Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In methanol under 735.5 Torr; for 2h; Ambient temperature; | 100% |
With hydrogen; nickel In ethanol at 20℃; | 96% |
Reduction; | 85% |
Conditions | Yield |
---|---|
With selenium; cobalt(II) chloride hexahydrate; nitrobenzene In methanol; water; dimethyl sulfoxide at 90℃; for 5h; Inert atmosphere; | 47% |
Multi-step reaction with 2 steps 1: potassium permanganate; tetrabutylammomium bromide 2: hydrogen; palladium on activated charcoal View Scheme |
Conditions | Yield |
---|---|
With selenium; nitrobenzene; sodium hydroxide In methanol; water; dimethyl sulfoxide at 90℃; for 5h; Inert atmosphere; | 54% |
2-carboxy-4-chlorophenyl azide
5-chloroanthranilic acid
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate; sodium iodide In acetonitrile at 20℃; for 0.583333h; | 92% |
5-chloro-1H-indole
5-chloroanthranilic acid
Conditions | Yield |
---|---|
Stage #1: 5-chloro-1H-indole With bromamine B; sodium hydroxide; palladium dichloride In water; acetonitrile at 60℃; for 3.66667h; pH=12; Stage #2: In water Acidic conditions; | 95% |
With ruthenium trichloride; osmium(VIII) oxide; bromamine B; sodium hydroxide In water; acetonitrile at 39.84℃; for 5.5h; | 95% |
anthranilic acid
A
5-chloroanthranilic acid
B
3,5-dichloroantranilic acid
Conditions | Yield |
---|---|
With hydrogenchloride; dihydrogen peroxide In water; N,N-dimethyl-formamide at 45 - 50℃; for 15h; | A n/a B 85% |
With sulfuryl dichloride; diethyl ether |
2-bromo-5-chlorobenzoic acid
5-chloroanthranilic acid
Conditions | Yield |
---|---|
Stage #1: 2-bromo-5-chlorobenzoic acid With copper(l) iodide; sodium azide; ethanol; caesium carbonate at 20 - 95℃; Inert atmosphere; Sealed tube; Stage #2: With hydrogenchloride In water pH=2 - 3; | 68% |
5-chloroanthranilic acid
Conditions | Yield |
---|---|
Stage #1: resin-bound 5-chloro-2-nitrobenzoic acid With aluminium; nickel dichloride at 20℃; for 70h; Stage #2: With trifluoroacetic acid | 80% |
Conditions | Yield |
---|---|
With sodium hydroxide for 1h; Heating; | 96% |
With sodium hydroxide In tetrahydrofuran; ethanol; water at 50℃; for 3h; Inert atmosphere; |
Conditions | Yield |
---|---|
With sulfuryl dichloride In diethyl ether Reflux; | 72% |
With hydrogenchloride; sulfuryl dichloride In diethyl ether at 60 - 70℃; for 1.5h; | 35% |
With thermophilic flavin reductase from Bacillussubtilis WU-S2B; tryptophan halogenase from Streptomyces violaceusniger strain SPC6; flavin adenine dinucleotide; NADH; magnesium chloride In aq. phosphate buffer at 20℃; for 24h; pH=7.2; Catalytic behavior; Enzymatic reaction; regioselective reaction; | 8% |
Conditions | Yield |
---|---|
With nitric acid Reduzieren des Nitrierungsprodukts; | |
With nitric acid Reduzieren des Nitrierungsprodukts mit Schwefelammon; | |
With nitric acid Reduzieren des Nitrierungsprodukts mit Zinn und Salzsaeure; | |
Multi-step reaction with 2 steps 1: acetic anhydride; nitric acid / 20 °C 2: hydrogen; palladium on activated charcoal / 20 °C View Scheme |
5-chloroindole 2,3-dione
5-chloroanthranilic acid
Conditions | Yield |
---|---|
With dihydrogen peroxide; sodium hydroxide In water |
5-chloro-N,Nα-diacetyl-L-kynurenine methyl ester
5-chloroanthranilic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride / water / 4 h / Reflux 2: Pseudomonas fluorescens kynureninase / aq. phosphate buffer / 37 °C / pH 8 / Enzymatic reaction View Scheme |
(2S)-methyl 2-acetamido-4-(2'-acetamidophenyl)-4-oxobutanoate
5-chloroanthranilic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: N-chloro-succinimide; hydrogenchloride / acetic acid / 1 h / 20 °C 2: hydrogenchloride / water / 4 h / Reflux 3: Pseudomonas fluorescens kynureninase / aq. phosphate buffer / 37 °C / pH 8 / Enzymatic reaction View Scheme |
Conditions | Yield |
---|---|
durch Oxydation und Verseifung des Reaktionsproduktes; | |
Multi-step reaction with 2 steps 1: aqueous potassium permanganate; magnesium sulfate 2: aqueous hydrochloric acid View Scheme |
5-chloroanthranilic acid
Conditions | Yield |
---|---|
With hydrogenchloride |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: octacarbonyl dicobalt; benzene / 230 °C / 110326 Torr 2: aqueous NaOH View Scheme | |
Multi-step reaction with 2 steps 1: octacarbonyl dicobalt; benzene / 230 °C / 110326 Torr 2: aqueous NaOH View Scheme |
6-chloro-3-phenyl-2,4(1H,3H)-quinazolinedione
5-chloroanthranilic acid
Conditions | Yield |
---|---|
With sodium hydroxide |
3-(p-chlorophenyl)-6-chloro-2,4-(1H,3H)-quinazolinedione
5-chloroanthranilic acid
Conditions | Yield |
---|---|
With potassium hydroxide |
Conditions | Yield |
---|---|
With hydrogenchloride |
Conditions | Yield |
---|---|
With hydrogenchloride |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: aqueous acetic acid; sodium chlorate; aqueous hydrochloric acid 2: aqueous potassium permanganate; magnesium sulfate 3: aqueous hydrochloric acid View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: AlCl3; NaCl 2: aqueous KOH View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium permanganate 2: tin; aqueous hydrochloric acid View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: manganese peroxide; hydrochloric acid / 150 °C / im Druckrohr 2: fuming nitric acid / Reduzieren des Nitrierungsprodukts mit Zinn und Salzsaeure View Scheme |
Conditions | Yield |
---|---|
With Pseudomonas fluorescens kynureninase In aq. phosphate buffer at 37℃; pH=8; Kinetics; Enzymatic reaction; |
anthranilic acid
A
2-amino-3-chlorobenzoic acid
B
5-chloroanthranilic acid
Conditions | Yield |
---|---|
With Pseudomonas fluorescens BL915 halogenase F454K mutant; flavin adenine dinucleotide; NADH; magnesium chloride In aq. phosphate buffer at 30℃; for 1h; pH=7.4; Kinetics; Reagent/catalyst; Enzymatic reaction; |
chlorine
anthranilic acid
acetic acid
A
chloranil
B
5-chloroanthranilic acid
C
3,5-dichloroantranilic acid
sulfuryl dichloride
diethyl ether
anthranilic acid
5-chloroanthranilic acid
Conditions | Yield |
---|---|
unter Kuehlung; |
Conditions | Yield |
---|---|
With thionyl chloride at 0℃; for 12h; Reflux; | 100% |
With thionyl chloride at 0℃; for 12h; Reflux; | 100% |
With sulfuric acid at 60℃; for 72h; Inert atmosphere; | 94% |
benzoyl chloride
5-chloroanthranilic acid
6-chloro-2-phenyl-benzo[d][1,3]oxazin-4-one
Conditions | Yield |
---|---|
With sodium carbonate In tetrahydrofuran 5 deg C, 10 min, then room temperature overnight; | 100% |
at 140℃; for 3h; | 92% |
With sodium carbonate In tetrahydrofuran for 16h; | 92% |
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In methanol under 735.5 Torr; for 80h; Product distribution; Ambient temperature; | 100% |
5-chloroanthranilic acid
2-amino-5-chlorobenzyl alcohol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | 100% |
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h; | 100% |
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 3.5h; | 93% |
5-chloroanthranilic acid
trifluoroacetic anhydride
5-chloro-2-(2,2,2-trifluoroacetyl)aminobenzoic acid
Conditions | Yield |
---|---|
In 1,4-dioxane at 0 - 20℃; | 100% |
In 1,4-dioxane at 20℃; for 12h; | 67% |
In 1,4-dioxane at 0 - 20℃; for 3h; |
2-nitrophenyl bromide
5-chloroanthranilic acid
5-Chloro-2-(2-nitro-phenylamino)-benzoic acid
Conditions | Yield |
---|---|
With copper; potassium carbonate In pentan-1-ol at 150℃; Ullman coupling; | 100% |
acetic acid
5-chloroanthranilic acid
5-chloro-2-(1H-tetrazol-1-yl)benzoic acid
Conditions | Yield |
---|---|
With sodium azide; trimethyl orthoformate at 0 - 20℃; | 100% |
5-chloroanthranilic acid
naphthalene-1-carbonic acid chloride
6-chloro-2-(1-naphthalenyl)-4H-3,1-benzoxazin-4-one
Conditions | Yield |
---|---|
Stage #1: 5-chloroanthranilic acid; naphthalene-1-carbonic acid chloride With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; Stage #2: With HATU In DMF (N,N-dimethyl-formamide) at 20℃; for 1h; | 99% |
Conditions | Yield |
---|---|
With oxygen; copper diacetate; palladium diacetate; potassium iodide In acetonitrile at 60℃; under 760.051 Torr; for 4h; | 99% |
metazonic acid
5-chloroanthranilic acid
5-chloro-2-(2-nitrovinylamino)benzoic acid
Conditions | Yield |
---|---|
With hydrogenchloride In water at 20℃; for 18h; | 99% |
N,N-dimethyl-formamide dimethyl acetal
5-chloroanthranilic acid
methyl 5-chloro-2-(N,N-dimethyl-N'-formamidinyl)benzoate
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide Heating; | 98% |
Conditions | Yield |
---|---|
With isopentyl nitrite In 1,4-dioxane for 0.416667h; Heating; | 98% |
bis(trichloromethyl) carbonate
5-chloroanthranilic acid
5-Chloroisatoic anhydride
Conditions | Yield |
---|---|
In 1,2-dichloro-ethane for 4h; Reflux; | 98% |
In 1,2-dichloro-ethane for 3.25h; Reflux; | 98% |
In 1,2-dichloro-ethane at 80℃; | 97% |
Conditions | Yield |
---|---|
at 200℃; | 98% |
at 200℃; for 3h; | 80.5% |
at 180℃; for 3h; |
5-chloroanthranilic acid
5-bromosalicyclaldehyde
phenylboronic acid
(N-B)-2-bromo-10-chloro-6-phenyl-8H-dibenzo[d,h][1,3,7,2]dioxazaborecin-8-one
Conditions | Yield |
---|---|
In tetrachloromethane for 0.05h; Microwave irradiation; | 98% |
Conditions | Yield |
---|---|
With hydrogenchloride In water for 4h; Reflux; | 98% |
formamide
5-chloroanthranilic acid
6-chloroquinazolin-4-one
Conditions | Yield |
---|---|
at 150℃; for 16h; | 97% |
With acetic acid; diethylamine at 150℃; for 2h; Product distribution / selectivity; | 93.3% |
at 140℃; | 90% |
Conditions | Yield |
---|---|
Stage #1: terephthaloyl chloride; 5-chloroanthranilic acid In N,N-dimethyl acetamide at 4 - 11℃; for 4h; Cooling with ice; Stage #2: With acetic anhydride In N,N-dimethyl acetamide at 105 - 126℃; for 2h; | 97% |
4-fluoroboronic acid
3-methoxy-2-hydroxybenzaldehyde
5-chloroanthranilic acid
(N-B)-10-chloro-6-(4-fluorophenyl)-4-methoxy-8H-dibenzo[d,h][1,3,7,2]dioxazaborecin-8-one
Conditions | Yield |
---|---|
In tetrachloromethane for 0.05h; Microwave irradiation; | 97% |
4-fluoroboronic acid
5-chloroanthranilic acid
5-bromosalicyclaldehyde
(N-B)-2-bromo-10-chloro-6-(4-fluorophenyl)-8H-dibenzo[d,h][1,3,7,2]dioxazaborecin-8-one
Conditions | Yield |
---|---|
In tetrachloromethane for 0.05h; Microwave irradiation; | 97% |
4-ethylphenylboronic acid
3-methoxy-2-hydroxybenzaldehyde
5-chloroanthranilic acid
(N-B)-10-chloro-6-(4-ethylphenyl)-4-methoxy-8H-dibenzo[d,h][1,3,7,2]dioxazaborecin-8-one
Conditions | Yield |
---|---|
In tetrachloromethane for 0.05h; Microwave irradiation; | 97% |
3-methoxy-2-hydroxybenzaldehyde
5-chloroanthranilic acid
phenylboronic acid
(N-B)-10-chloro-4-methoxy-6-phenyl-8H-dibenzo[d,h][1,3,7,2]dioxazaborecin-8-one
Conditions | Yield |
---|---|
In tetrachloromethane for 0.05h; Microwave irradiation; | 97% |
Conditions | Yield |
---|---|
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide | 97% |
dichloroacethyl chloride
5-chloroanthranilic acid
6-Chloro-2-dichloromethyl-benzo[d][1,3]oxazin-4-one
Conditions | Yield |
---|---|
96% |
Conditions | Yield |
---|---|
With isopentyl nitrite In dichloromethane for 38h; Heating; | A 3% B 96% |
Conditions | Yield |
---|---|
With potassium carbonate In water; acetone | 96% |
With potassium carbonate In water; acetone | 96% |
chloroacetyl chloride
5-chloroanthranilic acid
1-Chloro-2-(2-carboxy-4-chlorophenyl)amino-2-oxoethane
Conditions | Yield |
---|---|
In toluene for 1h; Reflux; | 96% |
With pyridine In toluene at 20℃; for 6h; | 75% |
With sodium hydrogencarbonate; potassium carbonate In acetonitrile |
Cyclohexyl isocyanide
N-isocyaniminotriphenylphosphorane
5-Nitrosalicylaldehyde
5-chloroanthranilic acid
N3-[4-chloro-2-(1,3,4-oxadiazol-2-yl)phenyl]-N2-cyclohexyl-5-nitrobenzofuran-2,3-diamine
Conditions | Yield |
---|---|
Stage #1: Cyclohexyl isocyanide; 5-Nitrosalicylaldehyde; 5-chloroanthranilic acid In ethanol at 25℃; for 1h; Stage #2: N-isocyaniminotriphenylphosphorane In ethanol at 25℃; for 2h; | 96% |
The 2-Amino-5-chlorobenzoic acid is an organic compound with the formula C7H6ClNO2. The IUPAC name of this chemical is 2-amino-5-chlorobenzoic acid. With the CAS registry number 635-21-2, it is also named as 5-Chloro-2-aminobenzoic acid. The product's categories are Fine Chemical & Intermediates; Amino Acids and Derivatives; Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Benzoic Acid; Organic Acids; Acids & Esters; Anilines, Amides & Amines; Chlorine Compounds. Besides, it is a white to light yellow crystal powder, which should be stored in a closed cool and dry place. It is used for organic synthesis. It has inhibitory to herbicides and monoamine oxidase.
Physical properties about 2-Amino-5-chlorobenzoic acid are: (1)ACD/LogP: 2.44; (2)ACD/LogD (pH 5.5): 1.11; (3)ACD/LogD (pH 7.4): -0.44; (4)ACD/BCF (pH 5.5): 1.96; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 23.59; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 3; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 2; (11)Polar Surface Area: 29.54 Å2; (12)Index of Refraction: 1.648; (13)Molar Refractivity: 42.31 cm3; (14)Molar Volume: 116.1 cm3; (15)Polarizability: 16.77×10-24cm3; (16)Surface Tension: 65.9 dyne/cm; (17)Density: 1.476 g/cm3; (18)Flash Point: 160.3 °C; (19)Enthalpy of Vaporization: 61.76 kJ/mol; (20)Boiling Point: 341.5 °C at 760 mmHg; (21)Vapour Pressure: 3.09E-05 mmHg at 25°C.
Preparation: this chemical can be prepared by 5-chloro-2-nitro-benzoic acid. This reaction will need reagent tin and aqueous hydrochloric acid.
Uses of 2-Amino-5-chlorobenzoic acid: it can be used to produce 6-chloro-3H-quinazolin-4-one at temperature of 180 °C.
When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: Clc1cc(C(=O)O)c(N)cc1
(2)InChI: InChI=1/C7H6ClNO2/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3H,9H2,(H,10,11)
(3)InChIKey: IFXKXCLVKQVVDI-UHFFFAOYAN
(4)Std. InChI: InChI=1S/C7H6ClNO2/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3H,9H2,(H,10,11)
(5)Std. InChIKey: IFXKXCLVKQVVDI-UHFFFAOYSA-N
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