425-61-6

Basic information

• Product Name: 2,2,3,3-TETRAFLUORO-1,4-BUTANEDIOL
• Synonyms: 1,4-DIHYDROXY-2,2,3,3-TETRAFLUOROBUTANE;2,2,3,3-TETRAFLUOROBUTANE-1,4-DIOL;2,2,3,3-TETRAFLUORO-1,4-BUTANEDIOL;2,2,3,3-Tetrafluorobutane-1,4-diol 97%;2,2,3,3-Tetrafluorobutane-1,4-diol97%;2,2,3,3-Tetrafluoro-1,4-butanediol,98%;2,2,3,3-Tetrafluorobutanediol;NSC 95113
• CAS NO: 425-61-6
• Molecular Formula: C₄H₆F₄O₂
• Molecular Weight: 162.08
• EINECS: -0
• Product Categories: Organic Building Blocks;Oxygen Compounds;Polyols
• Mol File: 425-61-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 77-82 °C(lit.)
• Boiling Point: 110-112 °C13 mm Hg(lit.)
• Flash Point: 110-112°C/13mm
• Appearance: white crystalline powder
• Density: 1.3091 (estimate)
• Vapor Pressure: 0.000235mmHg at 25°C
• Refractive Index: 1.354
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 12.83±0.10(Predicted)
• Water Solubility: Soluble in water.
• BRN: 1745847
• CAS DataBase Reference: 2,2,3,3-TETRAFLUORO-1,4-BUTANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,3,3-TETRAFLUORO-1,4-BUTANEDIOL(425-61-6)
• EPA Substance Registry System: 2,2,3,3-TETRAFLUORO-1,4-BUTANEDIOL(425-61-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• RIDADR: 3276
• WGK Germany: 3
• HazardClass: IRRITANT, IRRITANT-HARMFUL
• Hazardous Substances Data: 425-61-6(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

Uses

2,2,3,3-Tetrafluoro-1,4-butanediol is a reactant used for the enzymic synthesis of silicone fluorinated aliphatic polyester amides.

InChI:InChI=1/C4H6F4O2/c5-3(6,1-9)4(7,8)2-10/h9-10H,1-2H2

Synthetic route

tetrafluorosuccinyl chloride (356-15-0) → 2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6)

Conditions	Yield
With sodium tetrahydroborate; sodium hydroxide In ethanol; water at 10 - 20℃; for 0.5h; pH=Ca. 9;	86.6%

perfluorosuccinic difluoride (679-13-0) → 2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6)

Conditions	Yield
Stage #1: perfluorosuccinic difluoride With sodium tetrahydroborate In isopropyl alcohol at 5 - 80℃; for 3h; Stage #2: With sulfuric acid In isopropyl alcohol at 35℃; for 1h;	53%

diethyl tetrafluorosuccinate (377-71-9) → 2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether

dimethyl tetrafluorosuccinate (356-36-5) → 2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether Heating;

2,2,3,3-tetrafluorobutane-1,4-diol diacetate (1220957-89-0) → 2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6)

Conditions	Yield
With sulfuric acid Product distribution / selectivity; Reflux;	64 %Chromat.

2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6) + trifluoromethylsulfonic anhydride (358-23-6) → trifluoro-methanesulfonic Acid 2,2,3,3-tetrafluoro-4-(trifluoro-methanesulfonyloxy)-butyl Ester (159760-17-5)

Conditions	Yield
Stage #1: 2,2,3,3-tetrafluorobutane-1,4-diol With pyridine In dichloromethane at 0℃; for 0.166667h; Stage #2: trifluoromethylsulfonic anhydride In dichloromethane at 20℃; for 12h;	100%
Stage #1: 2,2,3,3-tetrafluorobutane-1,4-diol With pyridine In dichloromethane at 20℃; Stage #2: trifluoromethylsulfonic anhydride In dichloromethane at 20℃;	95%
Stage #1: 2,2,3,3-tetrafluorobutane-1,4-diol With pyridine In dichloromethane for 0.25h; Stage #2: trifluoromethylsulfonic anhydride In dichloromethane at 20℃; for 13h;	92%

2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6) + p-toluenesulfonyl chloride (98-59-9) → 2,2,3,3-tetrafluorobutane-1,4-diyl bis(4-methylbenzenesulfonate) (122834-95-1)

Conditions	Yield
With pyridine at 55℃; for 24h;	96%
With pyridine at 0 - 55℃; for 24h;	94%
With pyridine at 0 - 55℃; for 24h;	94%
With pyridine at 55℃; for 24h;	94%
With pyridine at 0 - 55℃; for 24h;	94%

2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6) + propargyl bromide (106-96-7) → C10H10F4O2

Conditions	Yield
Stage #1: 2,2,3,3-tetrafluorobutane-1,4-diol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: propargyl bromide In tetrahydrofuran; mineral oil at 0 - 20℃;	94%

2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6) + benzyl bromide (100-39-0) → mono-O-benzyl-2,2,3,3-tetrafluorobutane-1,4-diol (521316-04-1)

Conditions	Yield
With potassium carbonate In acetonitrile for 16h; Inert atmosphere; Reflux;	93%
With potassium carbonate In acetone for 12h; Heating;	90%

isocyanate de chlorosulfonyle (1189-71-5) + 2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6) → 2,2,3,3-tetrafluorobutane-1,4-diyl dicarbamate (22084-73-7)

Conditions	Yield
In acetonitrile at 20℃;	89%

2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6) + 2,2-ethylenedioxy-4,4,6,6-tetrachlorocyclotriphosphazatriene (53943-77-4) → 1,1-(ethane-1',2'-dioxy)-3,3-(2',2',3',3'-tetrafluorobutane-1',4'-dioxy)-5,5-dichlorocyclotriphosphazene (1392324-64-9)

Conditions	Yield
With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 24h; Inert atmosphere; Cooling with ice;	85%

2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6) + 4-bromobenzenecarbonitrile (623-00-7) → 2,2,3,3-tetrafluoro-1,4-(bis-4-cyano-1-phenoxy)butane

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; caesium carbonate In toluene at 85℃; for 16h; Inert atmosphere;	85%

iodo(trimethylsilyl)methane (4206-67-1) + 2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6) → 2,2,3,3-tetrafluoro-4-((trimethylsilyl)methoxy)butanol (1465917-59-2)

Conditions	Yield
With potassium carbonate In acetone for 18h; Reflux;	83%

2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6) + 3-chloroprop-1-ene (107-05-1) → 1,4-bis(allyloxy)-1H,1H,4H,4H-perfluorobutane

Conditions	Yield
With tetrabutylammomium bromide; potassium hydroxide In 1,2-dimethoxyethane at 85℃; for 16h;	81.2%
With tetrabutylammomium bromide; potassium hydroxide In 1,2-dimethoxyethane at 85℃; for 16h;	81.2%

2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6) + pentafluorophenyl isocyanate (1591-95-3) → 2,2,3,3-tetrafluorobutane-1,4-diyl bis(N-pentafluorophenylcarbamate) (1610024-10-6)

Conditions	Yield
In acetonitrile at 20℃; for 4h; Inert atmosphere; Irradiation;	79%

2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6) + 1,2,3,3,3-pentafluoro-N-(1,1,2,2,2-pentafluoroethyl)-N-(trifluoromethyl)prop-1-en-1-amine → (E/Z)-1,3,3,3-tetrafluoro-N-(1,1,2,2,2-pentafluoroethyl)-2-[2,2,3,3-tetrafluoro-4-[(E/Z)-2-fluoro-2-[1,1,2,2,2-pentafluoroethyl(trifluoromethyl)amino]-1-(trifluoromethyl)vinyloxy]butoxy]-N-(trifluoromethyl)prop-1-en-1-amine

Conditions	Yield
With potassium hydroxide In acetonitrile at 20℃; for 17h;	77.95%

2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6) + phenyl isocyanate (103-71-9) → 2,2,3,3-tetrafluoro-4-hydroxybutyl N-phenylcarbamate (1610024-03-7)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 1h; Schlenk technique; Inert atmosphere;	74%

2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6) + allyl bromide (106-95-6) → 1,4-bis(allyloxy)-1H,1H,4H,4H-perfluorobutane

Conditions	Yield
With tetrabutylammomium bromide; potassium hydroxide In tert-butyl methyl ether; water at 50 - 56℃;	74%

2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6) + 9,9-Dichloro-1,4-dimethyl-7-phenyl-7λ4-thia-1,4,6,8,10-pentaaza-5λ5,9λ5-diphospha-spiro[4.5]deca-5(10),6,8-triene 7-oxide → 10,10,11,11-tetrafluoro-1,4-dimethyl-15-phenyl-8,13-dioxa-15λ4-thia-1,4,6,14,16-pentaaza-5λ5,7λ5-diphospha-dispiro[4.1.6.3]hexadeca-5(16),6,14-triene 15-oxide

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -80 - 20℃;	73%

2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6) + Methyl phenyldiazoacetate (22979-35-7) → C13H14F4O4

Conditions	Yield
In dichloromethane at 20℃; Irradiation;	73%

2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6) + phenyl isocyanate (103-71-9) → 2,2,3,3-tetrafluorobutane-1,4-diyl bis(N-phenylcarbamate) (1610024-06-0)

Conditions	Yield
In acetonitrile at 20℃; for 4h; Inert atmosphere; Irradiation;	71%

2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6) + phosphorochloridic acid bis-(2,2-difluoro-ethyl) ester (327189-70-8) → phosphoric acid 4-[bis-(2,2-difluoro-ethoxy)-phosphoryloxy]-2,2,3,3-tetrafluoro-butyl ester bis-(2,2-difluoro-ethyl) ester

Conditions	Yield
With triethylamine In diethyl ether at 20℃; for 20h;	65%

2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6) + 7,7,9,9-tetrachloro-1-oxa-4,6,8,10-tetraaza-5λ5,7λ5,9λ5-triphospha-spiro[4.5]deca-5,7,9-triene (64487-59-8) → 1,1-(2'-amino-1'-ethoxy)-3,3-(2',2',3',3'-tetrafluorobutane-1',4'-dioxy)-5,5-dichlorocyclotriphosphazene + 1,1-(2-amino-1-ethoxy)-3,3,5,5-bis(2,2,3,3-tetrafluorobutane-1,4-dioxy)cyclotriphosphazene

Conditions	Yield
With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 24h; Inert atmosphere; Cooling with ice;	A 64% B 16%

2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6) → C12H12Cl2F12N4O6P4 (1259405-22-5) + C16H16F16N4O8P4 (1259308-77-4)

Conditions	Yield
With octachlorocyclotetraphosphazene; sodium hydride In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;	A 3% B 60%

2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6) + C12H22O7S → C15H24F4O6

Conditions	Yield
Stage #1: 2,2,3,3-tetrafluorobutane-1,4-diol With sodium hydride In diethylene glycol dimethyl ether; mineral oil at 0℃; for 1h; Stage #2: C12H22O7S In diethylene glycol dimethyl ether; mineral oil at 0 - 90℃; for 8h;	56%

2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6) + tert-butylchlorodiphenylsilane (58479-61-1) → 4-((tert-butyldiphenylsilyl)oxy)-2,2,3,3-tetrafluorobutan-1-ol (164412-95-7)

Conditions	Yield
With dmap; TEA In dichloromethane	55%
With 1H-imidazole In dichloromethane	40%

2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6) + 2,2,4,4-Tetrachloro-7-methyl-1,3,5,7,11-pentaaza-2λ5,4λ5,6λ5-triphospha-spiro[5.5]undeca-1(6),2,4-triene (141100-39-2) → C8H14Cl2F4N5O2P3 + C12H18F8N5O4P3

Conditions	Yield
With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 23h; Inert atmosphere;	A 55% B 8%

2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6) → 2,2,3,3-tetrafluorobutane-1,4-diyl dinitrate (13848-88-9)

Conditions	Yield
With nitric acid; acetic acid at 0 - 20℃; for 3h;	53%

2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6) → C4H4Cl6F4N4O2P4 (1259308-69-4) + C4H4Cl6F4N4O2P4 (1259308-67-2) + C8H8Cl4F8N4O4P4 (1259308-73-0) + C8H8Cl4F8N4O4P4 (1259308-71-8)

Conditions	Yield
With octachlorocyclotetraphosphazene; sodium hydride In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;	A 1% B 49% C 4% D 9%

2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6) + methanesulfonyl chloride (124-63-0) → 2,2,3,3-tetrafluorobutane-1,4-diol bis(methanesulfonate) (117186-53-5)

Conditions	Yield
With triethylamine In chloroform at -30 - -25℃; for 1h;	47%

2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6) + bis(2,2,3,3-tetrafluoropropyl) chlorophosphate (65611-22-5) → phosphoric acid 4-[bis-(2,2,3,3-tetrafluoro-propoxy)-phosphoryloxy]-2,2,3,3-tetrafluoro-butyl ester bis-(2,2,3,3-tetrafluoro-propyl) ester

Conditions	Yield
With triethylamine In diethyl ether at 20℃; for 20h;	41%

2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6) + 2,2,2-Trifluoroethanesulfonyl chloride (1648-99-3) → 2,2,3,3-tetrafluorobutane-1,4-diol bis(2,2,2-trifluoroethanesulfonate) (117186-55-7)

Conditions	Yield
With triethylamine In chloroform at -30 - -25℃; for 1h;	32%

2,2,3,3-tetrafluorobutane-1,4-diol (425-61-6) + C10H22Cl8N10P6 (91651-24-0) → C26H38F16N10O8P6

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 96h; Inert atmosphere;	32%

Upstream product

• 356-36-5 dimethyl tetrafluorosuccinate 
• 356-15-0 tetrafluorosuccinyl chloride 
• 1220957-89-0 2,2,3,3-tetrafluorobutane-1,4-diol diacetate 
• 377-71-9 diethyl tetrafluorosuccinate 
• 679-13-0 perfluorosuccinic difluoride 

Downstream Products

• 1547-52-0 5,5,6,6-Tetrafluoro-1,3-dioxacycloheptan 

Relevant articles and documents

Method for preparing fluorine-containing dihydric alcohol from fluorine-containing cycloolefin

The invention discloses a method for preparing fluorine-containing dihydric alcohol from fluorine-containing cycloolefin. The method comprises the following steps: oxidizing fluorine-containing cycloolefin serving as a raw material by using an oxidizing agent and treating the fluorine-containing cycloolefin by using a strong alkali to generate a solid mixed salt containing corresponding fluorine-containing dicarboxylate, and then generating corresponding fluorine-containing binary acyl chloride under the action of an acylating chlorination reagent; and finally, enabling the fluorine-containing binary acyl chloride and a reducing agent to be subjected to a reduction reaction under the action of a solvent and a catalyst to obtain the corresponding fluorine-containing dihydric alcohol. The specific organic solvent and catalyst are adopted, and other conditions are matched, so that the fluorine-containing cycloolefin can be effectively promoted to generate corresponding fluorine-containing dihydric alcohol with high efficiency and high yield. The method has the advantages of easily available raw materials, simple process, convenience in operation, low cost and the like, and is suitable for large-scale production of fluorine-containing dihydric alcohol.

METHOD FOR PRODUCING TETRAFLUORO COMPOUND

Provided is a method for producing a tetrafluoro nitrogen-containing heterocyclic compound such as tetrafluoropyrrolidine in good yield and at low cost. The method comprises the steps of: (A) reacting a compound represented by the formula (I) with fluorine gas to produce a tetrafluoro compound represented by the formula (II), (B) converting the tetrafluoro derivative represented by the formula (II) to a compound represented by the formula (III), and (C) reacting the compound represented by the formula (III) with an amine compound represented by the formula NH2R9 to produce a tetrafluoro nitrogen-containing heterocyclic compound represented by the formula (IV) or salt thereof.