16499-88-0

Basic information

• Product Name: 3-Butoxypropanamine
• Synonyms: 1-Propanamine, 3-butoxy-;3-butoxy-1-propanamin;3-Butoxy-1-propanamine;3-n-Butoxy-1-propylamine;RARECHEM AL BW 0499;3-Butoxy-1-propylamine;3-butoxypropanamine;3-BUTOXYPROPYLAMINE
• CAS NO: 16499-88-0
• Molecular Formula: C₇H₁₇NO
• Molecular Weight: 131.22
• EINECS: 240-566-8
• Product Categories: Amino Alcohols;Organic Building Blocks;Oxygen Compounds
• Mol File: 16499-88-0.mol
• Article Data: 1

Chemical Properties

• Melting Point: -65 °C
• Boiling Point: 169-170 °C756 mm Hg(lit.)
• Flash Point: 146 °F
• Appearance: clear colorless liquid
• Density: 0.853 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.52mmHg at 25°C
• Refractive Index: n20/D 1.426(lit.)
• Storage Temp.: 2-8°C
• PKA: 9.77±0.10(Predicted)
• Water Solubility: miscible
• CAS DataBase Reference: 3-Butoxypropanamine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Butoxypropanamine(16499-88-0)
• EPA Substance Registry System: 3-Butoxypropanamine(16499-88-0)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-27-36/37/39-45
• RIDADR: UN 2735 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 16499-88-0(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

Uses

3-Butoxypropylamine may be used in the synthesis of N-functionalized bis(phosphino)amine ligands with ether, thioether and pyridyl tethers.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C7H17NO/c1-2-3-6-9-7-4-5-8/h2-8H2,1H3/p+1

Synthetic route

3-butoxypropanenitrile (6959-71-3) → 3-butoxypropylamine (16499-88-0)

Conditions	Yield
With methanol; ammonia; nickel at 100℃; under 66195.7 - 88260.9 Torr; Hydrogenation;
With lithium aluminium tetrahydride; diethyl ether
With hydrogen; nickel In ethanol
With hydrogen; Ni(Raney)

acrylonitrile (107-13-1) + butan-1-ol (71-36-3) → 3-butoxypropylamine (16499-88-0)

Conditions	Yield
With sodium; toluene

3-Chloropropionitrile (542-76-7) + butan-1-ol (71-36-3) → 3-butoxypropylamine (16499-88-0)

Conditions	Yield
With sodium; toluene

2-cyanoethyl ether (1656-48-0) + butan-1-ol (71-36-3) → 3-butoxypropylamine (16499-88-0)

Conditions	Yield
With sodium

3-butoxypropanenitrile (6959-71-3) + butan-1-ol (71-36-3) → 3-butoxypropylamine (16499-88-0)

Conditions	Yield
With sodium

acrylonitrile (107-13-1) + butan-1-ol (71-36-3) + sodium → propylamine (107-10-8) + 3-butoxypropylamine (16499-88-0)

3-Methoxypropionitrile (110-67-8) + butan-1-ol (71-36-3) + sodium → 3-butoxypropylamine (16499-88-0)

2-cyanoethyl ether (1656-48-0) + butan-1-ol (71-36-3) + sodium → 3-butoxypropylamine (16499-88-0)

tetrahydrofuran (109-99-9) + 3-butoxypropanenitrile (6959-71-3) + lithium alanate → 3-butoxypropylamine (16499-88-0) + butan-1-ol (71-36-3) + hydrogen

Conditions	Yield
at 30 - 35℃; Ausbeute bei unterschiedlichem Mengenverhaeltnis der Reaktionspartner;

diethyl ether (60-29-7) + 3-butoxypropanenitrile (6959-71-3) + lithium alanate → 3-butoxypropylamine (16499-88-0) + butan-1-ol (71-36-3) + hydrogen

Conditions	Yield
at 35℃; Ausbeute bei unterschiedlichem Mengenverhaeltnis der Reaktionspartner;

3-butoxypropylamine (16499-88-0) + 1-[(tert-butoxycarbonyl)methoxy]-2,6-bis{2'-[(tert-butoxycarbonyl)methoxy]-3'-formyl-5'-methylphenyl}-4-methylbenzene (273730-47-5) → 1-[(tert-butoxycarbonyl)methoxy]-2,6-bis{2'-[(tert-butoxycarbonyl)methoxy]-3'-(n-butoxypropylaminomethyl)-5'-methylphenyl}-4-methylbenzene (243129-88-6)

Conditions	Yield
Stage #1: 3-butoxypropylamine; 1-[(tert-butoxycarbonyl)methoxy]-2,6-bis{2'-[(tert-butoxycarbonyl)methoxy]-3'-formyl-5'-methylphenyl}-4-methylbenzene In ethanol at 20℃; for 0.5h; Condensation; Stage #2: With hydrogen; palladium on activated charcoal In ethanol at 20℃; Catalytic hydrogenation; Further stages.;	100%

3-butoxypropylamine (16499-88-0) + S-acrylic acid-N-butoxypropyl dithiocarbamate → N,N'-dibutoxypropyl thiourea + 3-mercaptopropionic acid (107-96-0)

Conditions	Yield
With sodium hydroxide In water at 70℃; for 2h;	A 98.5% B 95.7%

3-butoxypropylamine (16499-88-0) + C15H21NO6 (1603109-24-5) → C22H36N2O6

Conditions	Yield
In toluene Reflux;	95%

3-butoxypropylamine (16499-88-0) + S-acrylic acid-N-isopropoxypropyl dithiocarbamate → N-isopropoxypropyl-N'-butoxypropyl thiourea + 3-mercaptopropionic acid (107-96-0)

Conditions	Yield
With sodium hydroxide In water at 70℃; for 2.5h;	A 94.9% B 93.6%

4-methoxypyridine (620-08-6) + 3-butoxypropylamine (16499-88-0) → N-(3-butoxypropyl)pyridin-4-amine

Conditions	Yield
Stage #1: 3-butoxypropylamine With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 0.166667h; Inert atmosphere; Schlenk technique; Stage #2: 4-methoxypyridine In tetrahydrofuran; hexane at 60℃; for 0.5h; Inert atmosphere; Schlenk technique;	94%

diethylchlorophosphine (686-69-1) + 3-butoxypropylamine (16499-88-0) → C15H35NP2O

Conditions	Yield
With triethylamine In dichloromethane	87%
With triethylamine In dichloromethane at 20℃; for 20h;	87%

3-butoxypropylamine (16499-88-0) + 2α,3α-epoxy-5α-androstan-17β-ol (965-66-2) → 2β-(3-butoxypropylamino)-5α-androstane-3α,17β-diol (1031816-30-4)

Conditions	Yield
With gadolinium(III) trifluoromethanesulfonate In toluene at 150 - 190℃; for 2h;	82%

Tetrahydrothiopyran-4-one (1072-72-6) + formaldehyd (50-00-0) + 3-butoxypropylamine (16499-88-0) → 7-(3-butoxypropyl)-3-thia-7-azabicyclo[3.3.1]nonan-9-one (941579-43-7)

Conditions	Yield
With hydrogenchloride; acetic acid In methanol for 8h; Mannich cyclization; Heating;	78%

3-butoxypropylamine (16499-88-0) + N-((2S,3S)-3-trans-ethoxycarbonyloxiran-2-carbonyl)-L-phenylalanine (169499-08-5) → N-[N-[(2S,3S)-3-trans-ethoxycarbonyloxirane-2-carbonyl]-L-phenylalanyl]-1-amino-3-butoxypropane (174699-37-7)

Conditions	Yield
	75%

3-butoxypropylamine (16499-88-0) + 3,6-difluoro-9-(3-(3-fluoro-9H-carbazol-9-yl)-2-(oxiran-2-ylmethoxy)propyl)-9H-carbazole → 1-((3-butoxypropyl)amino)-3-((1-(3,6-difluoro-9H-carbazol-9-yl)-3-(3-fluoro-9H-carbazol-9-yl)propan-2-yl)oxy)propan-2-ol

Conditions	Yield
In isopropyl alcohol at 60℃; Sealed tube;	73.02%

3-butoxypropylamine (16499-88-0) + acrylonitrile (107-13-1) → 3-butoxypropyl-2-cyanoethylamine

Conditions	Yield
In methanol at 25℃; for 2h;	69%

3-butoxypropylamine (16499-88-0) + 1,4-dihydroxy-9,10-anthracenedione (81-64-1) → 1-(n-butoxypropylamino)-4-hydroxy-9,10-anthracenedione

Conditions	Yield
With morpholine; sodium tetrahydroborate In 1,4-dioxane; diethylene glycol dimethyl ether for 6h; Reflux;	61%

3-butoxypropylamine (16499-88-0) + 3-fluoro-9-(oxiran-2-ylmethyl)-9H-carbazole → 1-((3-butoxypropyl)amine)-3-(3-fluoro-9H-carbazol-9-yl)-2-propanol

Conditions	Yield
In ethanol at 60℃; Sealed tube;	59.09%

formaldehyd (50-00-0) + 3-butoxypropylamine (16499-88-0) + idronoxil (81267-65-4) → 4-(3-(3-butoxypropyl)-2,3,4,8-tetrahydrochromeno[6,7-e][1,3]oxazin-7-yl)phenol

Conditions	Yield
Stage #1: formaldehyd; 3-butoxypropylamine In ethanol; water at 45℃; for 1h; Mannich Aminomethylation; Stage #2: idronoxil In ethanol; water at 20℃; for 48h; Mannich Aminomethylation;	54%

(E)-3-{(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-((E)-2-methoxycarbonyl-vinyl)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-2-yl}-acrylic acid methyl ester (827025-82-1) + 3-butoxypropylamine (16499-88-0) → (E)-N-(3-Butoxy-propyl)-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-{(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-[(E)-2-(3-butoxy-propylcarbamoyl)-vinyl]-tetrahydro-pyran-2-yloxy}-tetrahydro-pyran-2-yl)-acrylamide (827025-92-3)

Conditions	Yield
With trimethylaluminum In dichloromethane; toluene at 20℃;	39%

3-butoxypropylamine (16499-88-0) + m-Fluorobenzonitrile (403-54-3) → 3-(3-butoxy-propylamino)-benzonitrile

Conditions	Yield
In dimethyl sulfoxide at 100℃; for 60h; Substitution;	38%

3-butoxypropylamine (16499-88-0) + 3,6-difluoro-9-(oxiran-2-ylmethyl)-9H-carbazole → 1-((3-butoxypropyl)amino)-3-(3,6-difluoro-9H-carbazol-9-yl)-2-propanol

Conditions	Yield
In ethanol at 60℃; Sealed tube;	34.44%

3-butoxypropylamine (16499-88-0) + D,L-lactide (95-96-5) → N-(3-butoxypropyl) lactamide (950500-93-3)

Conditions	Yield
at 20℃; under 760.051 Torr; for 96h;	25%

3-butoxypropylamine (16499-88-0) + N-acryloylaniline (2210-24-4) → N3-(3-anilino-3-oxopropyl)-N3-(3-butoxypropyl)-N1-phenyl-β-alaninamide

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 16h; Inert atmosphere; Reflux;	25%

3-butoxypropylamine (16499-88-0) + 1,4,5,8-naphthalenetetracarboxylic dianhydride (81-30-1) → 2,7-bis-(3-butoxy-propyl)-benzo[lmn][3,8]phenanthroline-1,3,6,8-tetraone

Conditions	Yield
With quinoline; zinc diacetate at 200℃; imidation;	10%

1,4-dibromo-butane (110-52-1) + 3-butoxypropylamine (16499-88-0) → 1-(3-butoxy-propyl)-pyrrolidine

Conditions	Yield
With potassium carbonate; benzene

1,5-dibromo-pentane (111-24-0) + 3-butoxypropylamine (16499-88-0) → 1-(3-butoxy-propyl)-piperidine

Conditions	Yield
With potassium carbonate; benzene

3-butoxypropylamine (16499-88-0) + 1-(1'-cyclohexenyl)-2-buten-1-one (91897-80-2) + (Z)-1-(cyclohexen-1-yl)-2-buten-1-one (91897-81-3) → 1-(3-butoxy-propyl)-2-methyl-octahydro-quinolin-4-one (101572-81-0)

Conditions	Yield
With methanol; water

3-butoxypropylamine (16499-88-0) + Tosyl isocyanate (4083-64-1) → N-(3-butoxy-propyl)-N'-(toluene-4-sulfonyl)-urea (101261-39-6)

3-butoxypropylamine (16499-88-0) + 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride (129-64-6) → 2-(3-butoxy-propyl)-(3ac,7ac)-3a,4,7,7a-tetrahydro-4r,7c-methano-isoindole-1,3-dione (101256-17-1)

Conditions	Yield
With toluene at 160℃;

Upstream product

• 107-13-1 acrylonitrile 
• 71-36-3 butan-1-ol 
• 542-76-7 3-Chloropropionitrile 
• 1656-48-0 2-cyanoethyl ether 
• 6959-71-3 3-butoxypropanenitrile 
• 60-29-7 diethyl ether 
• 109-99-9 tetrahydrofuran 
• 110-67-8 3-Methoxypropionitrile 

Downstream Products

• 124-22-1 n-Dodecylamine 
• 107-96-0 3-mercaptopropionic acid 
• 1061735-63-4 C₁₆H₂₉NO₃ 
• 174699-37-7 N-[N-[(2S,3S)-3-trans-ethoxycarbonyloxirane-2-carbonyl]-L-phenylalanyl]-1-amino-3-butoxypropane 
• 273730-50-0 1-[(tert-butoxycarbonyl)methoxy]-2,6-bis{2'-[(tert-butoxycarbonyl)methoxy]-3'-[N-(n-butoxypropyl)-p-toluenesulfonylamidemethyl]-5'-methylphenyl}-4-methylbenzene 
• 243129-95-5 1-[(tert-butoxycarbonyl)methoxy]-2,6-bis{2'-[(tert-butoxycarbonyl)methoxy]-3'-[N-(n-butoxypropyl)benzoylamidomethyl]-5'-methylphenyl}-4-methylbenzene 

Relevant articles and documents

Aldose epimerization by Ni(II): effect of ether-containig alkylenediamine ligands

Several N-substituted ethylenediamine (en) Ni(II) derivatives containing ether linkages were prepared in order to study the effect of ligand structure on C-2 epimerization of aldohexoses.The reagent consisted of a Ni(II)-alkyenediamine derivative in methanol.The presence of ether linkages in the ligand increased the solubilty of the complexes, and resulted in an increase in the rate of epimerization.Epimerization occured rapidly under mild conditions, and the same equilibrium point was reached regardless of whether the reaction was started from glucose or mannose.Among the ligands studied, N,N'-dialkylethylenediamine was the most effective in C-2 epimerization.