994-05-8

Basic information

• Product Name: TERT-AMYL METHYL ETHER
• Synonyms: METHYL-TERT-AMYL ETHER;METHYL 2-METHYL-2-BUTYL ETHER;METHYL-(2-METHYLBUT-2-YL)ETHER;1,1-DIMETHYLPROPYL METHYL ETHER;TERT-AMYL METHYL ETHER;2-methoxy-2-methyl-butan;2-Methoxy-2-methylbutane;2-methoxy-2-methyl-butane
• CAS NO: 994-05-8
• Molecular Formula: C₆H₁₄O
• Molecular Weight: 102.17
• EINECS: 213-611-4
• Product Categories: AM to AQGasoline, Diesel,&Petroleum;A;A-BChemical Class;Alcohols;AliphaticAlphabetic;Alpha Sort;ASTM D5441Analytical Standards;ASTM Petroleum and Petrochemical;ASTM Petroleum Standards;Method Specific;Volatiles/ Semivolatiles
• Mol File: 994-05-8.mol
• Article Data: 27

Chemical Properties

• Melting Point: -105.78°C (estimate)
• Boiling Point: 85-86 °C(lit.)
• Flash Point: 11 °F
• Appearance: /
• Density: 0.77 g/mL at 25 °C(lit.)
• Vapor Pressure: 75mmHg at 25°C
• Refractive Index: n20/D 1.389(lit.)
• Storage Temp.: Flammables area
• Water Solubility: 12.35g/L(20 oC)
• Merck: 13,618
• BRN: 1731452
• CAS DataBase Reference: TERT-AMYL METHYL ETHER(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-AMYL METHYL ETHER(994-05-8)
• EPA Substance Registry System: TERT-AMYL METHYL ETHER(994-05-8)

Safety Data

• Hazard Codes: F,Xn,T
• Statements: 11-22-38-41-39/23/24/25-23/24/25-67
• Safety Statements: 16-26-39-45-36/37-33-23-9-7
• RIDADR: UN 3271 3/PG 2
• WGK Germany: 3
• RTECS: EK4421000
• F: 3
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 994-05-8(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR COLOURLESS LIQUID

Uses

Different sources of media describe the Uses of 994-05-8 differently. You can refer to the following data:
1. Fuel additive for gasoline.
2. TAME has been used as a reference standard for the determination of the analyte in Catalonian groundwater and soil samples by purge-and-trap gas chromatography/mass spectrometry (P&T-GC/MS) and in aqueous solutions by solid-phase microextraction (SPME) combined with GC-MS. It may be used as a reference standard for the identification of the analyte in gasoline-contaminated groundwater by GC combined with various detectors/quantification methods such as photoionization detector (PID), flame ionization detector (FID), or MS.

General Description

tert-Amyl methyl ether is an fuel ether oxygenate and has been quantitated in water by membrane extraction ion mobility spectrometry. tert-Amyl methyl ether is also referred to as 2-methoxy-2-methyl butane. Kinetics of ion exchange resin (Amberlyst 18) catalyzed tert-amyl methyl ether reactions have been investigated.

Flammability and Explosibility

Highlyflammable

InChI:InChI=1/C6H14O/c1-5-6(2,3)7-4/h5H2,1-4H3

Synthetic route

tert-Amyl alcohol (75-85-4) + methyl iodide (74-88-4) → tert-Amyl methyl ether (994-05-8)

Conditions	Yield
With sodium hydride; 1-n-butyl-2,3-dimethylimidazolium hexafluorophosphate at 25℃; for 2h; Williamson synthesis;	87%
With potassium hydride 1.)THF, 2 h, reflux, 2.) 0.5 h at 20 deg C, reflux, 1 h; Multistep reaction;

methanol (67-56-1) + tert-Amyl alcohol (75-85-4) → 2-methyl-but-2-ene (513-35-9) + tert-Amyl methyl ether (994-05-8) + 2-Methyl-1-butene (563-46-2)

Conditions	Yield
With Amberlyst-36 In 1,4-dioxane at 80℃; for 4h; Kinetics; Mechanism; Reagent/catalyst; Temperature; Autoclave;	A n/a B 71.37% C n/a
UDCaT-6 at 120℃; Product distribution; Activation energy; Further Variations:; Catalysts; Temperatures; space time;	A n/a B 18% C n/a

2-(benzotriazol-1-yl)-2-methoxypropane (123622-12-8) + EtMgX → tert-Amyl methyl ether (994-05-8)

Conditions	Yield
In diethyl ether Heating;	60%

methanol (67-56-1) + 2,2-dimethyl-1-propyl phenyl selenide (96503-15-0) → tert-Amyl methyl ether (994-05-8) + methyl t-butylmethyl ether (1118-00-9) + diphenyl diselenide (1666-13-3)

Conditions	Yield
With naphthalene-1,4-dicarbonitrile for 8h; Ambient temperature; Irradiation;	A 15% B 35% C 50%

methanol (67-56-1) + tert-Amyl alcohol (75-85-4) → tert-Amyl methyl ether (994-05-8)

Conditions	Yield
With hydrogen; iodine at 100℃; under 60004.8 Torr; for 0.5h;	42%
With Amberlyst 15 at 49.9℃; Product distribution; Rate constant; Kinetics; various reaction conditions;
With sulfuric acid
With Amberlyst 15 at 49.9℃;

diazomethane (186581-53-3, 908094-01-9) + tert-Amyl alcohol (75-85-4) → tert-Amyl methyl ether (994-05-8)

Conditions	Yield
With tetrafluoroboric acid; dichloromethane
With boron trifluoride diethyl etherate
silica gel Ambient temperature;	99 % Chromat.

methanol (67-56-1) + 2-methyl-but-2-ene (513-35-9) → tert-Amyl methyl ether (994-05-8)

Conditions	Yield
With sodium hydroxide; sodium tetrahydroborate; mercury(II) diacetate Product distribution; other alcohols and mercuric salts;
aluminosilicate catalyst at 99.9℃; Equilibrium constant; other temp.;
With Amberlyst 16 at 49.9℃; under 5250.4 Torr; Equilibrium constant; Thermodynamic data; var. temp.; ΔH;

methanol (67-56-1) + 2-Methyl-1-butene (563-46-2) → tert-Amyl methyl ether (994-05-8)

Conditions	Yield
aluminosilicate catalyst at 99.9℃; Equilibrium constant; Thermodynamic data; other temp., ΔH, ΔG, ΔS;
With Amberlyst 16 at 49.9℃; under 5250.4 Torr; Equilibrium constant; Thermodynamic data; var. temp.; ΔH;
(i) Hg(OAc)2, (ii) aq. NaOH, NaBH4; Multistep reaction;

methanol (67-56-1) + 2,2-dimethyl-1-propyl phenyl selenide (96503-15-0) → tert-Amyl methyl ether (994-05-8) + methyl t-butylmethyl ether (1118-00-9)

Conditions	Yield
With naphthalene-1,4-dicarbonitrile Irradiation;

methanol (67-56-1) + C31H30N(1+)*BF4(1-) (90886-05-8) → 2-methyl-but-2-ene (513-35-9) + tert-Amyl methyl ether (994-05-8)

Conditions	Yield
at 150℃; Yield given. Yields of byproduct given;

methanol (67-56-1) + C32H32N(1+)*BF4(1-) (90886-07-0) → 2-methyl-but-2-ene (513-35-9) + tert-Amyl methyl ether (994-05-8)

Conditions	Yield
at 150℃; Rate constant; Thermodynamic data; ΔH(excit.). ΔS(excit.);

deuteromethanol (1455-13-6) + C31H30N(1+)*BF4(1-) (90886-05-8) → 2-methyl-but-2-ene (513-35-9) + tert-Amyl methyl ether (994-05-8)

Conditions	Yield
at 150℃; Yield given. Yields of byproduct given;

methanol (67-56-1) + 2-methyl-but-2-ene (513-35-9) + sulfuric acid (7664-93-9) → tert-Amyl methyl ether (994-05-8)

Conditions	Yield
at 95℃;

methanol (67-56-1) + i-Amyl alcohol (123-51-3) → 2-methyl-but-2-ene (513-35-9) + tert-Amyl methyl ether (994-05-8) + 2-Methyl-1-butene (563-46-2) + 3-Methyl-1-butene (563-45-1)

Conditions	Yield
Stage #1: i-Amyl alcohol at 310 - 330℃; Stage #2: methanol With fibrous sulfonated cation exchanger at 90℃; under 6000.48 Torr; Title compound not separated from byproducts;

methanol (67-56-1) + tert-Amyl alcohol (75-85-4) → 2-methyl-but-2-ene (513-35-9) + tert-Amyl methyl ether (994-05-8) + 2-Methyl-1-butene (563-46-2) + 3-Methyl-1-butene (563-45-1)

Conditions	Yield
Dowex msm 31 at 70℃; under 6000.48 Torr; Product distribution; Further Variations:; Catalysts; Temperatures;

methanol (67-56-1) + 2-methyl-but-2-ene (513-35-9) → tert-Amyl alcohol (75-85-4) + tert-Amyl methyl ether (994-05-8)

Conditions	Yield
With Amberlyst(R) 15; water at 40℃;

3-Methyl-1-butene (563-45-1) → tert-Amyl methyl ether (994-05-8)

methanol (67-56-1) + isopentene → tert-Amyl methyl ether (994-05-8)

Conditions	Yield
With phenolic resin containing sulfonic groups In toluene at 79.84℃; under 2250.23 Torr; Autoclave; Inert atmosphere;

tert-Amyl methyl ether (994-05-8) + cabergoline (81409-90-7) → Form TAME cabergoline

Conditions	Yield
Stage #1: tert-Amyl methyl ether; cabergoline at 41 - 50℃; for 0.25h; Stage #2: cabergoline at 0 - 27℃; for 16.5h;	88.8%

tert-Amyl methyl ether (994-05-8) + 2-allyl-4-methylphenol (6628-06-4) → 2-allyl-6-tert-amyl-4-methylphenol (139573-21-0)

Conditions	Yield
tin(IV) chloride In dichloromethane Ambient temperature;	88%

tert-Amyl methyl ether (994-05-8) + [IrH2(bis(2-(diisopropylphosphino)-4-methylphenyl)amide)] (872682-19-4) → (N(C6H3(CH3)P(iPr)2)2)Ir(tert-amyl methyl ether(-2H))

Conditions	Yield
With norbornene In further solvent(s) byproducts: norbornane, H2; (inert atm.); keeping mixt. of iridium compd. and norbornene in tert-amyl methyl ether at room temp. for 2 h, heating for 20 min; evapn., dissolving in pentane, filtration, drying, NMR and MS;	87%

2-allyl-6-methylphenol (3354-58-3) + tert-Amyl methyl ether (994-05-8) → 2-allyl-4-tert-amyl-6-methylphenol (139553-36-9)

Conditions	Yield
tin(IV) chloride In dichloromethane for 16h; Ambient temperature;	82%

tert-Amyl methyl ether (994-05-8) + 3-n-Pentadecylphenol (501-24-6) → 2-tert-amyl-5-n-pentadecylphenol (139553-41-6)

Conditions	Yield
tin(IV) chloride In dichloromethane for 16h; Ambient temperature;	80%

Estragole (140-67-0) + tert-Amyl methyl ether (994-05-8) → 4-allyl-2-tert-amylanisole (139553-40-5)

Conditions	Yield
tin(IV) chloride In dichloromethane for 16h; Ambient temperature;	73%

tert-Amyl methyl ether (994-05-8) + 2,2,2-trichloroethyl 2-(4-bromophenyl)-2-diazoacetate (1641528-26-8) → 2,2,2-trichloroethyl (R)-2-(4-bromophenyl)-3-(tert-pentyloxy)propanoate

Conditions	Yield
With dirhodium tetrakis[(R)-(1-(biphenyl)-2,2-diphenylcyclopropanecarboxylate)] In dichloromethane at 0℃; enantioselective reaction;	70%

4-allylguaiacol (97-53-0) + tert-Amyl methyl ether (994-05-8) → 4-allyl-2-tert-amyl-6-methoxyphenol (139553-38-1)

Conditions	Yield
tin(IV) chloride In dichloromethane for 16h; Ambient temperature;	65%

tert-Amyl methyl ether (994-05-8) → 2-methyl-but-2-ene (513-35-9) + 2-Methyl-1-butene (563-46-2)

Conditions	Yield
With γ-Al2O3 at 250℃; flow reactor;	A 51% B 49 % Chromat.
With NaX zeolite at 200℃; flow reactor;	A 78 % Chromat. B 22%
With γ-Al2O3 at 300℃; Product distribution; variation of temperatures and reagent;	A 52 % Chromat. B 48 % Chromat.

[N-(trifluoromethylsulfonyl)imino][4-(trifluoromethyl)phenyl]-λ3-bromane (957188-75-9) + tert-Amyl methyl ether (994-05-8) → N-[(1,1-dimethylpropoxy)methyl]trifluoromethanesulfonamide (1378022-09-3)

Conditions	Yield
at 20℃; for 2h; Inert atmosphere; regioselective reaction;	51%

tert-Amyl methyl ether (994-05-8) + 2-Allylphenol (1745-81-9) → 2-allyl-4,6-di-tert-amylphenol (139553-37-0)

Conditions	Yield
tin(IV) chloride In dichloromethane for 16h; Ambient temperature;	35%

tert-Amyl methyl ether (994-05-8) → methanol (67-56-1) + 2-methyl-but-2-ene (513-35-9)

Conditions	Yield
aluminosilicate catalyst at 99.9℃; Equilibrium constant; other temp.;
With acid at 59.85℃; Equilibrium constant;

tert-Amyl methyl ether (994-05-8) → formaldehyd (50-00-0) + 2-methyl-2-butanol nitrate (21823-36-9) + tert-pentyl formate (757-88-0)

Conditions	Yield
With nitrate radical In gas at -16.1 - 89.9℃; under 750.06 Torr; Mechanism; Kinetics;

tert-Amyl methyl ether (994-05-8) → methanol (67-56-1) + 2-Methyl-1-butene (563-46-2)

Conditions	Yield
aluminosilicate catalyst at 99.9℃; Equilibrium constant; Thermodynamic data; other temp., ΔG0m, ΔS0m, ΔH0m;
With acid at 59.85℃; Equilibrium constant;

tert-Amyl methyl ether (994-05-8) → methanol (67-56-1) + 2-methyl-but-2-ene (513-35-9) + 2-Methyl-1-butene (563-46-2) + 3-Methyl-1-butene (563-45-1)

Conditions	Yield
KU-23 sulfonic acid ion exchange resin at 69.9℃; Equilibrium constant; Product distribution; other temperatures;

tert-Amyl methyl ether (994-05-8) → 2-methyl-but-2-ene (513-35-9)

Conditions	Yield
With methanol; Amberlyst 16 at 49.9℃; under 5250.4 Torr; Equilibrium constant; var. temp.;
With Amberlyst 15 In methanol at 24.85℃; Equilibrium constant; Further Variations:; Temperatures; Decomposition;

tert-Amyl methyl ether (994-05-8) → 2-Methyl-1-butene (563-46-2)

Conditions	Yield
With methanol; Amberlyst 16 at 49.9℃; under 5250.4 Torr; Equilibrium constant; var. temp.;
With Amberlyst 15 In methanol at 24.85℃; Equilibrium constant; Further Variations:; Temperatures; Decomposition;

tert-Amyl methyl ether (994-05-8) → methanol (67-56-1) + 2-methyl-but-2-ene (513-35-9) + propene (187737-37-7) + ethene (74-85-1) + 2-Methyl-1-butene (563-46-2) + isobutene (115-11-7)

Conditions	Yield
With oxygen at 300℃; Mechanism; Rate constant; anti-knock effect; oxidative degradation;

Upstream product

• 186581-53-3 diazomethane 
• 75-85-4 tert-Amyl alcohol 
• 67-56-1 methanol 
• 513-35-9 2-methyl-but-2-ene 
• 563-46-2 2-Methyl-1-butene 
• 96503-15-0 2,2-dimethyl-1-propyl phenyl selenide 
• 1455-13-6 deuteromethanol 
• 90886-05-8 C₃₁H₃₀N⁽¹⁺⁾*BF₄^(1-) 
• 74-88-4 methyl iodide 
• 7664-93-9 sulfuric acid 
• 123622-12-8 2-(benzotriazol-1-yl)-2-methoxypropane 
• 563-45-1 3-Methyl-1-butene 
• 123-51-3 i-Amyl alcohol 
• 90886-07-0 C₃₂H₃₂N⁽¹⁺⁾*BF₄^(1-) 

Downstream Products

• 139553-40-5 4-allyl-2-tert-amylanisole 
• 139553-41-6 2-tert-amyl-5-n-pentadecylphenol 
• 67-56-1 methanol 
• 513-35-9 2-methyl-but-2-ene 
• 50-00-0 formaldehyd 
• 21823-36-9 2-methyl-2-butanol nitrate 
• 757-88-0 tert-pentyl formate 
• 563-46-2 2-Methyl-1-butene 
• 563-45-1 3-Methyl-1-butene 
• 139573-21-0 2-allyl-6-tert-amyl-4-methylphenol 
• 79-20-9 acetic acid methyl ester 
• 75-07-0 acetaldehyde 
• 67-64-1 acetone 
• 181134-54-3 3-methoxy-3-methylbutanal 

Relevant articles and documents

Kinetics of liquid phase synthesis of tert-amyl methyl ether from tert-amyl alcohol and methanol catalyzed by ion exchange resin

Synthesis of tert-amyl methyl ether (TAME) from methanol (MeOH) and tert-amyl alcohol (TAA) in the liquid phase was studied by using an ion exchange resin, Amberlyst l5 (A15) in the H+ form. Experiments were carried out in a stirred batch reactor under atmospheric pressure. The effects of catalyst size, agitation speed, temperatures, feed ratio and water on the reaction rate were investigated. Both of intraparticle and external diffusion effects could be neglected in this system. The dehydration of TAA could be decreased by increasing the ratio of MeOH/TAA and the reaction rates were greatly inhibited by water. A kinetic model which considered the inhibition of water was proposed. The experimental results agreed well with the model.

Preparation of a novel sulfonated carbon catalyst for the etherification of isopentene with methanol to produce tert-amyl methyl ether

A novel method for the preparation of acid carbon catalyst from glucose and 4-hydroxybenzenesulfonic acid (p-HBSA) was reported. Glucose was first hydrolyzed to hydroxymethylfurfural that reacted with p-HBSA (a phenol compound) to form a phenolic (PF)-like resin containing -SO3H groups. The resin was carbonized and sulfonated further in concentrated sulfuric acid at 443 K to form an amorphous carbon material with a surface area of 22 m2/g. This acidic carbon contained 3.1 mmol/g of strong surface acid sites (-SO3H), and thus exhibited good catalytic activity for the etherification of isopentene with methanol to produce tert-amyl methyl ether.

In situ 13C DEPT-MRI as a tool to spatially resolve chemical conversion and selectivity of a heterogeneous catalytic reaction occurring in a fixed-bed reactor

The distortionless enhancement by polarisation transfer (DEPT) nuclear magnetic resonance (NMR) technique, combined with magnetic resonance imaging (MRI), has been used to provide the first in situ spatially-resolved and quantitative measurement of chemical conversion and selectivity within a fixed-bed reactor using natural abundance 13C NMR. The Royal Society of Chemistry 2005.