3851-87-4

Basic information

• Product Name: 3,5,5-Trimethylhexanoyl peroxide
• Synonyms: bis(3,5,5-trimethylhexanoyl) peroxide;3,5,5-Trimethylhexanoyl peroxide;3，5，5-Trimethyl caproyl peroxide;Di(3,5,5-trimethylhexanoyl) peroxide;Peroxide, bis(3,5,5-trimethyl-1-oxohexyl);Di-(3,5,5-trimethylhexanoyl)-peroxid21;Initiating agent CP-10;Dinonanoyl peroxide
• CAS NO: 3851-87-4
• Molecular Formula: C₁₈H₃₄O₄
• Molecular Weight: 314.46
• EINECS: 223-356-0
• Mol File: 3851-87-4.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 359.5 °C at 760 mmHg
• Flash Point: 149.8 °C
• Appearance: /
• Density: 0.943 g/cm³
• Vapor Pressure: 2.37E-05mmHg at 25°C
• Refractive Index: 1.445
• Water Solubility: 10mg/L at 5℃
• CAS DataBase Reference: 3,5,5-Trimethylhexanoyl peroxide(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5,5-Trimethylhexanoyl peroxide(3851-87-4)
• EPA Substance Registry System: 3,5,5-Trimethylhexanoyl peroxide(3851-87-4)

Safety Data

• RIDADR: 3106
• HazardClass: 5.2
• PackingGroup: II
• Hazardous Substances Data: 3851-87-4(Hazardous Substances Data)

Usage

General Description

3,5,5-Trimethylhexanoyl peroxide is a hazardous organic compound that is commonly used as a radical initiator in polymerization reactions and as a curing agent in the production of certain plastics and rubbers. It is a colorless to pale yellow liquid with a characteristic odor, and it is highly flammable and reactive. Exposure to 3,5,5-Trimethylhexanoyl peroxide can cause irritation to the skin, eyes, and respiratory tract, and prolonged or repeated exposure may lead to more serious health effects including dermatitis and sensitization. Due to its potential hazards, proper handling and storage procedures are necessary when working with this substance, and it is important to follow all safety guidelines and precautions when using it in industrial processes.

InChI:InChI=1/C18H34O4/c1-13(11-17(3,4)5)9-15(19)21-22-16(20)10-14(2)12-18(6,7)8/h13-14H,9-12H2,1-8H3

Synthetic route

3,5,5-trimethylhexanoic acid (3302-10-1) → bis(3,5,5-trimethylhexanoyl) peroxide (3851-87-4)

Conditions	Yield
With dihydrogen peroxide In pentane at 70 - 80℃; for 8h; Solvent; Temperature;	94%
With dmap; dihydrogen peroxide; dicyclohexyl-carbodiimide In dichloromethane at -5 - 0℃; for 2h; Inert atmosphere;	72%
Stage #1: 3,5,5-trimethylhexanoic acid With dmap; dihydrogen peroxide In dichloromethane at -15℃; for 0.166667h; Inert atmosphere; Stage #2: With dicyclohexyl-carbodiimide In dichloromethane at -15 - 10℃; for 1.5h; Inert atmosphere;

isononanoyl chloride (36727-29-4) → bis(3,5,5-trimethylhexanoyl) peroxide (3851-87-4)

Conditions	Yield
With dihydrogen peroxide In water at 26 - 32℃;	92%
With dihydrogen peroxide; potassium hydroxide In water at 5 - 40℃; for 0.0166667h; Temperature; Flow reactor;	92.3%

1,3-Benzothiazole (95-16-9) + bis(3,5,5-trimethylhexanoyl) peroxide (3851-87-4) → C15H21NS

Conditions	Yield
With iron(III) trifluoromethanesulfonate In acetonitrile at 80℃; for 5h; Inert atmosphere; Schlenk technique; Green chemistry;	83%

2-methylquinoline (91-63-4) + bis(3,5,5-trimethylhexanoyl) peroxide (3851-87-4) → 2-methyl-4-(2,4,4-trimethylpentyl)quinoline

Conditions	Yield
With trifluorormethanesulfonic acid In acetonitrile at 80℃; for 12h; Inert atmosphere; Schlenk technique;	73%

2-Vinylnaphthalene (827-54-3) + bis(3,5,5-trimethylhexanoyl) peroxide (3851-87-4) + phenylboronic acid (98-80-6) → 2-(4,6,6-trimethyl-1-phenylheptyl)naphthalene

Conditions	Yield
With tetrakis(actonitrile)copper(I) hexafluorophosphate; 2,6-bis[4′-isopropyloxazolin-2′-yl]pyridine; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 12h; Schlenk technique; Inert atmosphere;	69%

phenylacetylene (536-74-3) + bis(3,5,5-trimethylhexanoyl) peroxide (3851-87-4) → C16H24O

Conditions	Yield
Stage #1: phenylacetylene; bis(3,5,5-trimethylhexanoyl) peroxide With iron(III) trifluoromethanesulfonate In tetrahydrofuran at 60℃; for 1h; Schlenk technique; Inert atmosphere; Sealed tube; Stage #2: With trifluorormethanesulfonic acid In tetrahydrofuran at 100℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube;	68%

styrene (100-42-5) + bis(3,5,5-trimethylhexanoyl) peroxide (3851-87-4) → C16H25F

Conditions	Yield
With tris(bipyridine)ruthenium(II) dichloride hexahydrate; copper diacetate; triethylamine tris(hydrogen fluoride) In 1,2-dichloro-ethane at 20℃; for 24h; Schlenk technique; Inert atmosphere; Irradiation;	60%

bis(3,5,5-trimethylhexanoyl) peroxide (3851-87-4) → 2,2,4-trimethylpentane (540-84-1) + 2,4,4-trimethylpentan-1-ol (16325-63-6) + 2,2,4,7,9,9-hexamethyldecane (72493-27-7) + 3,5,5-trimethylhexanoic acid (3302-10-1) + bis(3,5,5-trimethylhexanoic) anhydride (94376-47-3) + 2,4,4-trimethylpentyl 3,5,5-trimethylhexanoate

Conditions	Yield
With pentadecane at 80℃; under 750060 Torr; Product distribution; Rate constant; Thermodynamic data; var. of temp., pressure, solvent, EA, ΔV(excit.);	A 0.625 mol B 0.009 mol C 0.394 mol D 0.038 mol E 0.005 mol F 0.126 mol

bis(3,5,5-trimethylhexanoyl) peroxide (3851-87-4) → 3,5,5-trimethylhexanoic acid (3302-10-1) + 2,4,4-trimethylpentyl 3,5,5-trimethylhexanoate

Conditions	Yield
With 2-methylundecane In acetonitrile at 70℃; under 1500120 Torr; for 16h; Rate constant; Thermodynamic data; Kinetics; var. of solvent, temp., pressure, without additive, EA, ΔV(excit.);

bis(3,5,5-trimethylhexanoyl) peroxide (3851-87-4) → 2,4,4-trimethylpentyl radical + 3,5,5-trimethylhexanoyloxyl radical

Conditions	Yield
With 5,5-Dimethyl-1-pyrroline N-oxide In benzene at 39.85℃; Product distribution; Further Variations:; Temperatures; Reagents; Decomposition;

phenylacetylene (536-74-3) + bis(3,5,5-trimethylhexanoyl) peroxide (3851-87-4) → C16H24 + ((E)-4,6,6-Trimethyl-hept-1-enyl)-benzene

Conditions	Yield
With N-hydroxyphthalimide; tris(4,4'-bis(tert-butyl)-2,2'-dipyridyl)ruthenium(II) dichloride; (R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine; N-ethyl-N,N-diisopropylamine; nickel dichloride In isopropyl alcohol for 6h; Inert atmosphere; Irradiation; Overall yield = 71 %; Overall yield = 77 mg;	A n/a B n/a

bis(3,5,5-trimethylhexanoyl) peroxide (3851-87-4) + 4-n-methylphenylacetylene (766-97-2) → C17H24

Conditions	Yield
With triethylamine; 4,4'-di-tert-butyl-2,2'-bipyridine; copper(l) chloride In acetonitrile at -10℃; Inert atmosphere;	80 mg

phenylacetylene (536-74-3) + bis(3,5,5-trimethylhexanoyl) peroxide (3851-87-4) → C16H23N3

Conditions	Yield
With trimethylsilylazide; copper(l) chloride In dichloromethane at 50℃; for 10h; Schlenk technique; regioselective reaction;	89 mg

Upstream product

• 36727-29-4 isononanoyl chloride 
• 3302-10-1 3,5,5-trimethylhexanoic acid 

Downstream Products

• 540-84-1 2,2,4-trimethylpentane 
• 16325-63-6 2,4,4-trimethylpentan-1-ol 
• 72493-27-7 2,2,4,7,9,9-hexamethyldecane 
• 3302-10-1 3,5,5-trimethylhexanoic acid 
• 94376-47-3 bis(3,5,5-trimethylhexanoic) anhydride 

Relevant articles and documents

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