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2,3-Dichlorophenol

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Name

2,3-Dichlorophenol

EINECS 209-399-8
CAS No. 576-24-9 Density 1.458 g/cm3
PSA 20.23000 LogP 2.69900
Solubility <0.1 g/100 mL at 20℃ Melting Point 56 °C
Formula C6H4Cl2O Boiling Point 206 °C at 760 mmHg
Molecular Weight 163.003 Flash Point 101.6 °C
Transport Information UN 2020 6.1/PG 3 Appearance Brown crystals (from ligroin, benzene).
Safety 26-28-61-45-36/37/39 Risk Codes 22-36/38-51/53-34
Molecular Structure Molecular Structure of 576-24-9 (2,3-Dichlorophenol) Hazard Symbols HarmfulXn; IrritantXi; DangerousN; CorrosiveC
Synonyms

NSC 60646;

Article Data 28

2,3-Dichlorophenol Synthetic route

95-50-1

1,2-dichloro-benzene

A

95-77-2

3,4-dichlorophenol

B

576-24-9

2,3-dichlorophenol

Conditions
ConditionsYield
With wild-type cytochrome P450cam In ethanol at 30℃; for 0.0333333h; pH=7.4; Enzyme kinetics; Further Variations:; Reagents; Oxidation;A 10%
B 90%
With oxygen; titanium(IV) oxide In perchloric acid at 23℃; for 0.25h; pH=1; Kinetics; Further Variations:; Catalysts; reaction time; UV-irradiation;
With (difluoroboryl)dimethylglyoximatocobalt(II) bis(acetonitrile); water; 3-cyano-1-methylquinolinium perchlorate In acetonitrile at 20℃; for 5h; Inert atmosphere; Irradiation;
Stage #1: 1,2-dichloro-benzene With formic acid; CoO40W12(5-)*16H2O*5K(1+); lithium formate at 25℃; for 3h; Electrochemical reaction;
Stage #2: With perchloric acid In diethyl ether; water at 20℃; for 0.166667h; Reagent/catalyst;
151169-74-3

2,3-dichlorobenzeneboronic acid

576-24-9

2,3-dichlorophenol

Conditions
ConditionsYield
With 10-methylacridine-3(10H)-one; oxygen; N-ethyl-N,N-diisopropylamine In water at 20℃; for 42h; Irradiation; Green chemistry;88%
1984-59-4

2,3-dichloroanisole

576-24-9

2,3-dichlorophenol

Conditions
ConditionsYield
With sodium methylate In N,N,N,N,N,N-hexamethylphosphoric triamide at 120℃;50%
108-43-0

3-monochlorophenol

A

583-78-8

2,5-dichlorophenol

B

95-77-2

3,4-dichlorophenol

C

576-24-9

2,3-dichlorophenol

D

1,7-dichlorodibenzofuran

Conditions
ConditionsYield
With oxygen; silica gel; copper dichloride at 350℃; Formation of xenobiotics; Further byproducts.;A 0.227%
B 0.027%
C 0.051%
D 0.115%
With oxygen; silica gel; copper dichloride at 375℃; Formation of xenobiotics; Further byproducts.;A 0.139%
B 0.019%
C 0.032%
D 0.2629%
108-43-0

3-monochlorophenol

A

583-78-8

2,5-dichlorophenol

B

95-77-2

3,4-dichlorophenol

C

576-24-9

2,3-dichlorophenol

D

95-95-4

2,4,5-trichlorophenol

Conditions
ConditionsYield
With oxygen; silica gel; copper dichloride at 300℃; Product distribution; Further Variations:; Temperatures;A 0.262%
B 0.044%
C 0.061%
D 0.021%
56962-00-6

2-amino-3-chlorophenol

576-24-9

2,3-dichlorophenol

Conditions
ConditionsYield
With hydrogenchloride Diazotization.Behandlung der Diazoniumsalz-Loesung mit CuCl2 und konz. wss. HCl;
56962-01-7

2-chloro-3-aminophenol

576-24-9

2,3-dichlorophenol

Conditions
ConditionsYield
With hydrogenchloride Diazotization.Behandlung der Diazoniumsalz-Loesung mit Kupfer-Pulver und wss. HCl;
67-56-1

methanol

124-41-4

sodium methylate

87-61-6

1,2,3-trichlorobenzene

A

87-65-0

2,6-Dichlorophenol

B

1984-59-4

2,3-dichloroanisole

C

576-24-9

2,3-dichlorophenol

Conditions
ConditionsYield
at 180℃; im Rohr;
87-61-6

1,2,3-trichlorobenzene

A

87-65-0

2,6-Dichlorophenol

B

576-24-9

2,3-dichlorophenol

Conditions
ConditionsYield
With methanol; sodium methylate at 180℃;
108-43-0

3-monochlorophenol

576-24-9

2,3-dichlorophenol

Conditions
ConditionsYield
With N-chloro-3-methyl-2,6-diphenylpiperidin-4-one; hydrogen cation In ethanol; water at 30℃; Product distribution; Thermodynamic data; ΔH(excit.), ΔS(excit.);
With N-chloro-3-methyl-2,6-diphenylpiperidin-4-one; hydrogen cation In ethanol; water at 30℃;

2,3-Dichlorophenol Consensus Reports

Reported in EPA TSCA Inventory.

2,3-Dichlorophenol Specification

The IUPAC name of this chemical is 2,3-Dichlorophenol. With the CAS registry number 576-24-9 and EINECS registry number 209-399-8, it is also named as Phenol,2,3-dichloro-. In addition, the molecular formula is C6H4Cl2O and the molecular weight is 163.001. It is a kind of light brown crystalline solid and belongs to the classes of Aromatic Phenols; Phenol Thiophenol Mercaptan; Chlorine Compounds; Phenols; Alphabetic; D; DIA - DIC; Organic Building Blocks; Oxygen Compounds. What's more, it is stable and incompatible with strong oxidizing agents, acid chlorides and acid anhydrides.

Physical properties about this chemical are: (1)ACD/LogP: 2.83; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.83; (4)ACD/LogD (pH 7.4): 2.59; (5)ACD/BCF (pH 5.5): 82.59; (6)ACD/BCF (pH 7.4): 47.9; (7)ACD/KOC (pH 5.5): 817.7; (8)ACD/KOC (pH 7.4): 474.31; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 9.23 Å2; (13)Index of Refraction: 1.593; (14)Molar Refractivity: 37.92 cm3; (15)Molar Volume: 111.7 cm3; (16)Polarizability: 15.03 ×10-24cm3; (17)Surface Tension: 47.8 dyne/cm; (18)Density: 1.458 g/cm3; (19)Flash Point: 101.6 °C; (20)Enthalpy of Vaporization: 46.03 kJ/mol; (21)Boiling Point: 206 °C at 760 mmHg; (22)Vapour Pressure: 0.169 mmHg at 25°C.

Preparation of 2,3-Dichlorophenol: it can be prepared by 1,2,3-trichlorobenzene. The 1,2,3-trichlorobenzene will become into salt by sulphonate. Then by means of high pressure hydrolysis, you can get 3,4-dichlorine-2-hydroxybenzenesulfonic acid. The sulfonateyl will be took off through sulfuric acid hydrolysis at last. In addition, it can be prepared by 2,3-dichloro-anisole. This reaction will need reagent sodium methoxide and solvent hexamethylphosphoric acid triamide. The yield is about 50% at reaction temperature of 50 °C.

2,3-Dichlorophenol can be prepared by 2,3-dichloro-anisole

Uses of 2,3-Dichlorophenol: it can be usd as intermediates to synthetize uric acid. In addition, it can react with thiophene-2-carbonyl chloride to get Thiophen-2-carbonsaeure-(2,3-dichlor)-phenylester. This reaction will need reagent pyridine and solvent tetrahydrofuran. The reaction time is one hour by heating. The yield is about 90%.

2,3-Dichlorophenol can react with thiophene-2-carbonyl chloride to get Thiophen-2-carbonsaeure-(2,3-dichlor)-phenylester

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed, irritating to eyes and skin. And it is toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. In addition, it may cause burns. It is refer to special instructions/safety data sheets. During using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If contact it with skin, wash immediately with plenty of soap-suds. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.). At last, avoid release to the environment.

You can still convert the following datas into molecular structure:
(1)SMILES: Clc1c(O)cccc1Cl
(2)InChI: InChI=1/C6H4Cl2O/c7-4-2-1-3-5(9)6(4)8/h1-3,9H
(3)InChIKey: UMPSXRYVXUPCOS-UHFFFAOYAZ

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 2376mg/kg (2376mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Toxicology Letters. Vol. 29, Pg. 39, 1985.

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