Product Name

  • Name

    4-Methylbenzoyl chloride

  • EINECS 212-864-8
  • CAS No. 874-60-2
  • Article Data54
  • CAS DataBase
  • Density 1.17 g/cm3
  • Solubility Reacts with water alcohol.
  • Melting Point -2 °C
  • Formula C8H7ClO
  • Boiling Point 226 °C at 760 mmHg
  • Molecular Weight 154.596
  • Flash Point 82.2 °C
  • Transport Information UN 3265 8/PG 2
  • Appearance clear colourless to slightly brownish liquid
  • Safety 26-36/37/39-45-24/25
  • Risk Codes 34
  • Molecular Structure Molecular Structure of 874-60-2 (4-Methylbenzoyl chloride)
  • Hazard Symbols CorrosiveC
  • Synonyms p-Toluoylchloride (6CI,7CI,8CI);4-Methylbenzoic acid chloride;4-Toluoyl chloride;p-Methylbenzoyl chloride;p-Toluic acid chloride;p-Toluyl chloride;
  • PSA 17.07000
  • LogP 2.37400

Synthetic route

p-Toluic acid
99-94-5

p-Toluic acid

4-methyl-benzoyl chloride
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%
4-tolyl iodide
624-31-7

4-tolyl iodide

4-nitro-benzoyl chloride
122-04-3

4-nitro-benzoyl chloride

A

p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

B

4-methyl-benzoyl chloride
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%
...Expand
carbon monoxide
201230-82-2

carbon monoxide

4-tolyl iodide
624-31-7

4-tolyl iodide

4-methyl-benzoyl chloride
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%
1-(4-methylphenyl)-1,2-ethanediol
13603-62-8

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

4-methyl-benzoyl chloride
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

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

A

chlorocarbonylbis(triphenylphosphine)rhodium(I)
15318-33-9, 16353-77-8, 13938-94-8

chlorocarbonylbis(triphenylphosphine)rhodium(I)

B

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

Conditions
ConditionsYield
With carbon monoxide In dichloromethane 25°C;A 81%
B n/a
tert-butyl 4-methylbenzoate
13756-42-8

tert-butyl 4-methylbenzoate

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

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

para-xylene

A

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

B

terephthaloyl chloride
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%
pyridine
110-86-1

pyridine

p-Toluic acid
99-94-5

p-Toluic acid

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

Conditions
ConditionsYield
With thionyl chloride
p-Toluic acid
99-94-5

p-Toluic acid

A

p-methylbenzoic anhydride
13222-85-0

p-methylbenzoic anhydride

B

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

Conditions
ConditionsYield
With phosphorus pentachloride
Benzotrichlorid
98-07-7

Benzotrichlorid

para-methylbenzamide
619-55-6

para-methylbenzamide

A

benzoyl chloride
98-88-4

benzoyl chloride

B

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

C

benzonitrile
100-47-0

benzonitrile

D

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

Conditions
ConditionsYield
at 130 - 140℃; reagiert aehnlich mit anderen Saeureamiden;
...Expand
Benzotrichlorid
98-07-7

Benzotrichlorid

para-methylbenzamide
619-55-6

para-methylbenzamide

A

4-methyl-N-(4-methylbenzoyl)-benzamide
732-93-4

4-methyl-N-(4-methylbenzoyl)-benzamide

B

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

C

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

D

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
at 140℃;
...Expand
p-Toluic acid
99-94-5

p-Toluic acid

A

benzoyl chloride
98-88-4

benzoyl chloride

B

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

Conditions
ConditionsYield
With Benzotrichlorid; iron(III) chloride In benzene at 55℃; Product distribution; Rate constant; Thermodynamic data; ΔE(excit.);
ortho-toluoyl chloride
933-88-0

ortho-toluoyl chloride

A

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

B

3-Methylbenzoyl chloride
1711-06-4

3-Methylbenzoyl chloride

Conditions
ConditionsYield
With benzene at 250℃; Product distribution; steel autoclave; var. temp and time;A 28 % Chromat.
B 5 % Chromat.
thionyl chloride
7719-09-7

thionyl chloride

p-Toluic acid
99-94-5

p-Toluic acid

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

hydrogenchloride
7647-01-0

hydrogenchloride

para-methylbenzamide
619-55-6

para-methylbenzamide

A

4-methyl-N-(4-methylbenzoyl)-benzamide
732-93-4

4-methyl-N-(4-methylbenzoyl)-benzamide

B

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

C

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

D

p-Toluic acid
99-94-5

p-Toluic acid

Conditions
ConditionsYield
at 140 - 150℃;
...Expand
p-toluidine
106-49-0

p-toluidine

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Reaktion ueber mehrere Stufen
2: concentrated sulfuric acid; H2O
3: PCl5
View Scheme
para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: concentrated sulfuric acid; H2O
2: PCl5
View Scheme
RhCl2COC6H4CH3(P(C6H5)3)2

RhCl2COC6H4CH3(P(C6H5)3)2

A

chlorocarbonylbis(triphenylphosphine)rhodium(I)
15318-33-9, 16353-77-8, 13938-94-8

chlorocarbonylbis(triphenylphosphine)rhodium(I)

B

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

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

C

4-methyl-benzoyl chloride

4-methyl-benzoyl chloride

Conditions
ConditionsYield
In further solvent(s) 83°C, in dichloroethane;
...Expand
RhCl2(COC6H4CH3)(P(C6H5)3)2

RhCl2(COC6H4CH3)(P(C6H5)3)2

A

chlorocarbonylbis(triphenylphosphine)rhodium(I)
15318-33-9, 16353-77-8, 13938-94-8

chlorocarbonylbis(triphenylphosphine)rhodium(I)

B

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

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

C

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

Conditions
ConditionsYield
In further solvent(s) 83°C, in dichloroethane, 1:1:1 molar ratio of the products;
...Expand
2-(4,5-Dihydro-1,3-oxazol-2-yl)aniline
3416-93-1

2-(4,5-Dihydro-1,3-oxazol-2-yl)aniline

p-Toluic acid
99-94-5

p-Toluic acid

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

Conditions
ConditionsYield
With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide
oxalyl dichloride
79-37-8

oxalyl dichloride

p-Toluic acid
99-94-5

p-Toluic acid

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

Conditions
ConditionsYield
In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h;
carbon monoxide
201230-82-2

carbon monoxide

para-bromotoluene
106-38-7

para-bromotoluene

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

Conditions
ConditionsYield
With bis(tri-t-butylphosphine)palladium(0); benzyltriphenylphosphonium chloride In toluene at 110℃; under 15201 Torr; for 24h; Autoclave; Glovebox;
4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

Conditions
ConditionsYield
With trichloroisocyanuric acid In dichloromethane at 20℃; for 120h; Inert atmosphere;
With tert.-butylhydroperoxide; N-chloro-succinimide; tris(2,2'-bipyridyl)ruthenium dichloride In acetonitrile at 20℃; for 24h; Sealed tube; Irradiation;
With trichloroisocyanuric acid In dichloromethane at 20℃; Inert atmosphere;
With trichloroisocyanuric acid In dichloromethane at 20℃; Inert atmosphere;
4-Methylbenzyl alcohol
589-18-4

4-Methylbenzyl alcohol

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

Conditions
ConditionsYield
With trichloroisocyanuric acid In dichloromethane at 20℃; for 120h; Inert atmosphere;
With trichloroisocyanuric acid In dichloromethane at 20℃; Inert atmosphere;
With trichloroisocyanuric acid In dichloromethane at 20℃; Inert atmosphere;
p-tolylCOPd(PtBu3)Cl

p-tolylCOPd(PtBu3)Cl

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

Conditions
ConditionsYield
With carbon monoxide In benzene-d6 at 20℃; under 3040.2 Torr; for 0.0833333h; Equilibrium constant; Pressure; Glovebox; Inert atmosphere;
2-Fluorobenzoyl chloride
393-52-2

2-Fluorobenzoyl chloride

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (Xantphos)Pd(4-C6H4NO2)(I) / benzene / 20 h / 90 °C / Sealed tube; Inert atmosphere
2: dichloromethane-d2 / 2 h / 50 °C / Sealed tube; Inert atmosphere
View Scheme
o-chlorobenzoyl chloride
609-65-4

o-chlorobenzoyl chloride

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (Xantphos)Pd(4-C6H4NO2)(I) / benzene / 20 h / 110 °C / Sealed tube; Inert atmosphere
2: dichloromethane-d2 / 2 h / 50 °C / Sealed tube; Inert atmosphere
View Scheme
4-Chlorocarbonyl-benzoic acid hexyl ester
4543-03-7

4-Chlorocarbonyl-benzoic acid hexyl ester

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (Xantphos)Pd(4-C6H4NO2)(I) / benzene / 20 h / 110 °C / Sealed tube; Inert atmosphere
2: dichloromethane-d2 / 2 h / 50 °C / Sealed tube; Inert atmosphere
View Scheme
(Xantphos)Pd(CO(C6H4CH3))(Cl)

(Xantphos)Pd(CO(C6H4CH3))(Cl)

4,5-bis(diphenylphosphino)-9,9-dimethylxanthene
161265-03-8

4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

A

bis(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)palladium

bis(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)palladium

B

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

Conditions
ConditionsYield
In dichloromethane-d2 at 50℃; for 2h; Sealed tube; Inert atmosphere;A n/a
B 27 %Spectr.
...Expand
1,3-Benzothiazole
95-16-9

1,3-Benzothiazole

trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

2,3-dihydro-3-(4-methylbenzoyl)-2-benzothiazolecarbonitrile
95479-50-8

2,3-dihydro-3-(4-methylbenzoyl)-2-benzothiazolecarbonitrile

Conditions
ConditionsYield
With aluminium trichloride In dichloromethane100%
With aluminium trichloride In dichloromethane for 72h; Ambient temperature;87%
With aluminium trichloride In dichloromethane for 72h; Ambient temperature;86%
...Expand
Benzophenone imine
1013-88-3

Benzophenone imine

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

Conditions
ConditionsYield
With pyridine for 2h;100%
With triethylamine In toluene for 3h; Ambient temperature;64%
methyl ribofuranoside

methyl ribofuranoside

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

methyl 2,3,5-tri-O-p-toluyl-D-ribofuranoside
86042-33-3

methyl 2,3,5-tri-O-p-toluyl-D-ribofuranoside

Conditions
ConditionsYield
In pyridine for 3h; Ambient temperature;100%
N-phenylsulfonylpyrrole
16851-82-4

N-phenylsulfonylpyrrole

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

1-(phenylsulfonyl)-3-(4-methylbenzoyl)pyrrole
97188-29-9

1-(phenylsulfonyl)-3-(4-methylbenzoyl)pyrrole

Conditions
ConditionsYield
With aluminium trichloride In dichloromethane for 0.5h; Ambient temperature;100%
With aluminium trichloride In dichloromethane for 2h; Ambient temperature;100%
With aluminium trichloride100%
neplanocin A
72877-50-0

neplanocin A

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

C27H25N5O5
142888-03-7

C27H25N5O5

Conditions
ConditionsYield
With pyridine for 1.33333h; Ambient temperature;100%
2-aminoacetophenone hydrochloride
5468-37-1

2-aminoacetophenone hydrochloride

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

4-Methyl-N-[1-(2-oxo-2-phenylethyl)]benzamide
82221-14-5

4-Methyl-N-[1-(2-oxo-2-phenylethyl)]benzamide

Conditions
ConditionsYield
With sodium hydrogencarbonate In ethyl acetate Ambient temperature;100%
With sodium carbonate at 20℃; for 2h; Acylation;82%
N-methoxylamine hydrochloride
593-56-6

N-methoxylamine hydrochloride

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

N-methoxy-4-methylbenzamide
25563-06-8

N-methoxy-4-methylbenzamide

Conditions
ConditionsYield
With potassium carbonate In water; ethyl acetate at 0 - 20℃; for 2h; Inert atmosphere;100%
With potassium carbonate In water; ethyl acetate at 0 - 20℃;99%
With potassium carbonate In water; ethyl acetate at 0 - 20℃;93%
ammonium thiocyanate
1147550-11-5

ammonium thiocyanate

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

4-methylbenzoyl isothiocyanate
16794-68-6

4-methylbenzoyl isothiocyanate

Conditions
ConditionsYield
With PEG-400 In ethyl acetate at 20℃;100%
In acetone for 1h; Heating;
C33H29N4OP
130774-67-3

C33H29N4OP

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

C41H36N4O2P(1+)*Cl(1-)
130774-82-2

C41H36N4O2P(1+)*Cl(1-)

Conditions
ConditionsYield
In benzene for 3h; Ambient temperature;100%

4-Methylbenzoyl chloride Consensus Reports

Reported in EPA TSCA Inventory.

4-Methylbenzoyl chloride 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,

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