802-93-7

Basic information

• Product Name: 1,3-BIS(2-HYDROXYHEXAFLUOROISOPROPYL)BENZENE
• Synonyms: alpha,alpha,alpha’,alpha’-tetrakis(trifluoromethyl)-3-benzenedimethanol;ALPHA,ALPHA,ALPHA',ALPHA'-TETRAKIS(TRIFLUOROMETHYL)-1,3-BENZENEDIMETHANOL;1,3-BIS (HEXAFLUORO 2-HYDROXY-2-PROPYL) BENZENE;1,3-BIS(HEXAFLUORO-2-HYDROXYISOPROPYL)BENZENE;1,3-BIS(HEXAFLUORO-ALPHA-HYDROXYISOPROPYL)BENZENE;1,3-BIS(ALPHA-HYDROXYHEXAFLUOROISOPROPYL)BENZENE;1,3-BIS(2-HYDROXYHEXAFLUOROISOPROPYL)BENZENE;1,3-BIS(1,1,1,3,3,3-HEXAFLUORO-2-HYDROXYPROPYL)BENZENE
• CAS NO: 802-93-7
• Molecular Formula: C₁₂H₆F₁₂O₂
• Molecular Weight: 410.16
• EINECS: 212-354-5
• Product Categories: Fluorenes, etc. (reagent for high-performance polymer research);Functional Materials;Reagent for High-Performance Polymer Research;Organic Building Blocks;Oxygen Compounds;Polyols
• Mol File: 802-93-7.mol

Chemical Properties

• Melting Point: 9-10°C
• Boiling Point: 209 °C(lit.)
• Flash Point: 207 °F
• Appearance: clear colorless to slightly yellow liquid
• Density: 1.659 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.387(lit.)
• Solubility: Difficult to mix.
• PKA: 8.61±0.15(Predicted)
• BRN: 2024879
• CAS DataBase Reference: 1,3-BIS(2-HYDROXYHEXAFLUOROISOPROPYL)BENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-BIS(2-HYDROXYHEXAFLUOROISOPROPYL)BENZENE(802-93-7)
• EPA Substance Registry System: 1,3-BIS(2-HYDROXYHEXAFLUOROISOPROPYL)BENZENE(802-93-7)

Safety Data

• Hazard Codes: Xi,C
• Statements: 36/37/38
• Safety Statements: 37/39-26
• RIDADR: 3265
• WGK Germany: 3
• RTECS: 212-354-5
• TSCA: T
• HazardClass: IRRITANT, CORROSIVE
• Hazardous Substances Data: 802-93-7(Hazardous Substances Data)

Usage

Uses

Used in Electrical Measurement Industry:
1,3-BIS(2-HYDROXYHEXAFLUOROISOPROPYL)BENZENE is used as a reference standard for calibrating and verifying the accuracy of electrical measurement instruments. Its specific properties allow it to provide precise and reliable measurements of electrical magnitudes, ensuring the accuracy and reliability of the instruments used in this industry.

Synthetic route

Hexafluoroacetone (684-16-2) + benzene (71-43-2) → 1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene (802-93-7)

Conditions	Yield
With aluminium trichloride at 50 - 54℃; for 6h;	86%
With aluminum (III) chloride at 51℃; Friedel-Crafts Acylation; Inert atmosphere;	70%

Hexafluoroacetone (684-16-2) + benzene (71-43-2) → 1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene (802-93-7) + 1,1,1,3,3,3-hexafluoro-2-phenylisopropyl alcohol (718-64-9) + 1,1,1,3,3,3-hexafluoro-2-[4-(2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl)-phenyl]-propan-2-ol (1992-15-0)

Conditions	Yield
With aluminium trichloride at 50 - 54℃; for 5h;	A 54% B 20% C 6%

1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene (802-93-7) → 5-Iodo-α,α,α',α'-tetrakis(trifluoromethyl)-1,3-benzenedimethanol (53173-72-1)

Conditions	Yield
With sulfuric acid; iodine for 7h; Ambient temperature;	89%
With sulfuric acid; sulfur trioxide; iodine at 70 - 72℃; for 2h;	77%
With fuming sulphuric acid; iodine at 70℃; for 2h;	70%

Methyl methanesulfonate (66-27-3) + 1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene (802-93-7) → 1,3-bis<1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl>benzene (53896-18-7)

Conditions	Yield
Stage #1: 1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene With sodium hydride In N,N-dimethyl-formamide at -20 - -10℃; Stage #2: Methyl methanesulfonate In N,N-dimethyl-formamide at 20℃; for 12h;	81%

4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecan-1-ol (1651-41-8) + 1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene (802-93-7) → 1,3-bis[1-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyloxy)-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]benzene

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In various solvent(s) at 20℃; for 1h;	61%

1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene (802-93-7) + dimethyl sulfoxide (67-68-5) → 1,3-bis(2-hydroxyhexafluoro-2-propyl)benzene DMSO complex

Conditions	Yield
at 120 - 125℃; for 5h;	43%

1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene (802-93-7) → 5-Iodo-α,α,α',α'-tetrakis(trifluoromethyl)-1,3-benzenedimethanol (53173-72-1) + 2,4,6-triiodo-1-(2-hydroxyhexafluoro-2-propyl)benzene

Conditions	Yield
With sulfur trioxide; iodine In sulfuric acid

1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene (802-93-7) + 2,2,2-trifluoroethyl trifluoromethanesulphonate (6226-25-1) → 1,3-bis[1-(2,2,2-trifluoroethoxy)-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]benzene

Conditions	Yield
Stage #1: 1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene With sodium hydride In N,N-dimethyl-formamide at -20 - -10℃; Stage #2: 2,2,2-trifluoroethyl trifluoromethanesulphonate In N,N-dimethyl-formamide at 60℃; for 6h;

1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene (802-93-7) → 1,3-bis(2-hydroxyhexafluoro-2-propyl)benzene DMSO complex

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / H2SO4, SO3, I2 / 2 h / 70 - 72 °C 2: 3.8 g / Cu, 2-iodoheptafluoropropane / 10 h / 135 - 140 °C View Scheme

1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene (802-93-7) → 1,3-bis(2-hydroxyhexafluoro-2-propyl)-5-(heptafluoro-n-propyl)benzene DMSO complex

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / H2SO4, SO3, I2 / 2 h / 70 - 72 °C 2: 87 percent / Cu / 135 - 140 °C View Scheme

1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene (802-93-7) → 3,5-bis(2-hydroxyhexafluoro-2-propyl)-2',3',4',5',6',-pentafluorobiphenyl DMSO complex

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / H2SO4, SO3, I2 / 2 h / 70 - 72 °C 2: 2.5 percent / Cu / 16 h / 145 °C View Scheme

1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene (802-93-7) → 1,3-bis(2-hydroxyhexafluoro-2-propyl)-5-(tridecafluoro-n-hexyl)benzene DMSO complex

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / H2SO4, SO3, I2 / 2 h / 70 - 72 °C 2: 78 percent / Cu / 135 - 140 °C View Scheme

1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene (802-93-7) → 1,3-bis(2-hydroxyhexafluoro-2-propyl)-5-(pentadecafluoro-n-heptyl)benzene DMSO complex

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / H2SO4, SO3, I2 / 2 h / 70 - 72 °C 2: 91 percent / Cu / 135 - 140 °C View Scheme

1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene (802-93-7) → 1,3-bis(2-hydroxyhexafluoro-2-propyl)-5-(heptadecafluoro-n-octyl)benzene DMSO complex

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / H2SO4, SO3, I2 / 2 h / 70 - 72 °C 2: 88 percent / Cu / 16 h / 120 - 125 °C View Scheme

1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene (802-93-7) → 3,5-bis<2,2,2-trifluoro-1-(2,2,2-trifluoroethoxy)-1-(trifluoromethyl)ethyl>iodobenzene (144369-52-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 89 percent / I2, 30percent H2SO4 / 7 h / Ambient temperature 2: 1.) NaH / 1.) DMF, 2.) DMF, 50 deg C, 35 min View Scheme

ethyl bromide (74-96-4) + 1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene (802-93-7) → C14H10F12O2

Conditions	Yield
aluminum (III) chloride at 50℃;

1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene (802-93-7) + 3-(triethoxypropyl) isocyanate (24801-88-5) → C32H48F12N2O10Si2 (813468-12-1)

Conditions	Yield
In toluene at 20 - 25℃; for 168h;

1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene (802-93-7) + methanesulfonyl chloride (124-63-0) → 1,3-bis-(1-methanesulfonyloxy-1-trifluoromethyl-2,2,2-trifluoro-ethyl)-benzene

Conditions	Yield
With triethylamine In dichloromethane

1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene (802-93-7) + Ethanesulfonyl chloride (594-44-5) → 1-(1-ethanesulfonyloxy-2,2,2-trifluoro-1-tri-fluoromethylethyl)-3-(2,2,2-trifluoro-1-hydroxy-1-tri-fluoromethylethyl)-benzene + 1,3-bis-(1-ethanesulfonyloxy-2,2,2-trifluoro-1-trifluoro-methylethyl)-benzene (161758-96-9)

Conditions	Yield
In hexane; N,N-dimethyl-formamide

1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene (802-93-7) + p-toluenesulfonyl chloride (98-59-9) → 1,3-bis-[2,2,2-trifluoro-1-(toluene-4-sulfonyloxy)-1-trifluoromethylethyl]-benzene

Conditions	Yield
In N,N-dimethyl-formamide

1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene (802-93-7) + 4-chlorobenzenesulfonyl chloride (98-60-2) → 1,3-bis-[1-(4-chlorobenzenesulfonyloxy)-2,2,2-trifluoro-1-trifluoromethylethyl]-benzene

Conditions	Yield
In N,N-dimethyl-formamide

triethylene + 1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene (802-93-7) + acryloyl chloride (814-68-6) → 1,3-Bis(2-hydroxyhexafluoro-2-propyl)benzene diacrylate (77974-91-5)

Conditions	Yield
In 1,1,2-Trichloro-1,2,2-trifluoroethane

1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene (802-93-7) + tetrabutyl-ammonium chloride (1112-67-0) → C12H6F12O2*Cl(1-)*C16H36N(1+)

Conditions	Yield
In [D3]acetonitrile at 24.84℃;

1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene (802-93-7) + tetrabutyl-ammonium chloride (1112-67-0) → 2C12H6F12O2*2C16H36N(1+)*2Cl(1-)

Conditions	Yield
In [D3]acetonitrile at 20℃;

1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene (802-93-7) + tetrabutylammomium bromide (1643-19-2) → C12H6F12O2*Br(1-)*C16H36N(1+)

Conditions	Yield
In [D3]acetonitrile at 24.84℃;

1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene (802-93-7) + tetrabutylammonium nitrate → C12H6F12O2*C16H36N(1+)*NO3(1-)

Conditions	Yield
In [D3]acetonitrile at 24.84℃;

1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene (802-93-7) + tetrabutylammonium dihydrogen phosphate → C12H6F12O2*C16H36N(1+)*H2O4P(1-)

Conditions	Yield
In [D3]acetonitrile at 24.84℃;

1,3-bis-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-benzene (802-93-7) + tetrabutylammonium acetate (10534-59-5) → C12H6F12O2*C16H36N(1+)*C2H3O2(1-)

Conditions	Yield
In [D3]acetonitrile at 24.84℃;

Upstream product

• 684-16-2 Hexafluoroacetone 
• 71-43-2 benzene 

Downstream Products

• 53173-72-1 5-Iodo-α,α,α',α'-tetrakis(trifluoromethyl)-1,3-benzenedimethanol 
• 53896-18-7 1,3-bis<1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl>benzene 
• 161758-96-9 1,3-bis-(1-ethanesulfonyloxy-2,2,2-trifluoro-1-trifluoro-methylethyl)-benzene 

Relevant articles and documents

A dendritic macromolecule fluorine - 19 magnetic resonance developer and its preparation method and application (by machine translation)

The invention discloses a dendritic macromolecule fluorine - 19 magnetic resonance developer and its preparation method and application. Developer of the present invention is to fluorine-containing dendritic macromolecule as the skeleton, peripheral end group is connected with the functional molecule, its preparation method comprises the following steps: through the Lewis acid under the catalysis of the Friedel-crafts reaction of hexafluoroacetone with benzene will double-trifluoromethyl tertiary alcohol introduction benzene, in fuming sulfuric acid under the action of the iodination reaction, and then introduced into the propynyl structure through the coupling reaction, hydrogenating the resultant fluorine-containing structure unit Q; phosphorus tribromide in Q through the primary conversion of hydroxy group to bromine, then in hydroxy Q with the bromo generating ether linkage synthesis of 1st on behalf of the dendritic macromolecule, repeated brominated and ether generating reaction to obtain 2nd, three generations of dendritic macromolecule, finally through the brominated 3rd on behalf of the branched chain with the ligand through ether bond and to obtain the developer of the present invention. Developer of the present invention can be used for magnetic resonance imaging and the quantitative, visual, transmission and release and the like field. (by machine translation)

PERFLUOROALKYLATION OF BENZENE DERIVATIVES. AN IMPROVED SYNTHESIS OF 1,3-BIS(2-HYDROXYHEXAFLUORO-2-PROPYL)-5-(PERFLUORO-n-ALKYL)BENZENES

A three-step high yield synthesis of various 1,3-bis(2-hydroxyhexafluoro-2-propyl)-5-perfluoro-n-alkyl) benzenes is described.Significant improvements in the iodination and perfluoro-alkylation of a perfluoroalkylbenzene diol have been achieved.Copper coupling of straight-chain perfluoroalkyl iodides with the iodobenzene derivative in DMSO gave the desired compounds as DMSO complexes in 78-91 percent yield.