88192-20-5

Basic information

• Product Name: 1-Butamine 4-azide
• Synonyms: 1-Butamine 4-azide;1-Butanamine, 4-azido-;4-Azidobutan-1-amine;4-Azidobutylamine;4-Azido-1-butanamine;1-Azido-4-aminobutane;4-Azidobutan-1-amine - A1951
• CAS NO: 88192-20-5
• Molecular Formula: C₄H₁₀N₄
• Molecular Weight: 114.149
• Mol File: 88192-20-5.mol
• Article Data: 24

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: 1-Butamine 4-azide(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Butamine 4-azide(88192-20-5)
• EPA Substance Registry System: 1-Butamine 4-azide(88192-20-5)

Safety Data

• Hazardous Substances Data: 88192-20-5(Hazardous Substances Data)

Usage

Uses

4-Azidobutylamine is weakly or non-mutagenic to Salmonella typhimurium.

InChI:InChI=1/C4H10N4/c5-3-1-2-4-7-8-6/h1-5H2

Synthetic route

1,4-diazidobutane (24345-72-0) → 4-azidobutan-1-amine (88192-20-5)

Conditions	Yield
With hydrogenchloride; triphenylphosphine In diethyl ether; water; ethyl acetate at 20℃; for 24h;	88%
With hydrogenchloride; water; triphenylphosphine In diethyl ether; ethyl acetate at 0 - 20℃; for 25h;	88%
With hydrogenchloride; triphenylphosphine In diethyl ether; water; ethyl acetate at 0 - 20℃; for 25h; Inert atmosphere;	88%

1-azido-4-isocyanatobutane (177489-76-8) → 4-azidobutan-1-amine (88192-20-5)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran for 4h; Heating;	83%

N-(4-azidobutyl)phthalimide (66917-06-4) → 4-azidobutan-1-amine (88192-20-5)

Conditions	Yield
With hydrazine hydrate In ethanol for 24h;	62%
With hydrazine hydrate In tetrahydrofuran at 60℃; for 4h;
With hydrazine In methanol Inert atmosphere;

1,4-diaminobutane (110-60-1) → 4-azidobutan-1-amine (88192-20-5)

Conditions	Yield
With triflic azide; potassium carbonate; copper(II) sulfate In methanol; water	61%

1-chloro-4-aminobutane hydrochloride → 4-azidobutan-1-amine (88192-20-5)

Conditions	Yield
With sodium azide In water at 80℃; for 15h;	50%

1,4-diaminobutane (110-60-1) → 1,4-diazidobutane (24345-72-0) + 4-azidobutan-1-amine (88192-20-5)

Conditions	Yield
With triflic azide; potassium carbonate; copper(II) sulfate In water for 18h; Inert atmosphere;	A 30% B 40%

N-t-butoxycarbonyl-4-azidobutylamine (129392-85-4) → 4-azidobutan-1-amine (88192-20-5)

Conditions	Yield
With hydrogenchloride In ethyl acetate at 20℃; for 72h;
With trifluoroacetic acid In dichloromethane at 20℃; for 16h;

1,4-diazidobutane (24345-72-0) + triphenylphosphine (603-35-0) → 4-azidobutan-1-amine (88192-20-5) + Triphenylphosphine oxide (791-28-6)

Conditions	Yield
With hydrogenchloride; water In diethyl ether; hexane at 0℃; modified Staudinger reaction;

1,4-dibromo-butane (110-52-1) → 4-azidobutan-1-amine (88192-20-5)

Conditions	Yield
With sodium azide In water; N,N-dimethyl-formamide at 80 - 85℃; for 8h;	343.7 g
Stage #1: 1,4-dibromo-butane With sodium azide In water; N,N-dimethyl-formamide at 80 - 90℃; for 12h; Stage #2: With hydrogenchloride; triphenylphosphine In water at 25 - 35℃; for 12h;

1-bromo-4-aminobutane (33977-38-7) → 4-azidobutan-1-amine (88192-20-5)

Conditions	Yield
With sodium azide In water at 80℃;	620 mg

di-tert-butyl dicarbonate (24424-99-5) + 4-azidobutan-1-amine (88192-20-5) → N-t-butoxycarbonyl-4-azidobutylamine (129392-85-4)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water	100%

benzyl chloroformate (501-53-1) + 4-azidobutan-1-amine (88192-20-5) → 4-azido-N-benzyloxycarbonyl-1-butylamine (123348-73-2)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 12h;	100%

2-Nitrobenzenesulfonyl chloride (1694-92-4) + 4-azidobutan-1-amine (88192-20-5) → N-(4-azido-butyl)-2-nitro-benzenesulfonamide

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water	100%

p-toluenesulfonyl chloride (98-59-9) + 4-azidobutan-1-amine (88192-20-5) → N-(4-azido-butyl)-4-methyl-benzenesulfonamide

Conditions	Yield
With sodium hydroxide In tetrahydrofuran; water	100%

2-hydroxy-2-methylpropanenitrile (75-86-5) + 4-azidobutan-1-amine (88192-20-5) → 2-(4-azidobutylamino)-2-methylpropionitrile (1220428-56-7)

Conditions	Yield
With sodium sulfate at 21℃; for 12h; Inert atmosphere;	99%

3-acetylenephenylamine (54060-30-9) + 4-azidobutan-1-amine (88192-20-5) → 1-(4-aminobutyl)-4-(3-aminophenyl)-1H-1,2,3-triazole

Conditions	Yield
With copper(II) sulfate; sodium L-ascorbate	95%

indomethacin pentafluorophenyl ester (65360-26-1) + 4-azidobutan-1-amine (88192-20-5) → N-(4-azidobut-1-yl)indomethacin amide

Conditions	Yield
In dichloromethane at 20℃; for 2h; Inert atmosphere;	94%

oxalic acid (144-62-7) + 4-azidobutan-1-amine (88192-20-5) → 4-azidobutylamine hemioxalate

Conditions	Yield
In ethanol for 0.5h;	94%

1,2-bis(bromomethyl)-4,5-dimethoxybenzene (26726-81-8) + 4-azidobutan-1-amine (88192-20-5) → 2-(4-azidobutyl)-5,6-dimethoxyisoindoline (1285549-10-1)

Conditions	Yield
With potassium carbonate; sodium iodide In N,N-dimethyl-formamide at 60℃; for 3h;	93%

vancomycin (1404-90-6) + 4-azidobutan-1-amine (88192-20-5) → C70H83Cl2N13O23

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide; N,N-dimethyl-formamide at 0 - 23℃;	93%

cholic acid (81-25-4) + 4-azidobutan-1-amine (88192-20-5) → 4-azidobutylamine cholate

Conditions	Yield
In tert-butyl methyl ether at 20 - 25℃; for 16h;	92%

N-(prop-2-ynyl)-2-(4-(trifluoromethyl)phenyl)diazenecarboxamide (1224434-04-1) + 4-azidobutan-1-amine (88192-20-5) → N-((1-(4-aminobutyl)-1H-1,2,3-triazol-4-yl)methyl)-2-(4-(trifluoromethyl)phenyl)diazenecarboxamide (1224434-34-7)

Conditions	Yield
With copper(ll) sulfate pentahydrate In methanol; water at 20℃; for 0.0833333h; Inert atmosphere; regioselective reaction;	91%

2',3'-O-isopropylideneinosine (2140-11-6) + 4-azidobutan-1-amine (88192-20-5) → N6-(4"-azidobutyl)-2',3'-(O-isopropylidene)adenosine (1616876-08-4)

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile Inert atmosphere;	91%

2',3'-O-isopropylidene inosine (2140-11-6) + 4-azidobutan-1-amine (88192-20-5) → N6-(4"-azidobutyl)-2',3'-(O-isopropylidene)adenosine (1616876-08-4)

Conditions	Yield
Stage #1: 2',3'-O-isopropylidene inosine With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; Inert atmosphere; Stage #2: 4-azidobutan-1-amine In acetonitrile at 20℃; Inert atmosphere;	91%

(±)-10-camphorsulphonic acid + 4-azidobutan-1-amine (88192-20-5) → 4-azidobutylamine camphorsulphonate

Conditions	Yield
In tert-butyl methyl ether at 20 - 25℃; for 16h;	91%

4-azidobutan-1-amine (88192-20-5) → putrescine dihydrochloride (333-93-7)

Conditions	Yield
With hydrogenchloride; hydrogen; palladium on activated charcoal In methanol under 3102.9 Torr; for 18h; Ambient temperature;	90%

4-azidobutan-1-amine (88192-20-5) + 4-(1-pyrene)butyric acid N-hydroxysuccinimide ester (114932-60-4) → 4-(pyren1-yl)butanoic acid N-4-azidobutylamide

Conditions	Yield
In tetrahydrofuran at 20℃; for 3h;	88%

ethacrynic acid (58-54-8) + 4-azidobutan-1-amine (88192-20-5) → 1-{4-[(4-azidobutylaminooxy)methyl]-2,3-dichlorophenyl}-2-methylenebutan-1-one (1284258-80-5)

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 1h; Inert atmosphere;	86%

fluoresceinyl 5-isothiocyanate (1173-43-9) + 4-azidobutan-1-amine (88192-20-5) → 1-(4-azidobutyl)-3-(6'-hydroxy-3,3'-dioxo-3',9a'-dihydro-3H-spiro[isobenzofuran-1,9'-xanthen]-6-yl)thiourea

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 12h;	86%

Cholesteryl chloroformate (7144-08-3) + 4-azidobutan-1-amine (88192-20-5) → C32H54N4O2

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 18h;	82%

3-(p-phenyl)benzoylpropionic acid (36330-85-5) + 4-azidobutan-1-amine (88192-20-5) → N-(4-azidobutyl)-4-(biphenyl-4-yl)-4-oxobutanamide (1284258-78-1)

Conditions	Yield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 1h; Inert atmosphere;	77%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 60℃; for 1h;	77%

4-azidobutan-1-amine (88192-20-5) + 5'(S)-[O4-(2,4,6-triisopropylbenzenesulfonyl)uracil-1-yl]-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester (389128-29-4) → 5'(S)-{N4-[1-(4-azidobutyl)]cytosin-1-yl}-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester (389128-30-7)

Conditions	Yield
In dichloromethane at 0℃; for 0.75h;	76%

O,O'-dibenzoyl-D-tartaric acid (17026-42-5) + 4-azidobutan-1-amine (88192-20-5) → 4-azidobutylamine dibenzoyl-L-tartrate

Conditions	Yield
In tert-butyl methyl ether at 20 - 25℃; for 16h;	75%

C34H52FN3O10 + 4-azidobutan-1-amine (88192-20-5) → C35H58FN5O10

Conditions	Yield
In water; acetonitrile at 55 - 65℃;	75%

4-azidobutan-1-amine (88192-20-5) + (R)-1,2-dithiolane-3-pentanoic acid (1200-22-2) → C12H22N4OS2

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In tetrahydrofuran at 0 - 20℃;	75%

(1'S,2'R,3'S,4'R,5'S)-4'-[6-(3-chlorobenzylamino)-2-(1,7-octadiynyl)-9H-purin-9-yl]-2',3'-dihydroxybicyclo[3.1.0]hexane-1'-carboxylic acid N-methylamide (1213770-15-0) + 4-azidobutan-1-amine (88192-20-5) → (1S,2R,3S,4R,5S)-4-(6-(3-chlorobenzylamino)-2-(6-(1-(4-aminobutyl)-1H-1,2,3-triazol-4-yl)hex-1-ynyl)-9H-purin-9-yl)-2,3-dihydroxybicyclo[3.1.0]hexane-1-carboxylic acid N-methylamide (1217299-63-2)

Conditions	Yield
With copper(II) sulphate hydrate; sodium L-ascorbate; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine In water; tert-butyl alcohol at 20℃; regioselective reaction;	73%

4-azidobutan-1-amine (88192-20-5) → 4-azido-1-butanol (54953-78-5)

Conditions	Yield
With sodium azide; trifluoromethylsulfonic anhydride In dichloromethane; water	70%

thiophene-2-carbaldehyde (98-03-3) + 4-azidobutan-1-amine (88192-20-5) → 4-azido-N-(thiophen-2-ylmethyl)butan-1-amine

Conditions	Yield
Stage #1: thiophene-2-carbaldehyde; 4-azidobutan-1-amine With triethylamine In methanol for 12h; Inert atmosphere; Reflux; Stage #2: With sodium tetrahydroborate In methanol at 0℃; for 1h; Inert atmosphere;	70%

Upstream product

• 33977-38-7 4-bromo-1-aminobutane 
• 24345-72-0 1,4-diazidobutane 
• 603-35-0 triphenylphosphine 
• 110-60-1 1,4-diaminobutane 
• 129392-85-4 N-t-butoxycarbonyl-4-azidobutylamine 
• 177489-76-8 1-azido-4-isocyanatobutane 
• 110-52-1 1,4-dibromo-butane 
• 66917-06-4 N-(4-azidobutyl)phthalimide 

Downstream Products

• 333-93-7 putrescine dihydrochloride 
• 389128-22-7 N⁶-[1-(4-azidobutyl)]-5'-O-dibenzyloxyphosphoryl-2',3'-didehydro-2',3'-dideoxyadenosine 
• 389128-30-7 5'(S)-{N⁴-[1-(4-azidobutyl)]cytosin-1-yl}-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester 
• 1284258-80-5 1-{4-[(4-azidobutylaminooxy)methyl]-2,3-dichlorophenyl}-2-methylenebutan-1-one 
• 1267640-80-1 4-azidobutan-1-amine hydrochloride 
• 1300732-55-1 4-azido-N-benzylbutyramide 

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