4-Chloro-2-methoxyaniline supplier

Name
4-CHLORO-2-ANISIDINE HYDROCHLORIDE
EINECS 202-251-3
CAS No. 93-50-5
Article Data30
CAS DataBase
Density 1.234 g/cm³
Solubility
Melting Point 52°C
Formula C₇H₈ClNO
Boiling Point 260 °C at 760 mmHg
Molecular Weight 157.6
Flash Point 108.9 °C
Transport Information
Appearance
Safety 36/37
Risk Codes 43
Molecular Structure
Hazard Symbols Xi
Synonyms o-Anisidine,4-chloro- (7CI,8CI);(4-Chloro-2-methoxyphenyl)amine;1-Amino-4-chloro-2-methoxybenzene;2-Amino-5-chloroanisole;2-Methoxy-4-chloroaniline;4-Chloro-2-anisidine;4-Chloro-2-methoxyaniline;4-Chloro-2-methoxybenzenamine;4-Chloro-o-anisidine;5-Chloro-2-aminoanisole;p-Chloro-o-anisidine;4-chloro-2-methoxyphenylamine;
PSA 35.25000
LogP 2.51200

Synthetic route

: 6627-53-8
1-chloro-3-methoxy-4-nitrobenzene

: 93-50-5
4-chloro-o-anisidine

Conditions

Conditions	Yield
With ammonium formate; platinum on activated charcoal In methanol	97%
With iron; acetic acid In methanol at 50℃; Inert atmosphere;	94%
Stage #1: With iron; ammonium chloride In water for 0.25h; Heating / reflux; Stage #2: 1-chloro-3-methoxy-4-nitrobenzene In water Heating / reflux; Stage #3: With hydrogenchloride; sodium hydroxide; sodium hydrogencarbonate Product distribution / selectivity; more than 3 stages;	91%

: 135055-92-4
Ethyl 4-chloro-2-methoxycarbanilate

: 93-50-5
4-chloro-o-anisidine

Conditions

Conditions	Yield
With potassium hydroxide In ethylene glycol at 160℃; for 1.5h;	94%

: 90-04-0
2-methoxy-phenylamine

: 93-50-5
4-chloro-o-anisidine

Conditions

Conditions	Yield
With copper dichloride; 1-hexyl-3-methylimidazol-1-ium chloride at 40℃; for 3h; regioselective reaction;	93%
With copper(II) choride dihydrate; lithium chloride hydrate In ethanol for 7h; Reflux; regioselective reaction;	76%

: tert-butyl (4-chloro-2-methoxyphenyl)carbamate

: 93-50-5
4-chloro-o-anisidine

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 2h;	85%

: 1092349-89-7
4-chloro-1-fluoro-2-methoxybenzene

: 93-50-5
4-chloro-o-anisidine

Conditions

Conditions	Yield
With 3,6‐di‐tert‐butyl‐9‐(2,6‐dimethylphenyl)‐10‐(4‐(trifluoromethyl)phenyl)acridin‐10‐iumtetrafluoroborate; ammonium carbamate In 2,2,2-trifluoroethanol; 1,2-dichloro-ethane at 45 - 50℃; for 18h; Irradiation; Inert atmosphere; Sealed tube;	57%

: 67-56-1
methanol

: 100-00-5
4-chlorobenzonitrile

: 93-50-5
4-chloro-o-anisidine

Conditions

Conditions	Yield
With fac-tris(2-phenylpyridinato-N,C2')iridium(III); methanesulfonic acid; triphenylphosphine In acetonitrile at 55℃; for 24h; Irradiation; Inert atmosphere;	28%

: 56-23-5
tetrachloromethane

: 24251-12-5
tertiary amyl hypochlorite

: 5877-56-5
N-benzylidene-2-methoxy-aniline

: 93-50-5
4-chloro-o-anisidine

...Expand

: 91-23-6
2-Nitroanisole

: 93-50-5
4-chloro-o-anisidine

Conditions

Conditions	Yield
With hydrogenchloride; tin(ll) chloride durch elektrochemische Reduktion;

: 91-23-6
2-Nitroanisole

A: 93-50-5
4-chloro-o-anisidine

B: 90-04-0
2-methoxy-phenylamine

Conditions

Conditions	Yield
With hydrogenchloride; tin

: 854910-68-2
N,N'-bis-(4-chloro-2-methoxy-phenyl)-urea

: 93-50-5
4-chloro-o-anisidine

Conditions

Conditions	Yield
With ammonium hydroxide at 150℃;
With sodium hydroxide at 175℃;

: 90-04-0
2-methoxy-phenylamine

A: 93-50-5
4-chloro-o-anisidine

B: 95-03-4
5-chloro-2-methoxyaniline

Conditions

Conditions	Yield
With chlorine

: 97-52-9
2-methoxy-4-nitrophenylamine

: 93-50-5
4-chloro-o-anisidine

: 7647-01-0
hydrogenchloride

: 91-23-6
2-Nitroanisole

Cu: Cu

: 93-50-5
4-chloro-o-anisidine

Conditions

Conditions	Yield
durch Elektroreduktion;

...Expand

: 7647-01-0
hydrogenchloride

: 91-23-6
2-Nitroanisole

SnCl2: SnCl2

: 93-50-5
4-chloro-o-anisidine

Conditions

Conditions	Yield
durch Elektroreduktion;

...Expand

: 7647-01-0
hydrogenchloride

: 91-23-6
2-Nitroanisole

tin: tin

A: 93-50-5
4-chloro-o-anisidine

B: 90-04-0
2-methoxy-phenylamine

...Expand

acetyl compound of 5-chloro-2-amino-phenol-methyl ether: acetyl compound of 5-chloro-2-amino-phenol-methyl ether

: 93-50-5
4-chloro-o-anisidine

Conditions

Conditions	Yield
With hydrogenchloride

diazotized 5-amino-2-acetylamino-anisole: diazotized 5-amino-2-acetylamino-anisole

: 93-50-5
4-chloro-o-anisidine

Conditions

Conditions	Yield
With hydrogenchloride; copper chloride

: 854910-68-2
N,N'-bis-(4-chloro-2-methoxy-phenyl)-urea

: ammonium hydroxide

: 93-50-5
4-chloro-o-anisidine

Conditions

Conditions	Yield
at 150℃;

: 854910-68-2
N,N'-bis-(4-chloro-2-methoxy-phenyl)-urea

aqueous NaOH-solution: aqueous NaOH-solution

: 93-50-5
4-chloro-o-anisidine

Conditions

Conditions	Yield
at 175℃;

: 57479-70-6
2-methoxy-4-chlorobenzoic acid

: 93-50-5
4-chloro-o-anisidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) diphenylphosphoryl azide, Et3N / 1) dioxane, 4 h, reflux 2) 6 h, reflux 2: 94 percent / KOH / ethane-1,2-diol / 1.5 h / 160 °C View Scheme

: 1226-63-7
1,3-bis(2-methoxyphenyl)urea

: 93-50-5
4-chloro-o-anisidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: nitrobenzene; chlorine 2: aqueous NaOH-solution / 175 °C View Scheme

: 88-73-3
2-Chloronitrobenzene

: 93-50-5
4-chloro-o-anisidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous potash 2: hydrochloric acid; SnCl2 / durch elektrochemische Reduktion View Scheme

: 611-07-4
5-chloro-2-nitrophenol

: 93-50-5
4-chloro-o-anisidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate; xylene 2: tin; hydrochloric acid View Scheme

: 28443-50-7
2-amino-5-chlorophenol

: 93-50-5
4-chloro-o-anisidine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydrogencarbonate / water / 0 - 20 °C 2: potassium carbonate / acetone / 6.5 h / 60 °C 3: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C View Scheme

: N-tert-butoxycarbonyl-2-hydroxy-4-chloroaniline

: 93-50-5
4-chloro-o-anisidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 6.5 h / 60 °C 2: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C View Scheme

: 93-50-5
4-chloro-o-anisidine

: 108-24-7
acetic anhydride

: 86412-57-9
N-(4-chloro-2-methoxyphenyl)acetamide

Conditions

Conditions	Yield
for 1h; Ambient temperature;	98%

: 24424-99-5
di-tert-butyl dicarbonate

: 93-50-5
4-chloro-o-anisidine

: tert-butyl (4-chloro-2-methoxyphenyl)carbamate

Conditions

Conditions	Yield
In tetrahydrofuran at 70℃;	95%
In tetrahydrofuran at 70℃;	95%

: 591-50-4
iodobenzene

: 93-50-5
4-chloro-o-anisidine

: 97026-57-8
4-Chloro-N-phenyl-o-anisidine

Conditions

Conditions	Yield
With potassium hydroxide In neat (no solvent) at 90℃; for 6h;	95%

: 93-50-5
4-chloro-o-anisidine

: 1567373-49-2
C7H9ClN2O*ClH

Conditions

Conditions	Yield
Stage #1: 4-chloro-o-anisidine With hydrogenchloride; acetic acid; sodium nitrite In water at 0 - 60℃; for 1.5h; Stage #2: With hydrogenchloride; tin(ll) chloride In water at 0℃; for 0.5h;	93%

: 93-50-5
4-chloro-o-anisidine

: 1609530-95-1
4,6-dichloro-N-methylnicotinamide

: 1609531-05-6
C14H13Cl2N3O2

Conditions

Conditions	Yield
With sodium hexamethyldisilazane In tetrahydrofuran; N,N-dimethyl acetamide for 0.333333h;	91%

: 93-50-5
4-chloro-o-anisidine

: 4755-77-5
Ethyl oxalyl chloride

: 1266620-66-9
C11H12ClNO4

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	90%

: 93-50-5
4-chloro-o-anisidine

: 122-51-0
orthoformic acid triethyl ester

: 1-(4-chloro-2-methoxyphenyl)-1H-tetrazole

Conditions

Conditions	Yield
With 1-n-butyl-3-methylimidazolium azide In water at 60℃; for 1.58333h; Green chemistry;	90%

: 93-50-5
4-chloro-o-anisidine

: 755027-21-5
4-chloro-1-iodo-2-methoxybenzene

Conditions

Conditions	Yield
Stage #1: 4-chloro-o-anisidine With sulfuric acid; sodium nitrite In water at 5℃; for 0.75h; Stage #2: With potassium iodide In water at 20℃;	88%
Diazotization;
Stage #1: 4-chloro-o-anisidine With sulfuric acid; sodium nitrite In water at 5 - 10℃; for 0.5h; Sandmeyer reaction; Stage #2: With potassium iodide In water at 20℃; for 1h;

: 93-50-5
4-chloro-o-anisidine

: 5-isocyanato-1H-indole-adamantane

: 1-(4-chloro-2-methoxyphenyl)-3-(1H-indol-2-adamantane-5-yl)urea

Conditions

Conditions	Yield
In toluene at 60℃; for 4h;	84.2%

: 93-50-5
4-chloro-o-anisidine

: 68-11-1
mercaptoacetic acid

: 4-chloro-2-methoxybenzenediazothioethanoic acid

Conditions

Conditions	Yield
Stage #1: 4-chloro-o-anisidine With phosphoric acid; sodium nitrite In water at 0℃; for 1.25h; Stage #2: mercaptoacetic acid In water for 1h; pH=Ca. 4;	83%

: 166538-98-3
8-chloro-4-oxo-4H-1-benzopyran-2-carboxylic acid

: 93-50-5
4-chloro-o-anisidine

: 8-chloro-N-(4-chloro-2-methoxyphenyl)-4-oxochromene-2-carboxamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 18h; Inert atmosphere;	80.3%

: 16722-38-6
6,8-dichloro-4-oxo-4H-chromene-2-carboxylic acid

: 93-50-5
4-chloro-o-anisidine

: 6,8-dichloro-N-(4-chloro-2-methoxyphenyl)-4-oxochromene-2-carboxamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 18h; Inert atmosphere;	80%

: 825-83-2
4-trifluoromethylbenzenethiol

: 93-50-5
4-chloro-o-anisidine

: 1-trifluoromethyl-4-[(4-chloro-2-methoxyphenyl)thio]benzene

Conditions

Conditions	Yield
With tert.-butylnitrite; C29H23N6Ru2(2+)2Cl(1-)6H2O; toluene-4-sulfonic acid In acetonitrile at 20℃; for 16h; Irradiation;	79%

: 14949-01-0
2-chloro-N-(4-sulfamoylphenyl)acetamide

: 93-50-5
4-chloro-o-anisidine

: 2-(4-Chloro-2-methoxy-phenylamino)-N-(4-sulfamoyl-phenyl)-acetamide

Conditions

Conditions	Yield
	68%

: 420-04-2
CYANAMID

: 93-50-5
4-chloro-o-anisidine

: 1610886-27-5
1-(4-chloro-2-methoxyphenyl)guanidine

Conditions

Conditions	Yield
With nitric acid In ethanol; water Reflux;	62%
Stage #1: 4-chloro-o-anisidine With nitric acid In ethanol; water Cooling with ice; Stage #2: CYANAMID In ethanol; water at 100℃; for 24h; Inert atmosphere;

: 349-94-0
3-chloro-6-(trifluoromethyl)pyridine

: 93-50-5
4-chloro-o-anisidine

: N-(4-chloro-2-methoxyphenyl)-6-(trifluoromethyl)pyridin-3-amine

Conditions

Conditions	Yield
With palladium diacetate; caesium carbonate; XPhos In toluene at 140℃; for 12h; Inert atmosphere; Sealed tube;	61.4%

: 1189-71-5
isocyanate de chlorosulfonyle

: 93-50-5
4-chloro-o-anisidine

: 820214-08-2
7-chloro-5-methoxy-2H-benzo[e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide

Conditions

Conditions	Yield
With aluminium trichloride In various solvent(s)	52%
Stage #1: isocyanate de chlorosulfonyle; 4-chloro-o-anisidine at -40 - 0℃; Stage #2: With aluminum (III) chloride at 0 - 110℃; for 0.5h; Stage #3: With water for 0.166667h; Time; Cooling with ice;	3.6 g

: 93-50-5
4-chloro-o-anisidine

: 36361-64-5
2-(4-biphenyl)-5-methyl-1,3,4-oxadiazole

: 3-biphenyl-4-yl-4-(4-chloro-2-methoxyphenyl)-5-methyl-4H-1,2,4-triazole

Conditions

Conditions	Yield
Stage #1: 4-chloro-o-anisidine; 2-(4-biphenyl)-5-methyl-1,3,4-oxadiazole With toluene-4-sulfonic acid In xylene at 150℃; for 14.5h; Stage #2: With hydrogenchloride In water; xylene Stage #3: With ammonia In methanol; dichloromethane; water	51%

: methyl cis-4-[5-[(hydrazinecarbonylformyl)amino]pyridin-2-yl]oxycyclohexane-1-carboxylate

: 93-50-5
4-chloro-o-anisidine

: 96989-50-3
di-2-pyridyl thionocarbonate

: (1s,4s)-methyl 4-(5-(5-(4-chloro-2-methoxyphenylamino)-1,3,4-oxadiazole-2-carboxamido)pyridin-2-yloxy)cyclohexanecarboxylate

Conditions

Conditions	Yield
Stage #1: 4-chloro-o-anisidine With sodium hydride In N,N-dimethyl-formamide Stage #2: di-2-pyridyl thionocarbonate In N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #3: methyl cis-4-[5-[(hydrazinecarbonylformyl)amino]pyridin-2-yl]oxycyclohexane-1-carboxylate With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride more than 3 stages;	49.8%

...Expand

: 32315-10-9
bis(trichloromethyl) carbonate

: 93-50-5
4-chloro-o-anisidine

: methyl 2-(methylamino)-5-oxo-5H-thieno[3,2-b]pyran-6-carboxylate

: methyl 2-(3-(4-chloro-2-methoxyphenyl)-1-methylureido)-5-oxo-5H-thieno[3,2-b]pyran-6-carboxylate

Conditions

Conditions	Yield
Stage #1: bis(trichloromethyl) carbonate; 4-chloro-o-anisidine In dichloromethane at 0℃; for 0.25h; Stage #2: methyl 2-(methylamino)-5-oxo-5H-thieno[3,2-b]pyran-6-carboxylate With triethylamine In dichloromethane at 16 - 25℃; for 2h;	39.61%

...Expand

: 39719-82-9
2-(4-ethoxy-phenyl)-5-methyl-[1,3,4]oxadiazole

: 93-50-5
4-chloro-o-anisidine

: 4-(4-chloro-2-methoxy-phenyl)-3-(4-ethoxy-phenyl)-5-methyl-4H-[1,2,4]triazole

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In xylene at 150℃; for 14.5h; Heating / reflux;	37%

: 93-50-5
4-chloro-o-anisidine

: 1-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)piperidine-3-carboxylic acid

: 76-05-1
trifluoroacetic acid

: N-(4-chloro-2-methoxyphenyl)-1-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)piperidine-3-carboxamide TFA salt

Conditions

Conditions	Yield
Stage #1: 4-chloro-o-anisidine; 1-(5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)piperidine-3-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 4h; Sealed tube; Stage #2: trifluoroacetic acid In water; N,N-dimethyl-formamide; acetonitrile	33%

...Expand

: (+/-)-4-oxo-2-pyrimidin-4-yl-1,6,7,8-tetrahydro-4H-pyrido[1,2-a]pyrimidine-9-carboxylic acid methyl ester

: 93-50-5
4-chloro-o-anisidine

: 1202639-25-5
(+/-)-4-oxo-2-pyrimidin-4-yl-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-9-carboxylic acid N-(4-chloro-2-methoxy-phenyl)-amide

Conditions

Conditions	Yield
In toluene for 16h; Reflux;	32%

: 93-50-5
4-chloro-o-anisidine

: 106-96-7
propargyl bromide

: 4-chloro-2-methoxy-N-(prop-2-yn-1-yl)aniline

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; chloroform at 70℃; for 6h;	26.71%
Stage #1: 4-chloro-o-anisidine With potassium carbonate In N,N-dimethyl-formamide at 53 - 55℃; for 0.5h; Inert atmosphere; Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	7%

4-Chloro-2-methoxyaniline Specification

The Benzenamine,4-chloro-2-methoxy-, with the CAS registry number 93-50-5 and EINECS registry number 202-251-3, has the systematic name and IUPAC name of 4-chloro-2-methoxy-aniline. It belongs to the product categories of Amines and Blocks. And the molecular formula of the chemical is C₇H₈ClNO. What's more, it should be stored in the dry and cool environment.

The characteristics of Benzenamine,4-chloro-2-methoxy- are as followings: (1)ACD/LogP: 2.14; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.13; (4)ACD/LogD (pH 7.4): 2.14 ; (5)#H bond acceptors: 2; (6)#H bond donors: 2; (7)#Freely Rotating Bonds: 2; (8)Polar Surface Area: 35.25 Å²; (9)Index of Refraction: 1.572; (10)Molar Refractivity: 42.06 cm³; (11)Molar Volume: 127.6 cm³; (12)Polarizability: 16.67×10^-24cm³; (13)Surface Tension: 42.3 dyne/cm; (14)Density: 1.234 g/cm³; (15)Flash Point: 108.9 °C; (16)Enthalpy of Vaporization: 49.77 kJ/mol; (17)Boiling Point: 260 °C at 760 mmHg; (18)Vapour Pressure: 0.0125 mmHg at 25°C.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: Nc1ccc(Cl)cc1OC
(2)InChI: InChI=1/C7H8ClNO/c1-10-7-4-5(8)2-3-6(7)9/h2-4H,9H2,1H3
(3)InChIKey: WOXLPNAOCCIZGP-UHFFFAOYAL

Product Name

4-CHLORO-2-ANISIDINE HYDROCHLORIDE

Synthetic route

4-Chloro-2-methoxyaniline Specification

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