2-Naphthylhydrazine hydrochloride supplier

Name
2-Naphthylhydrazine hydrochloride
EINECS
CAS No. 2243-58-5
Article Data8
CAS DataBase
Density 1.215g/cm3
Solubility
Melting Point 123 °C
Formula C₁₀H₁₀N₂^.HCl
Boiling Point 362.9 °C at 760 mmHg
Molecular Weight 194.664
Flash Point 203.9 °C
Transport Information
Appearance
Safety
Risk Codes R36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Hydrazine,(2-naphthyl)-, hydrochloride (6CI,7CI,8CI);Hydrazine, 2-naphthalenyl-,monohydrochloride (9CI);2-Hydrazinonaphthalene monohydrochloride;2-naphthalenyl hydrazine hydrochloride;
PSA 38.05000
LogP 3.70070

Synthetic route

: 580-13-2
2-bromonaphthalene

: 2243-58-5
2-naphthylhydrazine hydrochloride

Conditions

Conditions	Yield
Stage #1: 2-bromonaphthalene With potassium phosphate; copper(l) iodide; N,N′-bis(2,6-dimethylphenyl)oxalamide; cetyltrimethylammonim bromide In water at 80℃; for 0.25h; Schlenk technique; Inert atmosphere; Sealed tube; Stage #2: With hydrazine hydrate In water at 80℃; Inert atmosphere; Schlenk technique; Sealed tube; Stage #3: With hydrogenchloride In water pH=3 - 4; Inert atmosphere; Schlenk technique; Sealed tube;	70%
Multi-step reaction with 2 steps 1.1: s-BuLi / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C 1.2: tetrahydrofuran; cyclohexane / -78 - 20 °C 2.1: HCl / dioxane; propan-2-ol / 0.5 h / 60 °C View Scheme

Yield

Stage #1: 2-bromonaphthalene With potassium phosphate; copper(l) iodide; N,N′-bis(2,6-dimethylphenyl)oxalamide; cetyltrimethylammonim bromide In water at 80℃; for 0.25h; Schlenk technique; Inert atmosphere; Sealed tube;
Stage #2: With hydrazine hydrate In water at 80℃; Inert atmosphere; Schlenk technique; Sealed tube;
Stage #3: With hydrogenchloride In water pH=3 - 4; Inert atmosphere; Schlenk technique; Sealed tube;

70%

Multi-step reaction with 2 steps
1.1: s-BuLi / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C
1.2: tetrahydrofuran; cyclohexane / -78 - 20 °C
2.1: HCl / dioxane; propan-2-ol / 0.5 h / 60 °C
View Scheme

: 91-59-8
naphthalen-2-ylamine

: 2243-58-5
2-naphthylhydrazine hydrochloride

Conditions

Conditions	Yield
Stage #1: naphthalen-2-ylamine With hydrogenchloride; sodium nitrite In water for 1h; Cooling with ice; Stage #2: With tin(ll) chloride In water for 3.5h; Cooling with ice;	63%
With hydrogenchloride; tin(ll) chloride; sodium nitrite 1.) -5 deg C to 0 deg C, 0.75 h, 2.) 1 h; Multistep reaction;
Stage #1: naphthalen-2-ylamine With hydrogenchloride; sodium nitrite In water at 0℃; for 0.416667h; Stage #2: With hydrogenchloride; tin(ll) chloride In water at 0℃; for 0.5h;
Stage #1: naphthalen-2-ylamine With hydrogenchloride; sodium nitrite In water at -5 - 0℃; for 0.5h; Stage #2: With tin(ll) chloride In water at 0 - 20℃;

: 868394-40-5
di-tert-butyl 1-(naphthalene-2-yl)hydrazine-1,2-dicarboxylate

: 2243-58-5
2-naphthylhydrazine hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; isopropyl alcohol at 60℃; for 0.5h;

: 135-19-3
β-naphthol

: 2243-58-5
2-naphthylhydrazine hydrochloride

Conditions

Conditions	Yield
With hydrazine hydrate for 20h; Reflux;	296.5 g

: 1356907-02-2
2-(2,4-dimethyl-1,3-dioxolan-2-yl)acetic acid

: 2243-58-5
2-naphthylhydrazine hydrochloride

: 1192140-15-0
5-methyl-1-(naphthalen-2-yl)-1H-pyrazol-3-ol

Conditions

Conditions	Yield
Stage #1: 2-(2,4-dimethyl-1,3-dioxolan-2-yl)acetic acid With chloroformic acid ethyl ester; triethylamine In dichloromethane at 0℃; for 0.333333h; Stage #2: 2-naphthylhydrazine hydrochloride With triethylamine In dichloromethane at 20℃; for 3h; Product distribution / selectivity;	97%

: 2243-58-5
2-naphthylhydrazine hydrochloride

: cis-crotonin

: C29H29NO3

Conditions

Conditions	Yield
With acetic acid In ethanol for 1h; Reflux;	96%

: 2243-58-5
2-naphthylhydrazine hydrochloride

: 4381-25-3
S-methyl-S-phenylsulfoximine

: N-(2-naphthyl)-S-methyl-S-phenylsulfoximine

Conditions

Conditions	Yield
With oxygen; potassium acetate; copper(I) bromide In acetone at 20℃; for 12h; Schlenk technique;	88%

: 2243-58-5
2-naphthylhydrazine hydrochloride

: potassium phenyltrifluoborate

: 612-94-2
2-phenylnaphthalene

Conditions

Conditions	Yield
With diamminedichloropalladium(II); copper(II) choride dihydrate; potassium carbonate In water at 25℃; for 12h; Suzuki Coupling; Green chemistry;	87%

: 2243-58-5
2-naphthylhydrazine hydrochloride

: 78-93-3
butanone

: 55970-05-3
2,3-dimethylbenz<4,5>indole

Conditions

Conditions	Yield
With 4-methylbenzenesulfonic acid-based ionic liquid supported on silica gel In ethanol at 20℃; for 5h; Fischer Indole Synthesis;	86%
With acetic acid at 100℃; for 3h; Fischer Indole Synthesis; Inert atmosphere;

: 2243-58-5
2-naphthylhydrazine hydrochloride

: 529-34-0
3,4-dihydronaphthalene-1(2H)-one

: C20H15N

Conditions

Conditions	Yield
With acetic acid In ethanol for 3h; Heating;	85%

: 2243-58-5
2-naphthylhydrazine hydrochloride

: 530-93-8
1,2,3,4-tetrahydronaphthalen-2-one

: C20H17N

Conditions

Conditions	Yield
With acetic acid In ethanol for 3h;	85%

: 110-91-8
morpholine

: 201230-82-2
carbon monoxide

: 2243-58-5
2-naphthylhydrazine hydrochloride

: 26162-88-9
morpholino(naphthalen-2-yl)methanone

Conditions

Conditions	Yield
With oxygen; palladium diacetate; sodium carbonate; triphenylphosphine In 1,4-dioxane; dimethylsulfoxide-d6; carbon dioxide at 100℃; for 12h; Schlenk technique; liquid CO2;	83%
With oxygen; palladium diacetate; sodium carbonate; triphenylphosphine In 1,4-dioxane; dimethyl sulfoxide at 100℃; under 760.051 Torr; for 12h; Schlenk technique; Green chemistry;	83%

...Expand

: 2243-58-5
2-naphthylhydrazine hydrochloride

: 501-53-1
benzyl chloroformate

: C18H16N2O2

Conditions

Conditions	Yield
With pyridine In acetonitrile at 0 - 20℃; for 1.25h;	81%
With pyridine In acetonitrile

: 696-63-9
4-Methoxybenzenethiol

: 2243-58-5
2-naphthylhydrazine hydrochloride

: 51739-39-0
(4-methoxyphenyl)(naphthalen-2-yl)sulfane

Conditions

Conditions	Yield
With oxygen; palladium diacetate; sodium carbonate; tricyclohexylphosphine In toluene at 100℃; for 12h; Schlenk technique;	80%

: 2243-58-5
2-naphthylhydrazine hydrochloride

: 108-24-7
acetic anhydride

: 40880-56-6
N′-(naphthalen-2-yl)acetohydrazide

Conditions

Conditions	Yield
Stage #1: 2-naphthylhydrazine hydrochloride With potassium carbonate In water at 20℃; for 0.25h; Stage #2: acetic anhydride In ethyl acetate; toluene at 20℃; for 1h;	79%
With sodium hydroxide In tetrahydrofuran for 1h; Inert atmosphere; Schlenk technique;	61%

: 98-10-2
benzenesulfonamide

: 2243-58-5
2-naphthylhydrazine hydrochloride

: 7504-85-0
N-(naphthalen-2-yl)benzenesulfonamide

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; copper acetylacetonate; caesium carbonate In water; acetonitrile at 100℃; for 12h; Schlenk technique;	79%

: 1755-15-3
2-acetyldimedone

: 2243-58-5
2-naphthylhydrazine hydrochloride

: 3,6,6-trimethyl-1-(naphthalen-2-yl)-6,7-dihydro-1H-indazol-4(5H)-one

Conditions

Conditions	Yield
With pyridine In ethanol at 80℃; for 2h;	79%

: 108-31-6
maleic anhydride

: 2243-58-5
2-naphthylhydrazine hydrochloride

: 67945-32-8
6-hydroxy-2-(naphthalen-2-yl)pyridazin-3(2H)-one

Conditions

Conditions	Yield
With hydrogenchloride In water Reflux;	78.1%

: 2243-58-5
2-naphthylhydrazine hydrochloride

: 108-23-6
isopropyl chloroformate

: C14H16N2O2

Conditions

Conditions	Yield
With pyridine In acetonitrile at 0 - 20℃; for 1.25h;	78%
With pyridine In acetonitrile

: 2243-58-5
2-naphthylhydrazine hydrochloride

: 3-(anthracen-9-yl)-1-p-tolylprop-2-en-1-one

: 1337561-41-7
5-(anthracen-9-yl)-1-(naphthalene-2-yl)-3-p-tolyl-4,5-dihydro-1H-pyrazole

Conditions

Conditions	Yield
In ethanol for 4h; Reflux;	77%

: 2243-58-5
2-naphthylhydrazine hydrochloride

: C19H30O4

: C27H31NO2

Conditions

Conditions	Yield
Stage #1: C19H30O4 With hydrogenchloride In methanol for 1h; Reflux; Stage #2: 2-naphthylhydrazine hydrochloride With acetic acid In ethanol for 1h; Reflux;	77%

: 201230-82-2
carbon monoxide

: 2243-58-5
2-naphthylhydrazine hydrochloride

: 108-95-2
phenol

: 82408-29-5
phenyl naphthalene-2-carboxylate

Conditions

Conditions	Yield
With bis(diphenylphosphino)propanepalladium(II) dichloride; oxygen; sodium hydroxide at 100℃; under 760.051 Torr; for 12h; Schlenk technique; Molecular sieve; Green chemistry;	76%

...Expand

: 26465-81-6
3,3-dimethylindan-1-one

: 2243-58-5
2-naphthylhydrazine hydrochloride

: C21H17N

Conditions

Conditions	Yield
With hydrogenchloride; acetic acid In water for 12h; Reflux;	72%

: 201230-82-2
carbon monoxide

: 2243-58-5
2-naphthylhydrazine hydrochloride

: 536-74-3
phenylacetylene

: 1,5-di(naphthalen-2-yl)-3-phenyl-1H-pyrazole

Conditions

Conditions	Yield
With oxygen; palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 100℃; for 8h; Molecular sieve; Schlenk technique; regioselective reaction;	71%

...Expand

: 640-60-8
toluene-4-sulfonic acid phenyl ester

: 2243-58-5
2-naphthylhydrazine hydrochloride

: 83890-91-9
1-(2-naphthalenyl)-1-phenylhydrazine

Conditions

Conditions	Yield
Stage #1: toluene-4-sulfonic acid phenyl ester With potassium phosphate; palladium(II) trifluoroacetate; 2-(2-(dicyclohexylphosphino)-4,5-dimethoxyphenyl)-1-methyl-1H-indole; phenylboronic acid In N,N-dimethyl-formamide at 20℃; for 0.00833333h; Schlenk technique; Inert atmosphere; Sealed tube; Stage #2: 2-naphthylhydrazine hydrochloride In N,N-dimethyl-formamide at 100℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;	71%

Yield

Stage #1: toluene-4-sulfonic acid phenyl ester With potassium phosphate; palladium(II) trifluoroacetate; 2-(2-(dicyclohexylphosphino)-4,5-dimethoxyphenyl)-1-methyl-1H-indole; phenylboronic acid In N,N-dimethyl-formamide at 20℃; for 0.00833333h; Schlenk technique; Inert atmosphere; Sealed tube;
Stage #2: 2-naphthylhydrazine hydrochloride In N,N-dimethyl-formamide at 100℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;

71%

: 2243-58-5
2-naphthylhydrazine hydrochloride

: 615-79-2
ethyl 2,4-diketopentanoate

A: 330803-41-3
ethyl 5-methyl-1-(naphthalen-2-yl)-1H-pyrazole-3-carboxylate

B: 330803-40-2
ethyl 3-methyl-1-(2-naphthyl)-1H-pyrazole-5-carboxylate

Conditions

Conditions	Yield
Stage #1: 2-naphthylhydrazine hydrochloride; ethyl 2,4-diketopentanoate With acetic acid for 1h; Reflux; Stage #2: With sodium hydroxide In dichloromethane	A 66% B 7%

...Expand

: 1118-61-2
3-Aminocrotononitrile

: 2243-58-5
2-naphthylhydrazine hydrochloride

: 92166-17-1
3-methyl-1-(2-naphthyl)-1H-pyrazol-5-amine

Conditions

Conditions	Yield
Stage #1: 3-Aminocrotononitrile; 2-naphthylhydrazine hydrochloride With hydrogenchloride In water at 150℃; for 0.166667h; Microwave irradiation; Sealed tube; Green chemistry; Stage #2: With sodium hydroxide In water for 0.0833333h; Sonication; Green chemistry;	66%

: 1271-55-2
acetylferrocene

: 2243-58-5
2-naphthylhydrazine hydrochloride

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 1259930-40-9
3-ferrocenyl-1-(2-naphthyl)pyrazole-4-carbaldehyde

Conditions

Conditions	Yield
With sodium methoxide; POCl3; Na2CO3 In ethanol MeONa was added to soln. acetylferrocene and β-naphthylhydrazine*HCl in EtOH, refluxed for 1 h, cooled to r.t., ppt. was filtered off, washed with EtOH, dried over CaCl2 for 1 h, dissolved in DMF, POCl3 was added under Ar, stirred at r.t. for 18 h; react. mixt. was poured onto ice with water, ppt. was filtered off, washed with water and dried over Na2SO4, column chromy. on silica (benzene);elem. anal.;	65%

Yield

With sodium methoxide; POCl3; Na2CO3 In ethanol MeONa was added to soln. acetylferrocene and β-naphthylhydrazine*HCl in EtOH, refluxed for 1 h, cooled to r.t., ppt. was filtered off, washed with EtOH, dried over CaCl2 for 1 h, dissolved in DMF, POCl3 was added under Ar, stirred at r.t. for 18 h; react. mixt. was poured onto ice with water, ppt. was filtered off, washed with water and dried over Na2SO4, column chromy. on silica (benzene);elem. anal.;

65%

...Expand

: 2243-58-5
2-naphthylhydrazine hydrochloride

: methyl N-cyano-2-naphthimidate

: 1,3-di(naphthalen-2-yl)-1H-1,2,4-triazol-5-amine

Conditions

Conditions	Yield
Stage #1: 2-naphthylhydrazine hydrochloride With triethylamine In methanol at 20℃; for 0.5h; Inert atmosphere; Stage #2: methyl N-cyano-2-naphthimidate In methanol for 4h; Reflux; Inert atmosphere;	65%

: 16676-29-2
naltrexone Hydrochloride

: 2243-58-5
2-naphthylhydrazine hydrochloride

: 126642-60-2
17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3,14-dihydroxy-5',6'-benz-6,7-2',3'-indolomorphinan

Conditions

Conditions	Yield
With acetic acid for 4h; Heating;	60%

: 2243-58-5
2-naphthylhydrazine hydrochloride

: 65-85-0
benzoic acid

: 93323-38-7
N’-(naphthalen-2-yl)benzohydrazide

Conditions

Conditions	Yield
With 6-chloro-3-((dimethylamino)(dimethyliminio)methyl)-1H-benzo[d][1,2,3]triazol-3-ium-1-olatehexafluorophosphate(V); triethylamine In N,N-dimethyl-formamide at 20℃;	60%

: 2243-58-5
2-naphthylhydrazine hydrochloride

: 172168-01-3
ethyl 3-(3,5-dichlorophenyl)-3-oxopropanoate

: 907190-28-7
5-(3,5-dichlorophenyl)-2-(2-naphthyl)-2,4-dihydro-3H-pyrazol-3-one

Conditions

Conditions	Yield
Stage #1: 2-naphthylhydrazine hydrochloride; ethyl 3-(3,5-dichlorophenyl)-3-oxopropanoate In acetic acid Heating / reflux; Stage #2: With sodium hydroxide In water; acetic acid at 20℃; pH=6;	54%

2-Naphthylhydrazine hydrochloride Specification

The Hydrazine,2-naphthalenyl-, hydrochloride (1:1), with the CAS registry number 2243-58-5, has the systematic name and IUPAC name of naphthalen-2-ylhydrazine hydrochloride (1:1). It is a kind of organics, and should be stored in the dry and cool environment. And the molecular formula of the chemical is C₁₀H₁₀N₂^.HCl.

The characteristics of Hydrazine,2-naphthalenyl-, hydrochloride (1:1) are as followings: (1)ACD/LogP: 2.48; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.01; (4)ACD/LogD (pH 7.4): 2.47; (5)ACD/BCF (pH 5.5): 15.35; (6)ACD/BCF (pH 7.4): 44.13; (7)ACD/KOC (pH 5.5): 180.87; (8)ACD/KOC (pH 7.4): 519.92; (9)#H bond acceptors: 2; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 6.48 Å²; (13)Flash Point: 203.9 °C; (14)Enthalpy of Vaporization: 60.89 kJ/mol; (15)Boiling Point: 362.9 °C at 760 mmHg; (16)Vapour Pressure: 1.87E-05 mmHg at 25°C.

Uses of Hydrazine,2-naphthalenyl-, hydrochloride (1:1): It can react with (5a)-17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-one hydrochloride to produce 17-(cyclopropylmethyl)-6,7-dehydro-4,5a-epoxy-3,14-dihydroxy-5',6'-benz-6,7-2',3'-indolomorphinan. This reaction will need reagent glacial acetic acid. The reaction time is 4 hours with heating, and the yield is about 60%.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: Cl.c12ccccc1ccc(NN)c2
(2)InChI: InChI=1/C10H10N2.ClH/c11-12-10-6-5-8-3-1-2-4-9(8)7-10;/h1-7,12H,11H2;1H
(3)InChIKey: OXOQKRNEPBHINU-UHFFFAOYAA

Product Name

2-Naphthylhydrazine hydrochloride

Synthetic route

2-Naphthylhydrazine hydrochloride Specification

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