• Name

  3,5,5-Trimethylhexanoyl peroxide

• EINECS 223-356-0
• CAS No. 3851-87-4
• Article Data9
• CAS DataBase
• Density 0.943 g/cm³
• Solubility Soluble
• Melting Point 79oC
• Formula C₁₈H₃₄O₄
• Boiling Point 359.5 °C at 760 mmHg
• Molecular Weight 314.466
• Flash Point 149.8 °C
• Transport Information
• Appearance white crystals or powder
• Safety
• Risk Codes R8; R36/37/38; R22; R61; R20/21/22
• Molecular Structure
• Hazard Symbols O,Xi,Xn,T
• Synonyms Bis(3,5,5-trimethylhexanoyl) peroxide;Lup 219;Luperox 219;Peroyl 355;Trigonox 36;Trigonox 36C75;USP 355M;
• PSA 52.60000
• LogP 4.91260

Synthetic route

3302-10-1

3,5,5-trimethylhexanoic acid

3851-87-4

bis(3,5,5-trimethylhexanoyl) peroxide

Conditions

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;

36727-29-4

isononanoyl chloride

3851-87-4

bis(3,5,5-trimethylhexanoyl) peroxide

Conditions

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%

95-16-9

1,3-Benzothiazole

3851-87-4

bis(3,5,5-trimethylhexanoyl) peroxide

C15H21NS

Conditions

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

91-63-4

2-methylquinoline

3851-87-4

bis(3,5,5-trimethylhexanoyl) peroxide

2-methyl-4-(2,4,4-trimethylpentyl)quinoline

Conditions

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

827-54-3

2-Vinylnaphthalene

3851-87-4

bis(3,5,5-trimethylhexanoyl) peroxide

98-80-6

phenylboronic acid

2-(4,6,6-trimethyl-1-phenylheptyl)naphthalene

Conditions

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%

...Expand

536-74-3

phenylacetylene

3851-87-4

bis(3,5,5-trimethylhexanoyl) peroxide

C16H24O

Conditions

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%

100-42-5

styrene

3851-87-4

bis(3,5,5-trimethylhexanoyl) peroxide

C16H25F

Conditions

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%

3851-87-4

bis(3,5,5-trimethylhexanoyl) peroxide

A

540-84-1

2,2,4-trimethylpentane

B

16325-63-6

2,4,4-trimethylpentan-1-ol

C

72493-27-7

2,2,4,7,9,9-hexamethyldecane

D

3302-10-1

3,5,5-trimethylhexanoic acid

E

94376-47-3

bis(3,5,5-trimethylhexanoic) anhydride

F

2,4,4-trimethylpentyl 3,5,5-trimethylhexanoate

Conditions

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

...Expand

3851-87-4

bis(3,5,5-trimethylhexanoyl) peroxide

A

3302-10-1

3,5,5-trimethylhexanoic acid

B

2,4,4-trimethylpentyl 3,5,5-trimethylhexanoate

Conditions

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.);

3851-87-4

bis(3,5,5-trimethylhexanoyl) peroxide

A

2,4,4-trimethylpentyl radical

B

3,5,5-trimethylhexanoyloxyl radical

Conditions

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

536-74-3

phenylacetylene

3851-87-4

bis(3,5,5-trimethylhexanoyl) peroxide

A

C16H24

B

((E)-4,6,6-Trimethyl-hept-1-enyl)-benzene

Conditions

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

...Expand

3851-87-4

bis(3,5,5-trimethylhexanoyl) peroxide

766-97-2

4-n-methylphenylacetylene

C17H24

Conditions

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

536-74-3

phenylacetylene

3851-87-4

bis(3,5,5-trimethylhexanoyl) peroxide

C16H23N3

Conditions

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

3,5,5-Trimethylhexanoyl peroxide Chemical Properties

3,5,5-Trimethylhexanoyl peroxide Uses

3,5,5-Trimethylhexanoyl peroxide Safety Profile