538-93-2

Basic information

• Product Name: Isobutylbenzene
• Synonyms: (2-methylpropyl)-Benzene;1-Phenyl-2-methylpropane;2-Methylpropylbenzene;Benzene, isobutyl-;Benzene,(2-methylpropyl)-;benzene,2-methylpropyl-;i-Butylbenzene;isobutyl-benzen
• CAS NO: 538-93-2
• Molecular Formula: C₁₀H₁₄
• Molecular Weight: 134.22
• EINECS: 208-706-2
• Mol File: 538-93-2.mol
• Article Data: 80

Chemical Properties

• Melting Point: −51 °C(lit.)
• Boiling Point: 170 °C736 mm Hg(lit.)
• Flash Point: 131 °F
• Appearance: Clear colourless liquid
• Density: 0.853 g/mL at 25 °C(lit.)
• Vapor Pressure: 4.2 mm Hg ( 37.7 °C)
• Refractive Index: n20/D 1.486(lit.)
• Storage Temp.: Flammables area
• Solubility: 0.01g/l
• PKA: >14 (Schwarzenbach et al., 1993)
• Explosive Limit: 0.8-6%(V)
• Water Solubility: INSOLUBLE
• Merck: 14,5134
• BRN: 1852218
• CAS DataBase Reference: Isobutylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: Isobutylbenzene(538-93-2)
• EPA Substance Registry System: Isobutylbenzene(538-93-2)

Safety Data

• Hazard Codes: Xi,N
• Statements: 10-36/37/38-50/53
• Safety Statements: 26-36-61-60
• RIDADR: UN 3295 3/PG 3
• WGK Germany: 3
• RTECS: DA3550000
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 538-93-2(Hazardous Substances Data)

Usage

Chemical Properties

Isobutyl Benzene is an organic, aromatic, neutral and colourless liquid that has a specific gravity of around 0.852. Less dense than water and insoluble in water, soluble in ethanol, ether, benzene and acetone. Vapors heavier than air.

Physical properties

Clear, colorless, liquid with an odor resembling butylbenzene, tert-butylbenzene, ethylbenzene, or toluene. An odor threshold concentration of 80 μg/kg was reported (quoted, Verschueren, 1983)

Uses

Isobutylbenzene is used as an intermediate for perfumery and analgesic anti-inflammatory (Ibuprofen). It is also used as an internal standard in the study of increased pigmentation and floral scent levels in Pap1-transgenic petunia.

Definition

ChEBI: Isobutylbenzene is an alkylbenzene that is benzene carrying an isobutyl substituent.

Preparation

Isobutylbenzene synthesis: Isobutyrophenone, underwent a Wolff–Kishner reduction using hydrazine hydrate and strong base conditions to synthesize isobutyl benzene. The solvent for this reaction was replaced with the more sustainable solvent glycerol. The glycerol for this reaction was obtained from the synthesis of biodiesel. The reaction was allowed to heat at reflux (149–155 °C) for a period of three hours. An average 51 % yield of isobutyl benzene was obtained from the solar synthesis, compared to a 55 % yield from an in-lab, electrical heating analysis.

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 4343, 1951 DOI: 10.1021/ja01153a092Synthetic Communications, 26, p. 763, 1996 DOI: 10.1080/00397919608086751Tetrahedron Letters, 27, p. 6369, 1986 DOI: 10.1016/S0040-4039(00)87811-9

General Description

Isobutylbenzene is synthesized by the isopropylation at the side chain over Na, K and Cs exchanged zeolites.

Hazard

Moderate fire risk. Toxic in high concentration, a skin and eye irritant.

Environmental fate

Biological. Oxidation of isobutylbenzene by Pseudomonas desmolytica S44B1 and Pseudomonas convexa S107B1 yielded 3-isobutylcatechol and (+)-2-hydroxy-8-methyl-6-oxononanoic acid (Jigami et al., 1975). Chemical/Physical. Complete combustion in air yields carbon dioxide and water vapor. Isobutylbenzene will not hydrolyze because it has no hydrolyzable functional group.

InChI:InChI=1/C10H14/c1-9(2)8-10-6-4-3-5-7-10/h3-7,9H,8H2,1-2H3

Synthetic route

2-Methyl-1-phenyl-2-propanol (100-86-7) → 1-phenyl-2-methylpropane (538-93-2)

Conditions	Yield
With indium(III) chloride; diphenylsilyl chloride In 1,2-dichloro-ethane at 80℃; for 3h;	99%
With phosphorus; hydrogen iodide; iodine
With hydrogen; pyrographite at 300℃;
With platinum on activated charcoal; hydrogen at 300℃;
Multi-step reaction with 3 steps 1: 0 °C / Einleiten von HCl 2: magnesium; diethyl ether / Behandlung der erhaltenen Grignard-Verbindung mit Deutero-essigsaeure 3: platinum; ethanol / Hydrogenation View Scheme

(2E)-2-methyl-3-phenylallyl acetate (65693-16-5) → 1-phenyl-2-methylpropane (538-93-2)

Conditions	Yield
With sodium tetrahydroborate; nickel dichloride In methanol at 0℃; for 0.166667h;	95%

2-methylpropylmagnesium chloride (5674-02-2) + chlorobenzene (108-90-7) → 1-phenyl-2-methylpropane (538-93-2)

Conditions	Yield
With iron(II) chloride tetrahydrate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In tetrahydrofuran at 70℃; for 3h; Inert atmosphere;	92%

tert-butylbenzene (253185-03-4, 253185-04-5) + {Rh-bis(1,2-bis(diphenylphosphino)ethane))}ClO4 (30513-14-5) → hydrido{1,2-bis-(diphenylphosphino)ethane}rhodium (29189-87-5) + 1-phenyl-2-methylpropane (538-93-2)

Conditions	Yield
In benzonitrile Electrolysis; GC-MS;	A 90% B 10%

phenylmagnesium bromide + isobutyryl chloride (513-36-0) → 1-phenyl-2-methylpropane (538-93-2)

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; palladium diacetate; tricyclohexylphosphine In tetrahydrofuran at 20℃; for 20h; Kumada coupling;	72%

1,1-dimethyl-2-phenylethyl acetate (151-05-3) → 1-phenyl-2-methylpropane (538-93-2)

Conditions	Yield
With di-tert-butyl peroxide; (4-diphenylsilylphenyl)diphenylsilane at 140℃; for 15h;	71%
With di-tert-butyl peroxide; (4-diphenylsilylphenyl)diphenylsilane at 140℃; for 15h; Product distribution; alcohol deoxygenation via acetate; reaction with Ph3SiH;	71%

(+)-(1S,2S)-1-methyl-2-phenylcyclopropane (53403-04-6) → 1-phenyl-2-methylpropane (538-93-2)

Conditions	Yield
With C9H24B11N2(1+)*C24BF20(1-); hydrogen In benzene at 80℃; for 24h; Autoclave;	70%

1-methylene-2-phenylcyclopropane (29817-09-2, 22664-13-7) → 1-phenyl-2-methylpropane (538-93-2) + 1-butylbenzene (104-51-8) + sec-Butylbenzene (135-98-8, 36383-15-0)

Conditions	Yield
With hydrogen; palladium on activated charcoal In 2,2,4-trimethylpentane Thermodynamic data; ΔHH;	A 31.47% B 64.69% C 3.84%

methyl (E)-2-(2-methyl-1-phenylpropylidene)hydrazine-1-carboxylate → 1-phenyl-2-methylpropane (538-93-2) + 1,2-bis(2-methyl-1-phenylpropylidene)hydrazine (19838-99-4)

Conditions	Yield
With potassium hydroxide In 2,2'-[1,2-ethanediylbis(oxy)]bisethanol at 140℃; for 4h; Wolff-Kishner Reduction;	A 53% B 30%

methyl (2-methyl-1-phenylpropan-2-yl) oxalate → 1-phenyl-2-methylpropane (538-93-2)

Conditions	Yield
With 2-(2'-pyridyl)benzimidazole; diphenylsilane; magnesium chloride; nickel dichloride; zinc In N,N-dimethyl acetamide at 40℃; Inert atmosphere; Schlenk technique;	52%

diethylmethylsilane (760-32-7) + carbon monoxide (201230-82-2) + 1,1-dimethyl-2-phenylethyl acetate (151-05-3) → 2-methyl-1-phenyl-2-propene (3290-53-7) + 1-phenyl-2-methylpropane (538-93-2) + (2-methyl-1-propenyl)-benzene (768-49-0)

Conditions	Yield
dicobalt octacarbonyl In benzene at 140℃; under 38000 Torr;	A 45% B 11% C 17%

1-iodo-2-methyl-2-phenylpropane (19479-63-1) + acetophenone (98-86-2) → tert-butylbenzene (253185-03-4, 253185-04-5) + 1-phenyl-2-methylpropane (538-93-2) + phenyl-(3-phenyl-2,2-dimethyl-1-propyl)ketone + phenyl(3-phenyl-3-methyl-1-butyl)ketone

Conditions	Yield
With potassium tert-butylate In dimethyl sulfoxide for 1h; Substitution; Reduction; Rearrangement; Irradiation;	A n/a B n/a C 15.5% D 44.9%

1,1-dimethyl-2-phenylethyl acetate (151-05-3) + HSiPh3 (789-25-3) → 1-phenyl-2-methylpropane (538-93-2) + triphenylsilyl acetate (1929-33-5)

Conditions	Yield
With di-tert-butyl peroxide at 140℃; for 12h;	A 43% B n/a

1-iodo-4-isobutylbenzene (85609-09-2) + N-propionylmorpholine sodium enolate → 1-phenyl-2-methylpropane (538-93-2) + 2-(4-isobutylphenyl)-1-morpholinopropan-1-one

Conditions	Yield
With iron(II) sulfate In ammonia for 1.5h;	A 13% B 42%

verbenene (4080-46-0, 23733-90-6, 30460-81-2) → 1-phenyl-2-methylpropane (538-93-2) + cis-1-isopropyl-4-methyl-cyclohexane (6069-98-3) + isobutylcyclohexane (1678-98-4) + cis-o-menthane (6070-02-6, 6070-03-7, 16580-23-7, 19489-02-2, 19489-03-3) + trans-o-menthane (6070-02-6, 6070-03-7, 16580-23-7, 19489-02-2, 19489-03-3) + o-mentha-1(7),5,8-triene (76786-83-9)

Conditions	Yield
In benzene at 380 - 390℃; Product distribution; hydrogenation of the reaction mixture in AcOH on 2percentPd/C, r.t.;	A 15.2% B 6.7% C 35.3% D 8.2% E 19.6% F 29%

β-phenylisovaleryl peroxide (62726-47-0) → tert-butylbenzene (253185-03-4, 253185-04-5) + 2-methyl-1-phenyl-2-propene (3290-53-7) + 1-phenyl-2-methylpropane (538-93-2) + 2-methyl-2-phenyl-propan-1-ol (2173-69-5) + 3-methyl-3-phenylbutanoic acid (1010-48-6) + bineophyl (17648-05-4)

Conditions	Yield
In acetonitrile at 55℃; Product distribution; Rate constant; other solvents (benzene, cyclohexane), other temperature, ClCH2COOH as a reagent, possible ways of the products formation;	A 12.0 % Chromat. B 6.6 % Chromat. C 12.1 % Chromat. D 4.0 % Chromat. E 26.1% F 7.6 % Chromat.

2-Methyl-1-phenyl-2-propanol (100-86-7) → 2-methyl-1-phenyl-2-propene (3290-53-7) + 1-phenyl-2-methylpropane (538-93-2) + (2-methyl-1-propenyl)-benzene (768-49-0)

Conditions	Yield
With triphenyl phosphite; tetraethylammonium bromide In acetonitrile constant current electrolysis, 100 mA;	A n/a B 19% C 59 % Chromat.
With triphenyl phosphite; tetraethylammonium bromide In acetonitrile constant current electrolysis, 100 mA;	A n/a B 19 % Chromat. C 19%

(2-methyl-1-propenyl)-benzene (768-49-0) → 1-phenyl-2-methylpropane (538-93-2)

Conditions	Yield
Stage #1: (2-methyl-1-propenyl)-benzene With Dimethylphenylsilane; copper(l) chloride In various solvent(s) at 20℃; for 28h; Reduction; Stage #2: With water; toluene-4-sulfonic acid In various solvent(s) at 20℃; Hydrolysis;	8%
With ethanol; platinum Hydrogenation;
With hydrogen

isopropyl bromide (75-26-3) + benzylmagnesium chloride (6921-34-2) → 1-phenyl-2-methylpropane (538-93-2)

Conditions	Yield
at 0℃; for 1h;	8%

phosgene (75-44-5) + diethyl ether (60-29-7) + neophyl chloride (515-40-2) + phenylmagnesium bromide → tert-butylbenzene (253185-03-4, 253185-04-5) + 2-methyl-1-phenyl-2-propene (3290-53-7) + 1-phenyl-2-methylpropane (538-93-2) + (2-methyl-1-propenyl)-benzene (768-49-0)

bromobenzene (108-86-1) + Isobutyl bromide (78-77-3) → 1-phenyl-2-methylpropane (538-93-2)

Conditions	Yield
With sodium

bromobenzene (108-86-1) + Isobutyl iodide (513-38-2) → 1-phenyl-2-methylpropane (538-93-2)

Conditions	Yield
With sodium; benzene

diisopropyl sulfate (2973-10-6) + phenylmagnesium bromide (1589-82-8) → 1-phenyl-2-methylpropane (538-93-2)

Conditions	Yield
With diethyl ether

Isobutyl bromide (78-77-3) + phenylmagnesium bromide → 1-phenyl-2-methylpropane (538-93-2)

Conditions	Yield
at 100℃;
With diethyl ether

3-methyl-3-phenylbutanal (6325-41-3) → tert-butylbenzene (253185-03-4, 253185-04-5) + 1-phenyl-2-methylpropane (538-93-2)

Conditions	Yield
With di-tert-butyl peroxide

2,2,4,4,-Tetramethyl-1-phenyl-3-pentanon (80958-97-0) → 1-phenyl-2-methylpropane (538-93-2)

Conditions	Yield
With sodium amide; benzene
With sodium amide; xylene

2,2,4,4-tetramethyl-1,5-diphenyl-pentan-3-one (153339-36-7) → 1-phenyl-2-methylpropane (538-93-2)

Conditions	Yield
With sodium amide; benzene
With sodium amide; xylene

isobutylmagnesium bromide (926-62-5) + phenylmagnesium bromide → 1-phenyl-2-methylpropane (538-93-2)

Conditions	Yield
With silver(I) bromide; diethyl ether

isopropylmagnesium bromide (920-39-8) + phenylmagnesium bromide (1589-82-8) → 1-phenyl-2-methylpropane (538-93-2)

Conditions	Yield
With silver(I) bromide; diethyl ether

1-phenyl-2-methylpropane (538-93-2) → 1-iodo-4-isobutylbenzene (85609-09-2)

Conditions	Yield
With Barluenga reagent; trifluorormethanesulfonic acid In dichloromethane for 0.5h; Ambient temperature;	100%
With silver(I) nitrite; iodine In dichloromethane at 20℃; for 96h;	70%
With silver(I) nitrite; iodine In dichloromethane at 20℃; for 96h;	70%
With iodine; iodic acid; acetic acid

1-phenyl-2-methylpropane (538-93-2) + ethyl 2-chloro-2-methylthio-acetate (145628-18-8, 56078-31-0) → ethyl α-methylthio-(p-isobutylphenyl)acetate (75280-07-8)

Conditions	Yield
tin(IV) chloride In dichloromethane for 0.666667h; Ambient temperature;	100%
tin(IV) chloride In dichloromethane for 0.666667h; Ambient temperature; Yield given;

1-phenyl-2-methylpropane (538-93-2) + Heptanoic acid chloride (2528-61-2) → 4'-Isobutylheptanophenone (148367-02-6)

Conditions	Yield
Stage #1: Heptanoic acid chloride With aluminium trichloride In dichloromethane at 0℃; for 0.5h; Stage #2: 1-phenyl-2-methylpropane In dichloromethane at 0℃; for 1h; Friedel-Crafts acylation;	99.7%

1-phenyl-2-methylpropane (538-93-2) + butyryl chloride (141-75-3) → 1-(4-isobutyl-phenyl)-1-butanone (104483-01-4)

Conditions	Yield
Stage #1: butyryl chloride With aluminium trichloride In dichloromethane at 0℃; for 0.5h; Stage #2: 1-phenyl-2-methylpropane In dichloromethane at 0℃; for 1h; Friedel-Crafts acylation;	99.3%

1-phenyl-2-methylpropane (538-93-2) + propionyl chloride (79-03-8) → 4-isobutylpropiophenone (59771-24-3)

Conditions	Yield
Stage #1: propionyl chloride With aluminium trichloride In dichloromethane at 0℃; for 0.5h; Stage #2: 1-phenyl-2-methylpropane In dichloromethane at 0℃; for 1h; Friedel-Crafts acylation;	99.2%
With aluminum (III) chloride In neat (no solvent) at 87℃; under 10343.2 Torr; for 0.0166667h; Temperature; Pressure; Friedel-Crafts Acylation;	95%
With aluminium trichloride In carbon disulfide below 5 deg C, 1.5 h, then room temp., overnight;	88%

1-phenyl-2-methylpropane (538-93-2) + n-valeryl chloride (638-29-9) → 1-(4-isobutylphenyl)pentan-1-one (148367-01-5)

Conditions	Yield
Stage #1: n-valeryl chloride With aluminium trichloride In dichloromethane at 0℃; for 0.5h; Stage #2: 1-phenyl-2-methylpropane In dichloromethane at 0℃; for 1h; Friedel-Crafts acylation;	99.1%
Stage #1: 1-phenyl-2-methylpropane; n-valeryl chloride In Petroleum ether at 20℃; for 0.25h; Stage #2: With trifluorormethanesulfonic acid In Petroleum ether for 10h; Reflux;	79.6%
With sodium hydrogencarbonate; aluminium chloride In dichloromethane

succinic acid anhydride (108-30-5) + 1-phenyl-2-methylpropane (538-93-2) → 4-(4-isobutylphenyl)-4-oxobutanoic acid (73120-67-9)

Conditions	Yield
Stage #1: succinic acid anhydride; 1-phenyl-2-methylpropane With aluminum (III) chloride In 1,1-dichloroethane at 20℃; for 1h; Heating / reflux; Stage #2: With hydrogenchloride In 1,1-dichloroethane; water at 20℃; for 0.166667h;	99%
With aluminium trichloride In 1,2-dichloro-ethane for 4h;	93%
With aluminium trichloride In nitrobenzene at 100℃; for 4h; Friedel Crafts succinoylation;	80%

1-phenyl-2-methylpropane (538-93-2) + diethyl methylthio(chloro)methanephosphonate (28975-74-8) → [(4-Isobutyl-phenyl)-methylsulfanyl-methyl]-phosphonic acid diethyl ester (107126-09-0)

Conditions	Yield
With tin(IV) chloride In dichloromethane for 0.666667h; Ambient temperature;	99%

1-phenyl-2-methylpropane (538-93-2) → 1-(4-isobutyl-phenyl)-ethanone (38861-78-8)

Conditions	Yield
With boron trifluoride; sulfur dioxide; acetic anhydride	98.7%

1-phenyl-2-methylpropane (538-93-2) + acetyl chloride (75-36-5) → 1-(4-isobutyl-phenyl)-ethanone (38861-78-8)

Conditions	Yield
With aluminum (III) chloride In dichloromethane at -10℃; for 1h;	97%
With aluminium trichloride In dichloromethane at 25℃; for 12h;	95%
With aluminum (III) chloride In dichloromethane at 0℃; for 1.5h;	95%

1-phenyl-2-methylpropane (538-93-2) → 4-bromo-isobutylbenzene (57181-82-5)

Conditions	Yield
With hydrogen bromide; dihydrogen peroxide In 1,2-dichloro-ethane for 8h; Cooling with ice; Irradiation;	95%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 1h; Bromination; Heating;	67%
With Diethyl 2-bromomalonate In benzene at 70℃; Rate constant; Irradiation; k(rel);
With Diethyl 2-bromomalonate In benzene at 70℃; Irradiation;

1-phenyl-2-methylpropane (538-93-2) + 4-(tert-butyl)phenyl sulfamate → C20H27NO3S

Conditions	Yield
With tert-butyl isocyanide; [bis(acetoxy)iodo]benzene; dirhodium(II) tetrakis[N-tetrafluorophthaloyl-(S)-tert-leucinate] at 20℃; for 16h; regioselective reaction;	95%

1-phenyl-2-methylpropane (538-93-2) + Diethyl ketomalonate (609-09-6) → diethyl (4-isobutylphenyl)tartronate (83026-13-5)

Conditions	Yield
With tin(IV) chloride In dichloromethane 1.) 0 deg C, 10 min, 2.) 20 deg C, 3 h;	94%

1-phenyl-2-methylpropane (538-93-2) + n-octanoic acid chloride (111-64-8) → 1-(4'-Isobutylphenyl)octan-1-one (93673-09-7)

Conditions	Yield
With aluminium trichloride In tetrachloromethane at 0℃; for 1h;	94%
Stage #1: n-octanoic acid chloride With aluminium trichloride In dichloromethane at 0℃; for 0.5h; Stage #2: 1-phenyl-2-methylpropane In dichloromethane at 0℃; for 1h; Friedel-Crafts acylation;	77.3%

1-phenyl-2-methylpropane (538-93-2) → phenyl isopropyl ketone (611-70-1)

Conditions	Yield
With tert.-butylhydroperoxide; RuIII-Montmorillonite K10 In acetonitrile for 4h; Heating;	94%
With Oxone; potassium bromide In nitromethane at 20℃; for 24h;	90%
With potassium permanganate; Tulsion T-42 exchange resin In dichloromethane; tert-butyl alcohol at 20℃; for 5h; oxidative cleavage;	88%

(phenylthio)acetic acid chloride (7031-27-8) + 1-phenyl-2-methylpropane (538-93-2) → 4-isobutyl-α-(phenylthio)acetophenone (122657-57-2)

Conditions	Yield
With aluminium trichloride for 1h; Ambient temperature;	91%

1-phenyl-2-methylpropane (538-93-2) + methyloxirane (75-56-9, 16033-71-9) → ibuprofen (15687-27-1)

Conditions	Yield
Stage #1: methyloxirane With aluminum (III) chloride at 20 - 30℃; for 0.5h; Green chemistry; Stage #2: 1-phenyl-2-methylpropane In water at 30 - 80℃; Green chemistry; Stage #3: With sulfuric acid; dihydrogen peroxide at 60 - 80℃; for 5h; Temperature; Reagent/catalyst; Green chemistry;	91%

1-phenyl-2-methylpropane (538-93-2) + Benzylidenemalononitrile (2700-22-3) → 2-(3-methyl-1,2-diphenylbutyl)malononitrile

Conditions	Yield
With 9-(2-mesityl)-10-methylacridinium perchlorate; 1,2-dibromomethane at 50℃; for 24h; Irradiation;	91%

1-phenyl-2-methylpropane (538-93-2) + Hexanoyl chloride (142-61-0) → 4'-isobutylhexanophenone (146922-67-0)

Conditions	Yield
Stage #1: Hexanoyl chloride With aluminium trichloride In dichloromethane at 0℃; for 0.5h; Stage #2: 1-phenyl-2-methylpropane In dichloromethane at 0℃; for 1h; Friedel-Crafts acylation;	90.5%
aluminium trichloride In dichloromethane

10%-hydrochloric acid + 1-phenyl-2-methylpropane (538-93-2) → 4-isobutylpropiophenone (59771-24-3)

Conditions	Yield
aluminium chloride In dichloromethane; propionyl chloride	90.2%

1-phenyl-2-methylpropane (538-93-2) + pivaloyl chloride (3282-30-2) → 2,2-dimethyl-4'-isobutylpropiophenone (139155-61-6)

Conditions	Yield
zinc In toluene at 70℃; for 6h; Acylation;	90%

(methylthio)acetyl chloride (35928-65-5) + 1-phenyl-2-methylpropane (538-93-2) → 4-isobutyl-α-(methylthio)acetophenone (122657-55-0)

Conditions	Yield
With aluminium trichloride In dichloromethane for 1h; Ambient temperature;	89%

1-phenyl-2-methylpropane (538-93-2) + chloroacetyl chloride (79-04-9) → p-isobutylphenylacetic acid chloride (38588-43-1)

Conditions	Yield
With aluminium trichloride In 1,2-dichloro-ethane at 0 - 5℃; for 4h;	89%

1-phenyl-2-methylpropane (538-93-2) → 1-isobutyl-2,4-dinitro-benzene (552333-50-3)

Conditions	Yield
With sulfuric acid; nitric acid at 0 - 20℃; for 0.5h;	89%

1-phenyl-2-methylpropane (538-93-2) + acetic anhydride (108-24-7) → 1-(4-isobutyl-phenyl)-ethanone (38861-78-8)

Conditions	Yield
With aluminium trichloride In dichloromethane at 0℃; for 1h;	88%
With aluminium trichloride In dichloromethane at -5 - 28℃; Acylation;	70%
With trifluoroacetic acid at 100℃; for 56h; Friedel-Crafts Acylation; Inert atmosphere;	65%

1-phenyl-2-methylpropane (538-93-2) + chloroacetyl chloride (79-04-9) → 4-(isobutyl)phenacyl chloride (56374-25-5)

Conditions	Yield
With aluminium trichloride In 1,2-dichloro-ethane at 0 - 5℃; for 3.5h;	87%
With aluminum (III) chloride; bismuth(III) chloride In dichloromethane at 0 - 5℃; Friedel Crafts acylation;	87%

Upstream product

• 75-44-5 phosgene 
• 60-29-7 diethyl ether 
• 515-40-2 neophyl chloride 
• 78-77-3 Isobutyl bromide 
• 6325-41-3 3-methyl-3-phenylbutanal 
• 920-39-8 isopropylmagnesium bromide 
• 1589-82-8 phenylmagnesium bromide 
• 75-30-9 2-iodo-propane 
• 100-44-7 benzyl chloride 
• 78-84-2 isobutyraldehyde 
• 71-43-2 benzene 
• 187737-37-7 propene 
• 1121-53-5 benzyl sodium 
• 108-88-3 toluene 

Downstream Products

• 108-88-3 toluene 
• 71-43-2 benzene 
• 101789-77-9 2-(4-isobutyl-benzoyl)-benzoic acid 
• 68018-45-1 1-tert-butyl-4-(2-methylpropyl)benzene 
• 1678-98-4 isobutylcyclohexane 
• 10342-60-6 1-isobutyl-4-nitrobenzene 
• 552333-50-3 1-isobutyl-2,4-dinitro-benzene 
• 80304-54-7 (1-bromo-2-methylpropyl)benzene 
• 2051-99-2 1-bromo-4-isobutylbenzene 
• 72511-13-8 (2-methyl-1-nitro-propyl)-benzene 
• 161767-97-1 4-isobutylbenzenesulfonamide 
• 85609-09-2 1-iodo-4-isobutylbenzene 
• 115-11-7 isobutene 
• 38861-78-8 1-(4-isobutyl-phenyl)-ethanone 

Relevant articles and documents

Synthesis of 1-(3-tert-butyldimethylsiloxy)phenyl-5,5-dimethyl-2,7,8-trioxabicyclo[4.2.0] octanes: New dioxetanes giving high chemiexcitation yields in thermolysis and in fluoride-induced CIEEL-decay

Dioxetanes with annelated six-membered ring, 1-(3-tert-butyldimethylsiloxy)phenyl-5,5-dimethyl-2,7,8-trioxabicyclo[4.2.0] octanes (2a-2c) were synthesized by singlet oxygenation of the corresponding aryl-substituted dihydropyrans (3). Thermolysis of 2a-2c gave the corresponding ketoesters (5a-5c) as a normal decomposition product together with a considerable amount (23-26%) of ester (6) derived from Norrish type I reaction of the triplet-excited ester (5). On the other hand, treatment with tetrabutylammonium fluoride (TBAF) in DMSO induced rapid decomposition of 2 to emit blue light in high chemiexcitation yield (72-75%) of the oxyanion of a ketoester (10). These results show that the chemiexcitation efficiency of dioxetanes (2) was higher than that of their five-membered ring analog (1) not only for thermolysis and but also for the base-induced CIEEL.

Site-Specific Alkene Hydromethylation via Protonolysis of Titanacyclobutanes

Methyl groups are ubiquitous in biologically active molecules. Thus, new tactics to introduce this alkyl fragment into polyfunctional structures are of significant interest. With this goal in mind, a direct method for the Markovnikov hydromethylation of alkenes is reported. This method exploits the degenerate metathesis reaction between the titanium methylidene unveiled from Cp2Ti(μ-Cl)(μ-CH2)AlMe2 (Tebbe's reagent) and unactivated alkenes. Protonolysis of the resulting titanacyclobutanes in situ effects hydromethylation in a chemo-, regio-, and site-selective manner. The broad utility of this method is demonstrated across a series of mono- and di-substituted alkenes containing pendant alcohols, ethers, amides, carbamates, and basic amines.

Photocatalytic transfer hydrogenolysis of aromatic ketones using alcohols

A mild method of photocatalytic deoxygenation of aromatic ketones to alkyl arenes was developed, which utilized alcohols as green hydrogen donors. No hydrogen evolution during this transformation suggested a mechanism of direct hydrogen transfer from alcohols. Control experiments with additives indicated the role of acid in transfer hydrogenolysis, and catalyst characterization confirmed a larger number of Lewis acidic sites on the optimal Pd/TiO2 photocatalyst. Hence, a combination of hydrogen transfer sites and acidic sites may be responsible for efficient deoxygenation without additives. The photocatalyst showed reusability and achieved selective reduction in a variety of aromatic ketones.