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91-59-8 Usage

Chemical properties

2-Naphthylamine is also known as β-Naphthylamine, it is white to pink shiny flaky crystal, it is volatile with water vapor. It is harmful, carcinogenic, the International Institute for Cancer Research (IARC) put benzidine, 2-Naphthylamine and 4-aminobiphenyl as a human carcinogen (evidence), we should be particularly careful. The relative density is 1.0614 (98/4℃), m.p. is 111~113℃, boiling point is 306℃. It is insoluble in water, but soluble in hot water, ethanol, ether and benzene etc. Aqueous solution is blue fluorescence. It can be reducted by heat silver nitrate ammonia solution. It is synthesized by 2-naphthol with ammonia and ammonium sulfite in a high pressure system. 2-Naphthylamine is an important dye intermediates, can be used in the manufacture of dyes, phthalocyanine dyes, reactive dyes (Reactive brilliant orange K-7R, active golden XG, active golden KM-G, Reactive Yellow KM-RN, big red group B) and J acid. It can also be used as organic analytical reagents and fluorescent indicator, and also as a synthesis of organic materials. It can enter from the respiratory tract, gastrointestinal tract and skin. Long-term exposure β-Naphthylamine can cause bladder cancer. It can cause weak stimulation of the skin, contact dermatitis, and methemoglobinemia. After the diagnosis of bladder cancer should be early surgery. Prevention should be carried out from the reform process firstly, 1-naphthylamine acetic acid should be used in place of β-Naphthylamine. Production equipment should be tightly closed to prevent the escape of toxic vapors and dusts. structure of 2-naphthylamine

Uses

Different sources of media describe the Uses of 91-59-8 differently. You can refer to the following data:
1. Amino and nitrite of Aminonaphthalene can form diazonium salt, and can turn into a variety of hydrocarbon derivatives of naphthalene, it can be used in the manufacture of dyes and organic synthesis, also used as indicators of organic analytical reagents and fluorescent agents.
2. It is listed as a known human carcinogen. Used in manufacturing of dyes, as antioxidant in rubber
3. An amine compound used for research purposes
4. 2-Naphthylamine was widely used in themanufacture of dyes and in rubber. Currently, its use is curtailed because of thehealth hazard.

Production method

Since the nitration of naphthalene can not obtain 2-nitro-naphthalene, so the producing methods is different from 1-Naphthylamine. 2-Naphthylamine is derived by 2-naphthol pressurized ammonia solution.

Chemical Properties

2-Naphthylamine is a white to red crystals with a faint, aromatic odor. Darkens in air to a reddish-purple color.

Physical properties

White crystals becomes purplish-red on exposure to air. Odor threshold concentrations ranged from 1.4 to 1.9 mg/m3 (quoted, Keith and Walters, 1992).

Production Methods

2-Naphthylamine was previously produced in substantial amounts for nearly 50 years but is no longer produced commercially. It is now used exclusively for research, and only rarely. It was formerly used in the manufacture of dyestuffs and as an antioxidant in the rubber industry. Prior to termination of its domestic production and use in the dye and rubber industries, an estimated 1000 U.S. workers were possibly exposed to 2-naphthylamine by inhalation and dermal routes. Currently, laboratory technicians and scientists who use the compound for research purposes may constitute the group with the greatest risk of potential exposure.

Definition

ChEBI: 2-naphthylamine is a naphthylamine carrying the amino group at position 2. It has a role as a carcinogenic agent.

Synthesis Reference(s)

Journal of the American Chemical Society, 75, p. 2014, 1953 DOI: 10.1021/ja01104a525Synthesis, p. 830, 1980 DOI: 10.1055/s-1980-29225

General Description

A white to reddish colored solid in the form of flakes. Slightly soluble in hot water and denser than water. Toxic by ingestion, inhalation and skin absorption. Used to make dyes and agricultural chemicals.

Air & Water Reactions

2-Naphthylamine darkens in air to a reddish-purple color (oxidizes). Slightly soluble in hot water and denser than water. Napthyl amines can be slowly hydrolyzed, releasing NH3 as a byproduct [N.L. Drake, Org. React. 1, (1942), 105].

Reactivity Profile

2-Naphthylamine is a weak base. 2-Naphthylamine is incompatible with strong oxidizing agents and strong acids. 2-Naphthylamine is also incompatible with nitrous acid. 2-Naphthylamine reduces warm ammoniacal silver nitrate.

Hazard

Toxic by ingestion, inhalation, skin absorption; a confirmed carcinogen. Causes bladder cancer.

Health Hazard

2-Naphthylamine poses a severe health haz ard because of its carcinogenicity. Admin istration of this compound by all routesresulted in cancers in various tissues in testanimals. It caused tumors in the kidney, blad der, liver, lungs, skin, and blood tissues.There is sufficient evidence that this com pound causes bladder cancer in humans aftera latent period of several years.The toxicity of 2-naphthylamine is lowto moderate. However, high doses can pro duce severe acute toxic effects. The routesof exposures are ingestion, skin contact, andinhalation of its dusts or vapors. The acutetoxic symptoms are similar to those produced by 1-naphthylamine: hemorrhagic cystitis or methemoglobinemia (causing hypoxiaor inadequate supply of oxygen to tissues),respiratory distress, and hematuria (blood inurine).LD50 value, oral (rats): 727 mg/kg.

Fire Hazard

Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

Safety Profile

Confirmed human carcinogen with experimental neoplastigenic and tumorigenic data. Long and continued exposure to even small amounts may produce tumors and cancers of the bladder. Poison by intraperitoneal route. Moderately toxic by ingestion. Experimental reproductive effects. Human mutation data reported. A very toxic chemical in any of its physical forms, such as flake, lump, dust, liquid, or vapor. It can be absorbed into the body through the lungs, the gastrointestinal tract, or the skin. Combustible when exposed to heat or flame. At elevated temperatures it evolves a vapor that is flammable and explosive. Incompatible with nitrous acid. When heated to decomposition it emits toxic fumes of NOx.

Potential Exposure

2-Naphthylamine is presently used only for research purposes. It is present as an impurity in α-naphthylamine. It is as an intermediate in the preparation of other compounds. 2-Naphthylamine was widely used in the manufacture of dyestuffs; as an antioxidant for rubber; and in rubber coated cables.

Carcinogenicity

2-Naphthylamine is known to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in humans.

Environmental fate

Photolytic. Low et al. (1991) reported that the photooxidation of aqueous primary amine solutions by UV light in the presence of titanium dioxide resulted in the formation of ammonium and nitrate ions. Chemical/Physical. Kanno et al. (1982) studied the aqueous reaction of 2-naphthylamine and other substituted aromatic hydrocarbons (aniline, toluidine, 1-naphthylamine, phenol, cresol, pyrocatechol, resorcinol, hydroquinone, and 1-naphthol) with hypochlorous acid in the presence of ammonium ion. They reported that the aromatic ring was not chlorinated as expected but was cleaved by chloramine forming cyanogen chloride. At lower pHs, the amount of cyanogen chloride formed increased (Kanno et al., 1982). 2-Naphthylamine will not hydrolyze because it does not contain a hydrolyzable functional group (Kollig, 1993). At influent concentrations of 10, 1.0, 0.1, and 0.01 mg/L, the GAC adsorption capacities were 300, 150, 75, and 37 mg/g, respectively (Dobbs and Cohen, 1980).

Shipping

UN1650 β-Naphthylamine, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Purification Methods

Sublime the amine at 180o in a stream of nitrogen. Crystallise it from hot water (charcoal) or *benzene. Dry it under vacuum in a drying pistol. The styphnate has m 194-195o (from EtOH). [Beilstein 12 H 1265, 12 III 2989, 12 IV 3122.] CARCINOGEN.

Incompatibilities

A weak base. Dust may form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Incompatible with nitrous acid.

Waste Disposal

Controlled incineration whereby oxides of nitrogen are removed from the effluent gas by scrubber, catalyst, or thermal device. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal.

Check Digit Verification of cas no

The CAS Registry Mumber 91-59-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 1 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 91-59:
(4*9)+(3*1)+(2*5)+(1*9)=58
58 % 10 = 8
So 91-59-8 is a valid CAS Registry Number.
InChI:InChI=1/C10H9N/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7H,11H2

91-59-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-naphthylamine

1.2 Other means of identification

Product number -
Other names 2-Naftylamine

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:91-59-8 SDS

91-59-8Synthetic route

2-nitronaphthalene
581-89-5

2-nitronaphthalene

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With LaCu0.67Si1.33; hydrogen In isopropyl alcohol at 120℃; under 22502.3 Torr; for 96h; Autoclave;96%
With hydrazine hydrate; zinc In methanol at 20℃; for 0.0833333h;94%
With borane-ammonia complex; copper(II) oxide In methanol at 50℃; for 0.333333h;94%
2-acetylaminonaphthalene
581-97-5

2-acetylaminonaphthalene

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With hydrogenchloride In ethanol; water Inert atmosphere; Reflux;96%
With hydrogenchloride; water In ethanol for 7h; Reflux;96%
With hydrogenchloride; water In ethanol for 1h; Reflux;92%
N-2(hydroxybenzyl)-β-naphthylamine
95639-94-4

N-2(hydroxybenzyl)-β-naphthylamine

A

C21H18O3

C21H18O3

B

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
at 230℃; under 10 Torr; for 0.0833333h; Product distribution; pyrolysis without solvent;A n/a
B 95%
2-naphthyl triflate
3857-83-8

2-naphthyl triflate

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
Stage #1: 2-naphthyl triflate With bis(bis(trimethylsilyl)amido)zinc(II); tri-tert-butyl phosphine; tetrabutylammomium bromide; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 50℃; for 9h;
Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether
95%
2-bromonaphthalene
580-13-2

2-bromonaphthalene

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With bis(triphenylphosphine)nickel(II) chloride; lithium hexamethyldisilazane In toluene at 100℃; for 2h; Glovebox; Sealed tube;95%
With ammonium hydroxide; copper(l) iodide; N,N-dimethylethylenediamine In dimethyl sulfoxide at 130℃; for 12h; Reagent/catalyst; Sealed tube; Inert atmosphere;89%
Stage #1: 2-bromonaphthalene With magnesium In tetrahydrofuran Inert atmosphere;
Stage #2: With C10H17NO In tetrahydrofuran; toluene at -78℃; for 2h; Inert atmosphere;
Stage #3: With ammonium chloride In tetrahydrofuran; water; toluene Reagent/catalyst; Inert atmosphere;
89%
1,1,1,3,3,3-hexamethyl-2-naphthalen-2-yl-disilazane

1,1,1,3,3,3-hexamethyl-2-naphthalen-2-yl-disilazane

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With hydrogenchloride; water In methanol at 20℃; for 1h;94%
With hydrogenchloride In diethyl ether
β-naphthol
135-19-3

β-naphthol

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With sulfur dioxide; ammonia In water for 0.5h; Bucherer reaction; Irradiation;93%
With ammonium hydroxide; ammonium sulfite monohydrate In water at 180℃;93%
With sodium tetrahydroborate; 5%-palladium/activated carbon; hydrazine hydrate; lithium hydroxide In 1,4-dioxane at 170℃; for 16h; Molecular sieve; Inert atmosphere;85%
2-chloronaphthalene
91-58-7

2-chloronaphthalene

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With ammonium sulfate; (R)-(-)-1-[(SP)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; bis(tri-ortho-tolylphosphine)palladium(0); sodium t-butanolate In 1,4-dioxane at 100℃; for 12h; Inert atmosphere; Glovebox;93%
With ammonium sulfate; C39H45FeNNiP2; sodium t-butanolate In 2-methyltetrahydrofuran at 100℃; for 7h; Reagent/catalyst; Solvent; Inert atmosphere; Glovebox; Autoclave;86%
naphthalene-2-boronic acid
32316-92-0

naphthalene-2-boronic acid

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With sodium hydroxide; hydroxylamine-O-sulfonic acid In acetonitrile at 20℃; for 16h;92%
With sodium hydroxide; hydroxylamine-O-sulfonic acid In water; acetonitrile at 100℃; for 0.25h; Microwave irradiation;87%
With copper(I) oxide; ammonium hydroxide; air In methanol at 20℃; for 16h;86%
With caesium carbonate; O-(2,4-dinitrophenyl)hydroxylamine In toluene at 25℃; for 24h; Temperature; Solvent; Reagent/catalyst; Inert atmosphere;84%
With N-Bromosuccinimide; N-methoxylamine hydrochloride; bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile at 20℃;74%
3-dicyanomethylene-3,4-dihydro-1H-naphth<2,1-d><1,3>oxazin-1-one
79894-40-9

3-dicyanomethylene-3,4-dihydro-1H-naphth<2,1-d><1,3>oxazin-1-one

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With hydrogenchloride In water for 55h; Heating;91%
2-hydrazinonaphthalene
2243-57-4

2-hydrazinonaphthalene

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With titanium(III) chloride; water In ethanol for 4h; Reflux; Inert atmosphere;91%
With titanium tetrachloride; magnesium In tetrahydrofuran at 20℃; Inert atmosphere;90%
With Molybdenum(III) Reagent In tetrahydrofuran; water for 3.5h; Heating;64%
2-iodonaphthalene
612-55-5

2-iodonaphthalene

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With ammonium hydroxide; copper(l) iodide In dimethyl sulfoxide at 130℃; for 12h; Sealed tube; Inert atmosphere;91%
Multi-step reaction with 2 steps
1: chlorotris(triphenylphosphine)cobalt(I); bis[2-(diphenylphosphino)phenyl] ether / toluene / 12 h / 100 °C
2: hydrogenchloride; water / methanol / 1 h / 20 °C
View Scheme
2-azidonaphthalene
20937-86-4

2-azidonaphthalene

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With dicobalt octacarbonyl In water at 20℃; for 3.5h;90%
With water for 5h; Inert atmosphere; UV-irradiation; Sealed tube; chemoselective reaction;48%
With (pyrolysis) In decalin at 122.1 - 152.5℃; Kinetics;
N-(diphenylmethylene)-2-naphthaleneamine
200712-40-9

N-(diphenylmethylene)-2-naphthaleneamine

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran at 20℃; Catalytic behavior; Reagent/catalyst; Solvent;89%
With hydrogenchloride In tetrahydrofuran; water at 20℃;25 mg
C13H13NO3S

C13H13NO3S

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With methanol; toluene-4-sulfonic acid at 23℃; for 24h; Inert atmosphere;89%
methyl 2-naphthyl ketone
93-08-3

methyl 2-naphthyl ketone

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With methanesulfonic acid; O-benzenesulfonyl-acetohydroxamic acid ethyl ester In ethanol at 20℃; for 24h; Reagent/catalyst; Solvent;89%
With methanol; O-benzenesulfonyl-acetohydroxamic acid ethyl ester; toluene-4-sulfonic acid at 23℃; for 24h; Inert atmosphere;81%
2-naphthyl diethylcarbamate
61912-14-9

2-naphthyl diethylcarbamate

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With ammonium sulfate; C43H60ClFeNNiP2; sodium t-butanolate In o-xylene at 100℃; for 16h; Catalytic behavior; Solvent; Reagent/catalyst; Temperature; Inert atmosphere; Autoclave;87%
2,2'-azonaphthalene
582-08-1

2,2'-azonaphthalene

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With ammonium acetate; zinc In methanol at 20℃; for 0.05h;86%
2-Vinylnaphthalene
827-54-3

2-Vinylnaphthalene

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With methanesulfonic acid; trimethylsilylazide In tetrachloromethane at 80℃; for 4h;85%
2-nitronaphthalene
581-89-5

2-nitronaphthalene

A

naphthalene
91-20-3

naphthalene

B

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With formic acid In acetonitrile at 20℃; for 0.25h; Irradiation;A 17%
B 83%
naphthalen-2-yl tosylate
7385-85-5

naphthalen-2-yl tosylate

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; N-[2-(di(1-adamantyl)phosphino)phenyl]morpholine; ammonia; sodium t-butanolate In 1,4-dioxane at 20℃; for 20h; Inert atmosphere; chemoselective reaction;83%
With bis(tri-ortho-tolylphosphine)palladium(0); (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 50℃; for 24h; Inert atmosphere;67%
2-(naphthalen-2-yloxy)propanamide
82162-90-1

2-(naphthalen-2-yloxy)propanamide

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 140℃; for 6h; Green chemistry;81%
With potassium hydroxide at 140℃;111.6 mg
naphthalene-2-carboxylate
93-09-4

naphthalene-2-carboxylate

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With hydroxylamine hydrochloride Heating;80%
Stage #1: naphthalene-2-carboxylate With PPA; hydroxylamine hydrochloride at 20 - 160℃;
Stage #2: With potassium hydroxide In water
34%
With hydrogenchloride; PPA; hydroxylamine
1H-Naphtho<2,3-d><1,2,3>triazole
269-12-5

1H-Naphtho<2,3-d><1,2,3>triazole

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
In tetrahydrofuran; methanol for 1h; Irradiation;80%
naphthalene
91-20-3

naphthalene

A

1-amino-naphthalene
134-32-7

1-amino-naphthalene

B

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With tris-(2-chloro-ethyl)-amine; trifluorormethanesulfonic acid; trifluoroacetic acid In chloroform at 25℃; for 12h;A 77%
B 10%
With aluminium trichloride; hydroxylamine hydrochloride
Stage #1: naphthalene With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; N-(trifluoromethylsulfonyloxy)pyridinium trifluoromethanesulfonate In acetonitrile for 1.5h; Sealed tube; Inert atmosphere; Irradiation;
Stage #2: With piperidine In acetonitrile at 20℃; for 14h; Sealed tube; Inert atmosphere; Overall yield = 25 mg;
(NH4)2SO3

(NH4)2SO3

pyrographite
7440-44-0

pyrographite

β-naphthol
135-19-3

β-naphthol

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With hydrogenchloride; ammonium hydroxide In ethanol; water; toluene77%
1,2,3,4-tetrahydronaphthalen-2-one
530-93-8

1,2,3,4-tetrahydronaphthalen-2-one

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With ethene; 5%-palladium/activated carbon; ammonium acetate In acetonitrile at 90℃; under 760.051 Torr; for 3h; Reagent/catalyst; Schlenk technique;75%
potassium 2-naphthyltrifluoroborate

potassium 2-naphthyltrifluoroborate

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With caesium carbonate; O-(2,4-dinitrophenyl)hydroxylamine In water; toluene at 50℃; for 30h;74%
With sodium hydroxide; hydroxylamine-O-sulfonic acid In water; acetonitrile at 100℃; for 0.25h; Microwave irradiation;55%
2-(1-naphthyl)[1,3,2]dioxaborolane

2-(1-naphthyl)[1,3,2]dioxaborolane

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Conditions
ConditionsYield
With caesium carbonate; O-(2,4-dinitrophenyl)hydroxylamine In 1,4-dioxane; water at 100℃; for 24h;73%
furfural
98-01-1

furfural

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

(E)-1-(furan-2-yl)-N-(naphthalen-2-yl)methanimine
6233-18-7

(E)-1-(furan-2-yl)-N-(naphthalen-2-yl)methanimine

Conditions
ConditionsYield
In diethyl ether at 20℃; Inert atmosphere; Molecular sieve; Darkness;100%
chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

ethyl (naphthalen-2-yl)carbamate
5255-69-6

ethyl (naphthalen-2-yl)carbamate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 1h;100%
With sodium carbonate; benzene
With diethyl ether
at 130℃; for 0.0833333h; microwave irradiation;
With sodium hydrogencarbonate In dichloromethane; chloroform; water
acrylonitrile
107-13-1

acrylonitrile

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

3-(2-naphthylamino)propionitrile
38266-46-5

3-(2-naphthylamino)propionitrile

Conditions
ConditionsYield
With silica-supported aluminum chloride at 60℃; for 20h; Michael addition; Neat (no solvent);100%
With acetic acid at 60℃; for 20h;62%
With acetic acid; copper(l) chloride
1,1,1-trifluoro-4,4-diethoxy-3-buten-2-one
40657-29-2

1,1,1-trifluoro-4,4-diethoxy-3-buten-2-one

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

(E)-4-Ethoxy-1,1,1-trifluoro-4-(naphthalen-2-ylamino)-but-3-en-2-one
128648-68-0

(E)-4-Ethoxy-1,1,1-trifluoro-4-(naphthalen-2-ylamino)-but-3-en-2-one

Conditions
ConditionsYield
In acetonitrile for 18h; Ambient temperature;100%
N,N-diethylaminomethylene-1,1,1,5,5,5-hexafluoroacetylacetone
74888-65-6

N,N-diethylaminomethylene-1,1,1,5,5,5-hexafluoroacetylacetone

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

1,1,1,5,5,5-Hexafluoro-3-(naphthalen-2-ylaminomethylene)-pentane-2,4-dione

1,1,1,5,5,5-Hexafluoro-3-(naphthalen-2-ylaminomethylene)-pentane-2,4-dione

Conditions
ConditionsYield
With iron(III) chloride100%
N-α-Tosyl-4-cyanphenylalaninchlorid
80852-48-8

N-α-Tosyl-4-cyanphenylalaninchlorid

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

3-(4-Cyano-phenyl)-N-naphthalen-2-yl-2-(toluene-4-sulfonylamino)-propionamide
80852-67-1

3-(4-Cyano-phenyl)-N-naphthalen-2-yl-2-(toluene-4-sulfonylamino)-propionamide

Conditions
ConditionsYield
In benzene for 1.5h; Ambient temperature;100%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

naphthalen-2-yl-carbamic acid tert-butyl ester
454713-45-2

naphthalen-2-yl-carbamic acid tert-butyl ester

Conditions
ConditionsYield
In methanol at 100℃; for 6h;100%
Stage #1: di-tert-butyl dicarbonate With molybdenium(VI) dioxodichloride In dichloromethane at 20℃; for 0.5h;
Stage #2: naphthalen-2-ylamine In dichloromethane at 20℃; for 36h;
95%
With glycerol at 20℃; for 0.75h; Green chemistry; chemoselective reaction;94%
2-(2-nitroethenyl)thiophene
874-84-0, 34312-77-1

2-(2-nitroethenyl)thiophene

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

C16H14N2O2S
1140448-29-8

C16H14N2O2S

Conditions
ConditionsYield
In water at 20℃; Michael condensation;100%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

2-naphthylisocyanate
2243-54-1

2-naphthylisocyanate

Conditions
ConditionsYield
With sodium hydrogencarbonate In dichloromethane at 0℃; for 1.25h;100%
In dichloromethane at 0℃; Inert atmosphere;
In toluene at 95℃;
3,5-dichloro-[1,2,4]thiadiazole
2254-88-8

3,5-dichloro-[1,2,4]thiadiazole

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

C12H8ClN3S
1421694-69-0

C12H8ClN3S

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In cyclohexanol at 20 - 80℃; Reagent/catalyst; Temperature; Solvent; regioselective reaction;100%
acetic anhydride
108-24-7

acetic anhydride

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

2-acetylaminonaphthalene
581-97-5

2-acetylaminonaphthalene

Conditions
ConditionsYield
With vanadyl triflate In dichloromethane at 20℃; for 8h;99%
Stage #1: acetic anhydride With molybdenium(VI) dioxodichloride In dichloromethane at 20℃; for 0.5h;
Stage #2: naphthalen-2-ylamine In dichloromethane at 20℃; for 0.5h;
98%
With copper(II) ferrite In neat (no solvent) at 20℃; for 0.0833333h; Green chemistry;95%
benzaldehyde
100-52-7

benzaldehyde

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

benzyl-2-naphthylamine
13672-18-9

benzyl-2-naphthylamine

Conditions
ConditionsYield
With (2,6-dichlorophenyl)bis(2,3,5,6-tetrafluorophenyl)borane; hydrogen In tetrahydrofuran at 100℃; under 15201 Torr; for 6h; Sealed tube; Molecular sieve; Autoclave; Green chemistry;99%
With hydrogenchloride; platinum Hydrogenation;
With hydrogen In water at 80℃; under 22502.3 Torr; for 8h; Inert atmosphere; Autoclave; Green chemistry;79 %Chromat.
naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

1-bromo-2-naphthylamine
20191-75-7

1-bromo-2-naphthylamine

Conditions
ConditionsYield
With N-Bromosuccinimide; sulfonic acid functionalized silica In diethyl ether; acetonitrile at 20℃; for 0.0166667h;99%
With N-Bromosuccinimide at 20℃; for 0.0333333h; regioselective reaction;99%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃; for 1.5h;98%
2-phenylsulfanyl-[1,4]benzoquinone
18232-03-6

2-phenylsulfanyl-[1,4]benzoquinone

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

A

2-(phenylthio)benzene-1,4-diol
18231-96-4

2-(phenylthio)benzene-1,4-diol

B

2-(Naphthalen-2-ylamino)-5-phenylsulfanyl-[1,4]benzoquinone
128920-14-9

2-(Naphthalen-2-ylamino)-5-phenylsulfanyl-[1,4]benzoquinone

Conditions
ConditionsYield
In ethanol for 12h; Ambient temperature;A n/a
B 99%
2-chloroacenaphthylene-1-carbaldehyde
13152-84-6

2-chloroacenaphthylene-1-carbaldehyde

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

acenaphtho<1,2-b>benzoquinoline
238-05-1

acenaphtho<1,2-b>benzoquinoline

Conditions
ConditionsYield
With hydrogenchloride In ethanol Heating;99%
2,2-dimethylpropanoic anhydride
1538-75-6

2,2-dimethylpropanoic anhydride

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

N-naphthalen-2-yl-2,2-dimethyl-propanamide
201015-17-0

N-naphthalen-2-yl-2,2-dimethyl-propanamide

Conditions
ConditionsYield
With vanadyl triflate In dichloromethane at 20℃; for 42h;99%
Stage #1: 2,2-dimethylpropanoic anhydride With molybdenium(VI) dioxodichloride In dichloromethane at 20℃; for 0.5h;
Stage #2: naphthalen-2-ylamine In dichloromethane at 20℃; for 2.5h;
97%
With triethylamine In ethyl acetate at 80℃; Inert atmosphere; Sealed tube;40%
benzoic acid anhydride
93-97-0

benzoic acid anhydride

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

N-(naphthalen-2-yl)benzamide
18271-22-2

N-(naphthalen-2-yl)benzamide

Conditions
ConditionsYield
Stage #1: benzoic acid anhydride With molybdenium(VI) dioxodichloride In dichloromethane at 20℃; for 0.5h;
Stage #2: naphthalen-2-ylamine In dichloromethane at 20℃; for 50h;
99%
1,2-dimethoxyethane
110-71-4

1,2-dimethoxyethane

niobium pentachloride
10026-12-7

niobium pentachloride

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

Nb(N-2-naphthyl)Cl3(1,2-dimethoxyethane)
189813-51-2

Nb(N-2-naphthyl)Cl3(1,2-dimethoxyethane)

Conditions
ConditionsYield
With ZnCl2; pyridine In dichloromethane; toluene N2-atmosphere; addn. of 1 equiv. aniline and pyridine (in CH2Cl2) to mixt. of TaCl5 and DME with excess ZnCl2 (-40°C), stirring for 17 h; filtration, concn. (vac.), recrystn. (CH2Cl2/pentane); elem. anal.;99%
6,8-dimethoxy-1,3-dimethyl-2-benzopyrilium tetrafluoroborate

6,8-dimethoxy-1,3-dimethyl-2-benzopyrilium tetrafluoroborate

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

N,2'-naphthyl-6,8-dimethoxy-1,3-dimethylisoquinolinium tetrafluoroborate

N,2'-naphthyl-6,8-dimethoxy-1,3-dimethylisoquinolinium tetrafluoroborate

Conditions
ConditionsYield
In acetic acid at 20℃; for 8h;99%
naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

acetone
67-64-1

acetone

N-isopropylnaphthalen-2-amine
53622-39-2

N-isopropylnaphthalen-2-amine

Conditions
ConditionsYield
With iridium bromide; formic acid; zinc In water at 30℃; for 20h;99%
With sodium tetrahydroborate; sodium acetate; acetic acid In ethanol; water at 0 - 25℃;
copper diacetate
142-71-2

copper diacetate

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

2-acetylaminonaphthalene
581-97-5

2-acetylaminonaphthalene

Conditions
ConditionsYield
In acetic acid for 2.75h; Reflux; chemoselective reaction;99%
4-pentynoic acid
6089-09-4

4-pentynoic acid

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

N-(2-naphthylmethyl)pent-4-ynamide
1415976-72-5

N-(2-naphthylmethyl)pent-4-ynamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;99%
naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

3,4-dimethoxybenzoic acid chloride
3535-37-3

3,4-dimethoxybenzoic acid chloride

3,4-dimethoxy-N-(naphthalen-2-yl)benzamide
331270-79-2

3,4-dimethoxy-N-(naphthalen-2-yl)benzamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;99%
p-chlorophenylsulfonyl hydrazide
2751-25-9

p-chlorophenylsulfonyl hydrazide

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

1-((4-chlorophenyl)thio)naphthalen-2-amine

1-((4-chlorophenyl)thio)naphthalen-2-amine

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; propylene glycol dimethyl ether dimer at 100℃; for 12h; Schlenk technique;99%
With iodine; acetic acid In tetrahydrofuran at 100℃; for 5h;84%
p-bromophenylsulfonyl hydrazide
2297-64-5

p-bromophenylsulfonyl hydrazide

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

1-((4-bromophenyl)thio)naphthalen-2-amine

1-((4-bromophenyl)thio)naphthalen-2-amine

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; propylene glycol dimethyl ether dimer at 100℃; for 12h; Schlenk technique;99%
With iodine; acetic acid In tetrahydrofuran at 100℃; for 5h;86%
diphenyl diselenide
1666-13-3

diphenyl diselenide

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

1-(phenylselanyl)naphthalen-2-amine

1-(phenylselanyl)naphthalen-2-amine

Conditions
ConditionsYield
With iron(III) chloride; potassium iodide In dimethyl sulfoxide at 110℃; for 24h;99%
With iodine; dimethyl sulfoxide In neat (no solvent) at 80℃; for 24h; Sealed tube; Green chemistry; regioselective reaction;80%
With tert.-butylhydroperoxide; N-iodo-succinimide In water; N,N-dimethyl-formamide at 70℃; for 0.3h; regioselective reaction;65%
With Rose Bengal lactone In acetonitrile at 20℃; for 6h; Schlenk technique; Irradiation;43%
naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

diphenyldisulfane
882-33-7

diphenyldisulfane

1-(phenylsulfenyl)naphthalen-2-amine

1-(phenylsulfenyl)naphthalen-2-amine

Conditions
ConditionsYield
With iodine; dimethyl sulfoxide In neat (no solvent) at 80℃; for 0.5h; Sealed tube; Microwave irradiation; Green chemistry; regioselective reaction;99%
With iron(III) chloride; potassium iodide In dimethyl sulfoxide at 110℃; for 24h;98%
With tetra-(n-butyl)ammonium iodide; propylene glycol dimethyl ether dimer at 100℃; for 12h; Schlenk technique;97%
3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

2-(3-methoxyphenyl)naphtho[2,1-d]thiazole

2-(3-methoxyphenyl)naphtho[2,1-d]thiazole

Conditions
ConditionsYield
With sulfur; ammonium iodide In dimethyl sulfoxide; chlorobenzene at 140℃; for 24h; Molecular sieve;99%
sodium tetraphenyl borate
143-66-8

sodium tetraphenyl borate

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

N-Phenyl-2-naphthylamine
135-88-6

N-Phenyl-2-naphthylamine

Conditions
ConditionsYield
With copper(II) acetate monohydrate; triethylamine In acetonitrile at 20℃; for 24h; Chan-Lam Coupling;99%
tert-butyl (1-benzyl-2-oxoindolin-3-ylidene)carbamate
1373942-84-7

tert-butyl (1-benzyl-2-oxoindolin-3-ylidene)carbamate

naphthalen-2-ylamine
91-59-8

naphthalen-2-ylamine

(R)-tert-butyl (1-benzyl-3-(naphthalen-2-ylamino)-2-oxoindolin-3-yl)carbamate

(R)-tert-butyl (1-benzyl-3-(naphthalen-2-ylamino)-2-oxoindolin-3-yl)carbamate

Conditions
ConditionsYield
With C42H44N6O2 In dichloromethane at -20℃; for 2h; Temperature; enantioselective reaction;99%
With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((1S,2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)urea In tert-butyl methyl ether at -30℃; for 6h; enantioselective reaction;97%

91-59-8Relevant articles and documents

Mutagenicity and aromatic amine content of fumes from heated cooking oils produced in Taiwan

Chiang, Tai-An,Pei-Fen, Wu,Ying, Liao Su,Wang, Li-Fang,Ko, Ying Chin

, p. 125 - 134 (1999)

According to toxicological studies, there are several unidentified mutagens derived from cooking oil fumes appearing in kitchens of Chinese homes where women daily prepare food. Data are limited to an analysis of aromatic amines from cooking oil fumes, which are known to be carcinogenic for bladder cancer. Fume samples from three different commercial cooking oils frequently used in Taiwan were collected and analysed for mutagenicity in the almonella/microsome assay. Aromatic amines were extracted from the samples and identified by HPLC and confirmed by gas chromatography/mass spectrometry (GC/MS). Extracts from three cooking oil fumes were found to be mutagenic in the presence of S-9 mix. All samples contained 2-naphthylamine (2-NA) and 4-aminobiphenyl (4-ABP). Concentrations of 2-NA and 4-ABP were 31.5 and 35.7 μg/m3 in fumes from sunflower oil, 31.9 and 26.4 mg/m3 in vegetable oil, and 48.3 and 23.3 μg/m3 in refined-lard oil, respectively. Mutagenicities of the three cooking oil condensates were significantly reduced (P 0.05) by adding the antioxidant catechin (CAT) into the oils before heating. Significant difference existed between the amounts of aromatic amines with and without adding CAT (P 0.05). These results indicate that exposure to cooking oil fumes in Taiwan might be an important but controllable risk factor in the aetiology of bladder cancer. 1999 Published by Elsevier Science Ltd. All rights reserved.

Novel aminopeptidase specific for glycine from Actinomucor elegans.

Ito, Kiyoshi,Ma, Xiaohang,Azmi, Nik,Huang, Hua-Shan,Fujii, Mikio,Yoshimoto, Tadashi

, p. 83 - 88 (2003)

Glycyl aminopeptidase was purified 600-fold from a cell extract of Actinomucor elegans by ammonium sulfate fractionation and sequential chromatography on DEAE-Toyopearl, Toyopearl HW65C, and FPLC-Superdex 200 HR, with recovery of 3.3% of the activity. The enzyme highly specifically hydrolyzed Gly-X (amino acid, peptide, or arylamide) bonds. The enzyme hydrolyzed other amino acid residues but at a rate of less than one fifth that with Gly. The order was Gly >> Ala >> Met > Arg > Ser > Leu. The Km value for glycyl-2-naphthylamide was 0.24 mM. The enzyme was most active at pH 8.0 with glycyl-2-naphthylamide as the substrate and its optimal temperature was 40 degrees C. The enzyme was inhibited by iodoacetic acid, and p-chloromercuribenzoate but not done by diisopropylfluorophosphate, o-phenanthroline, or EDTA. Magnesium and calcium had no effect on enzymic activity, but the activity was suppressed by cadmium, zinc, and copper ions. The molecular mass was estimated to be 320 kDa by gel filtration on FPLC-Superdex 200 HR and 56.5 kDa by SDS-PAGE, so the enzyme probably was a hexamer.

Inhibitory effects of quaternary ammonium compounds on lysosomal degradation of endogenous proteins

Matsumoto,Watanabe,Suga,Fujitani

, p. 516 - 518 (1989)

-

Composite of β-cyclodextrin and bentonite clay: a promising support for Pd immobilization and developing a catalyst for hydrogenation of nitroarenes under mild reaction condition

Koohestani, Fatemeh,Sadjadi, Samahe

supporting information, (2020/12/21)

In attempt to take advantages of naturally occurring compounds for the catalysis, a novel composite composed of β-cyclodextrin, dendrimer and bentonite clay is fabricated and utilized as a support for the stabilization of Pd nanoparticles. To prepare the support, bentonite is amino functionalized and then successively reacted with 2,4,6-trichloro-1,3,5-triazine and ethylenediamine to furnish a dendrimer of generation II on bentonite. Afterwards, the terminal functionalities of the dendrimer were adorned with cyclodextrin. Bentonite played role in the heterogenation of the catalyst and improvement of the stability of the composite while, cyclodextrins served as molecular shuttles and capping agent for the as-prepared Pd nanoparticles. Dendrimer with multi nitrogen atoms, on the other hand, improved Pd anchoring through electrostatic interactions. The catalyst was applied for the hydrogenation of nitroarenes under mild reaction condition in aqueous media in a selective manner. Notably, the catalyst could be recovered and reused repeatedly.

Selective Carbon-Carbon Bond Amination with Redox-Active Aminating Reagents: A Direct Approach to Anilines?

Qiu, Xu,Wang, Yachong,Su, Lingyu,Jin, Rui,Song, Song,Qin, Qixue,Li, Junhua,Zong, Baoning,Jiao, Ning

supporting information, p. 3011 - 3016 (2021/09/13)

Amines are among the most fundamental motifs in chemical synthesis, and the introduction of amine building blocks via selective C—C bond cleavage allows the construction of nitrogen compounds from simple hydrocarbons through direct skeleton modification. Herein, we report a novel method for the preparation of anilines from alkylarenes via Schmidt-type rearrangement using redox-active amination reagents, which are easily prepared from hydroxylamine. Primary amines and secondary amines were prepared from corresponding alkylarenes or benzyl alcohols under mild conditions. Good compatibility and valuable applications of the transformation were also displayed.

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