52927-22-7

Basic information

• Product Name: 6-Cyano-2-naphthol
• Synonyms: 6-CYANO-2-NAPHTHOL;6-HYDROXY-NAPHTHALENE-2-CARBONITRILE;6-HYDROXY-2-NAPHTHALENECARBONITRILE;6-HYDROXY-2-NAPHTHONITRILE;CYANO(6-)-2-NAPTHOL;6-CYANO-2-NAPHTHOL 99%;6-CYANO-2-NAPHTHALENOL;6-Cyano-2-naphthol ,99%
• CAS NO: 52927-22-7
• Molecular Formula: C₁₁H₇NO
• Molecular Weight: 169.18
• EINECS: 1806241-263-5
• Product Categories: Aromatics Compounds;Building Blocks for Liquid Crystals;Chalcones, etc. (Building Blocks for Liquid Crystals);Functional Materials;Aromatics;C10 to C27;Cyanides/Nitriles;Nitrogen Compounds;Intermediates;Intermediates & Fine Chemicals;Pharmaceuticals;alcohol|cyanide
• Mol File: 52927-22-7.mol
• Article Data: 31

Chemical Properties

• Melting Point: 165.5-170.5 °C(lit.)
• Boiling Point: 383.1 °C at 760 mmHg
• Flash Point: 185.5 °C
• Appearance: brown crystalline solid
• Density: 1.28 g/cm³
• Vapor Pressure: 2.04E-06mmHg at 25°C
• Refractive Index: 1.692
• Storage Temp.: -20?C Freezer
• Solubility: DMSO (Slightly), Ethanol, Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 8.57±0.40(Predicted)
• CAS DataBase Reference: 6-Cyano-2-naphthol(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Cyano-2-naphthol(52927-22-7)
• EPA Substance Registry System: 6-Cyano-2-naphthol(52927-22-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 52927-22-7(Hazardous Substances Data)

Usage

Chemical Properties

Brown Crystalline Solid

Uses

Different sources of media describe the Uses of 52927-22-7 differently. You can refer to the following data:
1. Intermediate of Nafamostat mesilate (N210000).
2. Reactant for:Palladium-catalyzed reductionNickel-catalyzed cross-coupling reactionsPalladium-catalyzed Heck reactions

General Description

6-Cyano-2-naphthol (6CN2) is an aromatic alcohol that can be synthesized from 6-bromo-2-naphthol. It is a superphotoacid with the ground state pKa* value of 8.4 and excited state pKavalue of 0.2, respectively. 6CN2 protonates PANI-ES (polyaniline emeraldine salt) to form PANI-EB (emeraldine base), which shows enhanced conductivity. The proton-transfer kinetics and photophysical behavior of 6CN2 have been investigated.

InChI:InChI=1/C11H7NO/c12-7-8-1-2-10-6-11(13)4-3-9(10)5-8/h1-6,13H

Synthetic route

6-cyanonaphthalen-2-yl 4-methylbenzenesulfonate (939822-86-3) → 6-cyano-2-naphthol (52927-22-7)

Conditions	Yield
With tetraethylammonium perchlorate; triethylamine In dimethyl sulfoxide at 20℃; for 6h; Electrolysis; Green chemistry;	94%

2-cyano-6-methoxynaphthalene (67886-70-8) → 6-cyano-2-naphthol (52927-22-7)

Conditions	Yield
	91%
With tetrachlorosilane; borontrifluoride acetic acid; lithium iodide In toluene; acetonitrile at 70℃; for 10h;	83%
With boron tribromide In dichloromethane at -78 - 20℃; for 16h; Inert atmosphere;	69%
With sodium cyanide In dimethyl sulfoxide at 160 - 170℃; for 12h;	62%
With boron tribromide

trifluoromethanesulfonic acid 6-cyano-naphthalen-2-yl ester (145369-29-5) → 6-cyano-2-naphthol (52927-22-7)

Conditions	Yield
With tetraethylammonium perchlorate; triethylamine In dimethyl sulfoxide at 20℃; for 9h; Electrolysis; Green chemistry;	91%

6-bromo-naphthalen-2-ol (15231-91-1) → 6-cyano-2-naphthol (52927-22-7)

Conditions	Yield
With CuCN In N,N-dimethyl-formamide at 160 - 170℃; for 3h;	83%
	56%
In ethanol; N,N-dimethyl-formamide
In ethanol; N,N-dimethyl-formamide

6-bromo-naphthalen-2-ol (15231-91-1) + copper(l) cyanide → 6-cyano-2-naphthol (52927-22-7)

Conditions	Yield
In N,N-dimethyl-formamide at 160 - 170℃; for 4h; Inert atmosphere;	83%
In N,N-dimethyl-formamide at 135℃; for 18h;	62%
In N,N-dimethyl-formamide at 150℃;	60%

6-hydroxynaphthalene-2-carbaldehyde (78119-82-1) → 6-cyano-2-naphthol (52927-22-7)

Conditions	Yield
With hydroxylamine hydrochloride In dimethyl sulfoxide at 100℃; for 1h;	70%

6-acetoxy-[2]naphthonitrile (860363-16-2) → 6-cyano-2-naphthol (52927-22-7)

Conditions	Yield
With potassium hydroxide

acetate of α,α,α',α'-tetrabromo-3,4-xylenol (78119-72-9) + acrylonitrile (107-13-1) → 6-cyano-2-naphthol (52927-22-7) + 7-hydroxynaphthalene-2-carbonitrile (130200-58-7)

Conditions	Yield
1) NaI, DMF; 2) hydrolysis; Yield given. Multistep reaction. Title compound not separated from byproducts;

benzoate of α,α,α',α'-tetrabromo-3,4-xylenol (78119-71-8) + acrylonitrile (107-13-1) → 6-cyano-2-naphthol (52927-22-7) + 7-hydroxynaphthalene-2-carbonitrile (130200-58-7)

Conditions	Yield
1) NaI, DMF; 2) NaOH, CH3OH; Yield given. Multistep reaction;
1) NaI, DMF; 2) NaOH, CH3OH; Yield given. Multistep reaction. Title compound not separated from byproducts;

6-bromonaphthalen-2-yl acetate (6343-72-2) + copper(I) cyanide (544-92-3) → 6-cyano-2-naphthol (52927-22-7)

Conditions	Yield
With pyridine; copper(II) sulfate In N,N-dimethyl-formamide

6-bromo-naphthalen-2-ol (15231-91-1) + copper(I) cyanide (544-92-3) → 6-cyano-2-naphthol (52927-22-7)

Conditions	Yield
With 1,3-dimethyl-2-imidazolidinone at 160℃; for 3h; Substitution;

2-Bromo-6-methoxynaphthalene (5111-65-9) → 6-cyano-2-naphthol (52927-22-7)

Conditions	Yield
With boron tribromide demethylation;

3,4-dimethylphenyl benzoate (3845-63-4) → 6-cyano-2-naphthol (52927-22-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 91 percent / bromosuccinimide, azoisobutyronitrile / CCl4 / 12 h / Heating; Irradiation 2: 91 percent / NBS, azoisobutyronitrile / CCl4 / 12 h / Heating 3: 1) NaI, DMF; 2) NaOH, CH3OH View Scheme
Multi-step reaction with 2 steps 1: 88.5 percent / bromosuccinimide, azoisobutyronitrile / CCl4 / 25 h / Heating; Irradiation 2: 1) NaI, DMF; 2) NaOH, CH3OH View Scheme

benzoate of α,α,α'-tribromo-3,4-xylenol → 6-cyano-2-naphthol (52927-22-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 91 percent / NBS, azoisobutyronitrile / CCl4 / 12 h / Heating 2: 1) NaI, DMF; 2) NaOH, CH3OH View Scheme

6-bromonaphthalen-2-yl acetate (6343-72-2) → 6-cyano-2-naphthol (52927-22-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: copper (II)-sulfate; pyridine / 180 - 190 °C 2: methanol. KOH-solution View Scheme

1-methyl-pyrrolidin-2-one (872-50-4) + 6-bromo-naphthalen-2-ol (15231-91-1) + iron(III) chloride → 6-cyano-2-naphthol (52927-22-7)

Conditions	Yield
With hydrogenchloride; CaCl2 In water

C11H9NO2 (1123760-79-1) → 6-cyano-2-naphthol (52927-22-7) + 6-cyano-1-naphthol (91059-47-1)

Conditions	Yield
With perchloric acid In water at 25℃; for 10h; Kinetics; Concentration;

β-naphthol (135-19-3) → 6-cyano-2-naphthol (52927-22-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: bromine / acetic acid 1.2: 3 h / Reflux 2.1: N,N-dimethyl-formamide / 4 h / 160 °C View Scheme
Multi-step reaction with 2 steps 1: acetic acid; tin; bromine / 3 h / Reflux 2: N,N-dimethyl-formamide / 4 h / 160 - 170 °C / Inert atmosphere View Scheme

6-methoxy-3,4-dihydro-1(2H)-naphthalenone (1078-19-9) → 6-cyano-2-naphthol (52927-22-7)

Conditions

Yield

Multi-step reaction with 6 steps 1.1: sodium hydride / tetrahydrofuran / 1 h / 0 - 20 °C 1.2: 2 h / 20 °C 2.1: sodium azide; trifluorormethanesulfonic acid / acetonitrile / 1 h / 0 - 20 °C 3.1: sodium tetrahydroborate / ethanol / 2 h / 0 - 20 °C 4.1: toluene-4-sulfonic acid / toluene / 16 h / Reflux 5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 16 h / 90 °C 6.1: boron tribromide / dichloromethane / 16 h / -78 - 20 °C / Inert atmosphere View Scheme

6-Methoxy-2-hydroxymethylen-1-tetralon (16252-53-2) → 6-cyano-2-naphthol (52927-22-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: sodium azide; trifluorormethanesulfonic acid / acetonitrile / 1 h / 0 - 20 °C 2: sodium tetrahydroborate / ethanol / 2 h / 0 - 20 °C 3: toluene-4-sulfonic acid / toluene / 16 h / Reflux 4: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 16 h / 90 °C 5: boron tribromide / dichloromethane / 16 h / -78 - 20 °C / Inert atmosphere View Scheme

1-hydroxy-2-cyano-6-methoxy-1,2,3,4-tetrahydronaphthalene (606494-99-9) → 6-cyano-2-naphthol (52927-22-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / toluene / 16 h / Reflux 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 16 h / 90 °C 3: boron tribromide / dichloromethane / 16 h / -78 - 20 °C / Inert atmosphere View Scheme

6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalene-2-carbonitrile (34093-07-7) → 6-cyano-2-naphthol (52927-22-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium tetrahydroborate / ethanol / 2 h / 0 - 20 °C 2: toluene-4-sulfonic acid / toluene / 16 h / Reflux 3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 16 h / 90 °C 4: boron tribromide / dichloromethane / 16 h / -78 - 20 °C / Inert atmosphere View Scheme

6-methoxy-3,4-dihydronaphthalene-2-carbonitrile (79215-28-4) → 6-cyano-2-naphthol (52927-22-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 16 h / 90 °C 2: boron tribromide / dichloromethane / 16 h / -78 - 20 °C / Inert atmosphere View Scheme

6-Hydroxy-2-naphthoic acid (16712-64-4) → 6-cyano-2-naphthol (52927-22-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide; thionyl chloride / 5 h / 70 °C 2.1: ammonium hydroxide / tetrahydrofuran; water / 16 h / 25 °C 3.1: trifluoroacetic anhydride / tetrahydrofuran / 0.5 h / 0 - 25 °C 3.2: 16 h / 25 °C View Scheme

6-hydroxynaphthalene-2-carboxamide (62529-01-5) → 6-cyano-2-naphthol (52927-22-7)

Conditions	Yield
Stage #1: 6-hydroxynaphthalene-2-carboxamide With trifluoroacetic anhydride In tetrahydrofuran at 0 - 25℃; for 0.5h; Stage #2: With pyridine In tetrahydrofuran at 25℃; for 16h;

C11H7ClO2 → 6-cyano-2-naphthol (52927-22-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: ammonium hydroxide / tetrahydrofuran; water / 16 h / 25 °C 2.1: trifluoroacetic anhydride / tetrahydrofuran / 0.5 h / 0 - 25 °C 2.2: 16 h / 25 °C View Scheme

6-bromo-naphthalen-2-ol (15231-91-1) + 4-cyanophenylboronic acid (126747-14-6) → 6-cyano-2-naphthol (52927-22-7)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 80℃; for 8h; Suzuki-Miyaura Coupling; High pressure; Inert atmosphere;

6-cyano-2-naphthol (52927-22-7) → 6-(aminomethyl)naphthalen-2-ol (199387-77-4)

Conditions	Yield
With ammonia; hydrogen; nickel In methanol; water	100%

6-cyano-2-naphthol (52927-22-7) + D-cysteine hydrochloride (32443-99-5) → (S)-2-(6-hydroxynaphthalen-2-yl)-4,5-dihydrothiazole-4-carboxylic acid (122364-82-3)

Conditions	Yield
With sodium hydroxide In ethanol at 80℃; for 5h;	100%

6-cyano-2-naphthol (52927-22-7) + benzyl bromide (100-39-0) → 6-(benzyloxy)-2-cyanonaphthalene (66217-29-6)

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃; Williamson Ether Synthesis;	100%

6-cyano-2-naphthol (52927-22-7) + 4-Methylbenzyl bromide (104-81-4) → 6-((4-methylbenzyl)oxy)-2-naphthonitrile

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃; Williamson Ether Synthesis;	98%

1-Bromopentane (110-53-2) + 6-cyano-2-naphthol (52927-22-7) → 6-(pentyloxy)-2-naphthonitrile

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃; Williamson Ether Synthesis;	98%

6-cyano-2-naphthol (52927-22-7) + (Z)-tert-butyl (3-methyl-5-oxo-1-phenyl-1H-pyrazol-4(5H)-ylidene) carbamate → tert-butyl ((7aS,10aS)-3-cyano-7a-methyl-10-oxo-9-phenyl-7a,8,9,10-tetrahydro-10aHnaphtho[1',2':4,5]furo[2,3-c]pyrazol-10a-yl)carbamate

Conditions	Yield
With 3-((3,5-bis(trifluoromethyl)benzyl)amino)-4-(((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione In dichloromethane at 20℃; for 1h; stereoselective reaction;	98%

6-cyano-2-naphthol (52927-22-7) + (Z)-tert-butyl (3-methyl-5-oxo-1-(p-tolyl)-1H-pyrazol-4(5H)-ylidene) carbamate → tert-butyl ((7aS,10aS)-3-cyano-7a-methyl-10-oxo-9-(p-tolyl)-7a,8,9,10-tetrahydro-10aHnaphtho[1',2':4,5]furo[2,3-c]pyrazol-10a-yl)carbamate

Conditions	Yield
With 3-((3,5-bis(trifluoromethyl)benzyl)amino)-4-(((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)amino)cyclobut-3-ene-1,2-dione In dichloromethane at 20℃; for 1h; stereoselective reaction;	98%

6-cyano-2-naphthol (52927-22-7) + 4-methylphenylboronic acid (5720-05-8) → 6-p-tolyl-2-naphthonitrile (944042-22-2)

Conditions	Yield
Stage #1: 6-cyano-2-naphthol With potassium phosphate; triethylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In 1,4-dioxane at 100℃; for 3h; Inert atmosphere; Stage #2: 4-methylphenylboronic acid With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In 1,4-dioxane at 100 - 110℃; Suzuki-Miyaura coupling; Inert atmosphere;	97%

1,1-Diphenylmethanol (91-01-0) + 6-cyano-2-naphthol (52927-22-7) → 5-benzhydryl-6-hydroxy-2-naphthonitrile

Conditions	Yield
With stannic bromide In dichloromethane at 20℃; for 24h; Friedel-Crafts Alkylation; Inert atmosphere;	97%

trifluoromethylsulfonic anhydride (358-23-6) + 6-cyano-2-naphthol (52927-22-7) → trifluoromethanesulfonic acid 6-cyano-naphthalen-2-yl ester (145369-29-5)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 48h;	95%
With triethylamine In dichloromethane at 20℃;	93%
With pyridine In dichloromethane at 20℃;	79.1%

6-cyano-2-naphthol (52927-22-7) + 2,5,8,11-tetraoxatridecan-13-ol tosylate (62921-76-0) → tetraethylene glycol methyl 6-cyano-2-naphthyl ether

Conditions	Yield
With potassium hydroxide In 1,2-dimethoxyethane at 80℃; for 16h; Williamson etherification;	95%

6-cyano-2-naphthol (52927-22-7) + p-toluenesulfonyl chloride (98-59-9) → 6-cyanonaphthalen-2-yl 4-methylbenzenesulfonate (939822-86-3)

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃; Williamson Ether Synthesis;	95%
With potassium carbonate In acetonitrile at 80℃; Williamson Ether Synthesis;	95%
Stage #1: 6-cyano-2-naphthol With triethylamine In dichloromethane at 0℃; for 0.166667h; Stage #2: p-toluenesulfonyl chloride In dichloromethane at 20℃; for 4h;	90%
With dmap; triethylamine In dichloromethane at 20℃;

6-cyano-2-naphthol (52927-22-7) + 4-methoxycarbonylphenylboronic acid (99768-12-4) → methyl 4-(2-cyanonaphthalen-6-yl)benzoate (1290542-49-2)

Conditions	Yield
Stage #1: 6-cyano-2-naphthol With potassium phosphate; triethylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In 1,4-dioxane at 100℃; for 3h; Inert atmosphere; Stage #2: 4-methoxycarbonylphenylboronic acid With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In 1,4-dioxane at 100 - 110℃; Suzuki-Miyaura coupling; Inert atmosphere;	95%

6-cyano-2-naphthol (52927-22-7) + Diphenylphosphine oxide (4559-70-0) → 6-(diphenylphosphoryl)-2-naphthonitrile (1378042-96-6)

Conditions	Yield
Stage #1: 6-cyano-2-naphthol With potassium carbonate; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In acetonitrile at 100℃; for 3h; Inert atmosphere; Stage #2: Diphenylphosphine oxide With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In acetonitrile at 100℃; for 18h; Inert atmosphere;	95%

6-cyano-2-naphthol (52927-22-7) + [(1,10-phenanthroline)2Cu][O2CCF2Cl] → 6-(difluoromethoxy)-2-naphthonitrile (1261682-37-4)

Conditions	Yield
With sodium hydroxide; phenol In N,N-dimethyl-formamide at 75℃; for 4h; Sealed tube; Inert atmosphere;	95%

di-isopropyl azodicarboxylate (2446-83-5) + 6-cyano-2-naphthol (52927-22-7) → C19H21N3O5

Conditions	Yield
With 1,3,4-triphenyl-1,2,4-triazolium hexafluorophosphate; potassium tert-butylate In chloroform at 20℃; for 4h; Inert atmosphere;	95%

6-cyano-2-naphthol (52927-22-7) + 1-bromo-7-(4-bromophenylthio)heptane → 1-(4-bromophenylthio)-7-(6-cyano-2-naphthyloxy)heptane

Conditions	Yield
With 18-crown-6 ether; potassium carbonate In acetonitrile for 12h; Williamson Ether Synthesis; Reflux;	95%

6-cyano-2-naphthol (52927-22-7) + methanesulfonyl chloride (124-63-0) → 6-cyanonaphthalen-2-yl methanesulfonate (939822-84-1)

Conditions	Yield
Stage #1: 6-cyano-2-naphthol With triethylamine In toluene at 0℃; for 0.166667h; Stage #2: methanesulfonyl chloride In toluene at 20℃; for 12h;	93%
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;	91%

6-cyano-2-naphthol (52927-22-7) + allyl bromide (106-95-6) → 6-(allyloxy)-2-naphthonitrile

Conditions	Yield
With caesium carbonate In acetonitrile at 70℃; for 4h;	93%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;

1-bromo-butane (109-65-9) + 6-cyano-2-naphthol (52927-22-7) → 6-(butyloxy)-2-naphthonitrile (66217-27-4)

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃; Williamson Ether Synthesis;	93%
With potassium carbonate In acetonitrile at 80℃; Williamson Ether Synthesis;	93%
With potassium carbonate In acetonitrile at 80℃;	93%

1-ethynyl-2-methylbenzene (766-47-2) + 6-cyano-2-naphthol (52927-22-7) → 2-(o-tolyl)naphtho[2,1-b]furan-7-carbonitrile

Conditions	Yield
With boron trifluoride diethyl etherate; 2,3-dicyano-5,6-dichloro-p-benzoquinone In chloroform; toluene at 80℃; for 2h; Inert atmosphere; Schlenk technique;	93%

trifluorormethanesulfonic acid (1493-13-6) + 6-cyano-2-naphthol (52927-22-7) → trifluoromethanesulfonic acid 6-cyano-naphthalen-2-yl ester (145369-29-5)

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	93%

styrene (100-42-5) + 6-cyano-2-naphthol (52927-22-7) → 6-isocyano-1-(1-phenylethyl)naphthalen-2-ol

Conditions	Yield
With phosphorous acid In water; 1,2-dichloro-ethane at 100℃; for 18h; Schlenk technique; regioselective reaction;	93%

6-cyano-2-naphthol (52927-22-7) → 5-bromo-6-hydroxy-2-naphthonitrile (1192026-57-5)

Conditions	Yield
With bromine; acetic acid at 20℃;	92%
With bromine; acetic acid at 25℃; for 2.5h;
With N-Bromosuccinimide In acetonitrile at 0 - 20℃; for 4h; Inert atmosphere;
With pyridinium perbromide hydrobromide In acetonitrile at 0℃;
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 25℃; Inert atmosphere; Schlenk technique;

1-phenyl-3-(trimethylsilyl)prop-2-yn-1-yl acetate (866562-23-4) + 6-cyano-2-naphthol (52927-22-7) → (R)-2-methylene-1-phenyl-1,2-dihydronaphtho[2,1-b]furan-7-carbonitrile

Conditions	Yield
With (S)-N-[(3,5-dimethylphenyl)(pyridin-2-yl)methylene]-1-[2-(diphenylphosphino)phenyl]ethanamine; copper(II) acetate monohydrate; N-ethyl-N,N-diisopropylamine In methanol at -20℃; for 12h; Schlenk technique; Inert atmosphere; enantioselective reaction;	92%
Stage #1: 1-phenyl-3-(trimethylsilyl)prop-2-yn-1-yl acetate; 6-cyano-2-naphthol With (S)-N-[(3,5-dimethylphenyl)(pyridin-2-yl)methylene]-1-[2-(diphenylphosphino)phenyl]ethanamine; copper(II) acetate monohydrate In methanol for 1h; Inert atmosphere; Stage #2: With N-ethyl-N,N-diisopropylamine In methanol for 24h; Inert atmosphere;	90%

6-cyano-2-naphthol (52927-22-7) + C10H9BrOS2 → 1-(3-bromobenzoyl)-2-(methylthio)-4,5-dioxo-4,5-dihydronaphtho[2,1-b]thiophene-8-carbonitrile

Conditions	Yield
Stage #1: 6-cyano-2-naphthol With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper(II) bis(trifluoromethanesulfonate) In acetic acid at 100℃; for 0.166667h; Stage #2: C10H9BrOS2 In acetic acid at 100℃; for 4h; chemoselective reaction;	92%

6-cyano-2-naphthol (52927-22-7) + bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride (68641-49-6) → 6-cyanonaphthalen-2-yl bis(2-oxo-3-oxazolidinyl)phosphoramide (1231261-78-1)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 20℃; Inert atmosphere;	91%

Upstream product

• 15231-91-1 6-bromo-naphthalen-2-ol 
• 67886-70-8 2-cyano-6-methoxynaphthalene 
• 6343-72-2 6-bromonaphthalen-2-yl acetate 
• 544-92-3 copper(I) cyanide 
• 78119-71-8 benzoate of α,α,α',α'-tetrabromo-3,4-xylenol 
• 107-13-1 acrylonitrile 
• 78119-72-9 acetate of α,α,α',α'-tetrabromo-3,4-xylenol 
• 860363-16-2 6-acetoxy-[2]naphthonitrile 
• 5159-60-4 6-cyano-naphthalene-2-carboxylic acid 
• 145369-29-5 trifluoromethanesulfonic acid 6-cyano-naphthalen-2-yl ester 
• 939822-86-3 6-cyanonaphthalen-2-yl 4-methylbenzenesulfonate 
• 126747-14-6 4-cyanophenylboronic acid 
• 62529-01-5 6-hydroxynaphthalene-2-carboxamide 
• 16712-64-4 6-Hydroxy-2-naphthoic acid 

Downstream Products

• 82720-63-6 4-hexylphenylmethyl 6-cyano-2-naphthyl ether 
• 58200-88-7 6-Amidino-2-naphthol 
• 5159-60-4 6-cyano-naphthalene-2-carboxylic acid 
• 5088-91-5 6-cyano-naphthalene-2-carboxylic acid methyl ester 
• 259199-36-5 (E)-2-cyano-6-[2-(4-hydroxyphenyl)vinyl]naphthalene 
• 259199-34-3 6-[2-(4-methoxy-phenyl)-vinyl]-naphthalene-2-carbonitrile 
• 259199-37-6 (E)-tert-butyl 4-[2-(6-cyano-2-naphthyl)vinyl]phenoxyacetate 
• 259199-39-8 tert-butyl 4-[2-(6-cyano-2-naphthyl)ethyl]phenoxyacetate 
• 170737-24-3 tert-butyl 4-(6-cyano-2-naphthalenecarboxamido)phenoxyacetate 
• 82957-06-0 6-amidino-2-naphthol methanesulfonate 
• 82955-64-4 6-amidino-2-naphthyl benzoate MSA salt 
• 84729-83-9 Cyclohexanecarboxylic acid 6-carbamimidoyl-naphthalen-2-yl ester; compound with methanesulfonic acid 
• 82956-71-6 (E)-3-Phenyl-acrylic acid 6-carbamimidoyl-naphthalen-2-yl ester; compound with methanesulfonic acid 
• 82955-68-8 3-Methyl-benzoic acid 6-carbamimidoyl-naphthalen-2-yl ester; compound with methanesulfonic acid 

Relevant articles and documents

Process for Preparing Nafamostat Mesilate and Intermediate Thereof

The present invention provides a method for efficiently producing astaxmostat mesylate through a simple process and a method for producing 6 - amidino -2 - naphthol mesylate in high yield under mild conditions.

A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions

A general electrochemical system for reductive hydrodefunctionalization is described, employing the inexpensive and easily available triethylamine (Et3N) as a sacrificial reductant. This protocol is characterized by facile operation, sustainable conditions, and exceptionally wide substrate scope covering the cleavage of C-halogen, N-S, N-C, O-S, O-C, C-C and C-N bonds. Notably, the selectivity and capability of reduction can be conveniently switched by simple incorporation or removal of an alcohol as a co-solvent.

3-Aryl-1,2,4-oxadiazole Derivatives Active Against Human Rhinovirus

The human rhinovirus (hRV) is the causative agent of the common cold that often aggravates respiratory complications in patients with asthma or chronic obstructive pulmonary disease. The high rate of mutations and variety of serotypes are limiting the development of anti-hRV drugs, which emphasizes the need for the discovery of novel lead compounds. Previously, we identified antiviral compound 1 that we used here as the starting material for developing a novel compound series with high efficacy against hRV-A and -B. Improved metabolic stability was achieved by substituting an ester moiety with a 1,2,4-oxadiazole group. Specifically, compound 3k exhibited a high efficacy against hRV-B14, hRV-A21, and hRV-A71, with EC50 values of 66.0, 22.0, and 3.7 nM, respectively, and a relevant hepatic stability (59.6 and 40.7% compound remaining after 30 min in rat and human liver microsomes, respectively). An in vivo study demonstrated that 3k possessed a desirable pharmacokinetic profile with low systemic clearance (0.158 L·h-1·kg-1) and modest oral bioavailability (27.8%). Hence, 3k appears to be an interesting candidate for the development of antiviral lead compounds.