895-85-2

Basic information

• Product Name: Peroxide, bis(4-methylbenzoyl)
• Synonyms: Peroxide, bis(4-methylbenzoyl);Bis-(4-methylbenzoyl)-peroxide;(4-methylbenzoyl) 4-methylbenzenecarboperoxoate;(4-methylphenyl)carbonyl 4-methylbenzenecarboperoxoate;4-methylbenzenecarboperoxoic acid (4-methylbenzoyl) ester
• CAS NO: 895-85-2
• Molecular Formula: C₁₆H₁₄O₄
• Molecular Weight: 270.28
• EINECS: 407-950-9
• Mol File: 895-85-2.mol
• Article Data: 16

Chemical Properties

• Melting Point: 143-144 °C (decomp)
• Boiling Point: 373.4°C (rough estimate)
• Flash Point: 177.9 °C
• Appearance: white paste
• Density: 1.2117 (rough estimate)
• Vapor Pressure: 1.14E-06mmHg at 25°C
• Refractive Index: 1.5447 (estimate)
• Solubility: 680 in mg/100g standard fat at 20 ℃
• Water Solubility: 43μg/L at 20℃
• CAS DataBase Reference: Peroxide, bis(4-methylbenzoyl)(CAS DataBase Reference)
• NIST Chemistry Reference: Peroxide, bis(4-methylbenzoyl)(895-85-2)
• EPA Substance Registry System: Peroxide, bis(4-methylbenzoyl)(895-85-2)

Safety Data

• Hazard Codes: E,N
• Statements: 2-7-50/53
• Safety Statements: 7-14-36/37/39-47-60-61
• RIDADR: 3102
• HazardClass: 5.2
• PackingGroup: II
• Hazardous Substances Data: 895-85-2(Hazardous Substances Data)

Usage

Flammability and Explosibility

Notclassified

InChI:InChI=1/C16H14O4/c1-11-3-7-13(8-4-11)15(17)19-20-16(18)14-9-5-12(2)6-10-14/h3-10H,1-2H3

Synthetic route

p-Toluic acid (99-94-5) → di-(4-methylbenzoyl)peroxide (895-85-2)

Conditions	Yield
With Eosin Y; triphenylphosphine In acetonitrile at 20℃; Irradiation;	91%
(i) N,N'-carbonyl-diimidazole, (ii) H2O2; Multistep reaction;

4-methyl-benzoyl chloride (874-60-2) → di-(4-methylbenzoyl)peroxide (895-85-2)

Conditions	Yield
With dihydrogen peroxide In diethyl ether; water for 0.166667h;	86%
With sodium peroxide
With dihydrogen peroxide; sodium hydroxide In water

4-methyl-benzaldehyde (104-87-0) → di-(4-methylbenzoyl)peroxide (895-85-2) + 4-methylperbenzoic acid (937-21-3) + p-Toluic acid (99-94-5)

Conditions	Yield
With oxygen; ozone; lithium chloride In tetrachloromethane at 50℃;	A 58.3% B n/a C n/a

para-chlorotoluene (106-43-4) → di-(4-methylbenzoyl)peroxide (895-85-2)

Conditions	Yield
With sodium peroxide; toluene
With sodium peroxide; cyclohexane
With toluene
With dihydrogen peroxide; acetone Behandeln des Reaktionsgemisches mit Natronlauge;

4-(methylbenzoyl)imidazoline (10347-11-2) → di-(4-methylbenzoyl)peroxide (895-85-2)

Conditions	Yield
With dihydrogen peroxide

4-methyl-benzoyl chloride (874-60-2) + ortho-toluoyl chloride (933-88-0) → di-(4-methylbenzoyl)peroxide (895-85-2) + 2-methylbenzoyl 4-methylbenzoyl peroxide (208726-49-2)

Conditions	Yield
With dihydrogen peroxide; sodium hydroxide In water at 10 - 20℃; for 1h; Industry scale;

2-acetylpropanoic acid ethyl ester (609-14-3) + di-(4-methylbenzoyl)peroxide (895-85-2) → C15H18O5

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; CHF3O3S*C10H24N2 In chloroform at 20℃; Schlenk technique; Inert atmosphere; enantioselective reaction;	90%

4-methyl-β-nitrostyrene (7559-36-6) + di-(4-methylbenzoyl)peroxide (895-85-2) → (E)-4,4'-dimethylstilbene (18869-29-9)

Conditions	Yield
In acetonitrile at 100℃; for 3h; Sealed tube; stereoselective reaction;	90%

di-(4-methylbenzoyl)peroxide (895-85-2) + 1,2-dichloro-ethane (107-06-2) → 2-chloroethyl 4-methyl benzoate (125288-33-7)

Conditions	Yield
With 1,10-Phenanthroline; oxygen; copper diacetate; sodium t-butanolate In dimethyl sulfoxide at 80℃; for 24h;	85%

di-(4-methylbenzoyl)peroxide (895-85-2) + benzylamine (100-46-9) → N-benzyl-4-methylbenzamide (5436-83-9)

Conditions	Yield
With bathophenanthroline; cobalt(II) diacetate tetrahydrate In 1,2-dichloro-ethane at 60℃; for 8h; Sealed tube;	85%

1-methyl-2(1H)-quinoxalinone (6479-18-1) + di-(4-methylbenzoyl)peroxide (895-85-2) → 1-methyl-3-(4-tolyl)quinoxalin-2(1H)-one

Conditions	Yield
In ethyl acetate at 80℃; for 24h; Sealed tube;	85%
In ethyl acetate at 20℃; for 3h; Irradiation; Green chemistry; regioselective reaction;	75%
In acetone at 80℃; for 12h; Autoclave; Green chemistry;	68%

2-phenylpyridine (1008-89-5) + di-(4-methylbenzoyl)peroxide (895-85-2) → 2-(4’-methyl-[1,1’-biphenyl]-2-yl)pyridine

Conditions	Yield
With palladium diacetate In acetic acid; acetonitrile for 2h; Heating; Inert atmosphere;	81%

di-(4-methylbenzoyl)peroxide (895-85-2) + benzene (71-43-2) → 4-Methylbiphenyl (644-08-6)

Conditions	Yield
at 100℃; for 12h; Sealed tube;	81%

di-(4-methylbenzoyl)peroxide (895-85-2) + 1-(2-hydroxyphenyl)-3-dimethylaminoprop-2-enone (106129-86-6, 1776-08-5) → 4-oxo-4H-chromen-3-yl 4-methylbenzoate

Conditions	Yield
In ethanol at 20℃; for 6h;	80%

8-amino quinoline (578-66-5) + di-(4-methylbenzoyl)peroxide (895-85-2) → 7-aminoquinolin-8-yl 4-methylbenzoate

Conditions	Yield
With air In water at 20℃; for 16h; Green chemistry;	80%

di-(4-methylbenzoyl)peroxide (895-85-2) + 2-isocyanobiphenyl (3128-77-6) → 6-(4′-methylphenyl)phenanthridine (47135-83-1)

Conditions	Yield
at 100℃; for 10h; Inert atmosphere;	77%

di-(4-methylbenzoyl)peroxide (895-85-2) + tris(2,4,6-trimethylphenyl)phosphine (23897-15-6) + tris(pentafluorophenyl)borate (1109-15-5) → C26H7BF15O2(1-)*C27H33P(1+)

Conditions	Yield
In dichloromethane Inert atmosphere; Glovebox;	77%

di-(4-methylbenzoyl)peroxide (895-85-2) + 8-(n-butyryl)aminoquinoline (33757-47-0) → 8-butyramidoquinolin-5-yl 4-methylbenzoate

Conditions	Yield
Stage #1: N-(quinolin-8-yl)butyramide With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In water at 80℃; for 0.5h; Stage #2: di-(4-methylbenzoyl)peroxide In water at 80℃; for 24h;	73%

di-(4-methylbenzoyl)peroxide (895-85-2) + N-(3-methylphenyl)-2,2-dimethylpropanamide (32597-29-8) → N-(4,4′-dimethyl-[1,1′-biphenyl]-2-yl)pivalamide (1029124-77-3)

Conditions	Yield
With trifluorormethanesulfonic acid; palladium diacetate In acetonitrile at 80℃; for 32h; Molecular sieve;	72%

di-(4-methylbenzoyl)peroxide (895-85-2) + trans-azobenzene (17082-12-1) → (E)-1-(4’-methyl-[1,1’-biphenyl]-2-yl)-2-phenyldiazene (1619236-92-8) + (Z)-1-(4'-methyl-[1,1'-biphenyl]-2-yl)-2-phenyl diazene (1619236-93-9)

Conditions	Yield
With palladium diacetate In chlorobenzene; acetonitrile at 130℃; for 24h; Sealed tube; regioselective reaction;	A 70% B n/a

di-(4-methylbenzoyl)peroxide (895-85-2) + 4-methyl-N-(quinolin-8-yl)benzamide (33757-49-2) → 8-(4-methylbenzamido)quinolin-5-yl 4-methylbenzoate

Conditions	Yield
With iron(III) chloride hexahydrate In toluene at 90℃; for 24h;	70%

di-(4-methylbenzoyl)peroxide (895-85-2) + 2,3-dimethyl-buta-1,3-diene (513-81-5) → C22H24O4

Conditions	Yield
With copper(I) bromide In 1,2-dichloro-benzene at 80℃; for 18h; Inert atmosphere; Schlenk technique;	67%

di-(4-methylbenzoyl)peroxide (895-85-2) + phenyl 2-pyridyl sulphoxide (89818-46-2) → 2-[(4'-methylbiphenyl-2-yl)sulfinyl]pyridine (1308400-03-4)

Conditions	Yield
With palladium diacetate; acetic acid In acetonitrile at 80℃; for 16h; Inert atmosphere; regioselective reaction;	66%

di-(4-methylbenzoyl)peroxide (895-85-2) + 1,4-dichlorobutane (110-56-5) → 4-methylbenzoic acid 4-chlorobutyl ester

Conditions	Yield
With 1,10-Phenanthroline; oxygen; copper diacetate; sodium t-butanolate In dimethyl sulfoxide at 80℃; for 24h;	65%

s-butyl chloride (78-86-4, 53178-20-4) + di-(4-methylbenzoyl)peroxide (895-85-2) → sec-butyl 4-methylbenzoate (100556-51-2)

Conditions	Yield
With 1,10-Phenanthroline; oxygen; copper diacetate; sodium t-butanolate In dimethyl sulfoxide at 80℃; for 24h;	65%

Upstream product

• 874-60-2 4-methyl-benzoyl chloride 
• 99-94-5 p-Toluic acid 
• 933-88-0 ortho-toluoyl chloride 
• 104-87-0 4-methyl-benzaldehyde 
• 10347-11-2 4-(methylbenzoyl)imidazoline 
• 106-43-4 para-chlorotoluene 

Downstream Products

• 251326-30-4 2-methyl-3-(4-methylphenyl)-1,4-naphthoquinone 
• 116031-20-0 3-trityl-benzoic acid methyl ester 
• 937-21-3 4-methylperbenzoic acid 
• 2396-02-3 p-tolyl 
• 3170-80-7 trichloromethyl radical 
• 23074-26-2 4-methylbenzoyloxyl radical 
• 78477-04-0 2-<(4-Chlorbenzoyl)cyclohexylamino>-6-hydroxy-4,4-dimethyl-2,5-cyclohexadien-1-on 
• 78477-05-1 2--6-hydroxy-4,4-dimethyl-2,5-cyclohexadien-1-on 
• 99-94-5 p-Toluic acid 
• 115228-92-7 (3-methylphenyl)triphenylmethane 
• 115228-81-4 triphenyl(3-chlorophenyl)methane 
• 125288-33-7 2-chloroethyl 4-methyl benzoate 
• 100556-51-2 sec-butyl 4-methylbenzoate 
• 5436-83-9 N-benzyl-4-methylbenzamide 

Relevant articles and documents

Aryl acyl peroxides for visible-light induced decarboxylative arylation of quinoxalin-2(1: H)-ones under additive-, metal catalyst-, and external photosensitizer-free and ambient conditions

Aryl radicals were generated for the first time from cheap and easily available aryl acyl peroxides in eco-friendly ethyl acetate under ambient conditions and visible-light illumination in the absence of any additive, metal catalyst, or external photosensitizer. The present arylation of quinoxalin-2(1H)-ones was chemo- and regioselective, and provided good access to various 3-arylquinoxalin-2(1H)-ones. This journal is

An unprecedented cobalt-catalyzed selective aroylation of primary amines with aroyl peroxides

A novel and facile cobalt-catalyzed selective aroylation of primary amines with aroyl peroxides was developed for the synthesis of aryl amides. It was unprecedented that C[sbnd]N bond formation product was selectively generated without the common N[sbnd]O bond formation product. Aroyl peroxides act as the sole aroylation reagent without additional base or oxidant. The reactions proceeded under mild conditions and showed broad substrates scope with a series of primary amines and aroyl peroxides.

Uncatalyzed, on water oxygenative cleavage of inert C-N bond with concomitant 8,7-amino shift in 8-aminoquinoline derivatives

Oxygenative cleavage of an inert CAr-NH2 bond with concomitant 1,2 amine migration in 8-aminoquinoline derivatives is reported in water at room temperature. The reaction is highly atom- and step-economical as both C- and N-containing fragments of the C-N bond cleavage are incorporated into the target molecule and is effected without the need for N-oxide. The reaction is scalable to gram level, and the products are useful as electrophilic partners for coupling reactions, ligands in catalysis and bioactive compounds.