111.187
  • Flash Point 27.5 °C
  • Transport Information UN 2733 3/PG 2
  • Appearance colorless to yellowish transparent liquid
  • Safety 26-36/37/39-45
  • Risk Codes 11-21/22-34
  • Molecular Structure Molecular Structure of 4079-68-9 (1-Diethylamino-2-propyne)
  • Hazard Symbols FlammableF, HarmfulXn, CorrosiveC
  • Synonyms 2-Propynylamine,N,N-diethyl- (6CI,7CI,8CI);1-(Diethylamino)-2-propyne;3-(Diethylamino)-1-propyne;3-(Diethylamino)propyne;3-(N,N-Diethylamino)propyne;Diethylpropargylamine;Golpanol DEP;N,N-Diethyl-2-propyn-1-amine;N,N-Diethyl-2-propynylamine;N,N-Diethylpropargylamine;NSC 63868;Propargyldiethylamine;1-Diethylamino-2-propyne (DEP);
  • PSA 3.24000
  • LogP 0.96140

Synthetic route

diethylamine
109-89-7

diethylamine

propargyl bromide
106-96-7

propargyl bromide

N,N-diethyl-2-propynylamine
4079-68-9

N,N-diethyl-2-propynylamine

Conditions
ConditionsYield
With potassium carbonate In toluene at 20℃; for 15h;94%
In tetrahydrofuran at 20℃; for 2h;72.26%
In diethyl ether71%
2-propynyl chloride
624-65-7

2-propynyl chloride

diethylamine
109-89-7

diethylamine

N,N-diethyl-2-propynylamine
4079-68-9

N,N-diethyl-2-propynylamine

Conditions
ConditionsYield
With sodium carbonate80%
Ambient temperature;27%
With ethanol; sodium carbonate
morpholine
110-91-8

morpholine

Diethyl-pent-4-en-2-ynyl-prop-2-ynyl-ammonium; bromide

Diethyl-pent-4-en-2-ynyl-prop-2-ynyl-ammonium; bromide

A

N,N-diethyl-2-propynylamine
4079-68-9

N,N-diethyl-2-propynylamine

B

4-pent-4-en-2-ynyl-morpholine
51034-07-2

4-pent-4-en-2-ynyl-morpholine

C

diethyl-(5-morpholin-4-yl-penta-2,3-dienyl)-amine

diethyl-(5-morpholin-4-yl-penta-2,3-dienyl)-amine

Conditions
ConditionsYield
In water at 13 - 20℃; Addition; elimination; Heating;A n/a
B n/a
C 32%
...Expand
dimethyl amine
124-40-3

dimethyl amine

Diethyl-pent-4-en-2-ynyl-prop-2-ynyl-ammonium; bromide

Diethyl-pent-4-en-2-ynyl-prop-2-ynyl-ammonium; bromide

A

N,N-diethyl-2-propynylamine
4079-68-9

N,N-diethyl-2-propynylamine

B

dimethyl(4-penten-2-ynyl)amine
2696-30-2

dimethyl(4-penten-2-ynyl)amine

C

N,N-diethyl-N',N'-dimethyl-penta-2,3-diene-1,5-diamine

N,N-diethyl-N',N'-dimethyl-penta-2,3-diene-1,5-diamine

Conditions
ConditionsYield
In water at 13 - 20℃; Addition; elimination; Heating;A n/a
B n/a
C 30%
...Expand
piperidine
110-89-4

piperidine

Diethyl-pent-4-en-2-ynyl-prop-2-ynyl-ammonium; bromide

Diethyl-pent-4-en-2-ynyl-prop-2-ynyl-ammonium; bromide

A

N,N-diethyl-2-propynylamine
4079-68-9

N,N-diethyl-2-propynylamine

B

1-pent-4-en-2-ynyl-piperidine
51034-06-1

1-pent-4-en-2-ynyl-piperidine

C

diethyl-(5-piperidin-1-yl-penta-2,3-dienyl)-amine

diethyl-(5-piperidin-1-yl-penta-2,3-dienyl)-amine

Conditions
ConditionsYield
In water at 13 - 20℃; Addition; elimination; Heating;A n/a
B n/a
C 29%
...Expand
N,N-diethyl-2-propynylamine
4079-68-9

N,N-diethyl-2-propynylamine

(E)-1-iodo-1-(4-butoxyphenyl)-3,3,3-trifluoropropene
1111072-24-2

(E)-1-iodo-1-(4-butoxyphenyl)-3,3,3-trifluoropropene

(E)-4-(4-butoxyphenyl)-N,N-diethyl-6,6,6-trifluorohex-4-en-2-yl-1-amine
1111072-36-6

(E)-4-(4-butoxyphenyl)-N,N-diethyl-6,6,6-trifluorohex-4-en-2-yl-1-amine

Conditions
ConditionsYield
With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium(0) at 50℃; for 8h; Sonogashira reaction;98%
N,N-diethyl-2-propynylamine
4079-68-9

N,N-diethyl-2-propynylamine

3-iodoandrosta-3,5-dien-17β-ol
1027346-42-4

3-iodoandrosta-3,5-dien-17β-ol

3-[3-(diethylamino)prop-1-yn-1-yl]androsta-3,5-dien-17β-ol

3-[3-(diethylamino)prop-1-yn-1-yl]androsta-3,5-dien-17β-ol

Conditions
ConditionsYield
With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; potassium carbonate; triphenylphosphine In dimethyl sulfoxide at 100℃; Sonogashira Cross-Coupling; Inert atmosphere;97%
N,N-diethyl-2-propynylamine
4079-68-9

N,N-diethyl-2-propynylamine

1-(4-methoxybenzyl)-1H-indole-2,3-dione
31541-32-9

1-(4-methoxybenzyl)-1H-indole-2,3-dione

(R)-3-(3-(diethylamino)prop-1-yn-1-yl)-3-hydroxy-1-(4-methoxybenzyl)indolin-2-one

(R)-3-(3-(diethylamino)prop-1-yn-1-yl)-3-hydroxy-1-(4-methoxybenzyl)indolin-2-one

Conditions
ConditionsYield
With silver tetrafluoroborate; C46H34F6N3O2P; triethylamine In toluene at 30℃; Molecular sieve; Inert atmosphere; enantioselective reaction;97%
N,N-diethyl-2-propynylamine
4079-68-9

N,N-diethyl-2-propynylamine

17α-(azidomethyl)-17β-hydroxyandrost-4-en-3-one

17α-(azidomethyl)-17β-hydroxyandrost-4-en-3-one

17β-hydroxy-17α-({4-[(diethylamino)methyl]-1H-1,2,3-triazol-1-yl}methyl)androst-4-en-3-one
1610593-31-1

17β-hydroxy-17α-({4-[(diethylamino)methyl]-1H-1,2,3-triazol-1-yl}methyl)androst-4-en-3-one

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In tetrahydrofuran; water at 50℃; for 16h;96%
N,N-diethyl-2-propynylamine
4079-68-9

N,N-diethyl-2-propynylamine

Ethyl 2-butynoate
4341-76-8

Ethyl 2-butynoate

(E)-6-Diethylamino-3-methyl-hex-2-en-4-ynoic acid ethyl ester

(E)-6-Diethylamino-3-methyl-hex-2-en-4-ynoic acid ethyl ester

Conditions
ConditionsYield
palladium diacetate; 5-tert-butyl-2-(2-diphenylphosphanyl-phenyl)oxazoline at 20℃; Addition; cross-coupling;95%
N,N-diethyl-2-propynylamine
4079-68-9

N,N-diethyl-2-propynylamine

1-bromo-4-tert-butylbenzene
3972-65-4

1-bromo-4-tert-butylbenzene

3-(4-(tert-butyl)phenyl)-N,N-diethylprop-2-yn-1-amine

3-(4-(tert-butyl)phenyl)-N,N-diethylprop-2-yn-1-amine

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane; bis(η3-allyl-μ-chloropalladium(II)) In N,N-dimethyl-formamide at 110℃; for 20h;95%
N,N-diethyl-2-propynylamine
4079-68-9

N,N-diethyl-2-propynylamine

2,7-diiodofluoren-9-one
16218-30-7

2,7-diiodofluoren-9-one

2,7-bis-(3-diethylamino-propyn-1-yl)-fluoren-9-one

2,7-bis-(3-diethylamino-propyn-1-yl)-fluoren-9-one

Conditions
ConditionsYield
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride In DMF (N,N-dimethyl-formamide) at 65℃; for 60h;95%
N,N-diethyl-2-propynylamine
4079-68-9

N,N-diethyl-2-propynylamine

2,7-dibromofluorene-9-one
14348-75-5

2,7-dibromofluorene-9-one

2,7-bis-(3-diethylamino-propyn-1-yl)-fluoren-9-one

2,7-bis-(3-diethylamino-propyn-1-yl)-fluoren-9-one

Conditions
ConditionsYield
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride In DMF (N,N-dimethyl-formamide) at 65℃; for 60h;95%
With copper(l) iodide; dichlorobis(tri-O-tolylphosphine)palladium; triethylamine In N,N-dimethyl-formamide at 65℃; Sonogashira coupling;
N,N-diethyl-2-propynylamine
4079-68-9

N,N-diethyl-2-propynylamine

(E)-1-bromo-4-(3,3,3-trifluoro-1-iodoprop-1-enyl)benzene
1111072-22-0

(E)-1-bromo-4-(3,3,3-trifluoro-1-iodoprop-1-enyl)benzene

(E)-4-(4-bromophenyl)-N,N-diethyl-6,6,6-trifluorohex-4-en-2-yl-1-amine
1111072-39-9

(E)-4-(4-bromophenyl)-N,N-diethyl-6,6,6-trifluorohex-4-en-2-yl-1-amine

Conditions
ConditionsYield
With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium(0) at 50℃; for 8h; Sonogashira reaction;95%
3β-acetoxy-16β-azido-17α-hydroxypregn-5-en-20-one

3β-acetoxy-16β-azido-17α-hydroxypregn-5-en-20-one

N,N-diethyl-2-propynylamine
4079-68-9

N,N-diethyl-2-propynylamine

3β-acetoxy-16β-{4-[(diethylamino)methyl]-1H-1,2,3-triazol-1-yl}-17α-hydroxypregn-5-en-20-one
1610593-41-3

3β-acetoxy-16β-{4-[(diethylamino)methyl]-1H-1,2,3-triazol-1-yl}-17α-hydroxypregn-5-en-20-one

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine In tetrahydrofuran; water at 50℃; for 20h;95%
N,N-diethyl-2-propynylamine
4079-68-9

N,N-diethyl-2-propynylamine

diphenylsilane
775-12-2

diphenylsilane

(E)-3-(diphenylsilyl)-N,N-diethylprop-2-en-1-amine

(E)-3-(diphenylsilyl)-N,N-diethylprop-2-en-1-amine

Conditions
ConditionsYield
With bis(acetylacetonate)nickel(II) In tetrahydrofuran at 30℃; Inert atmosphere;95%
With sodium triethylborohydride; cobalt acetylacetonate In tetrahydrofuran at 50℃; for 12h; Inert atmosphere; Schlenk technique; regioselective reaction;53%
N,N-diethyl-2-propynylamine

N,N-diethyl-2-propynylamine

2-Bromo-6-methoxynaphthalene
5111-65-9

2-Bromo-6-methoxynaphthalene

N,N-diethyl-3-(6-methoxynaphthalen-2-yl)prop-2-yn-1-amine

N,N-diethyl-3-(6-methoxynaphthalen-2-yl)prop-2-yn-1-amine

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane; bis(η3-allyl-μ-chloropalladium(II)) In N,N-dimethyl-formamide at 110℃; for 20h;94%
N,N-diethyl-2-propynylamine
4079-68-9

N,N-diethyl-2-propynylamine

4-bromo-benzaldehyde
1122-91-4

4-bromo-benzaldehyde

4-(3-(diethylamino)prop-1-ynyl)benzaldehyde

4-(3-(diethylamino)prop-1-ynyl)benzaldehyde

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane; bis(η3-allyl-μ-chloropalladium(II)) In N,N-dimethyl-formamide at 110℃; for 20h;94%
With potassium carbonate; palladium diacetate; N,N-diisopropyl-1,1-diphenylphosphanamine In tetrahydrofuran at 65℃; for 8h; Sonogashira reaction;89%
o-fluorobromobenzene
1072-85-1

o-fluorobromobenzene

N,N-diethyl-2-propynylamine
4079-68-9

N,N-diethyl-2-propynylamine

3-(diethylamino)-1-(2-fluorophenyl)propyne

3-(diethylamino)-1-(2-fluorophenyl)propyne

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane; bis(η3-allyl-μ-chloropalladium(II)) In N,N-dimethyl-formamide at 110℃; for 20h;93%
N,N-diethyl-2-propynylamine
4079-68-9

N,N-diethyl-2-propynylamine

o-trifluoromethylphenyl bromide
392-83-6

o-trifluoromethylphenyl bromide

3-(diethylamino)-1-(2-trifluoromethylphenyl)propyne

3-(diethylamino)-1-(2-trifluoromethylphenyl)propyne

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane; bis(η3-allyl-μ-chloropalladium(II)) In N,N-dimethyl-formamide at 110℃; for 20h;93%
N,N-diethyl-2-propynylamine
4079-68-9

N,N-diethyl-2-propynylamine

4-bromobenzenecarbonitrile
623-00-7

4-bromobenzenecarbonitrile

4-(3-(diethylamino)prop-1-yn-1-yl)benzonitrile

4-(3-(diethylamino)prop-1-yn-1-yl)benzonitrile

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane; bis(η3-allyl-μ-chloropalladium(II)) In N,N-dimethyl-formamide at 110℃; for 20h;93%
N,N-diethyl-2-propynylamine
4079-68-9

N,N-diethyl-2-propynylamine

p-trifluoromethylphenyl bromide
402-43-7

p-trifluoromethylphenyl bromide

N,N-diethyl-3-(4-(trifluoromethyl)phenyl)prop-2-yn-1-amine

N,N-diethyl-3-(4-(trifluoromethyl)phenyl)prop-2-yn-1-amine

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane; bis(η3-allyl-μ-chloropalladium(II)) In N,N-dimethyl-formamide at 110℃; for 20h;93%
N,N-diethyl-2-propynylamine
4079-68-9

N,N-diethyl-2-propynylamine

3-cyclopropyl-3,7-dihydro-1-(5-oxohexyl)-7-n-propyl-1H-purine-2,6-dione

3-cyclopropyl-3,7-dihydro-1-(5-oxohexyl)-7-n-propyl-1H-purine-2,6-dione

A

3-Cyclopropyl-1-(8-diethylamino-5-hydroxy-5-methyl-6-octynyl)-7-propylxanthine

3-Cyclopropyl-1-(8-diethylamino-5-hydroxy-5-methyl-6-octynyl)-7-propylxanthine

B

3-Cyclopropyl-1-(8-diethylamino-5-hydroxy-5-methyl-6-octynyl)-7-propylxanthine hydrochloride
200554-76-3

3-Cyclopropyl-1-(8-diethylamino-5-hydroxy-5-methyl-6-octynyl)-7-propylxanthine hydrochloride

Conditions
ConditionsYield
A 93%
B n/a
...Expand
N,N-diethyl-2-propynylamine
4079-68-9

N,N-diethyl-2-propynylamine

P-tert-butyl-N-(2,4,6-tri(tert-butyl)phenyl)-λ3-iminophosphine
105350-87-6, 111426-74-5

P-tert-butyl-N-(2,4,6-tri(tert-butyl)phenyl)-λ3-iminophosphine

tert-butyl(3-diethylamino-1-propynyl)(2,4,6-tri-tert-butylphenylamino)phosphine

tert-butyl(3-diethylamino-1-propynyl)(2,4,6-tri-tert-butylphenylamino)phosphine

Conditions
ConditionsYield
In benzene at 100℃; for 10h;92%
3-Bromopyridine
626-55-1

3-Bromopyridine

N,N-diethyl-2-propynylamine
4079-68-9

N,N-diethyl-2-propynylamine

N,N-diethyl-3-(pyridin-3-yl)prop-2-yn-1-amine
24202-89-9

N,N-diethyl-3-(pyridin-3-yl)prop-2-yn-1-amine

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane; bis(η3-allyl-μ-chloropalladium(II)) In N,N-dimethyl-formamide at 110℃; for 20h;92%
With potassium carbonate; palladium diacetate; N,N-diisopropyl-1,1-diphenylphosphanamine In tetrahydrofuran at 65℃; for 8h; Sonogashira reaction;54%
N,N-diethyl-2-propynylamine
4079-68-9

N,N-diethyl-2-propynylamine

bromobenzene
108-86-1

bromobenzene

diethyl-(3-phenyl-prop-2-ynyl)-amine
22396-72-1

diethyl-(3-phenyl-prop-2-ynyl)-amine

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane; bis(η3-allyl-μ-chloropalladium(II)) In N,N-dimethyl-formamide at 110℃; for 20h;92%
With potassium carbonate; palladium diacetate; N,N-diisopropyl-1,1-diphenylphosphanamine In tetrahydrofuran at 65℃; for 8h; Sonogashira reaction;88%
N,N-diethyl-2-propynylamine
4079-68-9

N,N-diethyl-2-propynylamine

3-bromo-1-trifluoromethylbenzene
401-78-5

3-bromo-1-trifluoromethylbenzene

3-(diethylamino)-1-(3-trifluoromethylphenyl)propyne

3-(diethylamino)-1-(3-trifluoromethylphenyl)propyne

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane; bis(η3-allyl-μ-chloropalladium(II)) In N,N-dimethyl-formamide at 110℃; for 20h;92%
N,N-diethyl-2-propynylamine
4079-68-9

N,N-diethyl-2-propynylamine

(4-bromophenyl)(phenyl)methanone
90-90-4

(4-bromophenyl)(phenyl)methanone

1-(4-benzoylphenyl)-3-(diethylamino)propyne

1-(4-benzoylphenyl)-3-(diethylamino)propyne

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane; bis(η3-allyl-μ-chloropalladium(II)) In N,N-dimethyl-formamide at 110℃; for 20h;92%

1-Diethylamino-2-propyne Consensus Reports

Reported in EPA TSCA Inventory.

1-Diethylamino-2-propyne Specification

The N,N-Diethyl-2-propynylamine is an organic compound with the formula C7H13N. The IUPAC name of this chemical is N,N-diethylprop-2-yn-1-amine. With the CAS registry number 4079-68-9, it is also named as 2-Propyn-1-amine, N,N-diethyl-. In addition, this chemical is colorless to yellowish transparent liquid which is stable under normal temeprature and pressure. N,N-Diethyl-2-propynylamine is used as nickel plating leveling agent and brightener. When heated to decomposition it emits toxic fumes of NOx. Besides, it should be sealed in the container and stored in the ventilate and dry place.

The other characteristics of N,N-Diethyl-2-propynylamine can be summarized as: (1)ACD/LogP: 1.54; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.23; (4)ACD/LogD (pH 7.4): 0.37; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 11.22; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Index of Refraction: 1.446; (13)Molar Refractivity: 36.02 cm3; (14)Molar Volume: 135.1 cm3; (15)Polarizability: 14.28×10-24 cm3; (16)Surface Tension: 29.6 dyne/cm; (17)Enthalpy of Vaporization: 37.28 kJ/mol; (18)Vapour Pressure: 7.76 mmHg at 25°C; (19)Rotatable Bond Count: 3; (20)Exact Mass: 111.104799; (21)MonoIsotopic Mass: 111.104799; (22)Topological Polar Surface Area: 3.2; (23)Heavy Atom Count: 8; (24)Complexity: 83.8.

When you are using this chemical, please be cautious about it as the following:
It is highly flammable and can cause burns. It is also harmful by inhalation and in contact with skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure.
1. SMILES:C#CCN(CC)CC
2. InChI:InChI=1/C7H13N/c1-4-7-8(5-2)6-3/h1H,5-7H2,2-3H3 
3. InChIKey:JZJXKEWVUBVOEH-UHFFFAOYAT

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rabbit LD50 skin 570uL/kg (0.57mL/kg)   Toxicology and Applied Pharmacology. Vol. 28, Pg. 313, 1974.
rat LCLo inhalation 1000ppm/4H (1000ppm)   Toxicology and Applied Pharmacology. Vol. 28, Pg. 313, 1974.
rat LD50 oral 1540uL/kg (1.54mL/kg)   Toxicology and Applied Pharmacology. Vol. 28, Pg. 313, 1974.

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