79538-03-7

Basic information

• Product Name: 2,3,5,6-Tetrafluoro-4-methylbenzyl alcohol
• Synonyms: 4-METHYL-2,3,5,6-TETRAFLUOROBENZYL ALCOHOL;2,3,5,6-TETRAFLUORO-4-METHYLBENZYL ALCOHOL;2,3,5,6-TETRAFLUORO-4-METHYLBENYL ALCOHOL;4-METHYL-2,3,5,6-TETRAFLUOROBENZENEMETHANOL;(2,3,5,6-Tetrafluoro-4-Methylphenyl)Methanol;(4-Methyl-2,3,5,6-tetrafluorophenyl)methanol, 4-(Hydroxymethyl)-2,3,5,6-tetrafluorotoluene
• CAS NO: 79538-03-7
• Molecular Formula: C8H6F4O
• Molecular Weight: 194.13
• EINECS: 616-698-0
• Mol File: 79538-03-7.mol
• Article Data: 9

Chemical Properties

• Melting Point: 61-62°C
• Boiling Point: 201.367 °C at 760 mmHg
• Flash Point: 75.584 °C
• Appearance: /
• Density: 1.424 g/cm³
• Vapor Pressure: 0.189mmHg at 25°C
• Refractive Index: 1.462
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 12.95±0.10(Predicted)
• CAS DataBase Reference: 2,3,5,6-Tetrafluoro-4-methylbenzyl alcohol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,5,6-Tetrafluoro-4-methylbenzyl alcohol(79538-03-7)
• EPA Substance Registry System: 2,3,5,6-Tetrafluoro-4-methylbenzyl alcohol(79538-03-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• Hazardous Substances Data: 79538-03-7(Hazardous Substances Data)

Usage

Chemical Properties

Colorless solid

InChI:InChI=1/C8H6F4O/c1-3-5(9)7(11)4(2-13)8(12)6(3)10/h13H,2H2,1H3

Synthetic route

4-(hydroxymethyl)-2,3,5,6-tetrafluorobenzyl bromide (99705-46-1) → 2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7)

Conditions	Yield
With hydrogen; magnesium oxide; 5%-palladium/activated carbon In methanol; water at 50℃; under 1875.19 Torr; for 1 - 1.5h; Product distribution / selectivity;	89.4%
With hydrogen; 5%-palladium/activated carbon In methanol; water at 50℃; under 1875.19 Torr; Product distribution / selectivity;

formaldehyd (50-00-0) + 2,3,5,6-tetrafluorotoluene (5230-78-4) → 2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7)

Conditions	Yield
Stage #1: 2,3,5,6-tetrafluorotoluene With isopropylmagnesium chloride In tetrahydrofuran at 20℃; for 12h; Glovebox; Schlenk technique; Inert atmosphere; Stage #2: formaldehyd In tetrahydrofuran at 20℃; for 6h; Glovebox; Schlenk technique; Inert atmosphere;	71%

2,3,5,6-tetrafluoro-1,4-benzenedimethanol (92339-07-6) → 2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7) + 1,4-dimethyl-2,3,5,6-tetrafluorobenzene (703-87-7)

Conditions	Yield
With hydrogen; sponge cobalt catalyst in water-containing state In toluene at 160℃; under 3975.4 - 165017 Torr; for 0.5 - 1h; Product distribution / selectivity;	A 82 - 88 %Chromat. B 4 - 11 %Chromat.
With hydrogen; rhenium oxide-alumina catalyst In 1,4-dioxane at 220℃; under 36003.6 Torr; for 5h; Product distribution / selectivity;	A 58 %Chromat. B 14 %Chromat.
With hydrogen; sponge cobalt catalyst in a water-containing state In 1,4-dioxane at 160℃; under 3750.38 Torr; for 4h; Product distribution / selectivity;	A 40 %Chromat. B 7 %Chromat.
With hydrogen; palladium on activated charcoal In 1,4-dioxane at 220℃; under 67506.8 Torr; for 12h; Product distribution / selectivity;	A 37 %Chromat. B 6 %Chromat.

4-chloromethyl-2,3,5,6-tetrafluorobenzyl alcohol (99705-45-0) → 2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7)

Conditions	Yield
With hydrogen; 5%-palladium/activated carbon In water; butan-1-ol at 100℃; for 16h; Product distribution / selectivity; Inert atmosphere;

tetrahydro-2-[(4-methyl-2,3,5,6-tetrafluorophenyl)methoxy]-2H-pyran (289891-56-1) → 2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7)

Conditions	Yield
With toluene-4-sulfonic acid In ethanol for 0.5h; Reflux;

2,3,5,6-tetrafluoroterephthalaldehyde (3217-47-8) → 2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7) + 1,4-dimethyl-2,3,5,6-tetrafluorobenzene (703-87-7) + 2,3,5,6-tetrafluoro-1,4-benzenedimethanol (92339-07-6)

Conditions	Yield
With hydrogen; cobalt R400 In toluene at 120 - 150℃; under 3750.38 - 5625.56 Torr; for 10.5h; Product distribution / selectivity; Autoclave;

1,2,4,5-Tetrafluorobenzene (327-54-8) → 2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 2 h / -60 - -45 °C / Inert atmosphere 1.2: 0.5 h / -45 °C 2.1: n-butyllithium / hexane; diethyl ether / 1 h / -70 °C 2.2: -70 - 20 °C 3.1: lithium aluminium tetrahydride / diethyl ether / 1 h / 20 °C / Inert atmosphere; Reflux View Scheme

2,3,5,6-tetrafluorotoluene (5230-78-4) → 2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-butyllithium / hexane; diethyl ether / 1 h / -70 °C 1.2: -70 - 20 °C 2.1: lithium aluminium tetrahydride / diethyl ether / 1 h / 20 °C / Inert atmosphere; Reflux View Scheme

2,3,5,6-tetrafluoro-4-methylbenzoic acid (652-32-4) → 2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether at 20℃; for 1h; Inert atmosphere; Reflux;	200 mg

2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7) + trans-2,2-dimethyl-3-(2-chloropropenyl)cyclopropanecarboxylic acid chloride → trans-4-methyl-2,3,5,6-tetrafluorobenzyl 2,2-dimethyl-3-(2-chloropropenyl)cyclopropanecarboxylate

Conditions	Yield
With pyridine In toluene at 20℃; for 4h;	98%

2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7) + cis-((Z)-2-chloro-3,3,3-trifluoro-prop-1-enyl)-2,2-dimethylcyclopropane acyl chloride (393870-46-7) → tefluthrin

Conditions	Yield
With pyridine In toluene at 35 - 95℃; for 2h; Product distribution / selectivity;	96.5%

2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7) + (E/Z)-cis-3-(2-chloro-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid chloride → (1R-)trans-4-methyl-2,3,5,6-tetrafluorobenzyl 2,2-dimethyl-3-(2-chloropropenyl)cyclopropanecarboxylate

Conditions	Yield
With pyridine In hexane at 20℃; for 4h;	96%

2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7) + (E/Z)-trans-3-(2-Chloro-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid chloride → (1R)-cis-4-methyl-2,3,5,6-tetrafluorobenzyl 2,2-dimethyl-3-(2-chloropropenyl)cyclopropanecarboxylate

Conditions	Yield
With pyridine In hexane at 20℃; for 4h;	96%

2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7) → 2,3,5,6-tetrafluoro-4-methylbenzyl chloride (60903-84-6)

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 0℃;	95%

2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7) + methyl 1R-2,2-dimethyl-3-(1-propenyl)cyclopropane carboxylate → 2,3,5,6-tetrafluoro-4-methylbenzyl 1R-2,2-dimethyl-3-(1-propenyl)cyclopropane carboxylate

Conditions	Yield
With lithium methanolate In toluene at 122 - 127℃; for 8h;	94.7%
With lithium methanolate In n-heptane at 105 - 106℃; for 10h;	88.7%
With sodium methylate In methanol	55.5%

2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7) + cis-2,2-dimethyl-3-(2-chloropropenyl)cyclopropanecarboxylic acid chloride → cis-4-methyl-2,3,5,6-tetrafluorobenzyl 2,2-dimethyl-3-(2-chloropropenyl)cyclopropanecarboxylate

Conditions	Yield
With pyridine In 5,5-dimethyl-1,3-cyclohexadiene at 20℃; for 4h;	93%

2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7) + (1R)-trans-3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid chloride (4489-14-9) → (2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1R,3R)-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate (223419-26-9)

Conditions	Yield
With pyridine In tetrahydrofuran at 20℃; for 8h;	87%

2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7) + (1R)-trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid chloride (188023-87-2) → profluthrin

Conditions	Yield
With pyridine In tetrahydrofuran; ice-water; ethyl acetate	87%

2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7) + 2,2-dimethyl-1R-trans-3-(2,2-difluorovinyl)cyclopropanecarboxylic acid chloride → 2,3,5,6-tetrafluoro-4-methylbenzyl 2,2-dimethyl-1R-trans-3-(2,2-difluorovinyl)cyclopropanecarboxylate

Conditions	Yield
With pyridine In toluene at 18℃; for 4h;	85%

2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7) + cis-Z-(+) 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl-cyclopropane carboxylic acid chloride → tefluthrin

Conditions	Yield
In toluene at 20 - 95℃;	80%

2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7) + 9-bromo-1-nonene (89359-54-6) → 1,2,4,5-tetrafluoro-3-methyl-6-((non-8-en-1-yloxy)methyl)benzene

Conditions	Yield
Stage #1: 2,3,5,6-tetrafluoro-4-methylbenzyl alcohol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Williamson Ether Synthesis; Inert atmosphere; Stage #2: 9-bromo-1-nonene In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h; Williamson Ether Synthesis; Inert atmosphere;	80%

2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7) + methyl 1R-trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate → (2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1R,3R)-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate (223419-26-9)

Conditions	Yield
With lithium methanolate In n-heptane	77.4%

2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7) + trans-3-(2-chloro-vinyl)-2,2-dimethylcyclopropane carboxylic acid → trans-(2,3,5,6-tetrafluoro-4-methyl-benzyl)-3-(2-chlorovinyl)-2,2-dimethylcyclopropane-carboxylate

Conditions	Yield
Stage #1: trans-3-(2-chloro-vinyl)-2,2-dimethylcyclopropane carboxylic acid With thionyl chloride at 50℃; Stage #2: 2,3,5,6-tetrafluoro-4-methylbenzyl alcohol With pyridine In benzene	75%

2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7) + C8H11ClO2 → C16H15ClF4O2

Conditions	Yield
Stage #1: C8H11ClO2 With thionyl chloride at 50℃; Stage #2: 2,3,5,6-tetrafluoro-4-methylbenzyl alcohol With pyridine In benzene	75%

(1R)-trans-2,2-dimethyl-3-((Z)-1-propenyl)cyclopropanecarboxylic acid + 2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7) → (2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1R,3R)-2,2-dimethyl-3-((1Z)-1-propenyl)cyclopropanecarboxylate

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran; toluene

2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7) → (2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1R,3R)-3-formyl-2,2-dimethylcyclopropanecarboxylate (240494-67-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 87 percent / pyridine / tetrahydrofuran / 8 h / 20 °C 2: 82 percent / O3; dimethylsulfide / methanol; ethyl acetate / 12 h / 20 °C View Scheme

2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7) → (2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1R,3R)-2,2-dimethyl-3-((1Z)-1-propenyl)cyclopropanecarboxylate

Conditions	Yield
Multi-step reaction with 3 steps 1: 87 percent / pyridine / tetrahydrofuran / 8 h / 20 °C 2: 82 percent / O3; dimethylsulfide / methanol; ethyl acetate / 12 h / 20 °C 3: 67 percent / potassium tert-butoxide / tetrahydrofuran / 0.5 h / cooling View Scheme

2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7) + 2,2-dimethyl-3-(1-propenyl) cyclopropane methyl carboxylate (40447-55-0) → 2,3,5,6-tetrafluoro-4-methylbenzyl-3-(1-propenyl)-2,2-dimethylcyclopropanecarboxylate

Conditions	Yield
With lithium methanolate In n-heptane at 95 - 105℃; for 16h; Product distribution / selectivity; Heating / reflux;
With lithium methanolate In n-heptane at 95 - 105℃; for 17h; Product distribution / selectivity; Heating / reflux;

2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7) + (2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1R)-trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate + (1R)-trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid chloride (188023-87-2) → (2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1R)-trans-3-formyl-2,2-dimethyl-cyclopropanecarboxylate

Conditions	Yield
With pyridine; dimethylsulfide; p-toluenesulfonic acid monohydrate In tetrahydrofuran; methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; water; ethyl acetate; acetone

2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7) + diethylamino-sulfur trifluoride (38078-09-0) → 4-(fluoromethyl)-2,3,5,6-tetrafluorotoluene

Conditions	Yield
In dichloromethane

2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7) + (1R)-trans-3-(2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid (1052115-15-7) → 4-methyl-2,3,5,6-tetrafluorobenzyl (1R)-trans-3-((Z)-2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylate + 4-methyl-2,3,5,6-tetrafluorobenzyl (1R)-trans-3-((E)-2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylate

Conditions	Yield
With dicyclohexyl-carbodiimide; dmap In dichloromethane at 20℃; for 3h;	A n/a B n/a

2,3,5,6-tetrafluoro-4-methylbenzyl alcohol (79538-03-7) + C9H10ClF3O2 → tefluthrin

Conditions	Yield
zirconium(IV) chloride In xylene at 140℃; for 3h; Product distribution / selectivity;

Upstream product

• 92339-07-6 2,3,5,6-tetrafluoro-1,4-benzenedimethanol 
• 99705-46-1 4-(hydroxymethyl)-2,3,5,6-tetrafluorobenzyl bromide 
• 99705-45-0 4-chloromethyl-2,3,5,6-tetrafluorobenzyl alcohol 
• 289891-56-1 tetrahydro-2-[(4-methyl-2,3,5,6-tetrafluorophenyl)methoxy]-2H-pyran 
• 3217-47-8 2,3,5,6-tetrafluoroterephthalaldehyde 
• 50-00-0 formaldehyd 
• 5230-78-4 2,3,5,6-tetrafluorotoluene 
• 327-54-8 1,2,4,5-Tetrafluorobenzene 
• 652-32-4 2,3,5,6-tetrafluoro-4-methylbenzoic acid 

Downstream Products

• 223419-26-9 (2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1R,3R)-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate 
• 240494-67-1 (2,3,5,6-tetrafluoro-4-methylphenyl)methyl (1R,3R)-3-formyl-2,2-dimethylcyclopropanecarboxylate 
• 1462940-80-2 (R)-2,3,5,6-tetrafluoro-4-methylbenzyl 4-methyl-3-phenylpentanoate 
• 1462941-07-6 (R)-2,3,5,6-tetrafluoro-4-methylbenzyl 3-(4-methoxyphenyl)-4-(p-tolyl)butanoate 
• 1462940-81-3 (S)-2,3,5,6-tetrafluoro-4-methylbenzyl 4-methyl-3-phenylpentanoate 
• 1462941-09-8 (S)-2,3,5,6-tetrafluoro-4-methylbenzyl 3-(4-methoxyphenyl)-4-(p-tolyl)butanoate 
• 60903-84-6 4-methyl-2,3,5,6-tetrafluorobenzyl chloride 
• 1785-64-4 4,5,7,8,12,13,15,16-octafluoro(2.2)paracyclophane 

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