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Basic Information
CAS No.: 874-60-2
Name: 4-Methylbenzoyl chloride
Molecular Structure:
Molecular Structure of 874-60-2 (4-Methylbenzoyl chloride)
Formula: C8H7ClO
Molecular Weight: 154.596
Synonyms: p-Toluoylchloride (6CI,7CI,8CI);4-Methylbenzoic acid chloride;4-Toluoyl chloride;p-Methylbenzoyl chloride;p-Toluic acid chloride;p-Toluyl chloride;
EINECS: 212-864-8
Density: 1.17 g/cm3
Melting Point: -2 °C
Boiling Point: 226 °C at 760 mmHg
Flash Point: 82.2 °C
Solubility: Reacts with water alcohol.
Appearance: clear colourless to slightly brownish liquid
Hazard Symbols: CorrosiveC
Risk Codes: 34
Safety: 26-36/37/39-45-24/25
Transport Information: UN 3265 8/PG 2
PSA: 17.07000
LogP: 2.37400
Synthetic route
99-94-5

p-Toluic acid

874-60-2

4-methyl-benzoyl chloride

Conditions
ConditionsYield
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h; Reflux;100%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 35℃; for 1h;100%
With thionyl chloride; N,N-dimethyl-formamide at 90℃; for 2h;99.6%
624-31-7

4-tolyl iodide

122-04-3

4-nitro-benzoyl chloride

A

636-98-6

p-nitrobenzene iodide

B

874-60-2

4-methyl-benzoyl chloride

Conditions
ConditionsYield
With (Xantphos)Pd(4-C6H4NO2)(I) In benzene at 90℃; for 20h; Sealed tube; Inert atmosphere;A n/a
B 94%
201230-82-2

carbon monoxide

624-31-7

4-tolyl iodide

874-60-2

4-methyl-benzoyl chloride

Conditions
ConditionsYield
With bis(tri-t-butylphosphine)palladium(0); benzyltriphenylphosphonium chloride In toluene at 110℃; under 38002.6 Torr; for 24h; Glovebox; Autoclave; Inert atmosphere;93%
13603-62-8

1-(4-methylphenyl)-1,2-ethanediol

874-60-2

4-methyl-benzoyl chloride

Conditions
ConditionsYield
With tert-butylhypochlorite; lead acetate; dibenzoyl peroxide In toluene at 20℃; for 0.666667h;91%

RhCl2(C6H4CH3)(P(C6H5)3)2

A

15318-33-9, 16353-77-8, 13938-94-8

chlorocarbonylbis(triphenylphosphine)rhodium(I)

B

874-60-2

4-methyl-benzoyl chloride

Conditions
ConditionsYield
With carbon monoxide In dichloromethane 25°C;A 81%
B n/a
13756-42-8

tert-butyl 4-methylbenzoate

874-60-2

4-methyl-benzoyl chloride

Conditions
ConditionsYield
With phosphorus trichloride In acetonitrile at 80℃; for 3h; Schlenk technique;78%
106-42-3

para-xylene

A

874-60-2

4-methyl-benzoyl chloride

B

100-20-9

terephthaloyl chloride

Conditions
ConditionsYield
Stage #1: para-xylene With 5,10,15,20-tetrakis(4-methylphenyl)porphyrinatocopper(II); C40H32MnN8; oxygen at 180℃; under 2 Torr;
Stage #2: With thionyl chloride Reagent/catalyst; Temperature; Pressure;
A 59.4%
B 9.3%
Stage #1: para-xylene With 5,10,15,20-tetrakis(4-methylphenyl)porphyrinatocopper(II); C36H24MnN8; oxygen; cobalt(II) diacetate tetrahydrate at 180℃; under 15001.5 Torr;
Stage #2: With thionyl chloride Reagent/catalyst; Temperature; Pressure;
A 27.1%
B 37.1%
110-86-1

pyridine

99-94-5

p-Toluic acid

874-60-2

4-methyl-benzoyl chloride

Conditions
ConditionsYield
With thionyl chloride
99-94-5

p-Toluic acid

A

13222-85-0

p-methylbenzoic anhydride

B

874-60-2

4-methyl-benzoyl chloride

Conditions
ConditionsYield
With phosphorus pentachloride
98-07-7

Benzotrichlorid

619-55-6

para-methylbenzamide

A

98-88-4

benzoyl chloride

B

874-60-2

4-methyl-benzoyl chloride

C

100-47-0

benzonitrile

D

104-85-8

para-methylbenzonitrile

Conditions
ConditionsYield
at 130 - 140℃; reagiert aehnlich mit anderen Saeureamiden;
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The p-Toluoyl chloride is a kind of acidhalide compounds with cas registry number of 874-60-2. It has the EINECS registry number of 212-864-8. It is clear colourless to slightly brownish liquid which is sensitive to moisture. Both its systematic name and IUPAC name are the same which is called 4-methylbenzoyl chloride. This chemical is mainly used as the intermediates of liquid crystals.

The physical properties about this chemical are: (1)ACD/LogP: 2.67; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.67; (4)ACD/LogD (pH 7.4): 2.67; (5)ACD/BCF (pH 5.5): 62.93; (6)ACD/BCF (pH 7.4): 62.93; (7)ACD/KOC (pH 5.5): 674.9; (8)ACD/KOC (pH 7.4): 674.9; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.537; (13)Molar Refractivity: 41.32 cm3; (14)Molar Volume: 132.1 cm3; (15)Surface Tension: 38.3 dyne/cm; (16)Density: 1.17 g/cm3; (17)Flash Point: 82.2 °C; (18)Enthalpy of Vaporization: 46.25 kJ/mol; (19)Boiling Point: 226 °C at 760 mmHg; (20)Vapour Pressure: 0.0838 mmHg at 25°C ; (21)Refractive index: 1.5525-1.5545.

Preparation of p-Toluoyl chloride: it can be prepared by 4-methyl-benzoic acid with reagent Thionyl chloride at temperature of 60 ℃.

Uses of p-Toluoyl chloride: it can react with thiophene to produce thiophen-2-yl-p-tolyl-methanone in the presence of reagent 2-chloromercuri-thiophene at temperature of 70 - 120 ℃.

When you are using this chemical, please be cautious about it as the following:
This chemical causes burns. Wear suitable protective clothing, gloves and eye/face protection to avoid contact with skin and eyes, when using it. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Or if you feel unwell, seek medical advice immediately.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(Cl)c1ccc(cc1)C;
(2)InChI: InChI=1/C8H7ClO/c1-6-2-4-7(5-3-6)8(9)10/h2-5H,1H3;
(3)InChIKey: NQUVCRCCRXRJCK-UHFFFAOYAS

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 56mg/kg (56mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#04246,