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59-50-7

Basic Information
CAS No.: 59-50-7
Name: 4-Chloro-3-methylphenol
Article Data: 54
Molecular Structure:
Molecular Structure of 59-50-7 (4-Chloro-3-methylphenol)
Formula: C7H7ClO
Molecular Weight: 142.585
Synonyms: m-Cresol,4-chloro- (8CI);1-Chloro-2-methyl-4-hydroxybenzene;2-Chloro-5-hydroxytoluene;3-Methyl-4-chlorophenol;4-Chloro-3-cresol;4-Chloro-5-methylphenol;4-Chloro-m-cresol;6-Chloro-3-hydroxytoluene;Aptal;Baktol;Baktolan;Candaseptic;NSC 4166;Neopredisan;Ottafact;PCMC;Parmetol;Parol;Peritonan;Preventol CMK;Raschit;Raschit K;Rasen-Anicon;p-Chloro-m-cresol;para-Chloro-meta-cresol;
EINECS: 200-431-6
Density: 1.228 g/cm3
Melting Point: 63-65 °C
Boiling Point: 235 °C at 760 mmHg
Flash Point: 93.4 °C
Solubility: 4 g/L (20 ºC)
Appearance: white or pink crystals
Hazard Symbols: HarmfulXn; DangerousN; ToxicT; FlammableF
Risk Codes: 21/22-41-43-50-39/23/24/25-23/24/25-11-38
Safety: 26-36/37/39-61-45-36/37-16-7-28
Transport Information: UN 3077 9/PG 3
PSA: 20.23000
LogP: 2.35400
Synthetic route
108-39-4

3-methyl-phenol

59-50-7

4-Chloro-3-methylphenol

Conditions
ConditionsYield
With N-chloro-N-(benzenesulfonyl)benzenesulfonamide In acetonitrile at 20 - 25℃; for 0.166667h; Green chemistry;98.3%
With oxygen; lithium chloride; copper dichloride In acetic acid at 80℃; under 760.051 Torr; for 6h;81%
With oxone; potassium chloride In acetonitrile at 20℃; for 15h;73%
137-07-5

2-amino-benzenethiol

2,2-dimethyl-propionic acid 4-chloro-3-methyl-phenyl ester

A

59-50-7

4-Chloro-3-methylphenol

B

17626-88-9

2-(tert-butyl)benzo[d]thiazole

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; potassium carbonate at 100℃; for 2h; Hydrolysis; cyclization;A 98%
B n/a
599-85-9

toluene-4-sulfonic acid-(4-chloro-3-methyl-phenyl ester)

59-50-7

4-Chloro-3-methylphenol

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; potassium carbonate; thiophenol for 1h; Hydrolysis; Heating;95%
84196-13-4

4-chloro-3-methylphenyl benzoate

59-50-7

4-Chloro-3-methylphenol

Conditions
ConditionsYield
With potassium carbonate In 1-methyl-pyrrolidin-2-one at 100℃; for 3h;90%
With potassium fluoride; thiophenol In 1-methyl-pyrrolidin-2-one at 100℃; for 1h;80%
13334-71-9

1-chloro-4-methoxy-2-methylbenzene

59-50-7

4-Chloro-3-methylphenol

Conditions
ConditionsYield
With 1-N-ferrocenylmethyl benzimidazole tagged polymer In N,N-dimethyl-formamide Reflux;80%

2,2-dimethyl-propionic acid 4-chloro-3-methyl-phenyl ester

59-50-7

4-Chloro-3-methylphenol

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; potassium carbonate; thiophenol for 0.5h; Hydrolysis; Heating;70%
108-39-4

3-methyl-phenol

A

59-50-7

4-Chloro-3-methylphenol

B

615-74-7

2-chloro-5-methylphenol

C

608-26-4

2-chloro-m-cresol

Conditions
ConditionsYield
With NHCl2 In water pH=6.0; Product distribution; Further Variations:; Reagents; pH-values;A 50%
B 22%
C 28%
With sodium hydroxide; sodium hypochlorite; sodium nitrate at 4.85℃; Kinetics; Further Variations:; Temperatures;
With sodium hydroxide; tert-butylhypochlorite; sodium chloride at -35.15℃; Kinetics; Further Variations:; pH-values; conc.;

C7H7O3S(1-)*C10H15ClOP(1+)

59-50-7

4-Chloro-3-methylphenol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 60℃; for 1h; Inert atmosphere;46%
108-39-4

3-methyl-phenol

A

59-50-7

4-Chloro-3-methylphenol

B

615-74-7

2-chloro-5-methylphenol

C

13481-70-4

3-methyl-2,6-dichlorophenol

D

608-26-4

2-chloro-m-cresol

Conditions
ConditionsYield
With chloroamine In water pH=9.0; Product distribution; Further Variations:; Reagents; pH-values;A 23%
B 19.3%
C 10.1%
D 32.1%
95-49-8

2-methylchlorobenzene

A

59-50-7

4-Chloro-3-methylphenol

B

17849-38-6

2-Chlorobenzyl alcohol

C

3260-87-5

3-chloro-o-cresol

D

615-62-3

3-chloro-4-methylphenol

E

608-26-4

2-chloro-m-cresol

F

87-64-9

2-chloro-6-methylphenol

Conditions
ConditionsYield
With wild type cytochrome P450 CYP102A1 variants RLYF/A330P; oxygen; NADPH Enzymatic reaction;A 22%
B 15%
C 22%
D n/a
E 10%
F 28%
With wild type cytochrome P450 CYP102A1(P450Bm3); oxygen; NADPH Enzymatic reaction;A 24%
B 25%
C 28%
D n/a
E 7%
F 13%
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Consensus Reports

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

Specification

The IUPAC name of this chemical is 4-Chloro-3-methylphenol. With the CAS registry number 59-50-7 and EINECS 200-431-6, it is also named as Phenol,4-chloro-3-methyl-. In addition, the molecula formula is C7H7ClO and the molecular weight is 142.58. It belongs to the classes of Industrial/Fine Chemicals; Fluorobenzene; Biocides; Aromatic Phenols; Organics; Phenoles and thiophenoles; Highly Purified Reagents; Other Categories; Zone Refined Products. It is a kind of white or pink crystals.

Physical properties about this chemical are: (1)ACD/LogP: 2.89; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.89; (4)ACD/LogD (pH 7.4): 2.88; (5)#H bond acceptors: 1; (6)#H bond donors: 1; (7)#Freely Rotating Bonds: 1; (8)Polar Surface Area: 20.23 Å2; (9)Index of Refraction: 1.565; (10)Molar Refractivity: 37.85 cm3; (11)Molar Volume: 116 cm3; (12)Polarizability: 15 ×10-24cm3; (13)Surface Tension: 42.1 dyne/cm; (14)Density: 1.228 g/cm3; (15)Flash Point: 93.4 °C; (16)Enthalpy of Vaporization: 49.09 kJ/mol; (17)Boiling Point: 235 °C at 760 mmHg; (18)Vapour Pressure: 0.0335 mmHg at 25°C.

Preparation of 4-Chloro-3-methylphenol: it can be prepared by m-cresol and dichlorosulfuryl. You can add the m-cresol into the dichlorosulfuryl slowly with stirring. The reaction temperature should be controlled at 30-50 °C. And the reaction time is 16 hours. After the reaction, you should wash the product with water, then wash it with sodium carbonate solution until alkaline and wash with hot water to neutral at last. After separating the oil, you should dry the product with anhydrous calcium chloride. Then vacuum distillation the product after filtering the desiccant.

Uses of 4-Chloro-3-methylphenol: it can be used as preservative of baby cosmetics and protein shampoo. It also can be used in organic synthesis, such as dyes and film preservatives. And it can be used to get 2,6-dibromo-4-chloro-3-methyl-phenol. This reaction will need reagent NBS. The reaction time is 0.1 minute at reaction temperature of 5 °C. The yield is about 50%. It is a kind of solid phase reaction.

4-Chloro-3-methylphenol can be used to get 2,6-dibromo-4-chloro-3-methyl-phenol.

When you are using this chemical, please be cautious about it as the following:
It is highly flammable and harmful in contact with skin and if swallowed. And it is toxic by inhalation, in contact with skin and if swallowed and very toxic to aquatic organisms and. It has very serious irreversible effects and risk of serious damage to the eyes. In addition, it may cause sensitization by skin contact. When you are 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. And you should avoid release to the environment and refer to special instructions / safety data sheets. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.). You also should keep away from sources of ignition and keep container tightly closed. After contact with skin, you should wash immediately with plenty of soap-suds.

You can still convert the following datas into molecular structure:
(1)SMILES: Oc1ccc(Cl)c(C)c1
(2)InChI: InChI=1/C7H7ClO/c1-5-4-6(9)2-3-7(5)8/h2-4,9H,1H3
(3)InChIKey: CFKMVGJGLGKFKI-UHFFFAOYAE

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 70mg/kg (70mg/kg) BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Quarterly Journal of Pharmacy & Pharmacology. Vol. 12, Pg. 212, 1939.
mouse LD50 oral 600mg/kg (600mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Science Reports of the Research Institutes, Tohoku University, Series C: Medicine. Vol. 36(1-4), Pg. 10, 1989.
mouse LD50 subcutaneous 360mg/kg (360mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: TREMOR

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Quarterly Journal of Pharmacy & Pharmacology. Vol. 12, Pg. 212, 1939.
rat LD50 oral 1830mg/kg (1830mg/kg)   Personal Communication from P. Schmitz, Bayer AG, 5090 Leverkusen, Bayerwerk, Fed. Rep. Ger., April 4, 1986Vol. 04APR1986,
rat LD50 subcutaneous 400mg/kg (400mg/kg)   Quarterly Journal of Pharmacy & Pharmacology. Vol. 12, Pg. 212, 1939.