Benzoic acid,4-azido-2,3,5,6-tetrafluoro- supplier

Name
4-AZIDO-2,3,5,6-TETRAFLUOROBENZOIC ACID
EINECS
CAS No. 122590-77-6
Article Data22
CAS DataBase
Density
Solubility
Melting Point 140-141 °C
Formula C₇HF₄N₃O₂
Boiling Point
Molecular Weight 235.097
Flash Point
Transport Information
Appearance Colourless solid
Safety 26
Risk Codes 11-36/37/38
Molecular Structure
Hazard Symbols F,Xi
Synonyms 4-Azido-2,3,5,6-tetrafluorobenzoicacid;2,3,5,6-Tetrafluoro-4-azidobenzoic acid;
PSA 87.05000
LogP 2.33576

Synthetic route

: 122590-75-4
methyl 4-azidotetrafluorobenzoate

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

Conditions

Conditions	Yield
With sodium hydroxide In methanol; water at 25℃;	98%
With sodium hydroxide In methanol at 25℃; Hydrolysis;	98%
With water; sodium hydroxide In methanol at 20℃; for 25h;	96%

: 944-43-4
4-amino-2,3,5,6-tetrafluorobenzoic acid

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

Conditions

Conditions	Yield
Stage #1: 4-amino-2,3,5,6-tetrafluorobenzoic acid With sodium nitrite In trifluoroacetic acid for 1h; Stage #2: With sodium azide In diethyl ether for 2h; Further stages.;	95%
Stage #1: 4-amino-2,3,5,6-tetrafluorobenzoic acid With sulfuric acid; sodium nitrite In water at 0℃; for 0.666667h; Stage #2: With sodium azide In water at 20℃; for 1h;	80%
With sodium azide; sodium nitrite 1.) TFA, 0 deg C, 0.5 h; 2.) Et2O, 1 h; Yield given. Multistep reaction;
Stage #1: 4-amino-2,3,5,6-tetrafluorobenzoic acid With hydrogenchloride; sodium nitrite In water at 0℃; Stage #2: With sodium azide at 0℃;

: 122616-98-2
4-azidotetrafluorobenzamide

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

Conditions

Conditions	Yield
With sodium peroxide In water at 50℃; for 42h;	64%

: 126695-58-7
succinimidyl 4-azido-2,3,5,6-tetrafluorobenzoate

: 58066-85-6
hexadecylphosphocholine

A: phosphoric acid 2-(4-azido-2,3,5,6-tetrafluoro-benzoylamino)-ethyl ester hexadecyl ester

B: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

Conditions

Conditions	Yield
Title compound not separated from byproducts;

...Expand

: 36629-42-2
methyl pentafluorobenzoate

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / NaN3 / acetone; H2O / 16 h / Heating 2: 98 percent / aq. NaOH / methanol / 25 °C View Scheme
Multi-step reaction with 2 steps 1: 87 percent / sodium azide / acetone; H2O / 7 h / Heating 2: 95 percent / NaOH / H2O; methanol / 8 h / 25 °C View Scheme
Multi-step reaction with 2 steps 1: 87 percent / NaN3 / acetone; H2O / 8 h / Heating 2: 98 percent / 20percent aq. NaOH / methanol; H2O / 25 °C View Scheme

: 715-37-7
methyl 4-amino-2,3,5,6-tetrafluorobenzoate

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / TFA, NaNO2, NaN3 / 2.67 h / 0 °C 2: 94 percent / LiOH*H2O / methanol; H2O / 23 h / 25 °C View Scheme

: 773-82-0
Pentafluorobenzonitrile

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 18 percent / H2O2, (n-C4H9)4NHSO4, 20percent aq. NaOH / CH2Cl2 / 40 h / 25 °C 2: 64 percent / Na2O2 / H2O / 42 h / 50 °C View Scheme

: 652-31-3
2,3,4,5,6-pentafluorobenzamide

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 83 percent / NaN3 / acetone; H2O / 8 h / Heating 2: 64 percent / Na2O2 / H2O / 42 h / 50 °C View Scheme

: 602-94-8
Pentafluorobenzoic acid

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 96 percent / conc. H2SO4 / CCl4 / Heating 2: 87 percent / NaN3 / acetone; H2O / 8 h / Heating 3: 98 percent / 20percent aq. NaOH / methanol; H2O / 25 °C View Scheme

: 1423-15-0
perfluorophenyl azide

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

: 954-15-4
2,3,5,6-tetrafluoro-4-(methoxycarbonyl)benzoic acid

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

Conditions

Conditions	Yield
With sodium azide In water; acetone at 85℃; for 6h;

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

: 122590-78-7
4-Azido-2,3,5,6-tetrafluorobenzoyl Chloride

Conditions

Conditions	Yield
With phosphorus pentachloride In diethyl ether for 0.166667h;	100%
With phosphorus pentachloride In diethyl ether at 20℃; for 1h; Substitution;	100%
With sulfuryl dichloride In hexane Heating;	79%

: 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

: 126695-58-7
succinimidyl 4-azido-2,3,5,6-tetrafluorobenzoate

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 25℃;	99%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 25℃; for 34h;	99%
With dicyclohexyl-carbodiimide In acetonitrile	90%

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

: 126695-58-7
succinimidyl 4-azido-2,3,5,6-tetrafluorobenzoate

Conditions

Conditions	Yield
With EDAC; sodium sulfate In dichloromethane	94%

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

: 127099-85-8, 780722-26-1
N-Cyanoguanidine

: 4‐(5‐carbamimidamido‐1H‐tetrazol‐1‐yl)‐2,3,5,6‐tetrafluorobenzoic acid

Conditions

Conditions	Yield
With 5,10,15,20‐tetrakis‐(4‐sulfonatophenyl)‐porphyrin‐iron(III) chloride In ethanol; water at 60℃; for 43830h; Green chemistry;	90%

: 1202899-91-9
4-((4-aminobutyl)amino)-N2,N6-di(quinolin-3-yl)pyridine-2,6-dicarboxamide

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

: 1592668-55-7
4-((4-(4-azido-2,3,5,6-tetrafluorobenzamido)butyl)amino)-N2,N6-di(quinolin-3-yl)pyridine-2,6-dicarboxamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 24h;	88%

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

: 507-09-5
thioacetic acid

: 4-acetamido-2,3,5,6-tetrafluorobenzoic acid

Conditions

Conditions	Yield
Stage #1: 4-azido-2,3,5,6-tetrafluorobenzoic acid With sodium hydroxide In water Sonication; Stage #2: tiolacetic acid In water for 0.333333h; pH-value; Reagent/catalyst;	88%

: 1592668-43-3
4-((3-(2-(2-(3-aminopropoxy)ethoxy)ethoxy)propyl)amino)-N2,N6-di(quinolin-3-yl)pyridine-2,6-dicarboxamide

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

: 1592668-58-0
4-((1-(4-azido-2,3,5,6-tetrafluorophenyl)-1-oxo-6,9,12-trioxa-2-azapentadecan-15-yl)amino)-N2,N6-di(quinolin-3-yl)pyridine-2,6-dicarboxamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 24h;	87%

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

: 603-35-0
triphenylphosphine

: 2,3,5,6-tetrafluoro-4-[(triphenylphosphoranylidene)amino]benzoic acid

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 1h; Staudinger Azide Reduction; Inert atmosphere;	85%

: 864970-89-8
12-hydroxy-dodecanethioic acid S-propyl ester

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

: 864970-94-5
4-azido-2,3,5,6-tetrafluoro-benzoic acid 11-propylsulfanylcarbonyl-undecyl ester

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane	80.9%

: C25H24N4O

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

: C32H23F4N7O2

Conditions

Conditions	Yield
Stage #1: 4-azido-2,3,5,6-tetrafluorobenzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere; Stage #2: C25H24N4O With dmap In N,N-dimethyl-formamide at 20℃; for 8h; Inert atmosphere;	79%

: (R)-1-(1-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-1-(4-fluorophenyl)-2-phenylethyl)-3-(prop-2-ynyl)urea

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

: (R)-2,3,5,6-tetrafluoro-4-(4-((3-(1-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-1-(4-fluorophenyl)-2-phenylethyl)ureido)methyl)-1H-1,2,3-triazol-1-yl)benzoic acid

Conditions

Conditions	Yield
With copper(II) sulfate; sodium L-ascorbate In water; tert-butyl alcohol	78%

: 88192-19-2
3-azidopropylamine

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

: C10H7F4N7O

Conditions

Conditions	Yield
Stage #1: 4-azido-2,3,5,6-tetrafluorobenzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 0.166667h; Stage #2: 3-azidopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	78%

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

1,1'-carbonyldiimidazole: 1,1'-carbonyldiimidazole

: N-<(4-azidotetrafluorophenyl)carbonyl>imidazole

Conditions

Conditions	Yield
In tetrahydrofuran for 1.5h;	70%

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

: 126695-59-8
2,3,5,6-tetrafluoro-4-azidobenzyl alcohol

Conditions

Conditions	Yield
Stage #1: 4-azido-2,3,5,6-tetrafluorobenzoic acid With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 1h; Stage #2: With sodium tetrahydroborate In tetrahydrofuran at 20℃; for 2h;	70%

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

: 107-21-1
ethylene glycol

: ethane-1,2-diyl bis(4-azido-2,3,5,6-tetrafluorobenzoate)

Conditions

Conditions	Yield
Stage #1: 4-azido-2,3,5,6-tetrafluorobenzoic acid; ethylene glycol With dmap In dichloromethane at 20℃; for 0.5h; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	70%

: 1592668-41-1
4-((8-aminooctyl)amino)-N2,N6-di(quinolin-3-yl)pyridine-2,6-dicarboxamide

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

: 1592668-56-8
4-((8-(4-azido-2,3,5,6-tetrafluorobenzamido)octyl)amino)-N2,N6-di(quinolin-3-yl)pyridine-2,6-dicarboxamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 24h;	69%

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

: 4-sulfotetrafluorophenyl trifluoroacetate

: sodium; 4-(4-azido-2,3,5,6-tetrafluoro-benzoyloxy)-2,3,5,6-tetrafluoro-benzenesulfonate

Conditions

Conditions	Yield
With pyridine In acetonitrile at 35℃; for 5h;	68%

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

: 944-43-4
4-amino-2,3,5,6-tetrafluorobenzoic acid

Conditions

Conditions	Yield
With sodium L-ascorbate; copper(II) sulfate In tetrahydrofuran at 70℃; for 22h;	68%

: 4286-55-9
1-bromo-6-hexanol

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

: C13H12BrF4N3O2

Conditions

Conditions	Yield
Stage #1: 4-azido-2,3,5,6-tetrafluorobenzoic acid With thionyl chloride at 20℃; for 17h; Reflux; Stage #2: 1-bromo-6-hexanol With triethylamine In dichloromethane at 0 - 20℃; for 13h;	67%

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

: 252981-50-3
21-hydroxy-12,13-desoxyepothilone B

: 4-Azido-2,3,5,6-tetrafluoro-benzoic acid 4-[(E)-2-((Z)-(2S,9S,10S,11R,14S)-10,14-dihydroxy-5,9,11,13,13-pentamethyl-12,16-dioxo-oxacyclohexadec-4-en-2-yl)-propenyl]-thiazol-2-ylmethyl ester

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane at 0℃;	63%
With dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 2h;	63%

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

: 530-62-1
1,1'-carbonyldiimidazole

: N-<(4-azidotetrafluorophenyl)carbonyl>imidazole

Conditions

Conditions	Yield
In tetrahydrofuran at 25℃; for 1h;	60%

: 1-{2-[2-(2-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}ethoxy)ethoxy]ethyl}pyrrole-2,5-dione

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

: 2-{2-[2-(2-{2-[2-(2,5-dioxo-2,5-dihydropyrrol-1-yl)ethoxy]ethoxy}ethoxy)ethoxy]ethoxy}ethyl 4-azido-2,3,5,6-tetrafluorobenzoate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 4h;	60%

: 50-00-0
formaldehyd

: C13H24N4O4S

: 39687-95-1
isocyanoacetic acid methyl ester

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

: C25H30F4N8O8S

Conditions

Conditions	Yield
In methanol at 100℃; for 0.333333h; Microwave irradiation;	59%

...Expand

: 1-(2-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}ethyl)pyrrole-2,5-dione

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

: 2-(2-{2-[2-(2,5-dioxo-2,5-dihydropyrrol-1-yl)ethoxy]ethoxy}ethoxy)ethyl 4-azido-2,3,5,6-tetrafluorobenzoate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 4h;	59%

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

: 1949-55-9
methyl 3,5-diaminobenzoate

: 138724-23-9
Methyl 3-(4-Azido-2,3,5,6-tetrafluorobenzamido)-5-aminobenzoate

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In chloroform for 15h;	58%

: 24463-15-8
1-pyrenemethanol

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

: 1144517-32-7
1-[(4-azido-2,3,5,6-tetrafluorobenzoyloxy)methyl]pyrene

Conditions

Conditions	Yield
With 2-chloro-1-methyl-pyridinium iodide; triethylamine In dichloromethane at 20℃; for 4.5h; Inert atmosphere;	58%

: 122590-77-6
4-azido-2,3,5,6-tetrafluorobenzoic acid

: 75867-39-9
4-trimethylsilylethynyl aniline

: 1469890-54-7
4-azido-N-(4-(2-trimethylsilylethynyl)phenyl)-2,3,5,6-tetrafluorobenzamide

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In toluene at 60℃; for 24h;	58%

Benzoic acid,4-azido-2,3,5,6-tetrafluoro- Specification

The Benzoic acid,4-azido-2,3,5,6-tetrafluoro-, with the CAS registry number 122590-77-6, is also known as 4-Amino-3,5-dimethylbenzoic acid methyl ester. This chemical's molecular formula is C₇HF₄N₃O₂ and molecular weight is 235.1. What's more, its systematic name is 4-Azido-2,3,5,6-tetrafluorobenzoic acid and it belongs to the product categories of Nitric Oxide Reagents; Cross Linking Reagents; Photoaffinity Labels.

Physical properties of Benzoic acid,4-azido-2,3,5,6-tetrafluoro- are: (1)ACD/LogP: 3.16; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.08; (4)ACD/LogD (pH 7.4): 0.01; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1.02; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 38.66 Å²; (13)Feature 3D Acceptor Count: 2; (14)Feature 3D Anion Count: 1; (15)Feature 3D Ring Count: 1; (16)Effective Rotor Count: 2; (17)Conformer Sampling RMSD: 0.6; (18)CID Conformer Count: 3.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1(=C(C(=C(C(=C1F)F)N=[N+]=[N-])F)F)C(=O)O
(2)InChI: InChI=1S/C7HF4N3O2/c8-2-1(7(15)16)3(9)5(11)6(4(2)10)13-14-12/h(H,15,16)
(3)InChIKey: IOJFHZXQSLNAQJ-UHFFFAOYSA-N

Product Name

4-AZIDO-2,3,5,6-TETRAFLUOROBENZOIC ACID

Synthetic route

Benzoic acid,4-azido-2,3,5,6-tetrafluoro- Specification

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