3910-35-8

Basic information

• Product Name: 1-PHENYL-1,3,3-TRIMETHYLINDAN
• Synonyms: 1-Phenyl-1,3,3-trimethylindane;1,1,3-trimethyl-3-phenyl-2H-indene;1,3,3-TriMethyl-1-Phenylindine;Superfix;1-PHENYL-1,3,3-TRIMETHYLINDAN;1,1,3-trimethyl-3-phenylindane;1,1,3-trimethyl-3-phenylindan;1,3,3-Trimethyl-1-phenylindane
• CAS NO: 3910-35-8
• Molecular Formula: C₁₈H₂₀
• Molecular Weight: 236.3514
• EINECS: 223-467-4
• Mol File: 3910-35-8.mol
• Article Data: 69

Chemical Properties

• Melting Point: 52.5°C
• Boiling Point: 313.82°C (rough estimate)
• Flash Point: 156.5 °C
• Appearance: /
• Density: 1.0009
• Vapor Pressure: 0.00123mmHg at 25°C
• Refractive Index: 1.5681
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Dichloromethane; Ethyl Acetate
• CAS DataBase Reference: 1-PHENYL-1,3,3-TRIMETHYLINDAN(CAS DataBase Reference)
• NIST Chemistry Reference: 1-PHENYL-1,3,3-TRIMETHYLINDAN(3910-35-8)
• EPA Substance Registry System: 1-PHENYL-1,3,3-TRIMETHYLINDAN(3910-35-8)

Safety Data

• Hazardous Substances Data: 3910-35-8(Hazardous Substances Data)

Usage

Uses

1,1,3-Trimethyl-3-phenylindan is an intermediate in the synthesis of OctaInd (O237100). OctaInd is a commercial brominated flame retardant (BFR) used in styrenic and engineering thermoplastics.

InChI:InChI=1/C18H20/c1-17(2)13-18(3,14-9-5-4-6-10-14)16-12-8-7-11-15(16)17/h4-12H,13H2,1-3H3

Synthetic route

isopropenylbenzene (98-83-9) → 1,1,3-trimethyl-3-phenylindane (3910-35-8)

Conditions	Yield
iodine at 70℃; for 0.25h;	100%
With phosphotungstic acid In chloroform at 60℃; for 1.5h;	99%
With trifluoroacetic acid In dichloromethane	96%

cumenyl chloride (934-53-2) → 1,1,3-trimethyl-3-phenylindane (3910-35-8)

Conditions	Yield
With zinc diacetate In dichloromethane for 2h; Ambient temperature;	99%
Multi-step reaction with 2 steps 1: CD2Cl2 / -80 °C View Scheme

formaldehyd (50-00-0) + isopropenylbenzene (98-83-9) → 1,1,3-trimethyl-3-phenylindane (3910-35-8)

Conditions	Yield
With Ce3+-montmorillonite In toluene at 25℃; for 1h;	99%

isopropenylbenzene (98-83-9) → 1,1,3-trimethyl-3-phenylindane (3910-35-8) + 2,4-diphenyl-4-methyl-pent-1-ene (6362-80-7) + 4-methyl-2,4-diphenylpent-2-ene (22768-22-5, 22768-23-6, 6258-73-7)

Conditions	Yield
thiol-modified Al-loaded mesoporous silica In toluene at 120℃; for 2h;	A 97.1% B 0.7% C 1%
thiol-modified Al-loaded mesoporous silica In toluene at 80℃; for 2h;	A 37.5% B 16.9% C 42.8%
nafion resin; silica gel In various solvent(s) at 50℃; under 760 Torr; Product distribution; Rate constant; var. soluble liquid acids and resin-based solid acids as catalysts; var. time and solv.;

dimethylaluminum chloride (1184-58-3) + acetophenone (98-86-2) → 1,1,3-trimethyl-3-phenylindane (3910-35-8)

Conditions	Yield
In toluene at 120℃; for 24h; Schlenk technique; Inert atmosphere;	96%

1-methyl-1-phenylethyl alcohol (617-94-7) → 1,1,3-trimethyl-3-phenylindane (3910-35-8)

Conditions	Yield
iodine at 70℃; for 3h;	91%
With bismuth(III) bromide In 1,2-dichloro-ethane at 50℃; for 4h; Inert atmosphere;	82%
With 0.00044 wt% platinum nanoparticle supported on titanium oxide encapsulated in sulfated p-xylene polymer In nitromethane at 75℃; Irradiation; Inert atmosphere;	76%

dicumene (1889-67-4) → 1,1,3-trimethyl-3-phenylindane (3910-35-8) + acetophenone (98-86-2)

Conditions	Yield
With nitrosonium hexachloroantimonate In dichloromethane at 23℃; for 12h; Mechanism; Quantum yield; Product distribution; Irradiation; other solvent; other reactant; without irradiation;	A 90% B 2%
With nitrosonium hexachloroantimonate In dichloromethane at 23℃; for 12h; Irradiation;	A 90% B 2%

2-methyl-2-phenylpropionic acid (826-55-1) → 1,1,3-trimethyl-3-phenylindane (3910-35-8) + carbon monoxide (201230-82-2)

Conditions	Yield
With tungsten(VI) chloride In dichloromethane at 20℃; for 168h; Inert atmosphere; Schlenk technique;	A 88% B n/a

ethyl 3-phenylbut-2-enoate (1504-72-9, 13979-22-1, 945-93-7) → 1,1,3-trimethyl-3-phenylindane (3910-35-8)

Conditions	Yield
With trifluoroacetic acid at 80℃; for 24h; Reagent/catalyst; Temperature; Schlenk technique; Inert atmosphere;	86%

3-phenylbut-2-enoic acid (704-79-0, 704-80-3, 1199-20-8) → 1,1,3-trimethyl-3-phenylindane (3910-35-8)

Conditions	Yield
With trifluoroacetic acid at 80℃; for 24h; Inert atmosphere;	84%

diethyl α-(1-methyl-1-phenylethyl)malonate (78775-63-0) → 1,1,3-trimethyl-3-phenylindane (3910-35-8)

Conditions	Yield
With phosphoric acid at 90℃; for 1h;	83%

ethyl (Z)-3-phenylbut-2-enoate (945-93-7, 1504-72-9, 13979-22-1) → 1,1,3-trimethyl-3-phenylindane (3910-35-8)

Conditions	Yield
With trifluoroacetic acid at 80℃; for 24h; Schlenk technique; Inert atmosphere;	82%

(1-chloroethyl)benzene (672-65-1) + isopropenylbenzene (98-83-9) → 1,1,3-trimethyl-3-phenylindane (3910-35-8)

Conditions	Yield
zinc(II) chloride at 50℃; for 4h;	80%

2-(α,α-Dimethylbenzyl)malonsaeure (5243-41-4) → 1,1,3-trimethyl-3-phenylindane (3910-35-8)

Conditions	Yield
With PPA at 90℃; for 1h;	80%

2-cyano-3-methyl-3-phenyl-butyric acid ethyl ester (56264-36-9) → 1,1,3-trimethyl-3-phenylindane (3910-35-8)

Conditions	Yield
With PPA at 90℃; for 2h;	78%

1-methyl-1-phenylethyl alcohol (617-94-7) → 1,1,3-trimethyl-3-phenylindane (3910-35-8) + 2,4-diphenyl-4-methyl-pent-1-ene (6362-80-7) + 1,1-dimethyl-3-(2-methyl-2-phenylpropyl)-3-phenyl-2,3-dihydro-1H-indene (68305-40-8)

Conditions	Yield
With iron(III) chloride; 1,1,1,3',3',3'-hexafluoro-propanol; nitric acid at 20℃; for 3h; Catalytic behavior;	A 7 %Spectr. B 62% C 9 %Spectr.

trimethylaluminum (75-24-1) + dimethylaluminum chloride (1184-58-3) + acetophenone (98-86-2) → 1,1,3-trimethyl-3-phenylindane (3910-35-8) + isopropenylbenzene (98-83-9)

Conditions	Yield
In toluene at 120℃; for 24h; Schlenk technique; Inert atmosphere;	A 34% B 57%

1-methyl-1-phenylethyl alcohol (617-94-7) → 1,1,3-trimethyl-3-phenylindane (3910-35-8) + 1,1-dimethyl-3-(2-methyl-2-phenylpropyl)-3-phenyl-2,3-dihydro-1H-indene (68305-40-8)

Conditions	Yield
With iron(III) chloride; 1,1,1,3',3',3'-hexafluoro-propanol; nitric acid at 20℃; for 3h; Catalytic behavior;	A 57% B 18%

2,2-dimethyl-5-(1-methyl-1-phenylethyl)-1,3-dioxane-4,6-dione (81710-07-8) → 1,1,3-trimethyl-3-phenylindane (3910-35-8) + 3-methyl-3-phenylbutanoic acid (1010-48-6)

Conditions	Yield
With PPA at 90℃; for 2h;	A 52% B 26%

ethylene glycol (107-21-1) + acetophenone (98-86-2) → 1,1,3-trimethyl-3-phenylindane (3910-35-8)

Conditions	Yield
toluene-4-sulfonic acid In benzene for 18h; Heating;	42%

trimethylsilyl isothiocyanate (2290-65-5) + isopropenylbenzene (98-83-9) → 1,1,3-trimethyl-3-phenylindane (3910-35-8) + (1-isothiocyanato-1-methyl-ethyl)-benzene (25343-67-3)

Conditions	Yield
With iodine In dichloromethane	A 27% B 27%

methoxybenzene (100-66-3) + isopropenylbenzene (98-83-9) → 1,1,3-trimethyl-3-phenylindane (3910-35-8) + 1-(2-(4-methoxyphenyl)propan-2-yl)benzene (6623-93-4)

Conditions	Yield
With C16H22AuClN2; potassium tetrakis(pentafluorophenyl)borate In benzene at 20℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube;	A 7% B 25%

2-hydroxy-2-methyl-4.4-diphenyl-pentane (61455-18-3) → 1,1,3-trimethyl-3-phenylindane (3910-35-8)

Conditions	Yield
With hydrogenchloride; tin(IV) chloride; benzene

4-Methyl-3,4-diphenyl-pentanol-2 → 1,1,3-trimethyl-3-phenylindane (3910-35-8)

Conditions	Yield
With sulfuric acid

trimethylaluminum (75-24-1) + benzoic acid (65-85-0) → 1,1,3-trimethyl-3-phenylindane (3910-35-8)

Conditions	Yield
at 130 - 150℃; for 24h;

2,4-diphenyl-4-methyl-pent-1-ene (6362-80-7) → 1,1,3-trimethyl-3-phenylindane (3910-35-8)

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 1.5h; Ambient temperature;	0.98 g
With bismuth(III) bromide In 1,2-dichloro-ethane at 50℃; Inert atmosphere;

azocumene (5676-79-9) → Isopropylbenzene (98-82-8) + dicumene (1889-67-4) + 1,1,3-trimethyl-3-phenylindane (3910-35-8) + p-cumylcumene (62545-70-4) + 2-(Isopropyl-phenyl)-2-phenyl-propan (72235-66-6) + isopropenylbenzene (98-83-9)

Conditions	Yield
With silica surface at 55℃; Kinetics; Mechanism; Rate constant; energy data (ΔH(excit.), ΔS(excit.)); also photolysis at 25 deg C; labeling studies;

2-nitropropane (79-46-9) + benzene (71-43-2) → Isopropylbenzene (98-82-8) + 1,1,3-trimethylindene (2177-45-9) + 1,1,3-trimethyl-3-phenylindane (3910-35-8) + 2,2-diphenylpropane (778-22-3) + 3,3,3',3'-tetramethyl-1,1'-spiro-biindane (32507-26-9, 58343-29-6) + 1',3,3,3',3'-pentamethyl-1-(1'-indanyl-methylene)-indane (13864-90-9)

Conditions	Yield
With aluminium trichloride Product distribution; Mechanism; 2 h, room temp., 55 deg C, various periods of time;

isopropenylbenzene (98-83-9) → 1,1,3-trimethyl-3-phenylindane (3910-35-8) + 2,4-diphenyl-4-methyl-pent-1-ene (6362-80-7) + (E)-(4-methylpent-2-ene-2,4-diyl)dibenzene (22768-22-5)

Conditions	Yield
aluminum oxide; titanium(IV) oxide at 30℃; for 90h; Product distribution; Mechanism; variation of catalysts and reaction time;
With hydrogenchloride In cyclohexane; water at 170℃; for 12h; investigation of H-D exchange of styrenes in dilute acid at elevated temperatures; deuterium content not efficient;
With hydrogenchloride In cyclohexane; water at 170℃; for 12h;	A 3.7 % Chromat. B 31.7 % Chromat. C 32.6 % Chromat.

isopropenylbenzene (98-83-9) → 1,1,3-trimethyl-3-phenylindane (3910-35-8) + 1-phenyl-3-(2-phenyl-2-methylpropyl)-1,3-dimethylindan (41906-71-2)

Conditions	Yield
x In nitromethane at 25℃; for 0.0833333h; Yield given;
(BF4)2 In nitromethane at 25℃; for 1h; Yield given;

1,1,3-trimethyl-3-phenylindane (3910-35-8) → 1,3,3-trimethyl-5-nitro-1-(4-nitrophenyl)-2,3-dihydro-1H-indene (109751-35-1)

Conditions	Yield
With sulfuric acid; nitric acid In dichloromethane at 0 - 5℃;	83%

1,1,3-trimethyl-3-phenylindane (3910-35-8) → 1,3,3-trimethyl-5-nitro-1-(4-nitrophenyl)-2,3-dihydro-1H-indene (109751-35-1) + 1,3,3-trimethyl-6-nitro-1-(4-nitrophenyl)-2,3-dihydro-1H-indene (86126-32-1)

Conditions	Yield
With nitric acid at 60℃; for 6h; Reagent/catalyst; Temperature; Autoclave; Overall yield = 88.7 percent;	A 31% B 69%
With sulfuric acid; nitric acid In chloroform at 2 - 8℃; Temperature; Overall yield = 77.3 %; Overall yield = 25.2 g;	A 16.8 g B 8.4 g

1,1,3-trimethyl-3-phenylindane (3910-35-8) → 5-amino-1-(4'-aminophenyl)-1,3,3-trimethylindane + 6-amino-1-(4'-aminophenyl)-1,3,3-trimethylindane (54628-90-9)

Conditions	Yield
Stage #1: 1,1,3-trimethyl-3-phenylindane With nitric acid at 60℃; for 6h; Stage #2: With palladium 10% on activated carbon; hydrogen at 70℃; under 12001.2 - 15001.5 Torr; for 8h; Reagent/catalyst; Temperature; Pressure; Overall yield = 84 percent;	A 31% B 69%

1,1,3-trimethyl-3-phenylindane (3910-35-8) → 3,3,3',3'-tetramethyl-1,1'-spiro-biindane (32507-26-9, 58343-29-6)

Conditions	Yield
With aluminium trichloride

Upstream product

• 98-83-9 isopropenylbenzene 
• 617-94-7 1-methyl-1-phenylethyl alcohol 
• 7664-93-9 sulfuric acid 
• 7647-01-0 hydrogenchloride 
• 61455-18-3 2-hydroxy-2-methyl-4.4-diphenyl-pentane 
• 7646-78-8 tin(IV) chloride 
• 71-43-2 benzene 
• 3569-18-4 1,1,3-trimethyl-3-phenylindan-4',5-dicarboxylic acid 
• 79-46-9 2-nitropropane 
• 5676-79-9 azocumene 
• 107-21-1 ethylene glycol 
• 98-86-2 acetophenone 
• 6362-80-7 2,4-diphenyl-4-methyl-pent-1-ene 
• 1889-67-4 dicumene 

Downstream Products

• 54628-89-6 5-amino-1-(4'-aminophenyl)-1,3,3-trimethylindane 
• 54628-90-9 6-amino-1-(4'-aminophenyl)-1,3,3-trimethylindane 
• 109751-35-1 1,3,3-trimethyl-5-nitro-1-(4-nitrophenyl)-2,3-dihydro-1H-indene 
• 3569-18-4 1,1,3-trimethyl-3-phenylindan-4',5-dicarboxylic acid 
• 86126-32-1 1,3,3-trimethyl-6-nitro-1-(4-nitrophenyl)-2,3-dihydro-1H-indene 
• 135452-40-3 5-(2-chloro-2-methyl-1-oxo-prop-1-yl)-3-(4-(2-chloro-2-methyl-1-oxo-prop-1-yl)phenyl)-2,3-dihydro-1,1,3-trimethyl-1H-indene 
• 135452-41-4 2,3-dihydro-6-(2-chloro-2-methyl-1-oxopropyl)-1,1,3-trimethyl-3-[4-(2-chloro-2-methyl-1-oxopropyl)phenyl]-1H-indene 
• 10527-11-4 5-hydroxy-3-(4-hydroxyphenyl)-1,1,3-trimethylindane 
• 109252-41-7 5-hydroxy-1-(4'-hydroxyphenyl)-1,3,3-trimethylindan 

Relevant articles and documents

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A chemoselective route to either 4-methyl-2,4-diphenyl-2-pentene or 1,1,3-trimethyl-3-phenylindane from 2-phenylpropan-2-ol mediated by BiBr 3: A mechanistic study

The reaction of 2-phenylpropan-2-ol mediated by BiBr3 can, through control of the temperature, yield selectively either 4-methyl-2,4-diphenyl-2-pentene or 1,1,3-trimethyl-3-phenylindane. A reaction mechanism that proceeds via 1-methylstyrene is disclosed.

Preparation of a platinum nanoparticle catalyst located near photocatalyst titanium oxide and its catalytic activity to convert benzyl alcohols to the corresponding ethers

A novel platinum nanoparticle catalyst closely located near the surface of titanium oxide, PtNP/TiO2, has been prepared. This catalyst has both the properties of a photocatalyst and a metal nanoparticle catalyst, and acquired environmentally friendly catalytic activity, which cannot be achieved by just one of these catalysts, to afford ethers from benzyl alcohols under the wavelength of 420 nm.

Samarium triflate-catalyzed dimerization of vinylarenes

We report the preparation of substituted indanes and their dimeric isomers via the samarium triflate-mediated [Sm(OTf)3, 10 mol%] self-dimerization of vinylarenes in MeNO2 at 25 oC for 10 h. The diverse products were obtained in moderate to high yields. The synthesis involves a (3+2) annulation via the formation of carbon-carbon bonds. Plausible mechanisms are proposed and discussed. The investigation of various rare metal triflates catalyst loadings, reaction conditions, and substrate scope led to an operationally easy one-pot Friedel-Crafts reaction protocol.

Lewis Acid Catalyzed Transfer Hydromethallylation for the Construction of Quaternary Carbon Centers

The design and gram-scale synthesis of a cyclohexa-1,4-diene-based surrogate of isobutene gas is reported. Using the highly electron-deficient Lewis acid B(C6F5)3, application of this surrogate in the hydromethallylation of electron-rich styrene derivatives provided sterically congested quaternary carbon centers. The reaction proceeds by C(sp3)?C(sp3) bond formation at a tertiary carbenium ion that is generated by alkene protonation. The possibility of two concurrent mechanisms is proposed on the basis of mechanistic experiments using a deuterated surrogate.