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576-24-9

Basic Information
CAS No.: 576-24-9
Name: Phenol,2,3-dichloro-
Molecular Structure:
Molecular Structure of 576-24-9 (Phenol,2,3-dichloro-)
Formula: C6H4Cl2O
Molecular Weight: 163.001
Synonyms: NSC 60646;
EINECS: 209-399-8
Density: 1.458 g/cm3
Melting Point: 56 °C
Boiling Point: 206 °C at 760 mmHg
Flash Point: 101.6 °C
Solubility: <0.1 g/100 mL at 20℃
Appearance: Brown crystals (from ligroin, benzene).
Hazard Symbols: HarmfulXn; IrritantXi; DangerousN; CorrosiveC
Risk Codes: 22-36/38-51/53-34
Safety: 26-28-61-45-36/37/39
Transport Information: UN 2020 6.1/PG 3
PSA: 20.23000
LogP: 2.69900
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℃;
79435-99-7

5,6-Dichlorcyclohexan-3,5-dien-1,2-diol

A

591-35-5

3,5-dichlorophenol

B

95-77-2

3,4-dichlorophenol

C

576-24-9

2,3-dichlorophenol

Conditions
ConditionsYield
With hydrogenchloride at 23℃; for 24h; different reagent;
95-50-1

1,2-dichloro-benzene

A

87-65-0

2,6-Dichlorophenol

B

95-77-2

3,4-dichlorophenol

C

576-24-9

2,3-dichlorophenol

Conditions
ConditionsYield
With Pseudomonas putida 50802 at 30℃; for 100h; Mechanism; different reagents;
5.6-dichloro-phenol-disulfonic acid-(2.4)

5.6-dichloro-phenol-disulfonic acid-(2.4)

576-24-9

2,3-dichlorophenol

Conditions
ConditionsYield
With sulfuric acid Durchleiten von Wasserdampf;
diazotized 2.3-dichloro-aniline

diazotized 2.3-dichloro-aniline

576-24-9

2,3-dichlorophenol

Conditions
ConditionsYield
With sulfuric acid
7647-01-0

hydrogenchloride

603-84-9

2-chloro-3-nitrophenol

iron

iron

576-24-9

2,3-dichlorophenol

Conditions
ConditionsYield
Diazotierung des gebildeten Amins und Behandlung der Diazoniumsalz-Loesung mit Kupfer-Pulver und wss. HCl;
288-32-4

1H-imidazole

61925-85-7

2,3-dichlorophenyl acetate

A

2466-76-4

N-Acetylimidazole

B

576-24-9

2,3-dichlorophenol

Conditions
ConditionsYield
With sodium dodecyl-sulfate In water; acetonitrile at 25℃; pH=8.92; Kinetics; Acetylation;
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

Conditions
ConditionsYield
With sodium hydroxide; sodium hypochlorite; sodium nitrate at 24.85℃; Kinetics;
With sodium hydroxide; tert-butylhypochlorite; sodium chloride at 24.85℃; Kinetics; Further Variations:; pH-values; conc.;
With 1,3-dichloro-5,5-dimethylhydantoin; diisopropylamine hydrochloride In toluene at 0℃; for 4h; Darkness; Overall yield = 59 %; regioselective reaction;
935-95-5

2,3,5,6-tetrachlorophenol

A

87-65-0

2,6-Dichlorophenol

B

933-75-5

2,3,6-trichlorophenol

C

95-57-8

2-monochlorophenol

D

576-24-9

2,3-dichlorophenol

Conditions
ConditionsYield
With tetraethylammonium bromide In methanol Electrolysis; Further byproducts given. Title compound not separated from byproducts;
sewage sludge

sewage sludge

576-24-9

2,3-dichlorophenol

Conditions
ConditionsYield
With hydrogenchloride; air; sewage sludge ash at 400℃; Formation of xenobiotics;
61925-85-7

2,3-dichlorophenyl acetate

A

576-24-9

2,3-dichlorophenol

B

64-19-7

acetic acid

Conditions
ConditionsYield
With potassium chloride; water at 25℃; pH=12.7; Kinetics;
87-86-5

Pentachlorophenol

576-24-9

2,3-dichlorophenol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetraethylmmonium bromide / methanol / Electrolysis
2: tetraethylmmonium bromide / methanol / Electrolysis
View Scheme
92-59-1

N-benzyl-N-ethylaniline

1527472-72-5

2,3-dichlorophenyl picolinate

A

576-24-9

2,3-dichlorophenol

B

1199382-83-6

N-ethyl-N-phenylpicolinamide

C

N-benzyl-N-phenylpicolinamide

D

100-52-7

benzaldehyde

Conditions
ConditionsYield
In chlorobenzene at 115℃; for 24h; Green chemistry;
576-24-9

2,3-dichlorophenol

107-30-2

chloromethyl methyl ether

118166-34-0

2,3-dichlorophenyl methoxymethyl ether

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 50 - 60℃; for 0.666667h;100%
576-24-9

2,3-dichlorophenol

73686-46-1

2-methylbenzoic acid 2-pyridinyl ester

C14H10Cl2O2

Conditions
ConditionsYield
With potassium carbonate In 1,4-dioxane at 60℃; for 48h; Green chemistry;100%
576-24-9

2,3-dichlorophenol

77-78-1

dimethyl sulfate

1984-59-4

2,3-dichloroanisole

Conditions
ConditionsYield
Stage #1: 2,3-dichlorophenol With potassium carbonate In acetone for 0.5h;
Stage #2: dimethyl sulfate In acetone at 60℃; for 3h;
99.1%
Stage #1: 2,3-dichlorophenol With potassium hydroxide In toluene for 0.5h;
Stage #2: dimethyl sulfate In toluene at 100℃; for 5h;
Stage #3: With potassium hydroxide In toluene for 1h; Reflux;
96.6%
With alkali
576-24-9

2,3-dichlorophenol

A

108-43-0

3-monochlorophenol

B

108-95-2

phenol

Conditions
ConditionsYield
With 9,10-dihydroanthracene; water at 356.85℃; for 3h; Kinetics;A 99%
B 0.3%
1458-98-6

2-methyl-3-bromo-1-propene

576-24-9

2,3-dichlorophenol

1,2-dichloro-3-(2-methylallyloxy)benzene

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 25℃; for 18h;99%
576-24-9

2,3-dichlorophenol

6641-64-1

4,5-dichloro-2-nitroaniline

4-chloro-5-(2,3-dichlorophenoxy)-2-nitroaniline

Conditions
ConditionsYield
With potassium methanolate In N,N-dimethyl-formamide at 155℃; for 0.5h; Temperature; Reagent/catalyst; Microwave irradiation;98.5%
576-24-9

2,3-dichlorophenol

105-36-2

ethyl bromoacetate

37536-92-8

(dichloro-2,3 phenoxy)acetate d'ethyle

Conditions
ConditionsYield
With potassium carbonate In acetone at 50℃; for 3h;98%
With sodium ethanolate In ethanol for 2.5h; Heating;86%
Stage #1: 2,3-dichlorophenol With water; potassium carbonate for 0.2h; Metallation; Irradiation;
Stage #2: ethyl bromoacetate In benzene at 50℃; for 0.25h; Substitution; Irradiation;
82%
111-83-1

1-bromo-octane

576-24-9

2,3-dichlorophenol

1,2-Dichloro-3-octyloxybenzene

Conditions
ConditionsYield
With potassium carbonate In butanone for 24h; Heating;98%
576-24-9

2,3-dichlorophenol

541-41-3

chloroformic acid ethyl ester

207238-21-9

Carbonic acid 2,3-dichloro-phenyl ester ethyl ester

Conditions
ConditionsYield
With sodium hydroxide In water for 1.5h; Ambient temperature;98%
576-24-9

2,3-dichlorophenol

115314-14-2

(2s)-(+)-glycidyl 3-nitrobenzenesulfonate

134598-06-4

(2S)-2-([(2,3-dichlorophenyl)oxy]methyl)oxirane

Conditions
ConditionsYield
Stage #1: 2,3-dichlorophenol With potassium carbonate In acetone for 0.5h; Reflux;
Stage #2: (2s)-(+)-glycidyl 3-nitrobenzenesulfonate Cooling; Reflux;
96%
576-24-9

2,3-dichlorophenol

75-03-6

ethyl iodide

92514-07-3

1,2-dichloro-3-ethoxybenzene

Conditions
ConditionsYield
With potassium carbonate In acetone for 7h; Heating;95%
576-24-9

2,3-dichlorophenol

350-46-9

4-Fluoronitrobenzene

82239-20-1

1,2-dichloro-3-(4-nitrophenoxy)benzene

Conditions
ConditionsYield
With potassium carbonate In water; N,N-dimethyl-formamide at 110℃; for 5h;95%
591-50-4

iodobenzene

576-24-9

2,3-dichlorophenol

68486-28-2

2,3-dichlorodiphenyl ether

Conditions
ConditionsYield
With sodium hydroxide In neat (no solvent) at 90℃; for 6h; Green chemistry;95%
591-50-4

iodobenzene

201230-82-2

carbon monoxide

576-24-9

2,3-dichlorophenol

2,3-dichlorophenyl benzoate

Conditions
ConditionsYield
With N,N-dimethyl acetamide; triethylamine at 100℃; under 15001.5 Torr; for 4h; Autoclave;94%
576-24-9

2,3-dichlorophenol

2032-35-1

Bromoacetaldehyde diethyl acetal

1385058-09-2

C12H16Cl2O3

Conditions
ConditionsYield
With caesium carbonate In dimethyl sulfoxide at 95℃; for 12h;93%
Stage #1: 2,3-dichlorophenol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: Bromoacetaldehyde diethyl acetal In N,N-dimethyl-formamide for 72h; Reflux;
576-24-9

2,3-dichlorophenol

115314-14-2, 115314-17-5

(R)-glycidyl nosylate

198226-59-4

(2R)-2-([(2,3-dichlorophenyl)oxy]methyl)oxirane

Conditions
ConditionsYield
Stage #1: 2,3-dichlorophenol With potassium carbonate In acetone for 0.5h; Reflux;
Stage #2: (R)-glycidyl nosylate Cooling; Reflux;
92%
576-24-9

2,3-dichlorophenol

105-39-5

chloroacetic acid ethyl ester

2976-74-1

2,3-dichlorophenoxyacetic acid

Conditions
ConditionsYield
Stage #1: 2,3-dichlorophenol; chloroacetic acid ethyl ester With potassium carbonate; potassium iodide In water; N,N-dimethyl-formamide at 100℃; for 0.0666667h; Microwave irradiation;
Stage #2: With sodium hydroxide for 0.0833333h; Microwave irradiation;
91%
5271-67-0

2-Thiophenecarbonyl chloride

576-24-9

2,3-dichlorophenol

55901-84-3

Thiophen-2-carbonsaeure-(2,3-dichlor)-phenylester

Conditions
ConditionsYield
With pyridine In tetrahydrofuran for 1h; Heating;90%
16801-19-7

2-[2-(vinyloxy)ethoxymethyl]oxirane

576-24-9

2,3-dichlorophenol

98934-98-6

2-{2-[1-(2,3-Dichloro-phenoxy)-ethoxy]-ethoxymethyl}-oxirane

Conditions
ConditionsYield
With heptafluorobutyric Acid at 50 - 80℃;90%
4851-89-2

tris(chloromethyl)phosphine oxide

576-24-9

2,3-dichlorophenol

tris(2,3-dichlorophenoxymethyl)phosphine oxide

Conditions
ConditionsYield
With sodium In methanol for 7h; Heating;90%
576-24-9

2,3-dichlorophenol

10352-63-3

chloromethyl sodium sulfonate

sodium; (2,3-dichloro-phenoxy)-methanesulfonate

Conditions
ConditionsYield
With sodium hydroxide; water for 0.00833333h; Condensation; Irradiation;90%
576-24-9

2,3-dichlorophenol

535-11-5, 41978-69-2

Ethyl 2-bromopropionate

142836-15-5

C11H12Cl2O3

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 3h; Inert atmosphere;90%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 5h; Inert atmosphere;
576-24-9

2,3-dichlorophenol

108-95-2

phenol

Conditions
ConditionsYield
With borane-ammonia complex In water; isopropyl alcohol at 50℃; for 5h; Sealed tube;90%
In cyclohexane for 24h; UV-irradiation;9 %Chromat.
576-24-9

2,3-dichlorophenol

79-07-2

Chloroacetamide

57245-31-5

8-chloro-3,4-dihydro-2H-1,4-benzoxazin-3-one

Conditions
ConditionsYield
With caesium carbonate at 130℃; Microwave irradiation;89%
576-24-9

2,3-dichlorophenol

14301-31-6

2-chloro-N-(2-(3,4-dimethoxyphenyl)ethyl)acetamide

223686-69-9

2-(2,3-dichloro-phenoxy)-N-[2-(3,4-dimethoxy-phenyl)-ethyl]-acetamide

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 6h; Heating;88%
576-24-9

2,3-dichlorophenol

88-10-8

N,N-diethylcarbamyl chloride

1225288-00-5

2,3-dichlorophenyl N,N-diethyl O-carbamate

Conditions
ConditionsYield
Stage #1: 2,3-dichlorophenol With potassium carbonate In acetonitrile for 0.5h;
Stage #2: N,N-diethylcarbamyl chloride In acetonitrile for 5h; Reflux;
87%
7462-74-0

2-bromo-2-methylpropanamide

576-24-9

2,3-dichlorophenol

1226261-49-9

2-(2,3-dichlorophenoxy)-2-methylpropanamide

Conditions
ConditionsYield
Stage #1: 2,3-dichlorophenol With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;
Stage #2: 2-bromo-2-methylpropanamide In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere;
87%
350-30-1

3-chloro-4-fluoronitrobenzene

576-24-9

2,3-dichlorophenol

317336-87-1

3.chloro-4-(2,3-dichlorophenoxy)phenylamine

Conditions
ConditionsYield
Stage #1: 3-chloro-4-fluoronitrobenzene; 2,3-dichlorophenol With potassium hydrogencarbonate In N,N-dimethyl-formamide at 100℃; for 1.5h;
Stage #2: With hydrogenchloride; iron In ethanol; water at 110℃; for 3h;
Stage #3: With sodium hydrogencarbonate In water
86%
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    2,3-Dichlorophenol Basic information Product Name: 2,3-Dichlorophenol Synonyms: 2,3-DICHLOROPHENOL;2,3-dichloro-pheno;2 3-DICHLOROPHENOL 1000MG NEAT;2,3-DICHLOR-PHENOL;2,3-Dichlorophenol,98+%;Phenol, 2,3-dichloro-;2,3-DICHLOROPHENOL 99+%;2,

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    Phenol, 2,3-dichloro-

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Reported in EPA TSCA Inventory.

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.