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4-FLUORO-3-NITROPHENYL AZIDE is a chemical with a specific purpose. Lookchem provides you with multiple data and supplier information of this chemical.

28166-06-5

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28166-06-5 Usage

Purification Methods

Dissolve the azide in Et2O, dry it over MgSO4, filter, evaporate and recrystallise the residue from pet ether (b 20-40o) to give orange needles. Store it in a stoppered container at ~0o. The NMR has  7.75 (m 1H) and 7.35 (m 2H) in CDCl3. [Hagedorn et al. J Org Chem 43 2070 1978.]

Check Digit Verification of cas no

The CAS Registry Mumber 28166-06-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,8,1,6 and 6 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 28166-06:
(7*2)+(6*8)+(5*1)+(4*6)+(3*6)+(2*0)+(1*6)=115
115 % 10 = 5
So 28166-06-5 is a valid CAS Registry Number.
InChI:InChI=1/C6H4FN4O2/c7-5-2-1-4(9-10-8)3-6(5)11(12)13/h1-3,8H/q+1

28166-06-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name Benzene, 4-azido-1-fluoro-2-nitro-

1.2 Other means of identification

Product number -
Other names 4-azido-2-nitrofluorobenzene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:28166-06-5 SDS

28166-06-5Synthetic route

4-Fluoro-3-nitroaniline
364-76-1

4-Fluoro-3-nitroaniline

4-fluoro-3-nitrophenylazide
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

sodium azide

4-Fluoro-3-nitroaniline
364-76-1

4-Fluoro-3-nitroaniline

4-fluoro-3-nitrophenylazide
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;
4-fluoro-3-nitrophenylazide
28166-06-5

4-fluoro-3-nitrophenylazide

(1R,2R,3S,4R,5S)-4-(2-chloro-6-(prop-2-ynylamino)-9H-purin-9-yl)bicyclo[3.1.0]hexane-2,3-diol
1309943-98-3

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

(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
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%
4-fluoro-3-nitrophenylazide
28166-06-5

4-fluoro-3-nitrophenylazide

(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
1309943-74-5

(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

(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
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%
thiobenzoic acid
98-91-9

thiobenzoic acid

4-fluoro-3-nitrophenylazide
28166-06-5

4-fluoro-3-nitrophenylazide

N-(4-fluoro-3-nitrophenyl)-benzylamide
228425-41-0

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

Conditions
ConditionsYield
With 2,6-dimethylpyridine In methanol at 25℃; for 15h;95%
4-fluoro-3-nitrophenylazide
28166-06-5

4-fluoro-3-nitrophenylazide

(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
1309943-87-0

(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

(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
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%
4-fluoro-3-nitrophenylazide
28166-06-5

4-fluoro-3-nitrophenylazide

thioacetic acid
507-09-5

thioacetic acid

N-(4-fluoro-3-nitrophenyl)acetamide
351-32-6

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

Conditions
ConditionsYield
With 2,6-dimethylpyridine In methanol at 25℃; for 15h;94%
4-fluoro-3-nitrophenylazide
28166-06-5

4-fluoro-3-nitrophenylazide

(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

(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

MRS5223
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%
4-fluoro-3-nitrophenylazide
28166-06-5

4-fluoro-3-nitrophenylazide

(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
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

(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
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%
4-fluoro-3-nitrophenylazide
28166-06-5

4-fluoro-3-nitrophenylazide

(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
1309943-94-9

(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

(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
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-nitrophenylazide
28166-06-5

4-fluoro-3-nitrophenylazide

17α-aminomethyl-3,3-(dimethoxy)-5α-androstan-17β-ol
300350-92-9

17α-aminomethyl-3,3-(dimethoxy)-5α-androstan-17β-ol

17α-[(N-4-azido-2-nitrophenyl)aminomethyl]-3,3-dimethoxy-5α-androstan-17β-ol
300351-06-8

17α-[(N-4-azido-2-nitrophenyl)aminomethyl]-3,3-dimethoxy-5α-androstan-17β-ol

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; diethyl ether; ethanol91%
4-fluoro-3-nitrophenylazide
28166-06-5

4-fluoro-3-nitrophenylazide

(1R,2R,3S,4R,5S)-4-(2-chloro-6-(3-(hepta-1,6-diynyl)benzylamino)-9H-purin-9-yl)bicyclo[3.1.0]hexane-2,3-diol
1309943-86-9

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

(1R,2R,3S,4R,5S)-4-(2-chloro-6-(3-(5-(1-(4-fluoro-3-nitrophenyl)-1H-1,2,3-triazol-4-yl)pent-1-ynyl)benzylamino)-9H-purin-9-yl)bicyclo[3.1.0]hexane-2,3-diol
1309943-89-2

(1R,2R,3S,4R,5S)-4-(2-chloro-6-(3-(5-(1-(4-fluoro-3-nitrophenyl)-1H-1,2,3-triazol-4-yl)pent-1-ynyl)benzylamino)-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 dichloromethane; water; tert-butyl alcohol at 20℃;91%
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;91%
4-fluoro-3-nitrophenylazide
28166-06-5

4-fluoro-3-nitrophenylazide

(1R,2R,3S,4R,5S)-4-(2-chloro-6-(3-(nona-1,8-diynyl)benzylamino)-9H-purin-9-yl)bicyclo[3.1.0]hexane-2,3-diol
1309943-88-1

(1R,2R,3S,4R,5S)-4-(2-chloro-6-(3-(nona-1,8-diynyl)benzylamino)-9H-purin-9-yl)bicyclo[3.1.0]hexane-2,3-diol

(1R,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)bicyclo[3.1.0]hexane-2,3-diol
1309943-91-6

(1R,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)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;91%
4-fluoro-3-nitrophenylazide
28166-06-5

4-fluoro-3-nitrophenylazide

(1S,2R,3S,4R,5S)-4-[2-chloro-6-(3-(hepta-1,6-diynyl)phenylmethylamino)-9H-purin-9-yl]-2,3-dihydroxybicyclo[3.1.0]hexane-1-carboxylic acid N-methylamide
1309944-03-3

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

(1S,2R,3S,4R,5S)-4-[2-chloro-6-(3-(5-(1-(4-fluoro-3-nitrophenyl)-1H-1,2,3-triazol-4-yl)pent-1-ynyl)benzylamino)-9H-purin-9-yl]-2,3-dihydroxybicyclo[3.1.0]hexane-1-carboxylic acid N-methylamide
1309943-75-6

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

Conditions
ConditionsYield
With copper(II) sulfate; sodium L-ascorbate; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine In dichloromethane; water; tert-butyl alcohol at 20℃;90%
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;90%
4-fluoro-3-nitrophenylazide
28166-06-5

4-fluoro-3-nitrophenylazide

ethylenediamine
107-15-3

ethylenediamine

4-(2-aminoethyl)amino-3-nitro-phenylazide (napa)
64309-07-5

4-(2-aminoethyl)amino-3-nitro-phenylazide (napa)

Conditions
ConditionsYield
In dichloromethane for 24h; Ambient temperature;89%
In dichloromethane for 0.5h; Ambient temperature; in the dark;70%
4-fluoro-3-nitrophenylazide
28166-06-5

4-fluoro-3-nitrophenylazide

(1'S,2'R,3'S,4'R,5'S)-4'-[6-(3-chlorobenzylamino)-2-(1,6-heptadiynyl)-9H-purin-9-yl]-2',3'-dihydroxybicyclo[3.1.0]hexane-1'-carboxylic acid N-methylamide
1217299-55-2

(1'S,2'R,3'S,4'R,5'S)-4'-[6-(3-chlorobenzylamino)-2-(1,6-heptadiynyl)-9H-purin-9-yl]-2',3'-dihydroxybicyclo[3.1.0]hexane-1'-carboxylic acid N-methylamide

(1S,2R,3S,4R,5S)-4-(6-(3-chlorobenzylamino)-2-(5-(1-(4-fluoro-3-nitrophenyl)-1H-1,2,3-triazol-4-yl)pent-1-ynyl)-9H-purin-9-yl)-2,3-dihydroxybicyclo[3.1.0]hexane-1-carboxylic acid N-methylamide
1217299-57-4

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

Conditions
ConditionsYield
With copper(II) sulphate hydrate; sodium L-ascorbate In tetrahydrofuran; water at 20℃; regioselective reaction;89%
4-fluoro-3-nitrophenylazide
28166-06-5

4-fluoro-3-nitrophenylazide

C16H14O7
1285718-33-3

C16H14O7

C22H17FN4O9
1285718-37-7

C22H17FN4O9

Conditions
ConditionsYield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In dichloromethane; water at 20℃;87%
4-fluoro-3-nitrophenylazide
28166-06-5

4-fluoro-3-nitrophenylazide

6-methyl-2-oxo-1-(prop-2-yn-1-yl)-4-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile
1582270-75-4

6-methyl-2-oxo-1-(prop-2-yn-1-yl)-4-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile

1-((1-(4-fluoro-3-nitrophenyl)-1H-1,2,3-triazol-4-yl)methyl)-6-methyl-2-oxo-4-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile
1582270-94-7

1-((1-(4-fluoro-3-nitrophenyl)-1H-1,2,3-triazol-4-yl)methyl)-6-methyl-2-oxo-4-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile

Conditions
ConditionsYield
Stage #1: 6-methyl-2-oxo-1-(prop-2-yn-1-yl)-4-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile With copper(l) iodide In tetrahydrofuran at 20℃; for 0.5h;
Stage #2: 4-fluoro-3-nitrophenylazide In tetrahydrofuran for 12h;
86%
4-fluoro-3-nitrophenylazide
28166-06-5

4-fluoro-3-nitrophenylazide

6-phenyl-2-(prop-2-yn-1-yloxy)-4-(trifluoromethyl)nicotinonitrile
1336913-39-3

6-phenyl-2-(prop-2-yn-1-yloxy)-4-(trifluoromethyl)nicotinonitrile

2-((1-(4-fluoro-3-nitrophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-6-phenyl-4-(trifluoromethyl)nicotinonitrile
1582270-81-2

2-((1-(4-fluoro-3-nitrophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-6-phenyl-4-(trifluoromethyl)nicotinonitrile

Conditions
ConditionsYield
Stage #1: 6-phenyl-2-(prop-2-yn-1-yloxy)-4-(trifluoromethyl)nicotinonitrile With copper(l) iodide In tetrahydrofuran at 20℃; for 0.5h;
Stage #2: 4-fluoro-3-nitrophenylazide In tetrahydrofuran for 12h;
85%
4-fluoro-3-nitrophenylazide
28166-06-5

4-fluoro-3-nitrophenylazide

ethyl 2-(prop-2-ynyloxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate
1591994-08-9

ethyl 2-(prop-2-ynyloxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

ethyl 2-((1-(4-fluoro-3-nitrophenyl)-1H-1,2,3-triazole-4-yl)methoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate
1591994-28-3

ethyl 2-((1-(4-fluoro-3-nitrophenyl)-1H-1,2,3-triazole-4-yl)methoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Conditions
ConditionsYield
Stage #1: ethyl 2-(prop-2-ynyloxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate With copper(l) iodide In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;
Stage #2: 4-fluoro-3-nitrophenylazide In tetrahydrofuran at 20℃;
82%
4-fluoro-3-nitrophenylazide
28166-06-5

4-fluoro-3-nitrophenylazide

12-Aminododecanoic acid
693-57-2

12-Aminododecanoic acid

C18H27N5O4
58775-40-9

C18H27N5O4

Conditions
ConditionsYield
In methanol; N,N-dimethyl-formamide at 80℃;80%
1,6-Hexanediamine
124-09-4

1,6-Hexanediamine

4-fluoro-3-nitrophenylazide
28166-06-5

4-fluoro-3-nitrophenylazide

N'-(4-azido-2-nitrophenyl)hexane-1,6-diamine
64309-09-7

N'-(4-azido-2-nitrophenyl)hexane-1,6-diamine

Conditions
ConditionsYield
In methanol at 20℃; for 12h; Inert atmosphere;80%
Geraniol
106-24-1

Geraniol

4-fluoro-3-nitrophenylazide
28166-06-5

4-fluoro-3-nitrophenylazide

p-azido-o-nitrophenyl geranyl ether
106929-46-8

p-azido-o-nitrophenyl geranyl ether

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran for 14h; Ambient temperature;76%
4-fluoro-3-nitrophenylazide
28166-06-5

4-fluoro-3-nitrophenylazide

diethylamine
109-89-7

diethylamine

4-(N,N-diethylamino)-3-nitrophenylazide

4-(N,N-diethylamino)-3-nitrophenylazide

Conditions
ConditionsYield
In acetonitrile at 40℃; for 3h;67%
4-fluoro-3-nitrophenylazide
28166-06-5

4-fluoro-3-nitrophenylazide

(8R,9S,13S,14S,16S)-16-(4-Amino-but-2-ynyl)-3-(tert-butyl-dimethyl-silanyloxy)-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one
234765-89-0

(8R,9S,13S,14S,16S)-16-(4-Amino-but-2-ynyl)-3-(tert-butyl-dimethyl-silanyloxy)-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one

16α-(4-(4-azido-2-nitrophenylamino)-2-butynyl)estra-1,3,5(10)-triene-3,17β-diol

16α-(4-(4-azido-2-nitrophenylamino)-2-butynyl)estra-1,3,5(10)-triene-3,17β-diol

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide for 44h; Ambient temperature;59.9%
4-fluoro-3-nitrophenylazide
28166-06-5

4-fluoro-3-nitrophenylazide

histamine dichloride
56-92-8

histamine dichloride

water ethanol
180330-54-5

water ethanol

sodium carbonate
497-19-8

sodium carbonate

4(5)-[2-(4-azido-2-nitroanilino)ethyl]imidazole hydrochloride
79412-26-3

4(5)-[2-(4-azido-2-nitroanilino)ethyl]imidazole hydrochloride

Conditions
ConditionsYield
With hydrogenchloride58%
6-amino-1-hexanol
4048-33-3

6-amino-1-hexanol

4-fluoro-3-nitrophenylazide
28166-06-5

4-fluoro-3-nitrophenylazide

6-(4-Azido-2-nitro-phenylamino)-hexan-1-ol

6-(4-Azido-2-nitro-phenylamino)-hexan-1-ol

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane at 20℃; for 2h;55%
In 1,4-dioxane
Stage #1: 6-amino-1-hexanol; 4-fluoro-3-nitrophenylazide In 1,4-dioxane at 20℃; for 0.333333h;
Stage #2: With triethylamine In 1,4-dioxane at 20 - 55℃; for 16h;
16 g
4-pyrrol-1-yl-butylamine
98492-69-4

4-pyrrol-1-yl-butylamine

4-fluoro-3-nitrophenylazide
28166-06-5

4-fluoro-3-nitrophenylazide

C14H20N6O2

C14H20N6O2

Conditions
ConditionsYield
In tetrahydrofuran for 0.5h;54%
4-fluoro-3-nitrophenylazide
28166-06-5

4-fluoro-3-nitrophenylazide

3,3-(dimethoxy)-17α-aminopropyl-17β-hydroxy-5α-androstan-3-one
300350-96-3

3,3-(dimethoxy)-17α-aminopropyl-17β-hydroxy-5α-androstan-3-one

17α-[(N-4-azido-2-nitrophenyl)aminopropyl]-3,3-dimethoxy-5α-androstan-17β-ol
300351-12-6

17α-[(N-4-azido-2-nitrophenyl)aminopropyl]-3,3-dimethoxy-5α-androstan-17β-ol

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; diethyl ether; ethanol47%
4-fluoro-3-nitrophenylazide
28166-06-5

4-fluoro-3-nitrophenylazide

N-(2-aminoethyl)-N'-cyano-N''-<3-<3-(1-piperidinylmethyl)phenoxy>propyl>guanidine
140872-99-7

N-(2-aminoethyl)-N'-cyano-N''-<3-<3-(1-piperidinylmethyl)phenoxy>propyl>guanidine

C25H32N10O3
140873-16-1

C25H32N10O3

Conditions
ConditionsYield
With sodium carbonate In ethanol for 15h; Heating;45%
4-fluoro-3-nitrophenylazide
28166-06-5

4-fluoro-3-nitrophenylazide

C20H32N6O
140900-93-2

C20H32N6O

C26H34N10O3
140873-20-7

C26H34N10O3

Conditions
ConditionsYield
With sodium carbonate In ethanol for 15h; Heating;44%

28166-06-5Upstream product

28166-06-5Relevant academic research and scientific papers

Synthesis of Arylazide- and Diazirine-Containing CrAsH-EDT2 Photoaffinity Probes

Syeda, Shameem S.,Rice, Daren,Hook, Derek J.,Heckert, Leslie L.,Georg, Gunda I.

, p. 233 - 241 (2016)

Two photo-crosslinking biarsenical (CrAsH-EDT2)-modified probes were synthesized that are expected to be useful tools for tetracysteine-labeled proteins to facilitate the co-affinity purification of their DNA binding sequences and interacting proteins. In addition, improvements for the synthesis of CrAsH-EDT2 and N1-(4-azido-2-nitrophenyl)hexane-1,6-diamine are reported. Both photoprobes effectively entered HeLa cells (and the nucleus) and were dependent on the tetracysteine motif in recombinant DMRT1 (doublesex and Mab3-related transcription factor) to induce fluorescence, suggesting that their crosslinking abilities can be exploited for the identification of nucleic acids and proteins associated with a protein of interest.

BIS-BENZIMIDAZOLE COMPOUNDS AND METHODS OF USING SAME

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Paragraph 00767; 00768; 00771, (2019/06/05)

Provided herein are compounds and methods for modulating abnormal repeat expansions of gene sequences. More particularly, provided are inhibitors of RNA and the uses of such inhibitors in regulating nucleotide repeat expansions, e.g., to treat Myotonic Dystrophy Type 1 (DM1 ), Myotonic Dystrophy Type 2 (DM2), Fuchs dystrophy, Huntington Disease, Amyotrophic Lateral Sclerosis, or Frontotemporal Dementia.

Photoaffinity labeling via nitrenium ion chemistry: Protonation of the nitrene derived from 4-amino-3-nitrophenyl azide to afford reactive nitrenium ion pairs

Voskresenska, Valentyna,Wilson, R. Marshall,Panov, Maxim,Tarnovsky, Alexander N.,Krause, Jeanette A.,Vyas, Shubham,Winter, Arthur H.,Hadad, Christopher M.

supporting information; experimental part, p. 11535 - 11547 (2011/02/25)

Phenyl azides with powerful electron-donating substituents are known to deviate from the usual photochemical behavior of other phenyl azides. They do not undergo ring expansion but form basic nitrenes that protonate to form nitrenium ions. The photochemistry of the widely used photoaffinity labeling system 4-amino-3-nitrophenyl azide, 5, has been studied by transient absorption spectroscopy from femtosecond to microsecond time domains and from a theoretical perspective. The nitrene generation from azide 5 occurs on the S2 surface, in violation of Kasha's rule. The resulting nitrene is a powerful base and abstracts protons extremely rapidly from a variety of sources to form a nitrenium ion. In methanol, this protonation occurs in about 5 ps, which is the fastest intermolecular protonation observed to date. Suitable proton sources include alcohols, amine salts, and even acidic C-H bonds such as acetonitrile. The resulting nitrenium ion is stabilized by the electron-donating 4-amino group to afford a diiminoquinone-like species that collapses relatively slowly to form the ultimate cross-linked product. In some cases in which the anion is a good hydride donor, cross-linking is replaced by reduction of the nitrenium ion to the corresponding amine.

An easy access to aryl azides from aryl amines under neutral conditions

Das, Jagattaran,Patil, Santoshkumar N.,Awasthi, Riti,Narasimhulu, C. Prasad,Trehan, Sanjay

, p. 1801 - 1806 (2007/10/03)

A variety of substituted aryl amines were transformed into aryl azides using t-BuONO and moist NaN3 in t-BuOH in good to excellent yields. Smooth transformation was observed with anilines, having electron withdrawing and donating groups. Both acid- and base-sensitive groups survived the reaction conditions. Georg Thieme Verlag Stuttgart.

SURFACE FUNCTIONALISED ADHESION

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Page/Page column 26, (2010/02/11)

The invention describes a means of enhancing the adhesion and sealant qualities of adhesives through the addition of a surface modifier. The invention has particular relevance to the adhesion and sealing of tanned leather where surface functionality suitable for effective adhesion with known adhesives is impaired by loss of functionality of the leather surface. The invention is however equally applicable to the adhesion of articles made from other materials such as plastics and plastic composites where the surface chemistry of the article requires modification for improved adhesion.

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