2049-95-8

Basic information

• Product Name: tert-Amylbenzene
• Synonyms: T-PENTYLBENZENE;TERT-PENTYLBENZENE;T-AMYLBENZENE;TERT-AMYLBENZENE;(1,1-DIMETHYLPROPYL)BENZENE;2-METHYL-2-PHENYLBUTANE;2-phenyl-2-methylbutane;(1,1-dimethylpropyl)-benzen
• CAS NO: 2049-95-8
• Molecular Formula: C₁₁H₁₆
• Molecular Weight: 148.24
• EINECS: 218-076-0
• Mol File: 2049-95-8.mol
• Article Data: 14

Chemical Properties

• Melting Point: -44.72°C (estimate)
• Boiling Point: 188-191°C
• Flash Point: 65°C
• Appearance: /
• Density: 0,87 g/cm3
• Vapor Pressure: 0.764mmHg at 25°C
• Refractive Index: 1.4960
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: 10.5mg/L(25 oC)
• BRN: 2039053
• CAS DataBase Reference: tert-Amylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Amylbenzene(2049-95-8)
• EPA Substance Registry System: tert-Amylbenzene(2049-95-8)

Safety Data

• Safety Statements: 23-24/25
• RIDADR: UN1993 - class 3 - PG 3 - EHS - Flammable liquids, n.o.s., HI: a
• RTECS: DA6720000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 2049-95-8(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid

Uses

The presence of electrolyte additives enhances the performance of lithium ion batteries by improving their thermal stability and ionic conductivity. Additives also reduce the flammability of electrolytes and provide overcharge protection. t-Amyl benzene finds application as additive in lithium ion batteries and its addition in grade would be good expansion of our LIB portfolio.

Safety Profile

Mildly toxic by ingestion. Whenheated to decomposition it yields irritating fumes andsmoke.

InChI:InChI=1/C11H16/c1-4-11(2,3)10-8-6-5-7-9-10/h5-9H,4H2,1-3H3

Synthetic route

tert-Amyl alcohol (75-85-4) + benzene (71-43-2) → tery-amylbenzene (2049-95-8)

Conditions	Yield
With aluminum (III) chloride; iron(III) chloride at 0 - 5℃; for 6h; Large scale;	99.4%
With AlCl2
With iron(III) chloride
With aluminium trichloride

2-methyl-2-butylchloride (594-36-5) + benzene (71-43-2) → tery-amylbenzene (2049-95-8)

Conditions	Yield
With iron(III) chloride at 5℃; under 187.519 Torr; for 2.5h; Reagent/catalyst; Pressure;	98%
With boron trifluoride
With zirconium(IV) chloride

Isopropylbenzene (98-82-8) + ethene (74-85-1) → tery-amylbenzene (2049-95-8)

Conditions	Yield
at 160℃; for 1.5h; Inert atmosphere; Autoclave;	37.8%

Isopropylbenzene (98-82-8) + ethene (74-85-1) → 1,1-dimethylindan (4912-92-9) + tery-amylbenzene (2049-95-8)

Conditions	Yield
reagiert analog wie das Toluol;
With anthracene; potassium at 190 - 245℃;

Isopropylbenzene (98-82-8) → tery-amylbenzene (2049-95-8)

Conditions	Yield
With potassium graphite; ethene at 200℃; under 36775.4 Torr;
With ethene; anthracene; sodium at 200 - 225℃; under 22065.2 Torr;
With ethene; anthracene; potassium at 200 - 225℃; under 22065.2 Torr;
With ethene; n-pentylsodium at 140℃; under 22065.2 - 29420.3 Torr;
With ethene; sodium hydride at 250℃; under 29420.3 - 44130.5 Torr;

cumenyl chloride (934-53-2) → tery-amylbenzene (2049-95-8)

Conditions	Yield
With diethyl ether; ethylmagnesium bromide

(1-methyl-cyclobutyl)-cyclohexane (61208-95-5) → 2-phenylpentane (2719-52-0) + tery-amylbenzene (2049-95-8)

Conditions	Yield
at 250℃; Leiten ueber Platin-Aluminiumoxyd;

2-Methyl-1-butene (563-46-2) + benzene (71-43-2) → tery-amylbenzene (2049-95-8) + 1,4-di-tert-pentyl-benzene (3373-10-2)

Conditions	Yield
With sulfuric acid
With hydrogen fluoride
With sulfuric acid
With hydrogen fluoride

3-Methyl-1-butene (563-45-1) + benzene (71-43-2) → tery-amylbenzene (2049-95-8)

Conditions	Yield
With boron trifluoride
With aluminium chloride hydrogen chloride
With hydrogen fluoride
With aluminium trichloride

tert-Amyl alcohol (75-85-4) + benzene (71-43-2) → tery-amylbenzene (2049-95-8) + 1,4-di-tert-pentyl-benzene (3373-10-2)

Conditions	Yield
With AlCl2

2-methyl-but-2-ene (513-35-9) + benzene (71-43-2) → tery-amylbenzene (2049-95-8)

Conditions	Yield
With aluminium chloride hydrogen chloride
With hydrogen fluoride
With aluminium trichloride
With boron trifluoride

2-methyl-but-2-ene (513-35-9) + benzene (71-43-2) → tery-amylbenzene (2049-95-8) + 1,4-di-tert-pentyl-benzene (3373-10-2)

Conditions	Yield
With sulfuric acid
With hydrogen fluoride
With sulfuric acid
With hydrogen fluoride

2-methyl-2-butylchloride (594-36-5) + benzene (71-43-2) → tery-amylbenzene (2049-95-8) + 1,4-di-tert-pentyl-benzene (3373-10-2)

Conditions	Yield
With hydrogen fluoride at 0℃;

isopentyl ether (544-01-4) + benzene (71-43-2) → tery-amylbenzene (2049-95-8)

Conditions	Yield
With boron trifluoride at 150℃;

isopentyl ether (544-01-4) + benzene (71-43-2) → tery-amylbenzene (2049-95-8) + 1,4-di-tert-pentyl-benzene (3373-10-2)

Conditions	Yield
With boron trifluoride at 150℃; under 9561.6 Torr;

i-Amyl alcohol (123-51-3) + benzene (71-43-2) → tery-amylbenzene (2049-95-8)

Conditions	Yield
With sulfuric acid at 65℃;
With hydrogenchloride; zinc(II) chloride at 140 - 160℃;

2-bromo-2-methylbutane (507-36-8) + benzene (71-43-2) → tery-amylbenzene (2049-95-8)

Conditions	Yield
With aluminium trichloride

2,2-dimethyl-propanol-1 (75-84-3) + benzene (71-43-2) → tery-amylbenzene (2049-95-8)

Conditions	Yield
With sulfuric acid at 65℃;
With boron trifluoride at 60℃;

methyl-cyclobutane (598-61-8) + benzene (71-43-2) → tery-amylbenzene (2049-95-8)

Conditions	Yield
With sulfuric acid at 2 - 4℃;

1,4-di-tert-pentyl-benzene (3373-10-2) + benzene (71-43-2) → tery-amylbenzene (2049-95-8)

Conditions	Yield
With iron(III) chloride

3-chloro-1,1-dimethyl-1-phenylpropane (1459-04-7) → tery-amylbenzene (2049-95-8)

Conditions	Yield
With magnesium In diethyl ether
Multi-step reaction with 2 steps 1: (i) Mg, Et2O, (ii) aq. H2SO4 2: 1,1-dimethyl-propyl hydroperoxide View Scheme

4-Methyl-4-phenyl-1-pentanale (120384-23-8) → tery-amylbenzene (2049-95-8)

Conditions	Yield
With tert-amyl hydroperoxide

trimethylaluminum (75-24-1) + 1-phenyl-propan-1-one (93-55-0) → tery-amylbenzene (2049-95-8)

Conditions	Yield
bis(acetylacetonate)nickel(II) In toluene

methyl iodide (74-88-4) + isopropenylbenzene (98-83-9) → tery-amylbenzene (2049-95-8)

Conditions	Yield
With lithium In tetrahydrofuran

1-chloro-2-methylbutane (616-13-7) + benzene (71-43-2) → tery-amylbenzene (2049-95-8)

Conditions	Yield
With aluminium trichloride; nitromethane at 25℃; for 0.25h;

3-methyl-3-phenylbut-1-ene (18321-36-3) → tery-amylbenzene (2049-95-8)

Conditions	Yield
With hydrogen; triphenylphosphine; In tetrahydrofuran at 40.8℃; Rate constant; Mechanism; further rhodacarborane catalyst; also in the presence of bases, D2O, radical scavengers; labelled experiments;

2-methyl-3-phenylbutane (4481-30-5) + 2-Methyl-1-butene (563-46-2) → 2,2-dimethylbutyric acid (595-37-9) + methylbutane (78-78-4) + tery-amylbenzene (2049-95-8) + benzene (71-43-2)

Conditions	Yield
With trifluorormethanesulfonic acid; carbon monoxide In tetrachloromethane under 120 Torr; for 3h; Ambient temperature; Further byproducts given. Title compound not separated from byproducts;	A 4 % Chromat. B n/a C n/a D n/a

carbon monoxide (201230-82-2) + 2-Methyl-1-butene (563-46-2) + benzene (71-43-2) → 2,2,3-trimethylindan-1-one (10474-35-8) + tery-amylbenzene (2049-95-8) + 2-methyl-3-phenylbutane (4481-30-5) + (E)-3,3,6-Trimethyl-oct-5-en-4-one + (E)-3,3,6-Trimethyl-oct-6-en-4-one

Conditions	Yield
With trifluorormethanesulfonic acid In tetrachloromethane under 115 Torr; for 3h; Mechanism; Product distribution; Ambient temperature;	A 38 % Chromat. B n/a C n/a D n/a E n/a

2-Methyl-1-butene (563-46-2) + benzene (71-43-2) → tery-amylbenzene (2049-95-8) + 2-methyl-3-phenylbutane (4481-30-5) + (E)-3,3,6-Trimethyl-oct-5-en-4-one + (E)-3,3,6-Trimethyl-oct-6-en-4-one

Conditions	Yield
With trifluorormethanesulfonic acid; carbon monoxide In tetrachloromethane under 87400.1 Torr; for 3h; Ambient temperature; Further byproducts given. Title compound not separated from byproducts;

3-methyl-butan-2-one (563-80-4) + benzene (71-43-2) → tert-butylbenzene (253185-03-4, 253185-04-5) + tery-amylbenzene (2049-95-8) + 2-methyl-3-phenylbutane (4481-30-5)

Conditions	Yield
With isobutylaluminum dichloride for 24h; Ambient temperature;	A 31 % Chromat. B 1 % Chromat. C 68 % Chromat.

tery-amylbenzene (2049-95-8) → 1-iodo-4-(tertpentyl)benzene (860556-27-0)

Conditions	Yield
With sodium periodate; sulfuric acid; iodine; acetic acid In water at 30 - 40℃; for 5h; Temperature; Reagent/catalyst;	97%
With sodium periodate; sulfuric acid; iodine In acetic anhydride; acetic acid at 0 - 12℃; for 24.3333h;	96%
With iodine; iodic acid

phthalic anhydride (85-44-9) + tery-amylbenzene (2049-95-8) → 2-(4'-tert-amylbenzoyl)-benzoic acid (64164-99-4)

Conditions	Yield
With aluminum (III) chloride In chlorobenzene at 20 - 40℃; for 4h;	93.5%

phthalic anhydride (85-44-9) + tery-amylbenzene (2049-95-8) → 2-(t-amylbenzoyl)benzoic acid

Conditions	Yield
aluminium trichloride In chlorobenzene	70.4%

tery-amylbenzene (2049-95-8) → 4-tert-pentyl-bromobenzene (57263-21-5)

Conditions	Yield
With bromine; iron for 23h;	69%

phthalic anhydride (85-44-9) + sulfuric acid (7664-93-9) + tery-amylbenzene (2049-95-8) → 2-(t-amylbenzoyl)benzoic acid

Conditions	Yield
aluminium trichloride In n-heptane; water; chlorobenzene	65%

tery-amylbenzene (2049-95-8) + isobutyraldehyde (78-84-2) → (E)-2-methyl-3-(4-(tert-pentyl)phenyl)acrylaldehyde

Conditions	Yield
With dipotassium peroxodisulfate; palladium diacetate; trifluoroacetic acid; 3-amino propanoic acid at 60℃; for 24h; Sealed tube; stereoselective reaction;	61%

formaldehyd (50-00-0) + tery-amylbenzene (2049-95-8) → 1-chloromethyl-4-tert-pentylbenzene (28162-11-0)

Conditions	Yield
With hydrogenchloride; zinc(II) chloride

1,3-dichloro-3-methylbutane (624-96-4) + tery-amylbenzene (2049-95-8) → 1-(3-chloro-1,1-dimethyl-propyl)-4-tert-pentyl-benzene

Conditions	Yield
With aluminium trichloride; nitromethane

tery-amylbenzene (2049-95-8) + sodium methallylsulfonate (1561-92-8) → 2-methyl-2-(4-tert-pentyl-phenyl)-propane-1-sulfonic acid

Conditions	Yield
With sulfuric acid; boron trifluoride; 1,2-dichloro-ethane

tery-amylbenzene (2049-95-8) → 4-t-pentylcyclohexane (31797-64-5)

Conditions	Yield
With hydrogen; acetic acid; platinum

tery-amylbenzene (2049-95-8) → 1-(1,1-dimethylpropyl)-4-nitrobenzene (6284-98-6)

Conditions	Yield
With nitric acid; acetic anhydride; acetic acid at 30 - 40℃;
With nitric acid; acetic acid

tery-amylbenzene (2049-95-8) → 4-(1,1-dimethylpropyl)aniline (2049-92-5)

Conditions	Yield
With sulfuric acid; nitric acid Schuetteln des Reaktionsprodukts mit Zinn und wss.-aethanol.Salzsaeure;
Multi-step reaction with 2 steps 1: glacial acetic acid; fuming nitric acid View Scheme
Multi-step reaction with 2 steps 1: glacial acetic acid; acetic acid anhydride; HNO3 / 30 - 40 °C 2: nickel; ethanol / 100 °C / 58840.6 Torr / Hydrogenation View Scheme

tery-amylbenzene (2049-95-8) → 4-tert-pentyl-benzenesulfonic acid amide (781657-37-2)

Conditions	Yield
With chlorosulphuric acid; chloroform Erwaermen des danach isolierten Reaktionsprodukts mit Ammoniumcarbonat;

tery-amylbenzene (2049-95-8) → 4-(1,1-dimethylpropyl)benzenesulfonyl chloride (169677-20-7)

Conditions	Yield
With tetrachloromethane; chlorosulphuric acid
Multi-step reaction with 2 steps 1: chlorosulfonic acid / chloroform / 1.5 h / Inert atmosphere; Cooling with ice 2: thionyl chloride; N,N-dimethyl-formamide / 2 h / 80 °C View Scheme

tery-amylbenzene (2049-95-8) → N,N'-(4-tert-pentyl-m-phenylene)-bis-acetamide

tery-amylbenzene (2049-95-8) + acetyl chloride (75-36-5) → 1-(4-tert-pentyl-phenyl)-ethanone (67468-81-9)

Conditions	Yield
With carbon disulfide; aluminium trichloride

Upstream product

• 74-88-4 methyl iodide 
• 98-83-9 isopropenylbenzene 
• 7446-70-0 aluminium trichloride 
• 75-85-4 tert-Amyl alcohol 
• 71-43-2 benzene 
• 513-35-9 2-methyl-but-2-ene 
• 109-67-1 1-penten 
• 563-45-1 3-Methyl-1-butene 
• 98-82-8 Isopropylbenzene 
• 74-85-1 ethene 
• 120-12-7 anthracene 
• 7647-01-0 hydrogenchloride 
• 7664-93-9 sulfuric acid 
• 7727-15-3 aluminium bromide 

Downstream Products

• 67468-81-9 1-(4-(tert-pentyl)phenyl)ethan-1-one 
• 595-37-9 2,2-dimethylbutyric acid 
• 78-78-4 methylbutane 
• 10474-35-8 2,2,3-trimethylindan-1-one 
• 71-43-2 benzene 
• 4481-30-5 2-methyl-3-phenylbutane 
• 1007-26-7 (2,2-dimethyl-1-propyl)benzene 
• 65-85-0 benzoic acid 
• 62-23-7 4-nitro-benzoic acid 
• 851199-04-7 2-[4-(1,1-dimethylpropyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 13936-26-0 2-(4-pentylbenzoyl)benzene carboxylic acid 
• 6284-98-6 1-(1,1-dimethylpropyl)-4-nitrobenzene 
• 108-31-6 maleic anhydride 
• 85-44-9 phthalic anhydride 

Relevant articles and documents

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Synthesis method of tert-amylbenzene with controllable isomer content

The invention provides a synthesis method of tert-amylbenzene with controllable isomer content. The synthesis method comprises the following steps: 1) carrying out a substitution reaction on tert-amylalcohol and haloid acid to obtain a halopentane intermediate; 2) carrying out a Friedel-Crafts alkylation reaction on the halopentane intermediate and benzene under the catalysis of a Lewis acid to obtain tert-amylbenzene; wherein the Lewis acid is one of ZnCl2 and FeCl3 or a mixture of the ZnCl2 and the FeCl3; the temperature of the Friedel-Crafts alkylation reaction is -10 to 40 DEG C; the vacuum degree is absolute pressure of 2-75kPa; and the reaction time is 0.5-4 h. According to the synthesis method, by setting reasonable reaction steps, controlling reaction conditions, selecting a proper catalyst and the like, the isomerization ratio is reduced, and the tert-amyl product with high yield and high selectivity is obtained.

MANUFACTURING METHOD OF ALKYL SUBSTITUTED AROMATIC HYDROCARBON

PROBLEM TO BE SOLVED: To provide a manufacturing method capable of enhancing conversion ratio of aromatic hydrocarbon of a reaction substance and manufacturing alkyl substituted aromatic hydrocarbon at high selectivity and high yield. SOLUTION: There is provided a manufacturing method of alkyl substituted aromatic hydrocarbon (X-2) including a process for alkylating an alkyl group in aromatic hydrocarbon having the alkyl group having a hydrogen atom at an α position (X-1) with alkene, in which a solid base (D) derived from a composition containing an alkali earth metal compound (A) containing one or more kind of magnesium oxide, magnesium hydroxide, magnesium carbonate, calcium oxide, calcium hydroxide, and calcium carbonate, a potassium compound (B) containing one or more kind of potassium hydroxide, and potassium carbonate, and a metal sodium (C) is used as a reaction catalyst for alkylation. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT