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4-Fluoro-3-nitrophenyl azide
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Name

4-Fluoro-3-nitrophenyl azide

 EINECS 248-878-6
CAS No. 28166-06-5 Density N/A
PSA 95.57000 LogP 2.65166
Solubility N/A Melting Point 54-56 ºC
Formula C6H3FN4O2 Boiling Point N/A
Molecular Weight 182.114 Flash Point 113 °C
Transport Information N/A Appearance N/A
Safety 36/37/39-45 Risk Codes 5-11-23/24/25
Molecular Structure Molecular Structure of 28166-06-5 (4-Fluoro-3-nitrophenyl azide) Hazard Symbols ToxicT,FlammableF,IrritantXi
Synonyms

1-Fluoro-2-nitro-4-azidobenzene;2-Nitro-4-azidofluorobenzene;4-Azido-1-fluoro-2-nitrobenzene;4-Azido-2-nitrofluorobenzene;4-Azido-2-nitrophenyl fluoride;NSC 266503;

Article Data 9

4-Fluoro-3-nitrophenyl azide Synthetic route

364-76-1

4-Fluoro-3-nitroaniline

28166-06-5

4-fluoro-3-nitrophenylazide

Conditions
ConditionsYield
Stage #1: 4-Fluoro-3-nitroaniline With hydrogenchloride; sodium nitrite In water at 70℃;
Stage #2: With sodium azide In water at 70℃;		98%
With sodium azide; tert.-butylnitrite In tert-butyl alcohol at 20℃; for 1h;92%
Stage #1: 4-Fluoro-3-nitroaniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.25h;
Stage #2: With sodium azide In water at 20℃; for 0.5h;		75%
Stage #1: 4-Fluoro-3-nitroaniline With hydrogenchloride; sodium nitrite In water at 5℃; for 0.5h; Cooling with ice;
Stage #2: With sodium azide In water at 0℃;		73%
(i) aq. H2SO4, NaNO2, (ii) aq. NaN3; Multistep reaction;

sodium azide

364-76-1

4-Fluoro-3-nitroaniline

28166-06-5

4-fluoro-3-nitrophenylazide

Conditions
ConditionsYield
Stage #1: 4-Fluoro-3-nitroaniline With hydrogenchloride; sodium nitrite In water at 0℃; for 0.166667h;
Stage #2: sodium azide In water at 0℃; for 4.25h;
28166-06-5

4-fluoro-3-nitrophenylazide

1309943-98-3

(1R,2R,3S,4R,5S)-4-(2-chloro-6-(prop-2-ynylamino)-9H-purin-9-yl)bicyclo[3.1.0]hexane-2,3-diol

1309943-99-4

(1R,2R,3S,4R,5S)-4-(2-chloro-6-((1-(4-fluoro-3-nitrophenyl)-1H-1,2,3-triazol-4-yl)methylamino)-9H-purin-9-yl)bicyclo[3.1.0]hexane-2,3-diol

Conditions
ConditionsYield
With copper(II) sulfate; sodium L-ascorbate; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine In water; tert-butyl alcohol at 20℃;96%
With sodium ascorbate; copper(II) sulfate; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine In dichloromethane; water; tert-butyl alcohol at 20℃; Inert atmosphere;96%
28166-06-5

4-fluoro-3-nitrophenylazide

1309943-74-5

(1S,2R,3S,4R,5S)-4-[2-chloro-6-(3-(nona-1,8-diynyl)phenylmethylamino)-9H-purin-9-yl]-2,3-dihydroxybicyclo[3.1.0]hexane-1-carboxylic acid N-methylamide

1309943-77-8

(1S,2R,3S,4R,5S)-4-[2-chloro-6-(3-(7-(1-(4-fluoro-3-nitrophenyl)-1H-1,2,3-triazol-4-yl)hept-1-ynyl)benzylamino)-9H-purin-9-yl]-2,3-dihydroxybicyclo[3.1.0]hexane-1-carboxylic acid N-methylamide

Conditions
ConditionsYield
With sodium ascorbate; copper(II) sulfate; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine In dichloromethane; water; tert-butyl alcohol at 20℃; Inert atmosphere;96%
98-91-9

thiobenzoic acid

28166-06-5

4-fluoro-3-nitrophenylazide

228425-41-0

N-(4-fluoro-3-nitrophenyl)-benzylamide

Conditions
ConditionsYield
With 2,6-dimethylpyridine In methanol at 25℃; for 15h;95%
28166-06-5

4-fluoro-3-nitrophenylazide

1309943-87-0

(1R,2R,3S,4R,5S)-4-(2-chloro-6-(3-(octa-1,7-diynyl)benzylamino)-9H-purin-9-yl)bicyclo[3.1.0]hexane-2,3-diol

1309943-90-5

(1R,2R,3S,4R,5S)-4-(2-chloro-6-(3-(6-(1-(4-fluoro-3-nitrophenyl)-1H-1,2,3-triazol-4-yl)hex-1-ynyl)benzylamino)-9H-purin-9-yl)bicyclo[3.1.0]hexane-2,3-diol

Conditions
ConditionsYield
With sodium ascorbate; copper(II) sulfate; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine In dichloromethane; water; tert-butyl alcohol at 20℃; Inert atmosphere;95%
28166-06-5

4-fluoro-3-nitrophenylazide

507-09-5

thioacetic acid

351-32-6

N-(4-fluoro-3-nitrophenyl)acetamide

Conditions
ConditionsYield
With 2,6-dimethylpyridine In methanol at 25℃; for 15h;94%
28166-06-5

4-fluoro-3-nitrophenylazide

1213770-15-0

(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

1217299-58-5

MRS5223

Conditions
ConditionsYield
With copper(II) sulphate hydrate; sodium L-ascorbate In tetrahydrofuran; water at 20℃; regioselective reaction;94%
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In tetrahydrofuran; water at 20℃;94%
28166-06-5

4-fluoro-3-nitrophenylazide

1309944-05-5

(1S,2R,3S,4R,5S)-4-[2-chloro-6-(3-(octa-1,7-diynyl)phenylmethylamino)-9H-purin-9-yl]-2,3-dihydroxybicyclo[3.1.0]hexane-1-carboxylic acid N-methylamide

1309943-76-7

(1S,2R,3S,4R,5S)-4-[2-chloro-6-(3-(6-(1-(4-fluoro-3-nitrophenyl)-1H-1,2,3-triazol-4-yl)hex-1-ynyl)benzylamino)-9H-purin-9-yl]-2,3-dihydroxybicyclo[3.1.0]hexane-1-carboxylic acid N-methylamide

Conditions
ConditionsYield
With sodium ascorbate; copper(II) sulfate; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine In dichloromethane; water; tert-butyl alcohol at 20℃; Inert atmosphere;94%
28166-06-5

4-fluoro-3-nitrophenylazide

1309943-94-9

(1S,2R,3S,4R,5S)-4-(2-chloro-6-(prop-2-ynylamino)-9H-purin-9-yl)-2,3-dihydroxy-N-methylbicyclo[3.1.0]hexane-1-carboxamide

1309943-95-0

(1S,2R,3S,4R,5S)-4-(2-chloro-6-((1-(4-fluoro-3-nitrophenyl)-1H-1,2,3-triazol-4-yl)methylamino)-9H-purin-9-yl)-2,3-dihydroxy-N-methylbicyclo[3.1.0]hexane-1-carboxamide

Conditions
ConditionsYield
With copper(II) sulfate; sodium L-ascorbate; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine In water; tert-butyl alcohol at 20℃;92%
With sodium ascorbate; copper(II) sulfate; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine In dichloromethane; water; tert-butyl alcohol at 20℃; Inert atmosphere;92%

4-Fluoro-3-nitrophenyl azide Specification

The Benzene,4-azido-1-fluoro-2-nitro-, with the CAS registry number 2817-13-2, is also known as 2-Nitro-4-azidofluorobenzene. Its EINECS number is 248-878-6. This chemical's molecular formula is C6H3FN4O2 and formula weight is 182.11. What's more, its IUPAC name is 4-azido-1-fluoro-2-nitrobenzene. Its classification code is Mutation data. Its storage temperature is 2-8°C.It is used as an affinity label for insulin to give mono-azide-nitrophenyl-insulin derivatives. It is highly flammable. Once heated, it may cause an explosion. It is toxic by inhalation, in contact with skin and if swallowed. When using it, you should 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 where possible).

Physical properties about 4-Fluoro-3-nitrophenyl azide are:
(1)ACD/LogP:2.441; (2) # of Rule of 5 Violations:0; (3)ACD/LogD (pH 5.5):2.44; (4)ACD/LogD (pH 7.4):2.44; (5)ACD/BCF (pH 5.5):42.18; (6)ACD/BCF (pH 7.4):42.18; (7)ACD/KOC (pH 5.5): 506.86; (8)ACD/KOC (pH 7.4): 506.86; (9)#H bond acceptors: 6; (10)#H bond donors:0; (11)#Freely Rotating Bonds:2.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC(=C(C=C1N=[N+]=[N-])[N+](=O)[O-])F
(2)InChI: InChI=1S/C6H3FN4O2/c7-5-2-1-4(9-10-8)3-6(5)11(12)13/h1-3H
(3)InChIKey: VCTBSHQJICJJFV-UHFFFAOYSA-N

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