2-amino-5-chlorophenol
Conditions | Yield |
---|---|
With hydrazine hydrate In tetrahydrofuran at 25℃; for 0.5h; Inert atmosphere; | 89% |
With hydrazine In tetrahydrofuran; water at 25℃; for 0.5h; Inert atmosphere; | 88% |
N-(4-chloro-2-hydroxyphenyl)-2,6-difluorobenzamide
2-amino-5-chlorophenol
Conditions | Yield |
---|---|
With hydrazine hydrate at 100℃; for 3h; Sealed tube; | 85% |
5-chloro-2-nitrophenol
2-amino-5-chlorophenol
Conditions | Yield |
---|---|
With iron; ammonium chloride In ethanol; water for 1h; Reflux; | 81% |
With sodium hydroxide; sodium dithionite | |
With hydrogenchloride; tin(ll) chloride | |
With hydrazine hydrate In tetrahydrofuran at 100℃; for 10h; chemoselective reaction; | 93 %Chromat. |
N-(4-chlorophenyl)-O-pivaloylhydroxylamine
A
2-amino-5-chlorophenol
B
2,4-Dichloroaniline
C
N-(4-chloro-2-hydroxyphenyl)-2,2-dimethylpropanamide
D
p-benzoquinone
Conditions | Yield |
---|---|
In water; acetonitrile at 40℃; Rate constant; pH=1.0, μ=0.5M; other pH values; other N-aryl-O-pivaloylhydroxylamines; | A 3.6% B 53.2% C 8.3% D 3.8% |
N-(4-chloro-2-hydroxyphenyl)acetamide
2-amino-5-chlorophenol
Conditions | Yield |
---|---|
With hydrogenchloride |
2-Acetamido-5-chlorophenyl acetate
2-amino-5-chlorophenol
Conditions | Yield |
---|---|
With hydrogenchloride |
4-chlorobenzonitrile
2-amino-5-chlorophenol
Conditions | Yield |
---|---|
With sulfuric acid In ethanol (electrochemical reduction); |
α-ketoglutaric acid
1-chloro-4-nitroso-benzene
A
4-(4'-hydroxy-phenylamino)-4-oxo-butanoic acid
B
4-amino-phenol
C
2-amino-5-chlorophenol
D
N-(4-chloro-2-hydroxyphenyl)succinamic acid
Conditions | Yield |
---|---|
With thiamine pyrophosphate; α-ketoglutarate dehydrogenase; magnesium chloride In ethanol; water at 30℃; for 2h; KH2PO4 buffer; |
O-(m-chloro-phenyl)-hydroxylamine
A
3-monochlorophenol
B
4-amino-3-chlorophenol
C
2-amino-3-chlorophenol
D
2-amino-5-chlorophenol
Conditions | Yield |
---|---|
With trifluoroacetic acid at 60℃; for 13h; Product distribution; Rate constant; Kinetics; ΔH(excit.), ΔG(excit.), ΔS(excit.); |
1-chloro-4-nitroso-benzene
α-ketoglutaric acid disodium salt
A
4-(4'-hydroxy-phenylamino)-4-oxo-butanoic acid
B
4-amino-phenol
C
2-amino-5-chlorophenol
D
N-(4-chloro-2-hydroxyphenyl)succinamic acid
Conditions | Yield |
---|---|
With thiamine pyrophosphate; α-ketoglutarate dehydrogenase; magnesium chloride In water at 30℃; for 2h; 0.05M KH2PO4 buffer (pH 7.5); Further byproducts given. Yields of byproduct given; | A n/a B n/a C n/a D 2 mg |
1-chloro-4-nitroso-benzene
α-ketoglutaric acid disodium salt
A
4-(4'-hydroxy-phenylamino)-4-oxo-butanoic acid
B
2-amino-5-chlorophenol
C
N-(4-chlorophenyl)succinohydroxamic acid
D
N-(4-chloro-2-hydroxyphenyl)succinamic acid
Conditions | Yield |
---|---|
With thiamine pyrophosphate; α-ketoglutarate dehydrogenase; magnesium chloride In water at 30℃; for 2h; 0.05M KH2PO4 buffer (pH 7.5); Further byproducts given. Yields of byproduct given; | A n/a B n/a C 1.5 mg D 2 mg |
2-(benzylimino)-5-chlorophenyl pivalate
A
2-amino-5-chlorophenol
B
N-(4-chloro-2-hydroxyphenyl)-2,2-dimethylpropanamide
Conditions | Yield |
---|---|
In water; acetonitrile at 40℃; Rate constant; pH=1 (1N HCl), μ=0.5M (KCl); other pH value; | A 15 % Spectr. B 78 % Spectr. |
N-(4-chlorophenyl)-O-pivaloylhydroxylamine
A
2-azido-4-chlorobenzenamine
B
2-amino-5-chlorophenol
C
N-(4-chloro-2-hydroxyphenyl)-2,2-dimethylpropanamide
Conditions | Yield |
---|---|
With sodium azide; tris-(2-chloro-ethyl)-amine In water; acetonitrile at 20℃; Product distribution; Rate constant; Mechanism; |
2-amino-5-chlorophenol
Conditions | Yield |
---|---|
With hydrogenchloride In water at 100℃; for 0.75h; Hydrolysis; stirring; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium persulphate / KOH / ethanol; H2O / 8 h / stirring 2: HCl / H2O / 0.75 h / 100 °C / stirring View Scheme |
2-acetamidophenyl acetate
2-amino-5-chlorophenol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: chloroform; chlorine 2: aqueous hydrochloric acid View Scheme |
2-amino-phenol
2-amino-5-chlorophenol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 2: chloroform; chlorine 3: aqueous hydrochloric acid View Scheme |
acetic acid-(4-amino-2-hydroxy-anilide)
2-amino-5-chlorophenol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aqueous HCl; aqueous NaNO2 / Behandeln des Reaktionsgemisches mit wss.HCl und CuCl 2: aqueous HCl View Scheme |
6-chloro-2-mercaptobenzoxazole
2-amino-5-chlorophenol
Conditions | Yield |
---|---|
With hydrazine hydrate at 110℃; |
tetramethoxymethane
2-amino-5-chlorophenol
1-t-Butoxycarbonylpiperazine
tert-butyl 4-(6-chlorobenzo[d]oxazol-2-yl)piperazine-1-carboxylate
Conditions | Yield |
---|---|
With acetic acid In chloroform at 60℃; | 99% |
Stage #1: tetramethoxymethane; 2-amino-5-chlorophenol; 1-t-Butoxycarbonylpiperazine With acetic acid In chloroform at 60℃; for 16h; Inert atmosphere; Stage #2: With sodium hydroxide In chloroform; water at 20℃; Inert atmosphere; | 99% |
2-amino-5-chlorophenol
acetylenedicarboxylic acid diethyl ester
(Z)-3-ethoxycarbonylmethylene-7-chloro-3,4-dihydro-2H-1,4-benzoxazin-2-one
Conditions | Yield |
---|---|
at 20℃; for 0.0833333h; Michael addition; | 99% |
at 20℃; for 0.0833333h; |
2-amino-5-chlorophenol
dimethyl acetylenedicarboxylate
(Z)-3-methoxycarbonylmethylene-7-chloro-3,4-dihydro-2H-1,4-benzoxazin-2-one
Conditions | Yield |
---|---|
at 20℃; for 0.0666667h; Michael addition; | 98% |
In methanol at 20℃; for 1h; Inert atmosphere; | 83% |
In methanol at 20℃; for 2h; Inert atmosphere; | |
at 20℃; for 0.0666667h; |
iodobenzene
tert-butylisonitrile
2-amino-5-chlorophenol
6-chloro-2-phenylbenzo[d]oxazole
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; caesium carbonate; palladium dichloride In toluene for 2h; Reflux; Inert atmosphere; | 98% |
iodobenzene
tert-butylisonitrile
2-amino-5-chlorophenol
5-chloro-2-phenyl-1,3-benzoxazole
Conditions | Yield |
---|---|
With 1,1'-bis-(diphenylphosphino)ferrocene; caesium carbonate; palladium dichloride In toluene for 2h; Inert atmosphere; Reflux; | 98% |
2-amino-5-chlorophenol
benzaldehyde
mercaptoacetic acid
3-(4-chloro-2-hydroxyphenyl)-2-phenylthiazolidin-4-one
Conditions | Yield |
---|---|
With acetic acid In N,N-dimethyl-formamide at 110℃; for 0.15h; Microwave irradiation; | 98% |
2-amino-5-chlorophenol
4-nitrobenzaldehdye
mercaptoacetic acid
3-(4-chloro-2-hydroxyphenyl)-2-(4-nitrophenyl)thiazolidin-4-one
Conditions | Yield |
---|---|
With acetic acid In N,N-dimethyl-formamide at 110℃; for 0.15h; Microwave irradiation; | 98% |
2-chloro-benzaldehyde
2-amino-5-chlorophenol
mercaptoacetic acid
3-(4-chloro-2-hydroxyphenyl)-2-(2-chlorophenyl)thiazolidin-4-one
Conditions | Yield |
---|---|
With acetic acid In N,N-dimethyl-formamide at 110℃; for 0.166667h; Microwave irradiation; | 98% |
4-fluorobenzaldehyde
2-amino-5-chlorophenol
mercaptoacetic acid
3-(4-chloro-2-hydroxyphenyl)-2-(4-fluorophenyl)thiazolidin-4-one
Conditions | Yield |
---|---|
With acetic acid In N,N-dimethyl-formamide at 110℃; for 0.15h; Microwave irradiation; | 98% |
2-amino-5-chlorophenol
mercaptoacetic acid
3-Fluorobenzaldehyde
3-(4-chloro-2-hydroxyphenyl)-2-(3-fluorophenyl)thiazolidin-4-one
Conditions | Yield |
---|---|
With acetic acid In N,N-dimethyl-formamide at 110℃; for 0.15h; Microwave irradiation; | 98% |
2-amino-5-chlorophenol
4-hydroxy-benzaldehyde
mercaptoacetic acid
3-(4-chloro-2-hydroxyphenyl)-2-(4-hydroxyphenyl)thiazolidin-4-one
Conditions | Yield |
---|---|
With acetic acid In N,N-dimethyl-formamide at 110℃; for 0.15h; Microwave irradiation; | 98% |
2-amino-5-chlorophenol
1-Bromo-2-butanone
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 20℃; for 3h; Cooling with ice; | 98% |
Conditions | Yield |
---|---|
With 3,4,5-trihydroxybenzoic acid; oxygen; potassium carbonate; copper(l) chloride In water at 60℃; under 3750.38 Torr; for 6h; | 98% |
Conditions | Yield |
---|---|
With cobalt(II) sulfate; 3,4,5-trihydroxybenzoic acid; oxygen; sodium carbonate In water at 15℃; under 3750.38 Torr; for 40h; | 98% |
2-amino-5-chlorophenol
2-aminobenzaldehyde
Conditions | Yield |
---|---|
With scandium pentafluorobenzoate In toluene at 20℃; for 12h; | 97% |
2-amino-5-chlorophenol
2,4-dichlorobenzaldeyhde
mercaptoacetic acid
3-(4-chloro-2-hydroxyphenyl)-2-(2,4-dichlorophenyl)thiazolidin-4-one
Conditions | Yield |
---|---|
With acetic acid In N,N-dimethyl-formamide at 110℃; for 0.166667h; Microwave irradiation; | 97% |
2-amino-5-chlorophenol
4-methoxy-benzaldehyde
mercaptoacetic acid
3-(4-chloro-2-hydroxyphenyl)-2-(4-methoxyphenyl)thiazolidin-4-one
Conditions | Yield |
---|---|
With acetic acid In N,N-dimethyl-formamide at 110℃; for 0.133333h; Microwave irradiation; | 97% |
2-amino-5-chlorophenol
mercaptoacetic acid
2,4-Dimethoxybenzaldehyde
3-(4-chloro-2-hydroxyphenyl)-2-(2,4-dimethoxyphenyl)thiazolidin-4-one
Conditions | Yield |
---|---|
With acetic acid In N,N-dimethyl-formamide at 110℃; for 0.133333h; Microwave irradiation; | 97% |
pyridine-2-carbaldehyde
2-amino-5-chlorophenol
mercaptoacetic acid
3-(4-chloro-2-hydroxyphenyl)-2-(pyridin-2-yl)thiazolidin-4-one
Conditions | Yield |
---|---|
With acetic acid In N,N-dimethyl-formamide at 110℃; for 0.133333h; Microwave irradiation; | 97% |
2-amino-5-chlorophenol
2-amino-5-chlorophenol-4-sulphonic acid
Conditions | Yield |
---|---|
With sulfuric acid; sulfur trioxide Ambient temperature; | 96% |
1,1,1-trifluoro-4,4-diethoxy-3-buten-2-one
2-amino-5-chlorophenol
Conditions | Yield |
---|---|
In toluene for 0.183333h; Irradiation; | 96% |
dichlorodiphenoxymethane
2-amino-5-chlorophenol
1-t-Butoxycarbonylpiperazine
tert-butyl 4-(6-chlorobenzo[d]oxazol-2-yl)piperazine-1-carboxylate
Conditions | Yield |
---|---|
With triethylamine In toluene | 96% |
With triethylamine In toluene at 20℃; for 16h; Inert atmosphere; | 96% |
6-Amino-1,3-dimethylbarbituric acid
2-amino-5-chlorophenol
6-amino-1,3-dimethyl-5-[(4-chloro-2-hydroxyphenyl)diazenyl]uracil
Conditions | Yield |
---|---|
Stage #1: 2-amino-5-chlorophenol With sulfuric acid; acetic acid; zinc(II) chloride; sodium nitrite at 0 - 5℃; for 2h; Stage #2: 6-Amino-1,3-dimethylbarbituric acid With sodium hydroxide In water at 0 - 5℃; for 0.333333h; pH=7; | 96% |
4-chlorobenzaldehyde
2-amino-5-chlorophenol
mercaptoacetic acid
3-(4-chloro-2-hydroxyphenyl)-2-(4-chlorophenyl)thiazolidin-4-one
Conditions | Yield |
---|---|
With acetic acid In N,N-dimethyl-formamide at 110℃; for 0.15h; Microwave irradiation; | 96% |
thiophene-2-carbaldehyde
2-amino-5-chlorophenol
mercaptoacetic acid
3-(4-chloro-2-hydroxyphenyl)-2-(thiophen-2-yl)thiazolidin-4-one
Conditions | Yield |
---|---|
With acetic acid In N,N-dimethyl-formamide at 110℃; for 0.133333h; Microwave irradiation; | 96% |
4-methyl-1,3-thiazole-5-carbaldehyde
2-amino-5-chlorophenol
mercaptoacetic acid
3-(4-chloro-2-hydroxyphenyl)-2-(4-methylthiazol-5-yl)thiazolidin-4-one
Conditions | Yield |
---|---|
With acetic acid In N,N-dimethyl-formamide at 110℃; for 0.166667h; Microwave irradiation; | 96% |
2-amino-5-chlorophenol
mercaptoacetic acid
4-cyanobenzaldehyde
4-(3-(4-chloro-2-hydroxyphenyl)-4-oxothiazolidin-2-yl)benzonitrile
Conditions | Yield |
---|---|
With acetic acid In N,N-dimethyl-formamide at 110℃; for 0.15h; Microwave irradiation; | 96% |
acetic anhydride
2-amino-5-chlorophenol
N-(4-chloro-2-hydroxyphenyl)acetamide
Conditions | Yield |
---|---|
With acetic acid at 60℃; for 2h; | 95.8% |
In methanol at 20℃; for 0.5h; |
Conditions | Yield |
---|---|
In methanol at 20℃; for 0.0833333h; | 95% |
4-fluorobenzaldehyde
2-amino-5-chlorophenol
6-chloro-2-(4-fluorophenyl)benzo[d]oxazole
Conditions | Yield |
---|---|
With copper(II) ferrite; oxygen In toluene at 110℃; for 24h; Schlenk technique; Sealed tube; Green chemistry; | 95% |
With oxygen In toluene at 110℃; for 24h; Schlenk technique; Green chemistry; | 71% |
The 2-Amino-5-chlorophenol, with the CAS registry number 28443-50-7, is also known as Phenol, 2-amino-5-chloro-. It belongs to the product categories of Aromatic Phenols; Phenol & Thiophenol & Mercaptan; Phenoles and Thiophenoles; Organic Building Blocks; Oxygen Compounds; Phenols. Its EINECS registry number is 249-020-3. This chemical's molecular formula is C6H6ClNO and molecular weight is 143.57. What's more, its IUPAC name is the same with its product name. It should be stored in a cool, dry and well-ventilated place.
Physical properties about 2-Amino-5-chlorophenol are: (1)ACD/LogP: 1.457; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.44; (4)ACD/LogD (pH 7.4): 1.44; (5)ACD/BCF (pH 5.5): 7.19; (6)ACD/BCF (pH 7.4): 7.22; (7)ACD/KOC (pH 5.5): 140.95; (8)ACD/KOC (pH 7.4): 141.50; (9)#H bond acceptors: 2; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 46.25 Å2; (13)Index of Refraction: 1.651; (14)Molar Refractivity: 37.266 cm3; (15)Molar Volume: 102.094 cm3; (16)Polarizability: 14.773×10-24 cm3; (17)Surface Tension: 59.87 dyne/cm; (18)Density: 1.406 g/cm3; (19)Flash Point: 115.699 °C; (20)Enthalpy of Vaporization: 52.611 kJ/mol; (21)Boiling Point: 267.696 °C at 760 mmHg; (22)Vapour Pressure: 0.0050 mmHg at 25 °C.
Uses of 2-Amino-5-chlorophenol: (1) it is used as a dye intermediates; (2) it is used to produce other chemicals. For example, it can react with succinic acid anhydride to get N-(4-chloro-2-hydroxyphenyl)succinamic acid. The reaction occurs with solvents diethyl ether and CHCl3. The reaction time is 2 hours. The yield is 38 %.
When you are dealing with this chemical, you should be very careful. This chemical is inflammation to the skin, eyes and respiratory system. It may cause damage to health by inhalation, in contacting with skin and if swallowed. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1) SMILES: Clc1cc(O)c(N)cc1
(2) InChI: InChI=1S/C6H6ClNO/c7-4-1-2-5(8)6(9)3-4/h1-3,9H,8H2
(3) InChIKey: FZCQMIRJCGWWCL-UHFFFAOYSA-N
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