N-(benzyloxycarbonyl)dioctylamine
n-dioctylamine
Conditions | Yield |
---|---|
With N1,N1,N12,N12-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a:2,1'-c][1,4]diazepine-2,12-diamine In N,N-dimethyl-formamide for 72h; Inert atmosphere; Glovebox; UV-irradiation; | 99% |
With lithium triethylborohydride In tetrahydrofuran at 0 - 20℃; for 1h; | 72% |
With naphthalen-1-yl-lithium In tetrahydrofuran at 0℃; for 5h; | 71 % Chromat. |
n-dioctylamine
Conditions | Yield |
---|---|
With naphthalene; lithium In tetrahydrofuran; methanol at 20℃; for 3h; | 97% |
Conditions | Yield |
---|---|
With [{CyPN(H)P}Co(CH2SiMe3)]-BArF4 In toluene at 120℃; for 24h; Schlenk technique; Sealed tube; | 96% |
With hydrogen In 1,3,5-trimethyl-benzene at 140℃; under 760.051 Torr; for 24h; Reagent/catalyst; | 93% |
With Co2Rh2/C In toluene at 180℃; under 760.051 Torr; for 6h; Autoclave; Inert atmosphere; | 88% |
n-dioctylamine
Conditions | Yield |
---|---|
With C24H32N8Ni(2+)*2I(1-); sodium amalgam In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere; | 95% |
With N1,N1,N12,N12-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a:2,1'-c][1,4]diazepine-2,12-diamine In N,N-dimethyl-formamide at 20℃; for 72h; UV-irradiation; | 59% |
With C84H70N6P4 In toluene at 110℃; for 24h; Temperature; Inert atmosphere; | 56% |
n-dioctylamine
Conditions | Yield |
---|---|
Stage #1: N,N-dioctyltritylamine With naphthalene; lithium In tetrahydrofuran at 0℃; for 3.5h; Stage #2: With water In tetrahydrofuran at 0 - 20℃; | 90% |
Tri-n-octylamine
anthranilic acid amide
A
Octanal
B
n-dioctylamine
C
2-heptyl-3,4-dihydroquinazoline-4(3H)-one
Conditions | Yield |
---|---|
With diphenyl-phosphinic acid; oxygen In 1,4-dioxane at 25℃; for 12h; | A n/a B n/a C 82% |
Conditions | Yield |
---|---|
With 5-methyl-1,3,4-thiadiazol-2-amine; potassium carbonate In ethanol; water at 25℃; for 1h; | 81% |
Multi-step reaction with 2 steps 1: 1.) sodium hydride / 1.) DMF, 20 deg C, 1 h, 2.) 80 deg C, 18 h View Scheme | |
Multi-step reaction with 3 steps 1: 1.) sodium hydride / 1.) DMF, 20 deg C, 1 h, 2.) 80 deg C, 18 h 2: 1.) NaH / 1.) DMF, 1 h, 2.) 70 deg C, 6 h 3: 77 percent / NaBH4 / ethanol / 15 h / 60 °C View Scheme | |
Multi-step reaction with 2 steps 1: sodium hydride, trifluoroacetamide / dimethylformamide / 18 h / 80 °C View Scheme | |
Multi-step reaction with 3 steps 1: sodium hydride, trifluoroacetamide / dimethylformamide / 18 h / 80 °C 2: 1.) NaH / 1.) DMF, 1 h, 2.) 70 deg C, 6 h 3: 77 percent / NaBH4 / ethanol / 15 h / 60 °C View Scheme |
morpholine
n-Octylamine
A
N-1-octyl morpholine
B
n-dioctylamine
Conditions | Yield |
---|---|
With platinum-nickel nanoclusters on activated carbon; hydrogen at 180℃; under 760.051 Torr; Reagent/catalyst; Flow reactor; chemoselective reaction; | A 81% B 18% |
N-Octylideneoctylamine N-oxide
n-dioctylamine
Conditions | Yield |
---|---|
With 4,4'-di-tert-butylbiphenyl; lithium; nickel dichloride In tetrahydrofuran at 20℃; for 6h; | 80% |
N,N-Dioctyl-trifluoracetamid
n-dioctylamine
Conditions | Yield |
---|---|
With sodium tetrahydroborate In ethanol at 60℃; for 15h; | 77% |
Conditions | Yield |
---|---|
With lithium triethylborohydride In tetrahydrofuran at 0 - 20℃; for 1h; | 76% |
Tri-n-octylamine
1,2-diamino-benzene
A
2-heptyl-1H-benzoimidazole
B
n-dioctylamine
Conditions | Yield |
---|---|
With but-2-enenitrile; 10% Pd/C In water; toluene at 170℃; under 15514.9 Torr; for 1.5h; Microwave irradiation; Inert atmosphere; | A n/a B 76% |
Octanoic acid
A
n-Octylamine
B
octane
C
n-dioctylamine
D
caprylic acid octylamide
E
n-octanamide
Conditions | Yield |
---|---|
Stage #1: Octanoic acid With cyclopentyl methyl ether; ammonia at 200℃; under 4500.45 Torr; Sealed tube; Green chemistry; Stage #2: With cyclopentyl methyl ether; ammonia; hydrogen at 200℃; under 42004.2 Torr; for 6.5h; Reagent/catalyst; Cooling with ice; Green chemistry; | A 76% B 2% C 8% D 4% E 5% |
methyl octanate
A
n-Octylamine
B
octane
C
n-dioctylamine
D
caprylic acid octylamide
E
n-octanamide
Conditions | Yield |
---|---|
Stage #1: methyl octanate With cyclopentyl methyl ether; ammonia at 200℃; under 4500.45 Torr; Sealed tube; Green chemistry; Stage #2: With cyclopentyl methyl ether; ammonia; hydrogen at 200℃; under 42004.2 Torr; for 6.5h; Cooling with ice; Green chemistry; | A 76% B 11% C 8% D 7% E 5% |
n-dioctylamine
Conditions | Yield |
---|---|
Stage #1: N,N-dioctylmethanesulfonamide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.25h; Inert atmosphere; Stage #2: In tetrahydrofuran; hexane at 20℃; for 1h; Stage #3: With water In tetrahydrofuran; hexane | 72% |
With C84H70N6P4 In toluene at 110℃; for 48h; Inert atmosphere; | 6% |
With naphthalene; water; lithium 1.) THF, 20 deg C, 24 h; Yield given. Multistep reaction; |
n-dioctylamine
Conditions | Yield |
---|---|
With lithium triethylborohydride In tetrahydrofuran at 0 - 20℃; for 1h; | 66% |
Conditions | Yield |
---|---|
With 2-6-bis((1H-pyrazol-1-yl)methyl)pyridine; borane-ammonia complex; nickel(II) chloride hexahydrate In methanol at 25℃; for 0.5h; Reagent/catalyst; Inert atmosphere; chemoselective reaction; | 63% |
With hydrogen In neat (no solvent) at 110℃; under 5250.53 Torr; for 1h; Autoclave; | 30% |
With hydrogen at 90℃; under 18751.9 Torr; for 22h; Catalytic behavior; Autoclave; Sealed tube; | 22% |
With ethanol; nickel at 80℃; under 55163.1 Torr; Hydrogenation; |
Conditions | Yield |
---|---|
With ammonium carbonate In 5,5-dimethyl-1,3-cyclohexadiene for 24h; Inert atmosphere; Sealed tube; Reflux; | 61% |
pyrrolidine
n-Octylamine
A
Tri-n-octylamine
B
HRS-1-97
C
n-dioctylamine
Conditions | Yield |
---|---|
With hydrogen at 180℃; under 760.051 Torr; Flow reactor; chemoselective reaction; | A 16% B 61% C 22% |
Conditions | Yield |
---|---|
With ruthenium trichloride; triphenylphosphine In tetrahydrofuran at 185℃; for 8h; | A 58% B 21 % Chromat. |
With ruthenium trichloride; triphenylphosphine In tetrahydrofuran at 185℃; for 8h; Title compound not separated from byproducts; | A 47 % Chromat. B 51 % Chromat. |
In neat (no solvent) at 180℃; Reagent/catalyst; |
Conditions | Yield |
---|---|
With dicarbonyl(chloro)(η5-pentaphenylcyclopentadienyl)ruthenium(II); ammonia In tert-Amyl alcohol at 170℃; for 23.5h; Inert atmosphere; Schlenk technique; Autoclave; | A 13.5% B 43% |
With 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II); ammonia; water In tert-Amyl alcohol; tert-butyl methyl ether at 170℃; for 40h; pressure tube; Inert atmosphere; | A 71 %Chromat. B 25 %Chromat. |
n-Octylamine
N-butylamine
A
tributyl-amine
B
N-n-butyl-N-n-octylamine
C
n-dioctylamine
Conditions | Yield |
---|---|
With platinum-nickel nanoclusters on activated carbon; hydrogen at 190℃; under 760.051 Torr; Flow reactor; chemoselective reaction; | A 14.5% B 28% C 40.3% |
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 80℃; for 12h; | 30.8% |
With potassium carbonate In dimethyl sulfoxide at 80℃; for 12h; |
Conditions | Yield |
---|---|
With ethanol; ammonia at 140℃; | |
Multi-step reaction with 2 steps 1: 1.) sodium hydride / 1.) DMF, 20 deg C, 1 h, 2.) 80 deg C, 18 h View Scheme | |
Multi-step reaction with 3 steps 1: 1.) sodium hydride / 1.) DMF, 20 deg C, 1 h, 2.) 80 deg C, 18 h 2: 1.) NaH / 1.) DMF, 1 h, 2.) 70 deg C, 6 h 3: 77 percent / NaBH4 / ethanol / 15 h / 60 °C View Scheme | |
Multi-step reaction with 2 steps 1: sodium hydride, trifluoroacetamide / dimethylformamide / 18 h / 80 °C View Scheme | |
Multi-step reaction with 3 steps 1: sodium hydride, trifluoroacetamide / dimethylformamide / 18 h / 80 °C 2: 1.) NaH / 1.) DMF, 1 h, 2.) 70 deg C, 6 h 3: 77 percent / NaBH4 / ethanol / 15 h / 60 °C View Scheme |
Conditions | Yield |
---|---|
With ethanol; ammonia at 100℃; | |
With ammonia |
Conditions | Yield |
---|---|
With ammonia at 25℃; | |
With ammonia; sodium amide at -50℃; | |
With ammonia at 25℃; |
Conditions | Yield |
---|---|
With 1,4-dioxane; copper chromite at 275 - 290℃; under 147102 Torr; Hydrogenation; |
n-octyl methanesulfonate
2,2,2-trifluoro-N-octylacetamide
A
n-Octylamine
B
n-dioctylamine
Conditions | Yield |
---|---|
Yield given. Multistep reaction. Yields of byproduct given; |
Conditions | Yield |
---|---|
With borane pyridine In acetic acid; Petroleum ether for 4h; Yield given. Yields of byproduct given; |
1,2,3-Benzotriazole
formaldehyd
n-dioctylamine
1-(benzotriazol-1'-yl)methyl-N,N-dioctylamine
Conditions | Yield |
---|---|
1.) methanol, water, 7 h, 2.) Et2O, reflux, overnight; | 100% |
Conditions | Yield |
---|---|
100% |
Conditions | Yield |
---|---|
With 1,2-bis(diphenylphosphino)-1'-(diisopropylphosphino)-3',4-di-tert-butyl ferrocene; bis(η3-allyl-μ-chloropalladium(II)) In tetrahydrofuran at 20℃; for 20h; Tsuji-Trost amination; | 100% |
With (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane; bis(η3-allyl-μ-chloropalladium(II)) In tetrahydrofuran at 55℃; for 48h; | 99% |
With sodium chloride; bis(η3-allyl-μ-chloropalladium(II)); Tedicyp In water at 55℃; for 20h; | 80% |
Conditions | Yield |
---|---|
bis(η3-allyl-μ-chloropalladium(II)); Tedicyp In water at 55℃; for 20h; | 100% |
bis(η3-allyl-μ-chloropalladium(II)); (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane In water at 55℃; for 20h; | 100% |
Conditions | Yield |
---|---|
Stage #1: n-dioctylamine With n-butyllithium In tetrahydrofuran; hexane at -40℃; for 0.25h; Stage #2: N,N-diethyl-4-fluorobenzenesulfonamide In tetrahydrofuran; hexane at 20℃; for 24h; | 100% |
Conditions | Yield |
---|---|
In acetonitrile at 20℃; | 100% |
n-dioctylamine
6-chloropyrazine-2-carboxylic acid chloride
6-chloro-N,N-dioctylpyrazine-2-carboxamide
Conditions | Yield |
---|---|
With triethylamine In dichloromethane | 100% |
Conditions | Yield |
---|---|
In methanol at 20℃; for 0.0833333h; Solvent; Time; | 100% |
n-dioctylamine
Conditions | Yield |
---|---|
With dmap In dichloromethane at 20℃; for 0.5h; | 100% |
1,3,5-trichloro-2,4,6-triazine
n-dioctylamine
2-chloro-4,6-bis-(di-n-octylamino)-s-triazine
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 25h; Cooling with ice; | 99% |
With triethylamine In dichloromethane at 20℃; for 24h; | 97% |
With triethylamine In dichloromethane at 25℃; for 24h; | 97% |
Conditions | Yield |
---|---|
With triethylamine In diethyl ether at 0 - 20℃; for 2h; | 99% |
1,4-dioxane-2,6-dione
n-dioctylamine
2-(2-(di-n-octylamino)-2-oxoethoxy)acetic acid
Conditions | Yield |
---|---|
In acetone at 20℃; Product distribution / selectivity; | 98.1% |
In dichloromethane at 20℃; | 94.3% |
In dichloromethane at 20℃; Cooling with ice; | 94.2% |
Conditions | Yield |
---|---|
In toluene for 5h; Reflux; | 98% |
In benzene at 79.9℃; for 1h; | 87.6% |
n-dioctylamine
N-n-octylidene-n-octylamine
Conditions | Yield |
---|---|
With copper(ll) bromide; lithium tert-butoxide In tetrahydrofuran for 0.0833333h; | 98% |
Conditions | Yield |
---|---|
With sodium carbonate for 15h; Reflux; | 98% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 0.666667h; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With potassium carbonate In dichloromethane for 2h; | 98% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; | 97% |
In dichloromethane; triethylamine at 20℃; for 2h; | 96% |
With pyridine In dichloromethane at 20℃; Inert atmosphere; | 84% |
Conditions | Yield |
---|---|
bis(η3-allyl-μ-chloropalladium(II)); Tedicyp In water at 50℃; for 20h; | 97% |
With potassium carbonate; bis(η3-allyl-μ-chloropalladium(II)); (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane In water at 25℃; for 20h; | 97% |
With (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane; bis(η3-allyl-μ-chloropalladium(II)) In tetrahydrofuran at 25℃; for 24h; | 95% |
With 1,2-bis(diphenylphosphino)-1'-(diisopropylphosphino)-3',4-di-tert-butyl ferrocene; bis(η3-allyl-μ-chloropalladium(II)) In tetrahydrofuran at 50℃; for 20h; Tsuji-Trost amination; | 59% |
n-dioctylamine
3-tert-butyl-5-(chloromethyl)-2-hydroxybenzaldehyde
Conditions | Yield |
---|---|
In benzene for 6h; Heating; | 97% |
n-dioctylamine
N-octyl-α-heptylnitrone
Conditions | Yield |
---|---|
With Ti(OCH(CH3)2)N(CH2C6H3C(CH3)3O)3; dihydrogen peroxide In methanol; water at 60℃; for 3.5h; Inert atmosphere; chemoselective reaction; | 97% |
With Cumene hydroperoxide; C27H31NO4Ti; isopropyl alcohol In chloroform at 60℃; for 3h; Inert atmosphere; Molecular sieve; | 95% |
With dihydrogen peroxide In methanol at 60℃; for 8.5h; Reflux; | 76% |
With peroxomonosulfate; ethylenediaminetetraacetic acid; sodium hydrogencarbonate In tetrahydrofuran; water; acetonitrile at 5℃; for 2.33333h; Inert atmosphere; | 72% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0℃; for 4.5h; | 97% |
With dmap; triethylamine In dichloromethane at 20℃; for 2.5h; | 5.09 g |
Conditions | Yield |
---|---|
In toluene for 12h; Inert atmosphere; Reflux; | 97% |
n-dioctylamine
chloroacetyl chloride
N,N-di-n-octylcarbamoyl methyl chloride
Conditions | Yield |
---|---|
96% | |
With potassium carbonate In dichloromethane for 2h; | 95% |
With triethylamine In dichloromethane at 20℃; for 3h; Cooling with ice; Inert atmosphere; | 87.5% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 90 - 110℃; for 12h; | 96% |
Stage #1: n-dioctylamine; 11-bromo-undecanoic acid methyl ester In N,N-dimethyl-formamide for 0.25h; Stage #2: In N,N-dimethyl-formamide at 110℃; for 12h; | |
With potassium carbonate In N,N-dimethyl-formamide at 20 - 110℃; for 12h; |
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; polymer-bound triphenylphosphine In tetrahydrofuran at 20℃; for 12h; | 95% |
n-dioctylamine
(2,4,9,11,16,18,23,25-octakis(dioctylaminosulfonyl)phthalocyaninato)cobalt(II)
Conditions | Yield |
---|---|
In acetone extn. of (2,4,9,11,16,18,23,25-oktakis(sulfonyl chloride)phthalocyaninato)Co(II) into acetone; addn. of dioctylamine (1.5 equiv.); keeping at 30°C for 1 h; filtration, evapn.; chromy. on silica gel; using CHCl3-MeOH (10:1) as eluent; elem. anal.; | 95% |
Reported in EPA TSCA Inventory.
The CAS registry number of Dioctylamine is 1120-48-5. Its EINECS registry number is 214-311-6. The IUPAC name is N-octyloctan-1-amine. In addition, the molecular formula is C16H35N and the molecular weight is 241.46. It is also called di(n-octyl)amine. What's more, it is a kind of colourless to light yellow liquid and belongs to the classes of Amines; C11 to C38; Nitrogen Compounds. And it should be stored in a cool and dry place.
Physical properties about this chemical are: (1)ACD/LogP: 7.01; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 3.91; (4)ACD/LogD (pH 7.4): 4.01; (5)ACD/BCF (pH 5.5): 99.5; (6)ACD/BCF (pH 7.4): 124.14; (7)ACD/KOC (pH 5.5): 123.31; (8)ACD/KOC (pH 7.4): 153.84; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 14; (12)Polar Surface Area: 3.24 Å2; (13)Index of Refraction: 1.442; (14)Molar Refractivity: 79.76 cm3; (15)Molar Volume: 301.4 cm3; (16)Polarizability: 31.62 ×10-24cm3; (17)Surface Tension: 28.5 dyne/cm; (18)Density: 0.8 g/cm3; (19)Flash Point: 126.8 °C; (20)Enthalpy of Vaporization: 53.74 kJ/mol; (21)Boiling Point: 297.5 °C at 760 mmHg; (22)Vapour Pressure: 0.00134 mmHg at 25°C.
Preparation of Dioctylamine: it can be prepared by octanol and ammonia in the presence of solvent alumina or carbon. In addition, it also can be prepared by N,N-Dioctyl-trifluoracetamid. This reaction will need reagent NaBH4 and solvent ethanol. The reaction time is 15 hours at reaction temperature of 60 °C. The yield is about 77%.
Uses of Dioctylamine: it can be used as intermediate for the preparation of antistatic agent, softener, surfactant and fungicide. And it is also used as metal extraction agent and amine solvent. In addition, it can be used to get octanal. This reaction will need reagents mTFMB and KOH, and solvent ethyl acetate. The yield is about 70% at reaction temperature of -78 °C.
When you are using this chemical, please be cautious about it as the following:
This chemical can cause burns. And it is harmful if swallowed and irritating to eyes, respiratory system and skin. Moreover, it is very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. During using it, wear suitable protective clothing and gloves. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. And in case of accident or if you feel unwell, seek medical advice immediately (show label where possible). What's more, this material and/or its container must be disposed of as hazardous waste. You avoid release to the environment and you can refer to special instructions safety data sheet.
You can still convert the following datas into molecular structure:
(1)SMILES: N(CCCCCCCC)CCCCCCCC
(2)InChI: InChI=1/C16H35N/c1-3-5-7-9-11-13-15-17-16-14-12-10-8-6-4-2/h17H,3-16H2,1-2H3
(3)InChIKey: LAWOZCWGWDVVSG-UHFFFAOYAU
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