4459-18-1

Basic information

• Product Name: PERFLUORO-TERT-BUTYL IODIDE
• Synonyms: 1,1,1,3,3,3-Hexafluoro-2-iodo-2-(trifluoromethyl)propane;2-Iodoperfluoro-2-methylpropane;Nonafluoro-2-iodo-2-methylpropane;Perfluor-tert.-butyljodid;Propane,1,1,1,3,3,3-hexafluoro-2-iodo-2-(trifluoromethyl)-;Propane,hexafluoro-2-iodo-2-(trifluoromethyl)-;tert-Nonafluorobutyliodide;Tris(trifluoromethyl)iodomethane
• CAS NO: 4459-18-1
• Molecular Formula: C₄F₉I
• Molecular Weight: 345.93
• Mol File: 4459-18-1.mol

Chemical Properties

• Melting Point: 60 °C
• Boiling Point: 61
• Flash Point: 20°C
• Appearance: /
• Density: 2.1157 (estimate)
• CAS DataBase Reference: PERFLUORO-TERT-BUTYL IODIDE(CAS DataBase Reference)
• NIST Chemistry Reference: PERFLUORO-TERT-BUTYL IODIDE(4459-18-1)
• EPA Substance Registry System: PERFLUORO-TERT-BUTYL IODIDE(4459-18-1)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38
• Safety Statements: 37/39-26
• HazardClass: IRRITANT, TOXIC
• Hazardous Substances Data: 4459-18-1(Hazardous Substances Data)

Synthetic route

2-bromo-1,1,1,3,3,3-hexafluoro-2-trifluoromethyl-propane (754-43-8) → 1,1,1,3,3,3-hexafluoro-2-trifluoromethyl-propane (382-24-1) + perfluoro-tert-butyl iodide (4459-18-1)

Conditions	Yield
With sodium iodide In acetonitrile for 5h; Heating;	A 75.7% B 5.3%

2-chlorocarbonyloxy-1,1,1,3,3,3-hexafluoro-2-trifluoromethyl-propane (27746-96-9) → perfluoro-tert-butyl iodide (4459-18-1)

Conditions	Yield
With potassium iodide at 150 - 180℃; for 3h;	30.8%

iodotrifluoromethane (2314-97-8) + 3,3-bis(trifluoromethyl)diazirine (3024-50-8) → perfluoro-tert-butyl iodide (4459-18-1)

Conditions	Yield
at 150 - 155℃; for 10h;	9.8%

perfluoroisobutylene (382-21-8) → perfluoro-tert-butyl iodide (4459-18-1)

Conditions	Yield
With potassium fluoride; iodine; nitrobenzene

1,1,1,3,3,3-hexafluoro-2-nitroso-2-trifluoromethyl-propane (354-93-8) → perfluoro-tert-butyl iodide (4459-18-1)

Conditions	Yield
With iodine

perfluoropropylene (116-15-4) + iodotrifluoromethane (2314-97-8) → 1,1,1,2,2,3,3-heptafluoro-3-iodo-propane (754-34-7) + perfluoroisobutylene (382-21-8) + perfluoroisopropyl iodide (677-69-0) + 2-trifluoromethyl-perfluoropropyl iodide (1542-18-3) + perfluoro-tert-butyl iodide (4459-18-1) + 1,1,1,2-Tetrafluoro-2-iodo-butane

Conditions	Yield
at 360℃; Product distribution; nickel reactor; other temperatures, influence of reactor material;

perfluoropropylene (116-15-4) + iodotrifluoromethane (2314-97-8) → perfluoroisopropyl iodide (677-69-0) + 2-trifluoromethyl-perfluoropropyl iodide (1542-18-3) + perfluoro-tert-butyl iodide (4459-18-1) + 1,1,1,2-Tetrafluoro-2-iodo-butane

Conditions	Yield
at 360℃; Yield given. Further byproducts given. Yields of byproduct given;

2-bromo-1,1,1,3,3,3-hexafluoro-2-trifluoromethyl-propane (754-43-8) → iodotrifluoromethane (2314-97-8) + perfluoro-tert-butyl iodide (4459-18-1)

Conditions	Yield
With iodine Product distribution; Irradiation; multiple-photon IR laser excitation; different laser frequency and energy fluence;
With iodine Irradiation; Yield given. Yields of byproduct given;

benzenediazonium hexafluorophosphate (369-58-4) + C8F18I(1-)*C6H18N3S(1+) → 2-phenylazo-2-trifluoromethylperfluoropropane (38771-38-9) + perfluoro-tert-butyl iodide (4459-18-1) + C6H18N3S(1+)*F6P(1-)

Conditions	Yield
In tetrahydrofuran at 25℃;

C8F18I(1-)*C6H18N3S(1+) + methyl trifluoromethanesulfonate (333-27-7) → perfluoro-tert-butyl iodide (4459-18-1) + 1,1,1,3,3,3-hexafluoro-2-methyl-2-trifluoromethyl-propane (36553-69-2) + C6H18N3S(1+)*CF3O3S(1-)

Conditions	Yield
In dichloromethane at 25℃;

1,1,1,2,3,5,5,5-Octafluoro-2,3,4,4-tetrakis-trifluoromethyl-pentane (122432-75-1) → Perfluoro-2-iodo-3-methylbutane (7626-45-1) + perfluoroisopropyl iodide (677-69-0) + perfluoro-tert-butyl iodide (4459-18-1) + 1,1,1,2,4,4,4-Heptafluoro-2-iodo-3,3-bis-trifluoromethyl-butane

Conditions	Yield
With iodine at 161℃; for 48h;
With iodine at 201℃; for 48h;
With iodine at 201℃; for 48h; Rate constant; Thermodynamic data; other temp., activation energy;

perfluoro-tert-butyl iodide (4459-18-1) + triethylchlorogermane (994-28-5) → triethylfluorogermane (358-41-8)

Conditions	Yield
With hexaethylphosphoric triamide In dichloromethane byproducts: P(NEt2)3ClI; a soln. of ClGeEt3 and t-C4F9I in CH2Cl2 is cooled to -40 to -50°C with stirring in Ar, then a soln. of P(NEt2)3 in CH2Cl2 is added, stirred for 1-1.5 h, warmed to room temp. within 2-3 h; extd. (pentane), the extract is washed, dried, distd.;	87%

Cp*Rh(ethylene)2 (32613-78-8) + perfluoro-tert-butyl iodide (4459-18-1) + trimethylphosphane (594-09-2) → [(η5-pentamethylcyclopentadienyl)RhI(CH2CH2C(CF3)3)(trimethylphosphine)] (1349737-26-3)

Conditions	Yield
In toluene byproducts: CH2CH2; High Pressure; (N2, Schlenk technique); heating mixt. of rhodium compd. and phosphine deriv. in toluene at 120°C for 24 h, cooling to room temp., addn. of perfluoroisopropyl iodide, stirring for 40 min; evapn. in vac., extn. (n-pentane), evapn., elem. anal.;	80%
With CH3O(2)H In (2)H8-toluene byproducts: (CF3)2CF(2)H; High Pressure; (N2, Schlenk technique); heating toluene-d8 soln. of rhodium compd. and phosphine deriv. at 120°c for 24 h, treatment with tert-perfluorobutyl iodide and methanol-d1;

perfluoro-tert-butyl iodide (4459-18-1) + C12H20I2Ir + triphenylphosphine (603-35-0) → [Ir(η5-Cp*)(CH2CH2-t-C4F9)I(PPh3)]

Conditions	Yield
Stage #1: perfluoro-tert-butyl iodide; C12H20I2Ir In pentane at 20℃; for 18h; Inert atmosphere; Schlenk technique; Stage #2: triphenylphosphine In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; Schlenk technique;	77.6%

perfluoro-tert-butyl iodide (4459-18-1) + C12H20I2Ir → [Ir(η5-Cp*)(CH2CH2-t-C4F9)(μ-I)]2

Conditions	Yield
In pentane at 20℃; for 22h; Inert atmosphere; Schlenk technique;	64.2%

perfluoro-tert-butyl iodide (4459-18-1) + C12H20I2Rh + triphenylphosphine (603-35-0) → [Rh(η5-Cp*)(CH2CH2-t-C4F9)I(PPh3)]

Conditions	Yield
Stage #1: C12H20I2Rh; triphenylphosphine In toluene at 120℃; for 4h; Inert atmosphere; Schlenk technique; Stage #2: perfluoro-tert-butyl iodide In toluene at 20℃; for 1.5h; Inert atmosphere; Schlenk technique;	60.3%

[W(η-C5H5)2(η-ethylene)] + perfluoro-tert-butyl iodide (4459-18-1) → W(C5H5)2[CH2CH2C(CF3)3]I (191788-66-6)

Conditions	Yield
In tetrahydrofuran; benzene under N2; adding soln. of IC(CF3)3 in benzene to THF soln. of WCp2(C2H4), stirring for 15 min; removal of solvent in vacuo, dissolving residue in CH2Cl2, filtration, redn. of solvent vol., addn. of hexane; elem. anal.;	60%

Mo(η5-cyclopentadienyl)2(η2-C2H4) + perfluoro-tert-butyl iodide (4459-18-1) → Mo(C5H5)2[CH2CH2C(CF3)3]I (191788-62-2)

Conditions	Yield
In tetrahydrofuran; benzene under N2; adding soln. of IC(CF3)3 in benzene to THF soln. of MoCp2(C2H4), stirring for 0.5 h; removal of solvent, recrystn. from CH2Cl2/hexane; elem. anal.;	54%

Cp*Rh(ethylene)2 (32613-78-8) + perfluoro-tert-butyl iodide (4459-18-1) + trimethylphosphane (594-09-2) → [(η5-pentamethylcyclopentadienyl)RhI2(trimethylphosphine)] + [(η5-pentamethylcyclopentadienyl)RhI(CH2CH2C(CF3)3)(trimethylphosphine)] (1349737-26-3)

Conditions	Yield
In toluene byproducts: CH2CH2; (N2, Schlenk technique); addn. of tert-perfluorobutyl iodide to rhodium compd. in pentane, stirring for 20 h at room temp., evapn., dissolving in toluene, addn. of phosphine deriv., stirring for 3 h; evapn., extn. (n-pentane), evapn., chromy. (silica gel, diethyl ether/n-hexane (1:1)), evapn., elem. anal.;	A n/a B 52%

perfluoro-tert-butyl iodide (4459-18-1) + N-{2-(1,3-dioxoisoindolin-2-yl)acryloyl}-(1R,2S,4S)-bornane-10,2-sultam (1332724-61-4) → N-{(R)-2-(1,3-dioxoisoindolin-2-yl)-3-perfluoro-tert-butylpropanoyl}-(1R,2S,4S)-bornane-10,2-sultam (1430817-55-2)

Conditions	Yield
With tris-(trimethylsilyl)silane; sodium thiosulfate In dichloromethane; water at 20℃; UV-irradiation; Sealed tube; stereoselective reaction;	51%

perfluoro-tert-butyl iodide (4459-18-1) + (trimethylsilyl)diphenylphosphine (17154-34-6) → Ph2P(t-C4F9) (1202071-52-0)

Conditions	Yield
In hexane at -30 - 20℃; Inert atmosphere;	30%
In chloroform-d1 at 20℃; for 0.5h; Inert atmosphere;	30 %Spectr.

diazomethane (186581-53-3, 908094-01-9) + perfluoro-tert-butyl iodide (4459-18-1) → 1,1,1-trifluoro-4-iodo-2,2-bis-trifluoromethyl-butane (14115-45-8)

Conditions	Yield
In diethyl ether

ethene (74-85-1) + perfluoro-tert-butyl iodide (4459-18-1) → 1,1,1-trifluoro-4-iodo-2,2-bis-trifluoromethyl-butane (14115-45-8)

Conditions	Yield
With dicyclohexyl peroxydicarbonate

perfluoro-tert-butyl iodide (4459-18-1) → 1,1,1,3,3,3-hexafluoro-2-trifluoromethyl-propane (382-24-1)

Conditions	Yield
With diiron nonacarbonyl In hexane

1,4-dioxane-2,3-dione (3524-70-7) + perfluoro-tert-butyl iodide (4459-18-1) → 3-perfluoro-tert-butyl-3-hydroxy-1,4-dioxan-2-one (129282-33-3)

Conditions	Yield
With magnesium; ethylene dibromide 1.) ether, -25 deg C, 1.5 h, 2.) from -12 deg C to RT; Yield given. Multistep reaction;

perfluoro-tert-butyl iodide (4459-18-1) + fullerene-C60 (99685-96-8, 161105-99-3, 161106-00-9, 111138-12-6, 133318-63-5, 134053-11-5, 134931-35-4, 134931-36-5, 139703-76-7, 145633-27-8, 175414-73-0, 175414-74-1, 175414-75-2, 175519-12-7, 175519-13-8, 175519-14-9, 175519-15-0, 136376-46-0, 144906-37-6, 144906-38-7, 151767-00-9, 152882-97-8, 152882-98-9, 152882-99-0, 153062-34-1, 154171-74-1, 154171-75-2, 154333-99-0, 154334-00-6, 154397-63-4, 154460-59-0, 199456-56-9, 108739-25-9, 120329-57-9, 120329-58-0) → perfluoro-tert-butyl-C60

Conditions	Yield
In various solvent(s) at -48.1℃;

perfluoro-tert-butyl iodide (4459-18-1) + tris(dimethylamino)sulfonium1,1,1,3,3,3-hexafluoro-2-(trifluoromethyl)-2-propanide (100645-89-4) → C8F18I(1-)*C6H18N3S(1+)

Conditions	Yield
In tetrahydrofuran for 0.5h;	720 mg

perfluoro-tert-butyl iodide (4459-18-1) → perfluoroisobutylene (382-21-8)

Conditions	Yield
at 426.9 - 626.9℃;

perfluoro-tert-butyl iodide (4459-18-1) + oxalic acid diethyl ester (95-92-1) → ethyl 4,4,4-trifluoro-3,3-bis(trifluoromethyl)-2-oxobutyrate (129301-53-7)

Conditions	Yield
With magnesium; ethylene dibromide 1.) ether, -25 deg C, 1.5 h, 2.) from -12 deg C to RT; Yield given. Multistep reaction;

perfluoro-tert-butyl iodide (4459-18-1) + acetone (67-64-1) → 4,4,4-trifluoro-2-methyl-3,3-bis(trifluoromethyl)-2-butanol (129282-28-6)

Conditions	Yield
With magnesium; ethylene dibromide 1.) ether, -25 deg C, 1.5 h, 2.) from -12 deg C to RT; Yield given. Multistep reaction;

Upstream product

• 354-93-8 1,1,1,3,3,3-hexafluoro-2-nitroso-2-trifluoromethyl-propane 
• 116-15-4 perfluoropropylene 
• 2314-97-8 iodotrifluoromethane 
• 754-43-8 2-bromo-1,1,1,3,3,3-hexafluoro-2-trifluoromethyl-propane 
• 122432-75-1 1,1,1,2,3,5,5,5-Octafluoro-2,3,4,4-tetrakis-trifluoromethyl-pentane 
• 333-27-7 methyl trifluoromethanesulfonate 
• 3024-50-8 3,3-bis(trifluoromethyl)diazirine 
• 369-58-4 benzenediazonium hexafluorophosphate 
• 27746-96-9 2-chlorocarbonyloxy-1,1,1,3,3,3-hexafluoro-2-trifluoromethyl-propane 
• 382-21-8 perfluoroisobutylene 

Downstream Products

• 14115-45-8 β-(Perfluor-tert-butyl)-ethyl-jodid 
• 382-21-8 perfluoroisobutylene 
• 382-24-1 1,1,1,3,3,3-hexafluoro-2-trifluoromethyl-propane 
• 1202071-52-0 Ph₂P(t-C₄F₉) 

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