113798-74-6

Basic information

• Product Name: 2,3,6-TRIFLUOROPHENOL
• Synonyms: Phenol, 2,3,6-trifluoro- (9CI);2,3,6-Trifluorophenol 98%;2,3,6-Trifluorophenol98%;2,3,6-TRIFLUOROPHENOL
• CAS NO: 113798-74-6
• Molecular Formula: C₆H₃F₃O
• Molecular Weight: 148.08
• Product Categories: HALIDE;Phenol&Thiophenol&Mercaptan;Miscellaneous;Organic Building Blocks;Oxygen Compounds;Phenols;Aryl Fluorinated Building Blocks;Building Blocks;C6;C6 to C8;Chemical Synthesis;Fluorinated Building Blocks;Organic Building Blocks;Organic Fluorinated Building Blocks;Other Fluorinated Organic Building Blocks;Oxygen Compounds
• Mol File: 113798-74-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 33-37 °C(lit.)
• Boiling Point: 137°Cat760mmHg
• Flash Point: 147 °F
• Appearance: /
• Density: 1.456 g/cm
• Vapor Pressure: 5.81mmHg at 25°C
• Refractive Index: 1.471
• Storage Temp.: 2-8°C
• PKA: 6.45±0.15(Predicted)
• Water Solubility: Soluble in water (47.267 mg/L est.)
• BRN: 4976927
• CAS DataBase Reference: 2,3,6-TRIFLUOROPHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,6-TRIFLUOROPHENOL(113798-74-6)
• EPA Substance Registry System: 2,3,6-TRIFLUOROPHENOL(113798-74-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39-36
• RIDADR: UN 1325 4.1/PG 2
• WGK Germany: 3
• HazardClass: 4.1
• PackingGroup: III
• Hazardous Substances Data: 113798-74-6(Hazardous Substances Data)

Usage

Chemical Properties

clear light yellow liquid after melting

Uses

2,3,6-Trifluorophenol may be employed as model compound to investigate the site-selective functionalization of halogen-bearing phenols by organometallic approach.

General Description

2,3,6-Trifluorophenol is a fluorinated phenol. Biotransformation of 2,3,6-trifluorophenol has been studied by 19FNMR technique.

InChI:InChI=1/C6H3F3O/c7-3-1-2-4(8)6(10)5(3)9/h1-2,10H

Synthetic route

1,2,3,4-tetrafluorobenzene (551-62-2) → 2,3,6-trifluorophenol (113798-74-6)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide for 4h; Heating;

2,3,5-trifluoro-4-hydroxybenzoic acid (156839-10-0) → 2,3,6-trifluorophenol (113798-74-6)

Conditions	Yield
With sulfuric acid In 1-methyl-pyrrolidin-2-one; water

1-bromo-hexane (111-25-1) + 2,3,6-trifluorophenol (113798-74-6) → C12H15F3O

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 20℃;	100%

2,3,6-trifluorophenol (113798-74-6) + isopropyl bromide (75-26-3) → 2,3,6-trifluoroisopropoxybenzene

Conditions	Yield
With potassium carbonate In N-methyl-acetamide; water	94.2%

2,3,6-trifluorophenol (113798-74-6) + 2-Chloro-2-oxo-1,3,2-dioxaphospholane (6609-64-9) → C8H6F3O4P

Conditions	Yield
In dichloromethane at 0 - 20℃; for 12h;	93%

2,3,6-trifluorophenol (113798-74-6) + 2-chloro-1,3,2-dioxaphospholan (822-39-9) → 2-(2,3,6-trifluorophenoxy)-1,3,2-dioxaphospholane

Conditions	Yield
Stage #1: 2,3,6-trifluorophenol In dichloromethane at 20℃; for 0.5h; Stage #2: 2-chloro-1,3,2-dioxaphospholan In dichloromethane at 0 - 20℃; for 12h;	92%

2,3,6-trifluorophenol (113798-74-6) → 4-bromo-2,3,6-trifluorophenol (192446-70-1)

Conditions	Yield
With N-Bromosuccinimide In chloroform at 0℃; for 2h;	87%

2,3,6-trifluorophenol (113798-74-6) + chloromethyl methyl ether (107-30-2) → 1,2,4-trifluoro-3-(methoxymethoxy)benzene

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃;	87%

4-[4-(3-hydroxypropyl)phenyl]-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (642487-34-1) + 2,3,6-trifluorophenol (113798-74-6) → 4-{4-[3-(2,3,6-trifluorophenoxy)propyl]phenyl}-5,6-dihydro-2H-pyridine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (642487-39-6)

Conditions	Yield
With tributylphosphine; N-ethyl-N,N-diisopropylamine; 1,1'-azodicarbonyl-dipiperidine In toluene at 20 - 60℃; for 3h;	83%

2,3,6-trifluorophenol (113798-74-6) → 4-chloro-2,3,6-trifluorophenol

Conditions	Yield
With sodium hydroxide; chlorine In dichloromethane; water	82.5%

triisopropylsilyl chloride (13154-24-0) + 2,3,6-trifluorophenol (113798-74-6) → triisopropyl(2,3,6-trifluorophenoxy)silane

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 25℃; for 20h;	82%

(rac.)-(1R*,5S*)-3-[4-(3-hydroxypropyl)phenyl]-8-azabicyclo[3.2.1]oct-2-ene-2,8-dicarboxylic acid 8-tert-butyl ester 2-methyl ester + 2,3,6-trifluorophenol (113798-74-6) → (rac.)-(1R*,5S*)-3-{4-[3-(2,3,6-trifluorophenoxy)propyl]phenyl}-8-azabicyclo[3.2.1]oct-2-ene-2,8-dicarboxylic acid 8-tert-butyl ester 2-methyl ester

Conditions	Yield
With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine In toluene for 2h; Mitsunobu reaction; Heating / reflux;	78%

(rac)-(1RS,5SR)-7-[4-(3-hydroxy-propyl)-phenyl]-3,9-diaza-bicyclo[3.3.1]non-6-ene-3,6,9-tricarboxylic acid 3-tert-butyl ester 6-ethyl ester 9-(2,2,2-trichloro-1,1-dimethyl-ethyl) ester + 2,3,6-trifluorophenol (113798-74-6) → (rac)-(1RS,5SR)-7-{4-[3-(2,3,6-trifluoro-phenoxy)-propyl]-phenyl}-3,9-diaza-bicyclo[3.3.1]non-6-ene-3,6,9-tricarboxylic acid 3-tert-butyl ester 6-ethyl ester 9-(2,2,2-trichloro-1,1-dimethyl-ethyl) ester

Conditions	Yield
With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine In toluene for 0.5h; Mitsunobu reaction; Inert atmosphere; Reflux;	75%

2,3,6-trifluorophenol (113798-74-6) + tert-butyl 3-hydroxyazetidine-1-carboxylate (141699-55-0) → tert-butyl 3-(2,3,6-trifluorophenoxy)azetidin-1-carboxylate

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 0 - 20℃; for 72h;	72%

(S)-5-bromo-3-{2-[2-(2-tert-butyl-benzyl)-3-oxo-2,3-dihydro-pyridazin-4-yl]-butyrylamino}-4-oxo-pentanoic acid tert-butyl ester (1005751-88-1) + 2,3,6-trifluorophenol (113798-74-6) → (S)-3-{2-[2-(2-tert-butyl-benzyl)-3-oxo-2,3-dihydro-pyridazin-4-yl]-butyrylamino}-4-oxo-5-(2,3,6-trifluoro-phenoxy)-pentanoic acid tert-butyl ester (1005751-95-0)

Conditions	Yield
With potassium fluoride In N,N-dimethyl-formamide at 20℃; for 4h;	69%

sodium pyruvate (113-24-6) + 2,3,6-trifluorophenol (113798-74-6) → (S)-2-amino-3-(2,3,5-trifluoro-4-hydroxyphenyl)propanoic acid (182756-60-1)

Conditions	Yield
With tyrosine phenol-lyase; pyridoxal 5'-phosphate; ammonium acetate; 2-hydroxyethanethiol In water at 20℃; for 168h; pH=8;	50%
With ammonium acetate; tyrosine phenol lyase; 2-hydroxyethanethiol; pyridoxal 5'-phosphate at 20℃; pH=8.0;
With tyrosine phenol lyase; pyridoxal 5'-phosphate; ammonium acetate; 2-hydroxyethanethiol at 20℃; for 72h; pH=8; Enzymatic reaction;

4-(5-chloro-6-fluoropyridin-3-yl)-N-(ethylsulfonyl)-3-methoxybenzamide + 2,3,6-trifluorophenol (113798-74-6) → 4-(5-chloro-6-(2,3,6-trifluorophenoxy)-3-pyridinyl)-N-(ethylsulfonyl)-3-methoxybenzamide

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 120℃; for 15h;	30%

C24H36ClN3O7 + 2,3,6-trifluorophenol (113798-74-6) → C30H38F3N3O8

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 15h;	25%

4-(5-chloro-6-fluoro-3-pyridinyl)-3-methoxy-N-(methylsulfonyl)benzamide + 2,3,6-trifluorophenol (113798-74-6) → 4-(5-chloro-6-(2,3,6-trifluorophenoxy)-3-pyridinyl)-3-methoxy-N-(methylsulfonyl)benzamide

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 90℃;	21%

C20H28ClN3O4 + 2,3,6-trifluorophenol (113798-74-6) → C26H30F3N3O5

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 18℃; for 10h; Inert atmosphere;	21%

C18H26ClN3O4 + 2,3,6-trifluorophenol (113798-74-6) → C24H28F3N3O5

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 15h;	6.47%

C25H36ClN3O6 + 2,3,6-trifluorophenol (113798-74-6) → C31H38F3N3O7

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 15h;	5%

C19H28ClN3O5 + 2,3,6-trifluorophenol (113798-74-6) → C25H30F3N3O6

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 18℃; for 10h; Inert atmosphere;	4%

oxalyl dichloride (79-37-8) + 3-methoxy-N-(3-methoxyphenyl)benzenamine (92248-06-1) + 2,3,6-trifluorophenol (113798-74-6) → 2',3',6'-trifluoro-phenyl 1,6-dimethoxyacridine-9-carboxylate (177535-32-9)

Conditions	Yield
With pyridine; potassium hydroxide; aluminium trichloride; p-toluenesulfonyl chloride 1) CH2Cl2, reflux, 1 h; 2) CH2Cl2, rt, 25 min, reflux, 3 h; 3) reflux, 22 h; 4) 1 h; 5) rt; Multistep reaction;

9-acridinecarbonyl chloride (66074-67-7) + 2,3,6-trifluorophenol (113798-74-6) → Acridine-9-carboxylic acid 2,3,6-trifluoro-phenyl ester (172834-67-2)

Conditions	Yield
With pyridine In dichloromethane Ambient temperature;

2,3,6-trifluorophenol (113798-74-6) + 3-Methoxy-acridine-9-carbonyl chloride (178920-79-1) → 3-Methoxy-acridine-9-carboxylic acid 2,3,6-trifluoro-phenyl ester (172834-72-9)

Conditions	Yield
With pyridine In dichloromethane Ambient temperature;

2,3,6-trifluorophenol (113798-74-6) + 1,6-dimethoxy-4-methylacridine-9-carboxylic acid (197156-26-6) → 1,6-Dimethoxy-4-methyl-acridine-9-carboxylic acid 2,3,6-trifluoro-phenyl ester (197156-27-7)

Conditions	Yield
With pyridine; p-toluenesulfonyl chloride 1) 1 h; 2) pyridine, rt, overnight; Yield given. Multistep reaction;

2,3,6-trifluorophenol (113798-74-6) + 2-oxo-propionic acid (127-17-3) → (S)-2-amino-3-(2,3,5-trifluoro-4-hydroxyphenyl)propanoic acid (182756-60-1)

Conditions	Yield
With ammonium hydroxide; tyrosine phenollylase; pyridoxal 5'-phosphate; ammonium acetate; 2-hydroxyethanethiol In water Ambient temperature;
With tyrosine phenol lyase; ammonia Enzymatic reaction;
With ammonium hydroxide; tyrosine phenol lyase; pyridoxal 5'-phosphate; ammonium acetate; 2-hydroxyethanethiol at 20℃; pH=8; Darkness; Enzymatic reaction;

2,3,6-trifluorophenol (113798-74-6) + (S)-5-Bromo-3-{(S)-3-methyl-2-[2-(naphthalen-1-yloxy)-acetylamino]-butyrylamino}-4-oxo-pentanoic acid tert-butyl ester (265119-58-2) → (S)-3-{(S)-3-Methyl-2-[2-(naphthalen-1-yloxy)-acetylamino]-butyrylamino}-4-oxo-5-(2,3,6-trifluoro-phenoxy)-pentanoic acid tert-butyl ester

Conditions	Yield
With potassium fluoride; sodium iodide In N,N-dimethyl-formamide

α-chloro-N-(p-ethylphenyl)acetamide (20172-36-5) + 2,3,6-trifluorophenol (113798-74-6) → N-(4-ethyl-phenyl)-2-(2,3,6-trifluoro-phenoxy)-acetamide

Conditions	Yield
In isopropyl alcohol Heating;

2,3,6-trifluorophenol (113798-74-6) + aniline (62-53-3) → 2,3,6-trifluoro-4-phenylazophenol (849703-11-3)

Conditions	Yield
Stage #1: aniline With hydrogenchloride; sodium nitrite In water Stage #2: 2,3,6-trifluorophenol With sodium hydroxide; urea In water at 0 - 20℃;

Upstream product

• 551-62-2 1,2,3,4-tetrafluorobenzene 
• 156839-10-0 2,3,5-trifluoro-4-hydroxybenzoic acid 

Downstream Products

• 177535-32-9 2',3',6'-trifluoro-phenyl 1,6-dimethoxyacridine-9-carboxylate 
• 182756-60-1 (S)-2-amino-3-(2,3,5-trifluoro-4-hydroxyphenyl)propanoic acid 
• 875669-71-9 (S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(2,3,5-trifluoro-4-hydroxy-phenyl)-propionic acid 
• 197972-10-4 (S)-4-{(S)-2-[(S)-2-((S)-2-Amino-4-carboxy-butyrylamino)-3-carboxy-propionylamino]-3-carbamoyl-propionylamino}-4-[(S)-1-[(1S,2R)-1-((S)-1-carboxy-ethylcarbamoyl)-2-hydroxy-propylcarbamoyl]-2-(2,3,5-trifluoro-4-hydroxy-phenyl)-ethylcarbamoyl]-butyric acid 
• 177535-24-9 2',3',6'-Trifluorophenyl 1,10-dimethylacridan-9-carboxylate 
• 177535-25-0 2',3',6'-Trifluorophenyl 1-chloro-10-methylacridan-9-carboxylate 
• 1186393-84-9 2,3,6-trifluorophenylsulfamate 
• 1258001-96-5 tert-butyl 4-(5-cyano-4-((2,3,6-trifluorophenoxy)methyl)-1H-pyrazol-1-yl)piperidine-1-carboxylate 

Relevant articles and documents

Derivatives of 2, 3, 6-trifluorophenols and a process for their preparation

The present invention relates to compounds of the formula (1) STR1 where R is H, a straight-chain or branched alkyl radical with 1 to 6 carbons, a fluorinated straight-chain or branched alkyl radical with 1 to 6 carbons, a benzyl radical, or a benzyl radical substituted by an alkyl group or alkoxy group with 1 to 4 carbons each, or by halogen, X is H, Cl, Br or I, and X is different from R, and a process for their preparation.