32360-03-5

Basic information

• Product Name: 2-tert-Butyl-5-pentadecylphenol
• Synonyms: 2-(1,1-Dimethylethyl)-5-pentadecylphenol;2-tert-Butyl-5-pentadecylphenol
• CAS NO: 32360-03-5
• Molecular Formula: C₂₅H₄₄O
• Molecular Weight: 360.6163
• Mol File: 32360-03-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 43.5 °C(Solv: chloroform (67-66-3); hexane (110-54-3))
• Boiling Point: 458.4°Cat760mmHg
• Flash Point: 216.2°C
• Appearance: /
• Density: 0.897g/cm³
• Vapor Pressure: 5.05E-09mmHg at 25°C
• Refractive Index: 1.49
• PKA: 11.44±0.10(Predicted)
• CAS DataBase Reference: 2-tert-Butyl-5-pentadecylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-tert-Butyl-5-pentadecylphenol(32360-03-5)
• EPA Substance Registry System: 2-tert-Butyl-5-pentadecylphenol(32360-03-5)

Safety Data

• Hazardous Substances Data: 32360-03-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C25H44O/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-22-19-20-23(24(26)21-22)25(2,3)4/h19-21,26H,5-18H2,1-4H3

Synthetic route

tert-butyl methyl ether (1634-04-4) + 3-n-Pentadecylphenol (501-24-6) → 2-tert-butyl-5-n-pentadecylphenol (32360-03-5)

Conditions	Yield
tin(IV) chloride In dichloromethane for 16h; Ambient temperature;	98%

tertiary butyl chloride (507-20-0) + 3-n-Pentadecylphenol (501-24-6) → 2-tert-butyl-5-n-pentadecylphenol (32360-03-5)

Conditions	Yield
With zinc(II) chloride In acetone at 60℃; for 3h; Temperature;
With zinc(II) chloride In acetone at 50℃; for 5h;	31.2 g

2-tert-butyl-5-n-pentadecylphenol (32360-03-5) + ethylene dibromide (106-93-4) → 2-(2-bromo-ethoxy)-1-tert-butyl-4-pentadecyl-benzene

Conditions	Yield
With potassium hydroxide at 70℃; for 6h;	88%

2-tert-butyl-5-n-pentadecylphenol (32360-03-5) + allyl bromide (106-95-6) → 2-allyloxy-1-tert-butyl-4-n-pentadecylbenzene (502495-06-9)

Conditions	Yield
With potassium carbonate In acetone Heating;	80%

2-tert-butyl-5-n-pentadecylphenol (32360-03-5) + Cinnamyl bromide (4392-24-9) → 1-tert-butyl-4-n-pentadecyl-2-(3-phenylallyloxy)benzene

Conditions	Yield
With potassium carbonate In acetone Heating;	79%

2-tert-butyl-5-n-pentadecylphenol (32360-03-5) → 3-n-pentadecyl-6-tert-butyl-2,4-dinitrophenol

Conditions	Yield
With nitric acid In methanol at 20℃; for 0.5h;	79%

(E)-1-Bromo-2-butene (4784-77-4, 39616-19-8, 29576-14-5) + 2-tert-butyl-5-n-pentadecylphenol (32360-03-5) → 2-(but-2-enyloxy)-1-tert-butyl-4-n-pentadecylbenzene

Conditions	Yield
With potassium carbonate In acetone Heating;	77%

2-tert-butyl-5-n-pentadecylphenol (32360-03-5) → 2-tert-butyl-5-n-pentadecyl-1,4-benzoquinone (265310-65-4)

Conditions	Yield
With water; dihydrogen peroxide; acetic acid; methyltrioxorhenium(VII) at 25℃; for 12h; Catalytic oxidation;	71%
With poly(4-vinylpyridine) 25 percent cross-linked; dihydrogen peroxide; methyltrioxorhenium(VII) In ethanol; water at 40℃;
Multi-step reaction with 2 steps 1: K2CO3 / dimethylformamide / 12 h / 25 °C 2: 49 percent / H2O2; H2O; AcOH / methyltrioxorhenium(VII) / 12 h / 25 °C View Scheme

2-tert-butyl-5-n-pentadecylphenol (32360-03-5) → 3-n-pentadecyl-6-tert-butyl-2-nitrophenol + 2-tert-butyl-5-n-pentadecyl-4-nitrophenol

Conditions	Yield
With nitric acid In methanol at 20℃; for 0.5h;	A 15% B 69%

2-tert-butyl-5-n-pentadecylphenol (32360-03-5) → 2-tert-butyl-4-bromo-5-n-pentadecylphenol (172759-21-6)

Conditions	Yield
With bromine In tetrachloromethane at 0℃; for 0.25h;

2-tert-butyl-5-n-pentadecylphenol (32360-03-5) + methyl iodide (74-88-4) → 2-tert-Butyl-5-n-pentadecylphenyl methyl ether (265310-67-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 12h; Methylation;

2-tert-butyl-5-n-pentadecylphenol (32360-03-5) → 5-tert-butyl-3-nitro-2-pentadecyl-[1,4]benzoquinone

Conditions	Yield
Multi-step reaction with 2 steps 1: 15 percent / HNO3 / methanol / 0.5 h / 20 °C 2: 25 percent / methylrhenium trioxide; aq. H2O2; AcOH / 4 h / 80 °C View Scheme

2-tert-butyl-5-n-pentadecylphenol (32360-03-5) → 5-tert-butyl-3-nitro-2-pentadecyl-benzene-1,4-diol

Conditions	Yield
Multi-step reaction with 2 steps 1: 15 percent / HNO3 / methanol / 0.5 h / 20 °C 2: 26 percent / methylrhenium trioxide; aq. H2O2; AcOH / 4 h / 80 °C View Scheme

2-tert-butyl-5-n-pentadecylphenol (32360-03-5) → 4-[2-(2-tert-butyl-5-pentadecyl-phenoxy)-ethoxy]-benzaldehyde (699008-88-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 88 percent / KOH / 6 h / 70 °C 2: 60 percent / K2CO3 / acetone / 24 h / Heating View Scheme

2-tert-butyl-5-n-pentadecylphenol (32360-03-5) → 2-allyl-6-tert-butyl-3-n-pentadecylphenol

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / K2CO3 / acetone / Heating View Scheme

2-tert-butyl-5-n-pentadecylphenol (32360-03-5) → 6-tert-butyl-2-(1-methylallyl)-3-n-pentadecylphenol

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / K2CO3 / acetone / Heating View Scheme

2-tert-butyl-5-n-pentadecylphenol (32360-03-5) → 9-tert-butyl-6-n-pentadecyl-4,5-dihydro-3H-benzo[b]oxepin-2-one

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent / K2CO3 / acetone / Heating 2: 90 percent / 1,4-bis(diphenylphosphino)butane; H2 / Pd(OAc)2 / toluene / 24 h / 100 °C / 31028.9 Torr View Scheme

2-tert-butyl-5-n-pentadecylphenol (32360-03-5) → 2-tert-butyl-5-n-pentadecyl-4-(3-phenylallyl)phenol

Conditions	Yield
Multi-step reaction with 2 steps 1: 79 percent / K2CO3 / acetone / Heating View Scheme

2-tert-butyl-5-n-pentadecylphenol (32360-03-5) → 2-tert-Butyl-5-n-pentadecyl-p-hydroquinone (265310-66-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 71 percent / H2O2; H2O; AcOH / methyltrioxorhenium(VII) / 12 h / 25 °C 2: 100 percent / NaBH4 / ethanol; tetrahydrofuran / 1 h / 25 °C View Scheme
Multi-step reaction with 3 steps 1: K2CO3 / dimethylformamide / 12 h / 25 °C 2: 49 percent / H2O2; H2O; AcOH / methyltrioxorhenium(VII) / 12 h / 25 °C 3: 100 percent / NaBH4 / ethanol; tetrahydrofuran / 1 h / 25 °C View Scheme

2-tert-butyl-5-n-pentadecylphenol (32360-03-5) → 2,4-dibromo-6-tert-butyl-3-n-pentadecylphenol

Conditions	Yield
Multi-step reaction with 2 steps 1: Br2 / CCl4 / 0.25 h / 0 °C 2: Br2 / CCl4 / Heating View Scheme

2-tert-butyl-5-n-pentadecylphenol (32360-03-5) → 2,4,4-tribromo-6-tert-butyl-3-n-pentadecylphenol

Conditions	Yield
Multi-step reaction with 3 steps 1: Br2 / CCl4 / 0.25 h / 0 °C 2: Br2 / CCl4 / Heating 3: Br2, acetic acid / Ambient temperature View Scheme

formaldehyd (50-00-0) + 2-tert-butyl-5-n-pentadecylphenol (32360-03-5) → 2,2’-methylenebis(3-pentadecyl-6-tert-butylphenol)

Conditions	Yield
With sodium hydroxide In ethanol; water for 3h; Time; Reflux;
With sodium hydroxide In ethanol; water for 5h; Reflux;

Upstream product

• 507-20-0 tertiary butyl chloride 
• 501-24-6 3-n-Pentadecylphenol 
• 1634-04-4 tert-butyl methyl ether 

Downstream Products

• 265310-65-4 2-tert-butyl-5-n-pentadecyl-1,4-benzoquinone 
• 265310-67-6 2-tert-Butyl-5-n-pentadecylphenyl methyl ether 
• 502495-06-9 2-allyloxy-1-tert-butyl-4-n-pentadecylbenzene 
• 265310-66-5 2-tert-Butyl-5-n-pentadecyl-p-hydroquinone 
• 172759-21-6 2-tert-butyl-4-bromo-5-n-pentadecylphenol 
• 699008-88-3 4-[2-(2-tert-butyl-5-pentadecyl-phenoxy)-ethoxy]-benzaldehyde 

Relevant articles and documents

Phenolic compound as well as preparation method and application thereof

The invention provides a phenolic compound as well as a preparation method and application thereof. The structure of the phenolic compound is shown as a general formula (I), R1 and R1'can be the sameor different and are independently selected from CnH(2n+m), n is an integer ranging from 3 to 30, m is 1, -1, -3 or -5, R2 and R2' can be the same or different and are independently selected from C1-C8 straight chain or branched chain alkyl respectively; and R3 is selected from C1-C6 straight chain or branched chain alkylene. The phenolic compound provided by the invention has very excellent oxidation resistance, and can be used as an antioxidant in lubricating oil, lubricating grease, fuel oil, plastic and rubber. The preparation method disclosed by the invention is simple and feasible, and the yield and product purity are relatively high.

EFFECT OF METAL IONS IN ORGANIC SYNTHESIS. XXXV SIMPLE AND CONVENIENT AROMATIC ALKYLATION OF SOME ALKENYLPHENOL DERIVATIVES WITH tert-ALKYL METHYL ETHERS IN THE PRESENCE OF TIN(IV) CHLORIDE

A very mild, simple and convenient method for the aromatic alkylation of some alkenylphenol derivatives with tert-alkyl methyl ethers to give sterically hindered phenols useful as antioxidants is reported.The reaction occurs with good yields at room temperature and is promoted by tin(IV) chloride.