carbon dioxide
A
3,5-dichloro-4-hydroxybenzoic acid
B
2,4-dichloro-3-hydroxybenzoic acid
Conditions | Yield |
---|---|
Stage #1: (2,6-dichlorophenoxy)triethylsilane With sec.-butyllithium In tetrahydrofuran; cyclohexane at -75℃; for 0.75h; Stage #2: carbon dioxide In tetrahydrofuran; cyclohexane | A n/a B 70% |
Conditions | Yield |
---|---|
With hydrogenchloride; dihydrogen peroxide; acetic acid In water at 60℃; for 4h; Solvent; | 68% |
With hydrogenchloride; dihydrogen peroxide In water | 63.5% |
With chlorine; acetic acid |
3,5-dichloro-4-methoxybenzoic acid
3,5-dichloro-4-hydroxybenzoic acid
Conditions | Yield |
---|---|
With hydrogen iodide at 130 - 140℃; im geschlossenen Rohr; | |
With hydrogen iodide | |
With diazomethane |
Conditions | Yield |
---|---|
With antimonypentachloride |
ethyl 3,5-dichloro-4-hydroxybenzoate
3,5-dichloro-4-hydroxybenzoic acid
Conditions | Yield |
---|---|
With potassium hydroxide | |
With potassium hydroxide |
2-hydroxyl-5-carboxylbenzenesulfonic acid
3,5-dichloro-4-hydroxybenzoic acid
Conditions | Yield |
---|---|
With water; chlorine |
4-hydroxy-benzoic acid
A
3-chloro-4-hydroxybenzoic acid
B
3,5-dichloro-4-hydroxybenzoic acid
Conditions | Yield |
---|---|
With sodium hydroxide; sodium hypochlorite at 20℃; for 1h; pH > 12; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With sodium hydroxide; sodium hypochlorite at 20℃; for 1h; pH > 12; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
hydrogenchloride
dihydrogen peroxide
4-hydroxy-benzoic acid
A
3-chloro-4-hydroxybenzoic acid
B
3,5-dichloro-4-hydroxybenzoic acid
3,5-dichloro-4-methoxybenzoic acid
hydrogen iodide
3,5-dichloro-4-hydroxybenzoic acid
Conditions | Yield |
---|---|
at 130 - 140℃; im geschlossenen Rohr; |
Conditions | Yield |
---|---|
at 140℃; |
2-hydroxyl-5-carboxylbenzenesulfonic acid
water
chlorine
3,5-dichloro-4-hydroxybenzoic acid
3,3,5,5,6-pentachloro-4-oxo-cyclohex-1-enecarboxylic acid
3,5-dichloro-4-hydroxybenzoic acid
3,3,5,5,6-pentachloro-4-oxo-cyclohex-1-enecarboxylic acid
3,5-dichloro-4-hydroxybenzoic acid
A
3,5-dichloro-4-hydroxybenzoic acid
Conditions | Yield |
---|---|
at 165 - 175℃; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 89 percent / triethylamine / tetrahydrofuran / 12 h / 50 °C 2.1: sec-butyllithium / cyclohexane; tetrahydrofuran / 0.75 h / -75 °C 2.2: cyclohexane; tetrahydrofuran View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: lithium aluminum hydride 2: diazomethane View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: SO2Cl2 2: KOH-solution View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: KOH; methanol 2: nitric acid 3: hydriodic acid / 130 - 140 °C / im geschlossenen Rohr View Scheme |
2,6-dichloro-4-methylanisole
3,5-dichloro-4-hydroxybenzoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: nitric acid 2: hydriodic acid / 130 - 140 °C / im geschlossenen Rohr View Scheme |
Conditions | Yield |
---|---|
98% |
3,5-dichloro-4-hydroxybenzoic acid
3,5-dichloro-4-hydroxybenzyl alcohol
Conditions | Yield |
---|---|
With borane-THF In tetrahydrofuran at 0 - 20℃; for 13.25h; | 96% |
Stage #1: 3,5-dichloro-4-hydroxybenzoic acid With borane In tetrahydrofuran at 0 - 20℃; for 13.25h; Stage #2: With water In tetrahydrofuran; methanol at 0 - 20℃; for 5.25h; | 96% |
Stage #1: 3,5-dichloro-4-hydroxybenzoic acid With borane In tetrahydrofuran at 0 - 20℃; for 13.25h; Stage #2: With methanol; water at 0 - 20℃; for 5.25h; | 96% |
Stage #1: 3,5-dichloro-4-hydroxybenzoic acid With borane In tetrahydrofuran at 0 - 20℃; for 13.25h; Stage #2: With methanol; water In tetrahydrofuran at 0 - 20℃; for 5.25h; | 96% |
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / 6 h / Reflux 2: sodium tetrahydroborate / methanol / 3.5 h / Cooling with ice View Scheme |
chloro-trimethyl-silane
3,5-dichloro-4-hydroxybenzoic acid
3,5-dichloro-4-trimethylsiloxybenzoic acid trimethylsilyl ester
Conditions | Yield |
---|---|
With triethylamine In toluene for 2h; Heating; | 94% |
3,5-dichloro-4-hydroxybenzoic acid
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
With dmap; triethylamine In tetrahydrofuran at 0℃; for 0.5h; | 93% |
3,5-dichloro-4-hydroxybenzoic acid
allyl bromide
4-allyloxy-3,5-dichloro-benzoic acid
Conditions | Yield |
---|---|
Stage #1: 3,5-dichloro-4-hydroxybenzoic acid; allyl bromide With potassium hydroxide In ethanol for 24h; Stage #2: With hydrogenchloride In ethanol; water | 92% |
9-{[4-(Fluoro)phenyl]methyl}-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]-indole Mono Hydrochloride
3,5-dichloro-4-hydroxybenzoic acid
2-(3,5-Dichloro-4-hydroxy)benzoyl-9-[(4-fluorophenyl)methyl]1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole
Conditions | Yield |
---|---|
92% |
2,3-dihydro-1,1-dioxobenzothiazole
3,5-dichloro-4-hydroxybenzoic acid
(3,5-dichloro-4-hydroxyphenyl)(1,1-dioxo-1,2-dihydro-3H-1λ6-1,3-benzothiazol-3-yl)methanone
Conditions | Yield |
---|---|
Stage #1: 3,5-dichloro-4-hydroxybenzoic acid With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 60 - 70℃; for 12h; Inert atmosphere; Stage #2: 2,3-dihydro-1,1-dioxobenzothiazole In acetonitrile for 12h; Inert atmosphere; | 89.4% |
Conditions | Yield |
---|---|
Stage #1: 3,5-dichloro-4-hydroxybenzoic acid With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 60 - 70℃; for 12h; Inert atmosphere; Stage #2: 2-amino-benzenethiol In acetonitrile for 12h; Inert atmosphere; | 87.6% |
3-(tert-butyldimethylsilyloxy)benzylamine
3,5-dichloro-4-hydroxybenzoic acid
Conditions | Yield |
---|---|
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; ethyl acetate | 87% |
Conditions | Yield |
---|---|
With copper(I) oxide In quinoline at 220℃; for 6h; Autoclave; | 86% |
With quinoline at 190℃; | |
With methyllithium; calcium carbonate |
methanol
3,5-dichloro-4-hydroxybenzoic acid
methyl 3,5-dichloro-4-hydroxybenzoate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid for 6h; Reflux; | 84.9% |
With hydrogenchloride |
Conditions | Yield |
---|---|
Stage #1: 3,5-dichloro-4-hydroxybenzoic acid With 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 0.5h; Stage #2: C7H3(2)H4NS With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 2h; | 80% |
3,5-dichloro-4-hydroxybenzoic acid
4-decyloxybenzoyl chloride
Conditions | Yield |
---|---|
With pyridine at 20℃; for 30h; | 79.5% |
3,5-dichloro-4-hydroxybenzoic acid
methyl iodide
3,5-dichloro-4-methoxybenzoic acid
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 21h; | 77% |
With sodium hydroxide; potassium carbonate 1.) DMF, 55 deg C, 1 8 h, 2.) methanol, reflux, 4 h; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With perchloric acid at 25℃; for 0.566667h; Electrochemical reaction; | 76% |
carbon dioxide
A
3,5-dichloro-4-hydroxybenzoic acid
B
2,4-dichloro-3-hydroxybenzoic acid
Conditions | Yield |
---|---|
Stage #1: (2,6-dichlorophenoxy)triethylsilane With sec.-butyllithium In tetrahydrofuran; cyclohexane at -75℃; for 0.75h; Stage #2: carbon dioxide In tetrahydrofuran; cyclohexane | A n/a B 70% |
Conditions | Yield |
---|---|
With hydrogenchloride; dihydrogen peroxide; acetic acid In water at 60℃; for 4h; Solvent; | 68% |
With hydrogenchloride; dihydrogen peroxide In water | 63.5% |
With chlorine; acetic acid |
3,5-dichloro-4-methoxybenzoic acid
3,5-dichloro-4-hydroxybenzoic acid
Conditions | Yield |
---|---|
With hydrogen iodide at 130 - 140℃; im geschlossenen Rohr; | |
With hydrogen iodide | |
With diazomethane |
Conditions | Yield |
---|---|
With antimonypentachloride |
ethyl 3,5-dichloro-4-hydroxybenzoate
3,5-dichloro-4-hydroxybenzoic acid
Conditions | Yield |
---|---|
With potassium hydroxide | |
With potassium hydroxide |
2-hydroxyl-5-carboxylbenzenesulfonic acid
3,5-dichloro-4-hydroxybenzoic acid
Conditions | Yield |
---|---|
With water; chlorine |
4-hydroxy-benzoic acid
A
3-chloro-4-hydroxybenzoic acid
B
3,5-dichloro-4-hydroxybenzoic acid
Conditions | Yield |
---|---|
With sodium hydroxide; sodium hypochlorite at 20℃; for 1h; pH > 12; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With sodium hydroxide; sodium hypochlorite at 20℃; for 1h; pH > 12; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
hydrogenchloride
dihydrogen peroxide
4-hydroxy-benzoic acid
A
3-chloro-4-hydroxybenzoic acid
B
3,5-dichloro-4-hydroxybenzoic acid
3,5-dichloro-4-methoxybenzoic acid
hydrogen iodide
3,5-dichloro-4-hydroxybenzoic acid
Conditions | Yield |
---|---|
at 130 - 140℃; im geschlossenen Rohr; |
Conditions | Yield |
---|---|
at 140℃; |
2-hydroxyl-5-carboxylbenzenesulfonic acid
water
chlorine
3,5-dichloro-4-hydroxybenzoic acid
3,3,5,5,6-pentachloro-4-oxo-cyclohex-1-enecarboxylic acid
3,5-dichloro-4-hydroxybenzoic acid
3,3,5,5,6-pentachloro-4-oxo-cyclohex-1-enecarboxylic acid
3,5-dichloro-4-hydroxybenzoic acid
A
3,5-dichloro-4-hydroxybenzoic acid
Conditions | Yield |
---|---|
at 165 - 175℃; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 89 percent / triethylamine / tetrahydrofuran / 12 h / 50 °C 2.1: sec-butyllithium / cyclohexane; tetrahydrofuran / 0.75 h / -75 °C 2.2: cyclohexane; tetrahydrofuran View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: lithium aluminum hydride 2: diazomethane View Scheme |
This chemical is called Benzoic acid, 3,5-dichloro-4-hydroxy-, and its systematic name is 3,5-dichloro-4-hydroxybenzoic acid. With the molecular formula of C7H4Cl2O3, its molecular weight is 207.01. The CAS registry number of this chemical is 3336-41-2. Additionally, its product categories are Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Carboxylic Acids; Phenyls & Phenyl-Het; Acids & Esters; Chlorine Compounds; Phenols; Carboxylic Acids; C7.
Other characteristics of the Benzoic acid, 3,5-dichloro-4-hydroxy- can be summarised as followings: (1)ACD/LogP: 3.37; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.5; (4)ACD/LogD (pH 7.4): -0.54; (5)ACD/BCF (pH 5.5): 2.91; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 22.05; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 35.53 Å2; (13)Index of Refraction: 1.641; (14)Molar Refractivity: 44.85 cm3; (15)Molar Volume: 124.2 cm3; (16)Polarizability: 17.78×10-24cm3; (17)Surface Tension: 67.4 dyne/cm; (18)Density: 1.665 g/cm3; (19)Flash Point: 152.3 °C; (20)Enthalpy of Vaporization: 60.23 kJ/mol; (21)Boiling Point: 328.2 °C at 760 mmHg; (22)Vapour Pressure: 7.79E-05 mmHg at 25°C.
Uses of this chemical: The Benzoic acid, 3,5-dichloro-4-hydroxy- could react with chloro-trimethyl-silane, and obtain the 3,5-dichloro-4-trimethylsiloxybenzoic acid trimethylsilyl ester. This reaction needs the reagent of triethylamine, and the solvent of toluene. The yield is 94 %. In addition, this reaction should be taken for 2 hours. The other condition is heating.
When you are using this chemical, please be cautious about it as the following: This chemical is irritating to eyes, respiratory system and skin. You should wear suitable protective clothing if you use it. In case of contacting 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(cc(Cl)c1O)C(=O)O
2.InChI: InChI=1/C7H4Cl2O3/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1-2,10H,(H,11,12)
3.InChIKey: AULKDLUOQCUNOK-UHFFFAOYAH
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 650mg/kg (650mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) | Journal of Medicinal and Pharmaceutical Chemistry. Vol. 2, Pg. 213, 1960. |
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