1033463-31-8

Basic information

• Product Name: [3-chloro-5-(trifluoromethyl)-2-pyridinyl]methanol
• Synonyms: [3-chloro-5-(trifluoromethyl)-2-pyridinyl]methanol;3-Chloro-2-(hydroxymethyl)-5-(trifluoromethyl)pyridine;(3-chloro-5-(trifluoromethyl)pyridine-2-yl)methanol
• CAS NO: 1033463-31-8
• Molecular Formula: C₇H₅ClF₃NO
• Molecular Weight: 211.5689096
• Mol File: 1033463-31-8.mol
• Article Data: 1

Chemical Properties

• Melting Point: 36-38°
• Boiling Point: 225.3±35.0℃ (760 Torr)
• Flash Point: 90.1±25.9℃
• Appearance: /
• Density: 1.490±0.06 g/cm3 (20 ºC 760 Torr)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: [3-chloro-5-(trifluoromethyl)-2-pyridinyl]methanol(CAS DataBase Reference)
• NIST Chemistry Reference: [3-chloro-5-(trifluoromethyl)-2-pyridinyl]methanol(1033463-31-8)
• EPA Substance Registry System: [3-chloro-5-(trifluoromethyl)-2-pyridinyl]methanol(1033463-31-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 1033463-31-8(Hazardous Substances Data)

Usage

General Description

[3-chloro-5-(trifluoromethyl)-2-pyridinyl]methanol is a chemical compound with the molecular formula C7H5ClF3NO. It is a pyridine derivative with a chloro and a trifluoromethyl group attached to the 3 and 5 positions, respectively. The compound also contains a hydroxymethyl group attached to the pyridinyl ring. This chemical is commonly used in the pharmaceutical and agrochemical industries as an intermediate for the synthesis of various drugs and pesticides. It may also have potential applications in organic synthesis and medicinal chemistry. The compound's structure and properties make it a valuable building block for the development of new and improved products in these fields.

Synthetic route

3-chloro-5-trifluoromethylpyridine-2-carboxylic acid ethyl ester → (3-chloro-5-(trifluoromethyl)pyridin-2-yl)methanol (1033463-31-8)

Conditions	Yield
With methanol; sodium tetrahydroborate at 0 - 23℃; for 4h;	60%

2,3-dichloro-5-trifluoromethylpyridine (69045-84-7) → (3-chloro-5-(trifluoromethyl)pyridin-2-yl)methanol (1033463-31-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium diacetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium acetate / 6 h / 90 °C / 11377.6 Torr / Autoclave 2: methanol; sodium tetrahydroborate / 4 h / 0 - 23 °C View Scheme

2,6-dichloro-benzonitrile (1194-65-6) + (3-chloro-5-(trifluoromethyl)pyridin-2-yl)methanol (1033463-31-8) → fluopicolide (239110-15-7)

Conditions	Yield
With sulfuric acid In toluene at 100℃; Reagent/catalyst;	90.43%

(3-chloro-5-(trifluoromethyl)pyridin-2-yl)methanol (1033463-31-8) → 3-chloro-5-trifluoromethyl-2-bromomethylpyridine (1227502-50-2)

Conditions	Yield
With phosphorus tribromide In dichloromethane at 20℃; for 4.5h; Concentration; Cooling with ice;	89.2%

(3-chloro-5-(trifluoromethyl)pyridin-2-yl)methanol (1033463-31-8) → 3-chloro-5-(trifluoromethyl)picolinaldehyde (175277-50-6)

Conditions	Yield
With Dess-Martin periodane In dichloromethane at 0 - 23℃; for 3h;	57%

(3-chloro-5-(trifluoromethyl)pyridin-2-yl)methanol (1033463-31-8) + methanesulfonyl chloride (124-63-0) → [3-chloro-5-(trifluoromethyl)-2-pyridinyl]methyl methanesulfonate

Conditions	Yield
With triethylamine In dichloromethane at 0 - 25℃;

(3-chloro-5-(trifluoromethyl)pyridin-2-yl)methanol (1033463-31-8) → 2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)tetrahydro-2H-pyran-4-yl methanesulfonate

Conditions	Yield
Multi-step reaction with 2 steps 1: Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C 2: dichloromethane / 40 °C View Scheme

(3-chloro-5-(trifluoromethyl)pyridin-2-yl)methanol (1033463-31-8) → 3-chloro-5-(trifluoromethyl)-2-(4-((3-(trifluoromethyl)phenyl)thio)tetrahydro-2H-pyran-2-yl)pyridine

Conditions	Yield
Multi-step reaction with 3 steps 1: Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C 2: dichloromethane / 40 °C 3: caesium carbonate / acetonitrile / 40 °C / Inert atmosphere View Scheme

(3-chloro-5-(trifluoromethyl)pyridin-2-yl)methanol (1033463-31-8) → 3-chloro-5-(trifluoromethyl)-2-(4-((3-(trifluoromethyl)phenyl)sulfonyl)tetrahydro-2H-pyran-2-yl)pyridine

Conditions	Yield
Multi-step reaction with 4 steps 1: Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C 2: dichloromethane / 40 °C 3: caesium carbonate / acetonitrile / 40 °C / Inert atmosphere 4: Oxone / acetonitrile; water / 23 °C View Scheme

(3-chloro-5-(trifluoromethyl)pyridin-2-yl)methanol (1033463-31-8) → [cis-rac] 3-chloro-2-(4-methyl-4-((3-(trifluoromethyl)phenyl)sulfonyl)tetrahydro-2H-pyran-2-yl)-5-(trifluoromethyl)pyridine

Conditions	Yield
Multi-step reaction with 5 steps 1.1: Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C 2.1: dichloromethane / 40 °C 3.1: caesium carbonate / acetonitrile / 40 °C / Inert atmosphere 4.1: Oxone / acetonitrile; water / 23 °C 5.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.25 h / -78 °C 5.2: 23 °C View Scheme

(3-chloro-5-(trifluoromethyl)pyridin-2-yl)methanol (1033463-31-8) → 2-(4-methyl-4-((3-(trifluoromethyl)phenyl)sulfonyl)tetrahydro-2H-pyran-2-yl)-3-(methylthio)-5-(trifluoromethyl)pyridine

Conditions	Yield
Multi-step reaction with 6 steps 1.1: Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C 2.1: dichloromethane / 40 °C 3.1: caesium carbonate / acetonitrile / 40 °C / Inert atmosphere 4.1: Oxone / acetonitrile; water / 23 °C 5.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.25 h / -78 °C 5.2: 23 °C 6.1: pyridine / 60 °C View Scheme

(3-chloro-5-(trifluoromethyl)pyridin-2-yl)methanol (1033463-31-8) → [cis-rac] 3-methylsulfonyl-2-[4-methyl-4-[[3-(trifluoromethyl)phenyl]sulfonyl]-tetrahydro-pyran-2-yl]-5-(trifluoromethyl)-pyridine

Conditions

Yield

Multi-step reaction with 7 steps 1.1: Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C 2.1: dichloromethane / 40 °C 3.1: caesium carbonate / acetonitrile / 40 °C / Inert atmosphere 4.1: Oxone / acetonitrile; water / 23 °C 5.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.25 h / -78 °C 5.2: 23 °C 6.1: pyridine / 60 °C 7.1: Oxone / acetonitrile; tetrahydrofuran; water / 40 °C View Scheme

(3-chloro-5-(trifluoromethyl)pyridin-2-yl)methanol (1033463-31-8) → C20H19F6NO5S2 + C20H19F6NO5S2

Conditions

Yield

Multi-step reaction with 8 steps 1.1: Dess-Martin periodane / dichloromethane / 3 h / 0 - 23 °C 2.1: dichloromethane / 40 °C 3.1: caesium carbonate / acetonitrile / 40 °C / Inert atmosphere 4.1: Oxone / acetonitrile; water / 23 °C 5.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.25 h / -78 °C 5.2: 23 °C 6.1: pyridine / 60 °C 7.1: Oxone / acetonitrile; tetrahydrofuran; water / 40 °C 8.1: chiral-LC IC-column / ethanol; n-heptane / Resolution of racemate View Scheme

Upstream product

• 69045-84-7 2,3-dichloro-5-trifluoromethylpyridine 
• 128073-16-5 3-chloro-5-trifluoromethylpyridine-2-carboxylic acid ethyl ester 

Downstream Products

• 175277-50-6 3-chloro-5-(trifluoromethyl)picolinaldehyde 
• 239110-15-7 fluopicolide 
• 1227502-50-2 3-chloro-5-trifluoromethyl-2-bromomethylpyridine 

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