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874-60-2

Basic Information
CAS No.: 874-60-2
Name: Benzoyl chloride,4-methyl-
Molecular Structure:
Molecular Structure of 874-60-2 (Benzoyl chloride,4-methyl-)
Formula: C8H7ClO
Molecular Weight: 154.60
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;
98-07-7

Benzotrichlorid

619-55-6

para-methylbenzamide

A

732-93-4

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

B

874-60-2

4-methyl-benzoyl chloride

C

104-85-8

para-methylbenzonitrile

D

99-94-5

p-Toluic acid

Conditions
ConditionsYield
at 140℃;
99-94-5

p-Toluic acid

A

98-88-4

benzoyl chloride

B

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.);
933-88-0

ortho-toluoyl chloride

A

874-60-2

4-methyl-benzoyl chloride

B

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.
7719-09-7

thionyl chloride

99-94-5

p-Toluic acid

874-60-2

4-methyl-benzoyl chloride

7647-01-0

hydrogenchloride

619-55-6

para-methylbenzamide

A

732-93-4

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

B

874-60-2

4-methyl-benzoyl chloride

C

104-85-8

para-methylbenzonitrile

D

99-94-5

p-Toluic acid

Conditions
ConditionsYield
at 140 - 150℃;
106-49-0

p-toluidine

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
104-85-8

para-methylbenzonitrile

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

A

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

chlorocarbonylbis(triphenylphosphine)rhodium(I)

B

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

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

A

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

chlorocarbonylbis(triphenylphosphine)rhodium(I)

B

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

C

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;
3416-93-1

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

99-94-5

p-Toluic acid

874-60-2

4-methyl-benzoyl chloride

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

oxalyl dichloride

99-94-5

p-Toluic acid

874-60-2

4-methyl-benzoyl chloride

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

carbon monoxide

106-38-7

para-bromotoluene

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;
104-87-0

4-methyl-benzaldehyde

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;
589-18-4

4-Methylbenzyl alcohol

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

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;
393-52-2

2-Fluorobenzoyl 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
609-65-4

o-chlorobenzoyl 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
4543-03-7

4-Chlorocarbonyl-benzoic acid hexyl ester

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)

161265-03-8

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

A

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

B

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.
95-16-9

1,3-Benzothiazole

7677-24-9

trimethylsilyl cyanide

874-60-2

4-methyl-benzoyl chloride

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%
1013-88-3

Benzophenone imine

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

874-60-2

4-methyl-benzoyl chloride

86042-33-3

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

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

N-phenylsulfonylpyrrole

874-60-2

4-methyl-benzoyl chloride

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%
72877-50-0

neplanocin A

874-60-2

4-methyl-benzoyl chloride

142888-03-7

C27H25N5O5

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

2-aminoacetophenone hydrochloride

874-60-2

4-methyl-benzoyl chloride

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%
593-56-6

N-methoxylamine hydrochloride

874-60-2

4-methyl-benzoyl chloride

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%
1147550-11-5

ammonium thiocyanate

874-60-2

4-methyl-benzoyl chloride

16794-68-6

4-methylbenzoyl isothiocyanate

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

C33H29N4OP

874-60-2

4-methyl-benzoyl chloride

130774-82-2

C41H36N4O2P(1+)*Cl(1-)

Conditions
ConditionsYield
In benzene for 3h; Ambient temperature;100%
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    4-Methylbenzoyl chloride CAS: 874-60-2

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  • Benzoyl chloride,4-methyl- 874-60-2

  • Casno:

    874-60-2

    Benzoyl chloride,4-methyl- 874-60-2

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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,

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