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Butylamine (also known as 1-Butanamine, 1-Aminobutane, or other synonyms) is a primary aliphatic amine used as a reactant in nucleophilic aromatic substitution (SNAr) reactions, where its reactivity is influenced by steric effects and ring activation of substrates. It participates in cine-substitution reactions with metallabenzenes, forming both substitution products and kinetically favored five-membered rings due to its nucleophilicity. Butylamine also reacts with organo-tungsten pyrylium salts, exhibiting pseudo-first-order kinetics, and serves as a reagent in solvent-free microwave-assisted syntheses of cyano-2-aminopyridine derivatives. Additionally, it undergoes oxidation with dimethyldioxirane to yield products like oximes or nitroalkanes, depending on reaction conditions. Its versatility in organic transformations highlights its utility in synthetic chemistry.

109-73-9

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109-73-9 Usage

Chemical Description

Butylamine and cyclohexylamine are organic compounds used as solvents and reagents in chemical reactions.

Check Digit Verification of cas no

The CAS Registry Mumber 109-73-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 9 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 109-73:
(5*1)+(4*0)+(3*9)+(2*7)+(1*3)=49
49 % 10 = 9
So 109-73-9 is a valid CAS Registry Number.
InChI:InChI=1/C4H11N/c1-2-3-4-5/h2-5H2,1H3/p+1

109-73-9 Well-known Company Product Price

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  • TCI America

  • (B0707)  Butylamine  >99.0%(GC)(T)

  • 109-73-9

  • 25mL

  • 115.00CNY

  • Detail
  • TCI America

  • (B0707)  Butylamine  >99.0%(GC)(T)

  • 109-73-9

  • 500mL

  • 205.00CNY

  • Detail
  • Alfa Aesar

  • (L03575)  1-Butylamine, 99%   

  • 109-73-9

  • 100ml

  • 166.0CNY

  • Detail
  • Alfa Aesar

  • (L03575)  1-Butylamine, 99%   

  • 109-73-9

  • 500ml

  • 215.0CNY

  • Detail
  • Alfa Aesar

  • (L03575)  1-Butylamine, 99%   

  • 109-73-9

  • 2500ml

  • 509.0CNY

  • Detail
  • Sigma-Aldrich

  • (90893)  Butylamine  analytical reference material

  • 109-73-9

  • 90893-1ML

  • 553.41CNY

  • Detail
  • Sigma-Aldrich

  • (90893)  Butylamine  analytical reference material

  • 109-73-9

  • 90893-5ML

  • 2,196.09CNY

  • Detail

109-73-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name butan-1-amine

1.2 Other means of identification

Product number -
Other names n-Butylamine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:109-73-9 SDS

109-73-9Synthetic route

(E)-2-((butylimino)methyl)phenol
2565-54-0

(E)-2-((butylimino)methyl)phenol

cyclohexylamine
108-91-8

cyclohexylamine

A

N-(2-hydroxybenzylidene)cyclohexylamine
19028-72-9

N-(2-hydroxybenzylidene)cyclohexylamine

B

N-butylamine
109-73-9

N-butylamine

Conditions
ConditionsYield
In [D3]acetonitrile at 25℃; Equilibrium constant; Molecular sieve;A 100%
B n/a
C13H18N2O

C13H18N2O

cyclohexylamine
108-91-8

cyclohexylamine

A

C15H20N2O

C15H20N2O

B

N-butylamine
109-73-9

N-butylamine

Conditions
ConditionsYield
In [D3]acetonitrile at 25℃; Equilibrium constant; Molecular sieve;A 100%
B n/a
C12H18N2O2S

C12H18N2O2S

cyclohexylamine
108-91-8

cyclohexylamine

A

C14H20N2O2S

C14H20N2O2S

B

N-butylamine
109-73-9

N-butylamine

Conditions
ConditionsYield
In [D3]acetonitrile at 25℃; Equilibrium constant; Molecular sieve;A 100%
B n/a
propyl cyanide
109-74-0

propyl cyanide

N-butylamine
109-73-9

N-butylamine

Conditions
ConditionsYield
With sodium tetrahydroborate In water; dimethyl sulfoxide at 60℃; for 4.5h; High pressure; Green chemistry;99.9%
With sodium tetrahydroborate; nickel; sodium hydroxide In methanol; water at 30 - 60℃;93%
With [DBUH(+)][C4H9COO(-)]; water; potassium formate at 70℃; for 3h; Ionic liquid;82%
1-nitrobutane
627-05-4

1-nitrobutane

12percent nickel/Al-SBA-15 fiber

12percent nickel/Al-SBA-15 fiber

N-butylamine
109-73-9

N-butylamine

Conditions
ConditionsYield
With hydrogen In ethanol at 109.84℃; under 18751.9 Torr; for 7.5h; Autoclave; Green chemistry; chemoselective reaction;99%
butan-1-ol
71-36-3

butan-1-ol

N-butylamine
109-73-9

N-butylamine

Conditions
ConditionsYield
With ammonia; hydrogen at 200℃; under 3750.38 Torr; Reagent/catalyst; Temperature; Pressure;97.7%
With ammonia; nickel at 200℃;
With ammonia at 350 - 400℃; als Katalysatoren, eignen sich Cr2O3,NiO und SiO2 auf Al2O3;
butyraldehyde
123-72-8

butyraldehyde

N-butylamine
109-73-9

N-butylamine

Conditions
ConditionsYield
With ammonia; hydrogen In methanol at 30℃; for 15h; Autoclave;96%
With ammonium hydroxide; Ni6AlO(z); hydrogen at 80℃; under 2250.23 Torr; for 3h; Autoclave;83%
With (S)-1-phenyl-ethylamine; pyridoxal 5'-phosphate; pQR1108 In aq. phosphate buffer; dimethyl sulfoxide at 30℃; for 18h; pH=8; Enzymatic reaction;42%
1-nitrobutane
627-05-4

1-nitrobutane

N-butylamine
109-73-9

N-butylamine

Conditions
ConditionsYield
Stage #1: 1-nitrobutane In water; acetonitrile at 20℃; for 0.0833333h;
Stage #2: With sodium tetrahydroborate In water; acetonitrile at 20℃; for 0.333333h;
95%
Stage #1: 1-nitrobutane In water at 20℃; for 0.0166667h;
Stage #2: With sodium tetrahydroborate In water at 50℃; for 0.166667h;
93%
With triethylamine In water at 80℃; for 6h; Inert atmosphere; Green chemistry; chemoselective reaction;91%
N,N'-di-n-butylurea
1792-17-2

N,N'-di-n-butylurea

sodium p-toluenesulfonamide
18522-92-4

sodium p-toluenesulfonamide

A

N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide
64-77-7

N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide

B

N-butylamine
109-73-9

N-butylamine

Conditions
ConditionsYield
at 150℃; for 8h; Product distribution; other time;;A 94.5%
B n/a
at 150℃; for 5h;A 94.5%
B n/a
butan-1-ol
71-36-3

butan-1-ol

A

propyl cyanide
109-74-0

propyl cyanide

B

N-butylamine
109-73-9

N-butylamine

Conditions
ConditionsYield
With ammonia; zinc(II) oxide at 420℃;A 92.2%
B n/a
With ammonia; zinc(II) oxide at 340℃; Product distribution; 1:4 molar ratio n-butyl alcohol/NH3, other temperature (300-420 deg C), other catalyst (oxidized form of SMS-4 Zn-Cr-O);;A 86.7%
B 6%
butyraldehyde oxime
110-69-0

butyraldehyde oxime

N-butylamine
109-73-9

N-butylamine

Conditions
ConditionsYield
With sodium tetrahydroborate; nickel; sodium hydroxide In methanol; water at 20 - 30℃;90%
With nickel at 80 - 105℃; Hydrogenation;
With lithium aluminium tetrahydride; diethyl ether
With ethanol; aluminium amalgam
With sodium n-propoxide In propan-1-ol at 69.84℃; for 2h; Reagent/catalyst;98 %Chromat.
1-bromo-butane
109-65-9

1-bromo-butane

N-butylamine
109-73-9

N-butylamine

Conditions
ConditionsYield
With 5-methyl-1,3,4-thiadiazol-2-amine; triethylamine In ethanol; water at 25℃; for 1h;89%
With copper(ll) sulfate pentahydrate; ammonium hydroxide In PEG1000-DIL; methyl cyclohexane at 75℃; for 10h;85%
With 2-methoxy-ethanol; sodium tetraamidoalanate In benzene at 50℃; for 6h; Product distribution; further educt/reagent ratios, temperatures, reaction times;57%
tert-butyl butylcarbamate
59255-58-2

tert-butyl butylcarbamate

N-butylamine
109-73-9

N-butylamine

Conditions
ConditionsYield
With water at 100℃; for 13h;87%
N-Benzyl-N-butylamine
2403-22-7

N-Benzyl-N-butylamine

A

benzaldehyde
100-52-7

benzaldehyde

B

N-butylamine
109-73-9

N-butylamine

Conditions
ConditionsYield
With dipotassium peroxodisulfate; tris(2,2'-bipyridyl)ruthenium dichloride In water; acetonitrile at 20℃; for 12h; Irradiation;A 87%
B n/a
N-butyl-4-toluenesulfonamide
1907-65-9

N-butyl-4-toluenesulfonamide

N-butylamine
109-73-9

N-butylamine

Conditions
ConditionsYield
With cesium fluoride supported on Celite at 120℃; for 2.5h; chemoselective reaction;86%
5-chloro-valeric acid
1119-46-6

5-chloro-valeric acid

A

piperidine
110-89-4

piperidine

B

piperidin-2-one
675-20-7

piperidin-2-one

C

1-pentanamine
110-58-7

1-pentanamine

D

N-butylamine
109-73-9

N-butylamine

Conditions
ConditionsYield
Stage #1: 5-chloro-valeric 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; Cooling with ice; Green chemistry;
A 85%
B 9%
C 2%
D 2%
n-Butyl chloride
109-69-3

n-Butyl chloride

N-butylamine
109-73-9

N-butylamine

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; ammonium hydroxide In PEG1000-DIL; methyl cyclohexane at 75℃; for 10h;84%
With dibutyl ether; ammonia; water at 175℃;
With ammonia; water at 170℃;
With ammonia; water; dibutylamine at 175℃;
With tributyl-amine; ammonia; water at 175℃;
butyric acid
107-92-6

butyric acid

A

butanamide
541-35-5

butanamide

B

N-butyl-butyramide
10264-16-1

N-butyl-butyramide

C

dibutylamine
111-92-2

dibutylamine

D

N-butylamine
109-73-9

N-butylamine

Conditions
ConditionsYield
Stage #1: butyric 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; Cooling with ice; Green chemistry;
A 6%
B n/a
C 5%
D 80%
CuCl2(C4H9NH2)2
52518-95-3

CuCl2(C4H9NH2)2

bis(carbomethoxy)palladium bipyridine

bis(carbomethoxy)palladium bipyridine

dichloro(2,2'-bipyridine)palladium(II)
14871-92-2

dichloro(2,2'-bipyridine)palladium(II)

B

CuCl(bipyridine)
39583-95-4

CuCl(bipyridine)

C

methyl N-butylcarbamate
2594-21-0

methyl N-butylcarbamate

D

n-butylamine hydrochloride
3858-78-4

n-butylamine hydrochloride

E

N-butylamine
109-73-9

N-butylamine

Conditions
ConditionsYield
With nitrogen In tetrahydrofuran byproducts: CuCl; Pd-compd. in THF and CuCl2(BuNH2)2 in a Cu/Pd molar ratio of 4:1 are loaded sep. in the 2 branches of an inverted-Y glass reactor. Reactor is closed under N2, contents are mixed and stirred for 1 h.; IR, GC-MS and GLC anal. of liq. phase shows presence of BuNH2COOCH3. Filtn. of solid residue (anaerobic conditions), sepn. of PdCl2(bipy) from CuCl by addn. of MeOH soln. contg. bipy, IR, elem. anal. Removal of MeOH(vac.) gives CuCl(bipy). Elem. anal.;A n/a
B n/a
C 79%
D n/a
E n/a
C28H38N4O5
81539-78-8

C28H38N4O5

A

2,2'-diphthalimido-diethyl ether
43113-25-3

2,2'-diphthalimido-diethyl ether

B

N-butylamine
109-73-9

N-butylamine

Conditions
ConditionsYield
at 250℃;A 62%
B 75%
{(n-C4H9NH2)2BH2}{SC2H5}
24473-71-0

{(n-C4H9NH2)2BH2}{SC2H5}

A

tert-butylamine borane complex
1087352-20-2

tert-butylamine borane complex

B

N,N',N''-tri-n-butylborazine
2080-01-5

N,N',N''-tri-n-butylborazine

C

HB(NH-n-C4H9)2
2387-02-2

HB(NH-n-C4H9)2

D

N-butylamine
109-73-9

N-butylamine

E

ethanethiol
75-08-1

ethanethiol

Conditions
ConditionsYield
In not given byproducts: H2; thermal decomposition between 40 and 50°C;;A 33%
B 15%
C 15%
D n/a
E 75%
In not given
1-butyl-6-tolyl-2,5-dithiobiurea
125908-37-4

1-butyl-6-tolyl-2,5-dithiobiurea

A

2-(4'-methylphenylamino)-Δ2-1,3,4-thiadiazoline-5-thione
14731-25-0

2-(4'-methylphenylamino)-Δ2-1,3,4-thiadiazoline-5-thione

B

N-butylamine
109-73-9

N-butylamine

Conditions
ConditionsYield
With sodium hydroxide In water Heating;A 74%
B n/a
1-butyl-6-phenyl-2,5-dithiobiurea
2834-31-3

1-butyl-6-phenyl-2,5-dithiobiurea

A

N-butylamine
109-73-9

N-butylamine

B

5-phenylamino-3H-[1,3,4]thiadiazole-2-thione
10253-83-5

5-phenylamino-3H-[1,3,4]thiadiazole-2-thione

Conditions
ConditionsYield
With sodium hydroxide In water Heating;A n/a
B 73%
1-methyl-pyrrolidin-2-one
872-50-4

1-methyl-pyrrolidin-2-one

ammonium hydroxide
1336-21-6

ammonium hydroxide

propyl cyanide
109-74-0

propyl cyanide

N-butylamine
109-73-9

N-butylamine

Conditions
ConditionsYield
In methanol73%
butyl-N,N-diformylamine
55756-14-4

butyl-N,N-diformylamine

N-butylamine
109-73-9

N-butylamine

Conditions
ConditionsYield
With hydrogenchloride In water for 2h; Heating;72%
1-butyl-6-(4'-ethoxyphenyl)-2,5-dithiobiurea
125908-43-2

1-butyl-6-(4'-ethoxyphenyl)-2,5-dithiobiurea

A

2-(4'-ethoxyphenylamino)-Δ2-1,3,4-thiadiazoline-5-thione
68161-60-4

2-(4'-ethoxyphenylamino)-Δ2-1,3,4-thiadiazoline-5-thione

B

N-butylamine
109-73-9

N-butylamine

Conditions
ConditionsYield
With sodium hydroxide In water Heating;A 72%
B n/a
Butane-1,4-diol
110-63-4

Butane-1,4-diol

A

pyrrolidine
123-75-1

pyrrolidine

B

1-butylpyrrolidine
767-10-2

1-butylpyrrolidine

C

4-(pyrrolidin-1-yl)butan-1-ol
93264-47-2

4-(pyrrolidin-1-yl)butan-1-ol

D

1,4-di-(1-pyrrolidinyl)butane
41726-75-4

1,4-di-(1-pyrrolidinyl)butane

E

N-butylamine
109-73-9

N-butylamine

Conditions
ConditionsYield
With ammonia; hydrogen; iron RFC at 260℃; Product distribution; Mechanism; other temp. (280, 300, 310 deg C);A 71%
B 12%
C n/a
D n/a
E 9%
phthalic anhydride
85-44-9

phthalic anhydride

N-butylamine
109-73-9

N-butylamine

N-butylphthalimide
1515-72-6

N-butylphthalimide

Conditions
ConditionsYield
for 0.0333333h; microwave irradiation;100%
In decaethylene glycol at 120℃; for 6h;98%
In water at 90 - 180℃; for 0.8h; Inert atmosphere;96.2%
2-chloro-5-nitropyridine
4548-45-2

2-chloro-5-nitropyridine

N-butylamine
109-73-9

N-butylamine

N-(5-nitropyridin-2-yl)butylamine
26820-54-2

N-(5-nitropyridin-2-yl)butylamine

Conditions
ConditionsYield
In dimethyl sulfoxide at 25℃;100%
With ethanol
In methanol for 2h; Heating;
In dimethyl sulfoxide at 25℃; Kinetics;
In acetonitrile at 25℃; Kinetics; Further Variations:; amine concentration;
4-bromo-1,8-naphthalenedicarboxylic anhydride
81-86-7

4-bromo-1,8-naphthalenedicarboxylic anhydride

N-butylamine
109-73-9

N-butylamine

4-bromo-N-butylnaphthalimide
92874-17-4

4-bromo-N-butylnaphthalimide

Conditions
ConditionsYield
In ethanol at 78℃; for 4h;100%
In ethanol for 26h; Reflux;100%
for 3h; Reflux;94.5%
4-Nitrophenyl isocyanate
100-28-7

4-Nitrophenyl isocyanate

N-butylamine
109-73-9

N-butylamine

N-butyl-N'-(4'-nitrophenyl)urea
21260-50-4

N-butyl-N'-(4'-nitrophenyl)urea

Conditions
ConditionsYield
In 1,4-dioxane at 20℃; for 1h;100%
In 1,4-dioxane at 20 - 40℃; for 3h;100%
In 1,4-dioxane96%
2,4-Dinitrofluorobenzene
70-34-8

2,4-Dinitrofluorobenzene

N-butylamine
109-73-9

N-butylamine

2,4-dinitro-N-butylaniline
13059-86-4

2,4-dinitro-N-butylaniline

Conditions
ConditionsYield
With 2-hydroxypyridin In benzene at 25℃; Rate constant; other catalysts, other solvents, var. conc. of catalysts;100%
With 1-(1-butyl)-3-methylimidazolium tetrafluoroborate In acetonitrile at 25℃; Kinetics; Further Variations:; Reagents; Solvents;100%
at 25℃; for 2h;56%
benzaldehyde
100-52-7

benzaldehyde

N-butylamine
109-73-9

N-butylamine

N-benzylidenebutan-1-amine
1077-18-5

N-benzylidenebutan-1-amine

Conditions
ConditionsYield
With aluminum oxide for 5h; Milling;100%
at 20℃; for 2h;100%
With HC(CMeN(2,6-Et2C6H3)2)Al(μ-S)2AlHC(CMeN(2,6-Et2C6H3))2 In chloroform-d1 at 20℃; for 2h; Inert atmosphere;99%
phenyl isocyanate
103-71-9

phenyl isocyanate

N-butylamine
109-73-9

N-butylamine

N-butyl-N'-phenylurea
3083-88-3

N-butyl-N'-phenylurea

Conditions
ConditionsYield
Stage #1: phenyl isocyanate; N-butylamine In dichloromethane at 60℃;
Stage #2: With isatoic anhydride-N-(CH2)3-C8F17 In dichloromethane at 60℃; for 2.5h;
100%
at 20℃;98%
In hexane at 25℃; Cooling with ice;98%
1-amino-4-bromo-9,10-dioxoanthracene-2-sulphonic acid
116-81-4

1-amino-4-bromo-9,10-dioxoanthracene-2-sulphonic acid

N-butylamine
109-73-9

N-butylamine

1-amino-4-(butylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonic acid
101139-67-7

1-amino-4-(butylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate; copper(II) sulfate; iron(II) sulfate In water at 70 - 90℃; for 4h;100%
With copper(I) sulfate; water; sodium carbonate; copper(II) sulfate at 80 - 90℃;
N-butylamine
109-73-9

N-butylamine

2-Bromoacetyl bromide
598-21-0

2-Bromoacetyl bromide

2-bromo-N-butylacetamide
67056-04-6

2-bromo-N-butylacetamide

Conditions
ConditionsYield
With potassium carbonate In dichloromethane; water at 0 - 20℃; for 6.5h;100%
In dichloromethane at 0 - 20℃; for 1.5h; Inert atmosphere;96%
With potassium carbonate In dichloromethane; water at 0 - 20℃; for 12.5h;95%
N-butylamine
109-73-9

N-butylamine

ethyl acrylate
140-88-5

ethyl acrylate

ethyl N-(n-butyl)-b-aminopropionate
10494-81-2

ethyl N-(n-butyl)-b-aminopropionate

Conditions
ConditionsYield
In ethanol at 20℃; for 2h; Michael addition;100%
With poly(ethylene glycol) 2000; ruthenium trichloride at 50℃; for 8h; aza-Michael addition;96%
Stage #1: N-butylamine With cerous nitrate for 4h; Reflux;
Stage #2: ethyl acrylate for 8h; Time;
93.8%
N-butylamine
109-73-9

N-butylamine

2-nitrobenzyl chloride
610-14-0

2-nitrobenzyl chloride

N-butyl-2-nitrobenzamide
79903-04-1

N-butyl-2-nitrobenzamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; for 1h;100%
With sodium hydroxide
N-butylamine
109-73-9

N-butylamine

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

diethyl N-butylphosphoramidate
20465-03-6

diethyl N-butylphosphoramidate

Conditions
ConditionsYield
With potassium carbonate; potassium hydrogencarbonate; tetrabutylammomium bromide In tetrachloromethane; dichloromethane at 15 - 20℃; for 2h;100%
With copper(ll) bromide In ethyl acetate at 25℃; for 3h;92%
Stage #1: phosphonic acid diethyl ester With pyridine In acetonitrile
Stage #2: N-butylamine With iodine In acetonitrile for 0.0833333h;
85%
In tetrachloromethane; xylene
2-Chloro-3-nitropyridine
5470-18-8

2-Chloro-3-nitropyridine

N-butylamine
109-73-9

N-butylamine

N-(3-nitropyridin-2-yl)butylamine
26820-68-8

N-(3-nitropyridin-2-yl)butylamine

Conditions
ConditionsYield
In dimethyl sulfoxide at 25℃;100%
In methanol for 2h; Heating;
With potassium carbonate
In dimethyl sulfoxide at 25℃; Kinetics;
In acetonitrile at 25℃; Kinetics; Further Variations:; amine concentration;
4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

N-butylamine
109-73-9

N-butylamine

(E)-N-(4-fluorobenzylidene)butan-1-amine

(E)-N-(4-fluorobenzylidene)butan-1-amine

Conditions
ConditionsYield
In benzene at 80℃; for 2h;100%
In neat (no solvent) at 60℃; for 0.0666667h; Microwave irradiation;98%
In diethyl ether Ambient temperature;87%
acetic acid
64-19-7

acetic acid

N-butylamine
109-73-9

N-butylamine

N-butylacetamide
1119-49-9

N-butylacetamide

Conditions
ConditionsYield
zirconium(IV) oxide at 200℃; Product distribution; the liquid- and vapor-phase amidation were investigated with different heterogeneous catalysts;100%
zirconium(IV) oxide at 200℃;100%
With (1-methyl-3-(3-sulfopropyl)-1H-imidazol-3-ium)3[PW12O403-] In neat (no solvent) at 100℃; for 0.0833333h; Green chemistry;93%
N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

N-butylamine
109-73-9

N-butylamine

N2-n-butyl-N1,N1-dimethylformamidine
3717-82-6

N2-n-butyl-N1,N1-dimethylformamidine

Conditions
ConditionsYield
at 60℃;100%
ethyl acetate
141-78-6

ethyl acetate

N-butylamine
109-73-9

N-butylamine

N-butylacetamide
1119-49-9

N-butylacetamide

Conditions
ConditionsYield
zirconium(IV) oxide at 200℃;100%
With tin(IV) oxide at 200℃; further conditions: liquid phase, reflux;79%
With aluminum oxide; monoaluminum phosphate at 77℃;75%
With potassium tert-butylate at 95℃; for 0.05h; microwave irradiation;70%
butanoic acid ethyl ester
105-54-4

butanoic acid ethyl ester

N-butylamine
109-73-9

N-butylamine

N-butyl-butyramide
10264-16-1

N-butyl-butyramide

Conditions
ConditionsYield
at 40℃; for 1h; lipase SP 382 (from Candida sp.);100%
Stage #1: N-butylamine With TurboGrignard In tetrahydrofuran at 20℃; for 0.1h; Microreactor;
Stage #2: butanoic acid ethyl ester In tetrahydrofuran at 20℃; for 0.233333h; Bodroux reaction; Microreactor;
82%
1-chloro-4-methyl-2-nitro-benzene
89-60-1

1-chloro-4-methyl-2-nitro-benzene

N-butylamine
109-73-9

N-butylamine

N-butyl-4-methyl-2-nitroaniline
216591-86-5

N-butyl-4-methyl-2-nitroaniline

Conditions
ConditionsYield
at 92℃; for 96h; Inert atmosphere;100%
for 3.5h; Heating;
ethyl 5-oxo-2-phenyl-2,5-dihydroisoxazole-4-carboxaldehyde
4504-12-5

ethyl 5-oxo-2-phenyl-2,5-dihydroisoxazole-4-carboxaldehyde

N-butylamine
109-73-9

N-butylamine

N,N'-dibutyl-N''-phenylmethanetricarboxamide
146848-35-3

N,N'-dibutyl-N''-phenylmethanetricarboxamide

Conditions
ConditionsYield
In acetone at 25℃;100%
Irradiation; silica glass;80%
In acetone at 20℃; for 0.25h; Irradiation;37%
methanol
67-56-1

methanol

N-butylamine
109-73-9

N-butylamine

N,N-dimethylbutylamine
927-62-8

N,N-dimethylbutylamine

Conditions
ConditionsYield
chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II) at 100℃;100%
With Diethyl phosphonate Rate constant; Ambient temperature;
at 150℃; under 7500.75 Torr;
1,1,1,3,3,3-hexachloro-propan-2-one
116-16-5

1,1,1,3,3,3-hexachloro-propan-2-one

N-butylamine
109-73-9

N-butylamine

A

chloroform
67-66-3

chloroform

B

trichloro-acetic acid butylamide
31464-96-7

trichloro-acetic acid butylamide

Conditions
ConditionsYield
In hexaneA n/a
B 100%
4-hydroxy-4-methylhex-2-ynenitrile
32837-88-0

4-hydroxy-4-methylhex-2-ynenitrile

N-butylamine
109-73-9

N-butylamine

4-[(E)-Butylimino]-5-ethyl-5-methyl-4,5-dihydro-furan-2-ylamine
134965-70-1

4-[(E)-Butylimino]-5-ethyl-5-methyl-4,5-dihydro-furan-2-ylamine

Conditions
ConditionsYield
In dichloromethane at 40℃; for 24h;100%
5-(dimethylamino)naphth-1-ylsulfonyl chloride
605-65-2

5-(dimethylamino)naphth-1-ylsulfonyl chloride

N-butylamine
109-73-9

N-butylamine

(N,N-dimethylamino)-naphthalene-N-butyl-1-sulfonamide
55032-39-8

(N,N-dimethylamino)-naphthalene-N-butyl-1-sulfonamide

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 3.5h; Inert atmosphere;100%
90%
With triethylamine In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;88%
o-formylbenzonitrile
7468-67-9

o-formylbenzonitrile

N-butylamine
109-73-9

N-butylamine

3-(butylamino)isoindolin-1-one
93680-02-5

3-(butylamino)isoindolin-1-one

Conditions
ConditionsYield
at 20℃; for 6h;100%
With N,N,N,N-tetraethylammonium tetrafluoroborate In acetonitrile at 20℃; Electrolysis;85%

109-73-9Relevant articles and documents

Impact of solvent on Co/SiO2 activity and selectivity for the synthesis of n-butylamine from butyronitrile hydrogenation

Segobia,Trasarti,Apesteguía

, p. 62 - 66 (2015)

The impact of solvent on Co(9.8%)/SiO2 activity and selectivity for the synthesis of n-butylamine from butyronitrile hydrogenation was investigated using methanol, benzene, toluene and cyclohexane as solvents. In non-polar solvents, the yield of n-butylamine increased from 60% to 79% following the order cyclohexane toluene benzene. Nevertheless, the highest n-butylamine yield (91%) was obtained in methanol, a protic solvent. The solvent effect on the catalyst performance was interpreted by considering: i) the solvent-catalyst interaction strength and ii) the solvent polarity and its ability for H-bond formation with n-butylamine.

Kinetics of Amine Addition to Benzylidenemalonodialdehyde in 50percent Me2SO-50percent water

Bernasconi, Claude F.,Stronach, Michael W.

, p. 1993 - 2001 (1991)

The kinetics of the reaction of benzylidenemalonodialdehyde with piperidine, morpholine, n-butylamine, 2-methoxyethylamine, glycinamide, glycine ethyl ester, cyanomethylamine, and semicarbazide have been determined in 50percent aqueous Me2SO at 20 deg C.The reaction leads to a zwitterionic adduct, PhCH(RR'NH(1+))C(CHO)2(1-) (TA(+/-)), that is in fast acid-base equilibrium with the anionic adduct, PhCH(RR'N)C(CHO)2(1-) (TA(1-)).With strongly basic amines at high pH there is also attack of the amine on one of the carbonyl groups, which acts as a rapid preequilibrium.Rate constants for the formation of TA(+/-) (k1) and its reverse (k-1), as well as equilibrium constants (K1 = k1/k-1) and the pKa of TA(+/-) were determined for all the amines.Intrinsic rate constants (k0 = k1 = k-1 when K1 = 1) were calculated.The intrinsic rate constants are lower than those for amine addition to benzylidene Meldrum's acid.This is consistent with the greater role played by resonance in stabilizing TA(+/-) derived from benzylidenemalonodialdehyde.However, k0 for piperidine/morpholine addition to benzylidenemalonodialdehyde is much higher than for the reaction of benzylideneacetylacetone with the same amines, indicating that the rate-depressing effect of intramolecular hydrogen bonding in TA(+/-) derived from benzylidenemalonodialdehyde is much smaller than that in TA(+/-) derived from benzylideneacetylacetone.Even though semicarbazide is an α-effect nucleophile, no enhancement of k1 was observed, but K1, estimated on the basis of a structure-reactivity relationship, is larger than expected based on the pKa of the amine.This result is attributed to a low νnucn value.

Dynamic Covalent Switches and Communicating Networks for Tunable Multicolor Luminescent Systems and Vapor-Responsive Materials

Zou, Hanxun,Hai, Yu,Ye, Hebo,You, Lei

, p. 16344 - 16353 (2019)

Molecular switches are an intensive area of research, and in particular, the control of multistate switching is challenging. Herein we introduce a general and versatile strategy of dynamic covalent switches and communicating networks, wherein distinct states of reversible covalent systems can induce addressable fluorescence switching. The regulation of intramolecular ring/chain equilibrium, intermolecular dynamic covalent reactions (DCRs) with amines, and both permitted the activation of optical switches. The variation in electron-withdrawing competition between the fluorophore and 2-formylbenzenesulfonyl unit afforded diverse signaling patterns. The combination of switches in situ further enabled the creation of communicating networks for multistate color switching, including white emission, through the delicate control of DCRs in complex mixtures. Finally, reversible and recyclable multiresponsive luminescent materials were achieved with molecular networks on the solid support, allowing visualization of different types of vapors and quantification of primary amine vapors with high sensitivity and wide detection range. The results reported herein should be appealing for future studies of dynamic assemblies, molecular sensing, intelligent materials, and biological labeling.

Biocatalysed synthesis of chiral amines: continuous colorimetric assays for mining amine-transaminases

Gourbeyre, Léa,Heuson, Egon,Charmantray, Franck,Hélaine, Virgil,Debard, Adrien,Petit, Jean-Louis,de Berardinis, Véronique,Gefflaut, Thierry

, p. 904 - 911 (2021)

In the course of our research aimed at the design of new biocatalytic processes for the enantioselective synthesis of chiral amines, we have developed new continuous assays for the screening of amine-transaminase collections. These assays are based on the use of hypotaurine as an irreversible amine donor. This β-aminosulfinic acid is converted upon transamination into 2-oxoethylsulfinic acid, which instantaneously decomposes into acetaldehyde and sulfite ions that can be easily detected by spectrophotometry using Ellman's reagent. Two complementary assays were developed based on this titration method. Firstly, a direct assay allowed detection of various transaminases able to use hypotaurine as an amino donor. In a second coupled assay,l-alanine is used as a generic donor substrate of amine-transaminases and is regenerated using an auxiliary hypotaurine-transaminase. The powerful and complementary nature of both assays was demonstrated through the screening of a collection of 549 amine-transaminases from biodiversity, thus allowing the discovery of a variety of valuable new biocatalysts for use in synthetic processes.

Kinetic and equilibrium studies of σ-adduct formation and nucleophilic substitution in the reactions of trinitro-activated benzenes with aliphatic amines in acetonitrile

Crampton, Michael R.,Lord, Simon D.

, p. 369 - 376 (1997)

Rate and equilibrium constants are reported for reactions in acetonitrile of butylamine, pyrrolidine and piperidine with 1,3,5-trinitrobenzene, 1, and with ethyl 2,4,6-trinitrophenyl ether, 4a, and phenyl 2,4,6-trinitrophenyl ether, 4b. Rapid nucleophilic attack at unsubstituted ring-positions may yield anionic σ-adducts via zwitterionic intermediates, while slower attack at the 1-position of 4a and 4b may lead to substitution to give 2,4,6-trinitroaniline derivatives. Base catalysis in the substitution reaction reflects rate-limiting proton transfer which may be from the zwitterionic intermediates to amine in the case of 4b, or from a substituted ammonium ion to the ethoxy leaving group in the case of 4a. Comparisons with values in DMSO indicate that values of overall equilibrium constants for adduct formation are ca. 104 lower in acetonitrile, while rate constants for proton transfer are ca. 104 higher. These differences may reflect strong hydrogen-bonding between DMSO and -NH+ protons in ammonium ions and in zwitterions. In acetonitrile homoconjugation of substituted ammonium ions with free amine is an important factor.

SOLVATION OF PRIMARY AMINES: SHORT-RANGE SOLVATION OF PROTON TRANSFER COMPLEXES OF 2,4-DINITROPHENOL, AND n-BUTYLAMINE

Guo, Shuqiong,Scott, Ronald M.

, p. 307 - 313 (1990)

The short range solvation of the proton-transfer complex formed between 2,4-dinitrophenol and n-butylamine was studied in benzene solution containing small amounts of three ethers: n-propylether, tetrahydropyran, and dioxane.In all cases a pattern is observed in which solvation by the ether causes an increase in the equilibrium constant for the formation of the proton transfer complex until a plateau value is reached.This is followed on further increase of the ether concentration by a second rise followed by a second plateau.The equilibrium constants for each of thesolvation events and the number of solvent molecules reacting per amine molecule were calculated.The first step involves two solvent molecules per amine, and the second step involves a larger number.

Charged states of proteins. Reactions of doubly protonated alkyldiamines with NH3: Solvation or deprotonation. Extension of two proton cases to multiply protonated globular proteins observed in the gas phase

Peschke, Michael,Blades, Arthur,Kebarle, Paul

, p. 11519 - 11530 (2002)

The apparent gas-phase basicities (GBapp'S) of basic sites in multiply protonated molecules, such as proteins, can be approximately predicted. An approach used by Williams and co-workers was to develop an equation for a diprotonated system, NH

A new supported rhodium catalyst for selective hydrogenation of nitriles to primary amines

Witte, Peter T.

, p. 468 - 474 (2007)

Nitriles are converted to primary amines with high selectivity using a newly developed alumina-supported rhodium catalyst. The high selectivity is obtained without any additives, which are often used to prevent the formation of higher amines. The catalyst is active under mild conditions In various solvents, which makes it specifically suitable for use in pharmaceutical applications or for other substrates that can react with additives like strong acids or bases.

Electron Spin Resonance Monitoring of Ligand Ejection Reactions Following Solid-State Reduction of Cobalt Globin and Cobalt Protoporphyrin Complexes

Dickinson, L. Charles,Symons, M. C. R.

, p. 917 - 921 (1982)

Cobaltihemoglobin, isolated α and β chains, and cobaltimyoglobin in aqueous solution at neutral pH were irradiated at 77 K with 3 Mrd of 60Co γ-rays.These diamagnetic Co(III) species are converted to paramagnetic Co(II) species in high yield.The EPR spectra are identical with those of authentic six-coordinate cobalt(II) porphyrins.Upon partial annealing of the species, the EPR spectrum transforms irreversibly to that of a five-coordinate species, indicating that at 77 K these cobaltiglobins are cobaltichromes in analogy to the hemichromes of the native iron species.Differences are seen among all of the six-coordinate, reduced protein ligated species.This ejection of the sixth ligand with thermal annealing after addition of one electron to the dz2 orbital of the cobalt porphyrin also occurs in aqueous glasses of cobalt protoporphyrin IX in pyridine, n-butylamine, or quinuclidine.The five-coordinate species in aqueous media are stable with annealing to room temperature.

Selective Transformations of Triglycerides into Fatty Amines, Amides, and Nitriles by using Heterogeneous Catalysis

Jamil, Md. A. R.,Siddiki, S. M. A. Hakim,Touchy, Abeda Sultana,Rashed, Md. Nurnobi,Poly, Sharmin Sultana,Jing, Yuan,Ting, Kah Wei,Toyao, Takashi,Maeno, Zen,Shimizu, Ken-ichi

, p. 3115 - 3125 (2019)

The use of triglycerides as an important class of biomass is an effective strategy to realize a more sustainable society. Herein, three heterogeneous catalytic methods are reported for the selective one-pot transformation of triglycerides into value-added chemicals: i) the reductive amination of triglycerides into fatty amines with aqueous NH3 under H2 promoted by ZrO2-supported Pt clusters; ii) the amidation of triglycerides under gaseous NH3 catalyzed by high-silica H-beta (Hβ) zeolite at 180 °C; iii) the Hβ-promoted synthesis of nitriles from triglycerides and gaseous NH3 at 220 °C. These methods are widely applicable to the transformation of various triglycerides (C4–C18 skeletons) into the corresponding amines, amides, and nitriles.

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