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87-65-0

Basic Information
CAS No.: 87-65-0
Name: 2,6-Dichlorophenol
Article Data: 94
Molecular Structure:
Molecular Structure of 87-65-0 (2,6-Dichlorophenol)
Formula: C6H4Cl2O
Molecular Weight: 163.003
Synonyms: Phenol,2,6-dichloro-;NSC 60647;
EINECS: 201-761-3
Density: 1.458 g/cm3
Melting Point: 65 °C
Boiling Point: 219 °C at 760 mmHg
Flash Point: 94.9 °C
Solubility: <0.1 g/100 mL at 20 °C in water
Appearance: white or light purple crystals
Hazard Symbols: CorrosiveC, IrritantXi, ToxicT, FlammableF
Risk Codes: 34-36/38-39/23/24/25-23/24/25-11
Safety: 26-27-36/37/39-37/39-45-36/37-16
Transport Information: UN 2020 6.1/PG 3
PSA: 20.23000
LogP: 2.69900
Synthetic route
188645-80-9

tert-butyl (2,6-dichlorophenoxy)dimethylsilane

87-65-0

2,6-Dichlorophenol

Conditions
ConditionsYield
With lithium acetate In water; N,N-dimethyl-formamide at 70℃; for 3h; Inert atmosphere;94%
95-57-8

2-monochlorophenol

87-65-0

2,6-Dichlorophenol

Conditions
ConditionsYield
With 2,2,6,6-tetramethyl-piperidine; sulfuryl dichloride In toluene at 25℃; for 24h; Inert atmosphere; regioselective reaction;91%
With 1,3-dichloro-5,5-dimethylhydantoin; diisopropylamine hydrochloride In toluene at 0℃; for 4h; Darkness; regioselective reaction;78%
With tetrachloromethane; tert-butylhypochlorite
3336-41-2

3,5-dichloro-4-hydroxybenzoic acid

87-65-0

2,6-Dichlorophenol

Conditions
ConditionsYield
With copper(I) oxide In quinoline at 220℃; for 6h; Autoclave;86%
With quinoline at 190℃;
With methyllithium; calcium carbonate
83-38-5

2,6-dichlorobenzaldehyde

A

87-65-0

2,6-Dichlorophenol

B

50-30-6

2,6-dichlorobenzoic acid

Conditions
ConditionsYield
With selenium(IV) oxide; dihydrogen peroxide In tetrahydrofuran for 52h; Heating;A 4 % Chromat.
B 86%
95-57-8

2-monochlorophenol

A

87-65-0

2,6-Dichlorophenol

B

120-83-2

2,4-dichlorophenol

Conditions
ConditionsYield
With iron(III) chloride; diphenyl sulfide; boric acid at 40 - 80℃;A 13.31%
B 85.43%
With chloroamine In water pH=9.0; Product distribution; Further Variations:; Reagents; pH-values;A 23%
B 77%
With N-chlorobis(2-chloroethyl)amine; silica gel In tetrachloromethane at 25℃; Yield given. Yields of byproduct given;
With 2,3,4,4,5,6-hexachlorocyclohexa-2,5-dien-1-one In tetrachloromethane; N,N-dimethyl-formamide at 20℃; for 360h; other reagent; Yield given. Yields of byproduct given;
With aluminum (III) chloride; sulfuryl dichloride In neat (no solvent) at 25 - 55℃; for 3h; Reagent/catalyst; Temperature; regioselective reaction;A 5.7 %Chromat.
B 92.1 %Chromat.
3776-30-5

2,2,6,6-tetrachlorocyclohexanone

87-65-0

2,6-Dichlorophenol

Conditions
ConditionsYield
With triethylamine In toluene at 80℃; for 2.5h; Reagent/catalyst; Solvent; Time;84.4%
With triethylamine In N,N-dimethyl-formamide at 100℃; for 4h; Dehydrochlorination;30%
6267-90-9

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

87-65-0

2,6-Dichlorophenol

Conditions
ConditionsYield
With 12-TPA/SBA 15 In 1,4-dioxane at 110℃;75%
73852-17-2

2,6-dichlorophenylboronic acid

87-65-0

2,6-Dichlorophenol

Conditions
ConditionsYield
With ozone In ethanol; water at 20 - 30℃; for 0.583333h;73%

C11H12Cl2O

87-65-0

2,6-Dichlorophenol

Conditions
ConditionsYield
With 12-TPA/SBA 15 In 1,4-dioxane at 110℃;70%
108-95-2

phenol

A

87-65-0

2,6-Dichlorophenol

B

106-48-9

4-chloro-phenol

C

120-83-2

2,4-dichlorophenol

Conditions
ConditionsYield
With hydrogenchloride; sodium chlorate In water; acetic acid at 20℃; for 72h;A 4%
B 16%
C 65%
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Chemistry

Following is the structure of 2,6-Dichlorophenol (CAS NO.87-65-0):
                 

IUPAC Name: 2,6-Dichlorophenol
Molecular Formula: C6H4Cl2O
Molecular Weight: 163.001360 g/mol
EINECS: 201-761-3
Index of Refraction: 1.593
Molar Refractivity: 37.92 cm3
Molar Volume: 111.7 cm3
Density: 1.458 g/cm3
Flash Point: 94.9 °C
Melting Point: 65 °C
Storage temp.: 0-6 °C
Polarizability: 15.03 10-24cm3
Surface Tension: 47.8 dyne/cm
Enthalpy of Vaporization: 47.39 kJ/mol
Boiling Point: 219 °C at 760 mmHg
Vapour Pressure: 0.0828 mmHg at 25 °C
Water Solubility: <0.1 g/100 mL at 20 °C
Appearance of 2,6-Dichlorophenol (CAS NO.87-65-0): white or light purple crystals
Stability: Stable. Combustible. Incompatible with strong oxidizing agents, acid chlorides, acid anhydrides.
Product Categories: Aromatic Phenols; Phenoles and thiophenoles; Alpha sort; D; DAlphabetic; DIA - DIC; Pesticides & Metabolites; Volatiles/ Semivolatiles; Organic Building Blocks; Oxygen Compounds; Phenols
Canonical SMILES: C1=CC(=C(C(=C1)Cl)O)Cl
InChI: InChI=1S/C6H4Cl2O/c7-4-2-1-3-5(8)6(4)9/h1-3,9H
InChIKey: HOLHYSJJBXSLMV-UHFFFAOYSA-N

Uses

 2,6-Dichlorophenol (CAS NO.87-65-0) is used as intermediates of medicine, pesticide, dyes and organic synthesis.

Production

 2,6-Dichlorophenol (CAS NO.87-65-0) can be synthesized by 4-ethylparaben obtained.

Toxicity Data With Reference

1.    

skn-rbt 500 mg/24H SEV

    28ZPAK    Sbornik Vysledku Toxixologickeho Vysetreni Latek A Pripravku Marhold, J.V.,Institut Pro Vychovu Vedoucicn Pracovniku Chemickeho Prumyclu Praha,Czechoslovakia.: 1972,79.
2.    

eye-rbt 250 µg/24H SEV

    28ZPAK    Sbornik Vysledku Toxixologickeho Vysetreni Latek A Pripravku Marhold, J.V.,Institut Pro Vychovu Vedoucicn Pracovniku Chemickeho Prumyclu Praha,Czechoslovakia.: 1972,79.
3.    

ipr-rat LD50:390 mg/kg

    BJPCAL    British Journal of Pharmacology and Chemotherapy. 13 (1958),20.
4.    

orl-mus LD50:2120 mg/kg

    TOLED5    Toxicology Letters. 29 (1985),39.

Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program. Chlorophenol compounds are on the Community Right-To-Know List.

Safety Profile

Hazard Codes:C  ,Xi  ,T  ,F
Risk Statements:34-36/38-39/23/24/25-23/24/25-11
34:Causes burns 
36/38:Irritating to eyes and skin 
39/23/24/25:Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed 
23/24/25:Toxic by inhalation, in contact with skin and if swallowed 
11:Highly Flammable 
Safety Statements:26-27-36/37/39-37/39-45-36/37-16
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
27:Take off immediately all contaminated clothing 
36/37/39:Wear suitable protective clothing, gloves and eye/face protection 
37/39:Wear suitable gloves and eye/face protection 
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) 
36/37:Wear suitable protective clothing and gloves 
16:Keep away from sources of ignition - No smoking
RIDADR:UN 2020 6.1/PG 3
WGK Germany:2
RTECS:SK8750000
Hazard Note:Harmful/Corrosive
HazardClass:6.1
PackingGroup:III
Poison by intraperitoneal route. Moderately toxic by ingestion. A severe skin and eye irritant. When heated to decomposition it emits toxic fumes of Cl. See also CHLOROPHENOLS.

Specification

 2,6-Dichlorophenol , its cas register number 87-65-0. It also can be called 2,6-Dichlorfenol [Czech] ; 2,6-Dichlorophenol ; BRN 1447806 ; CCRIS 2511 ; HSDB 4240 ; NSC 60647 ; and Phenol, 2,6-dichloro- . Its classification code are Skin / Eye Irritant and TSCA Flag T [Subject to the Section 4 test rule under TSCA].
 2,6-Dichlorophenol (CAS NO.87-65-0) is stable. It should avoid the condition like incompatible materials. It is not compatible with incompatible materials, acid chlorides, acid anhydrides. And also prevent it to broken down into hazardous decomposition products: hydrogen chloride, carbon monoxide, carbon dioxide. However, its hazardous polymerization will not occur.