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307-24-4

Basic Information
CAS No.: 307-24-4
Name: Undecafluorohexanoic acid
Molecular Structure:
Molecular Structure of 307-24-4 (Undecafluorohexanoic acid)
Formula: C6HF11O2
Molecular Weight: 314.05
Synonyms: Hexanoicacid, undecafluoro- (6CI,7CI,8CI,9CI);NSC 5213;Perfluoro-1-pentanecarboxylicacid;Perfluorohexanoic acid;Undecafluorocaproic acid;Undecafluorohexanoicacid;
EINECS: 206-196-6
Density: 1.722 g/cm3
Melting Point: 14 °C
Boiling Point: 143 °C at 760 mmHg
Flash Point: 40.3 °C
Solubility:
Appearance: colourless liquid
Hazard Symbols: CorrosiveC; ToxicT
Risk Codes: 34-37
Safety: 26-36/37/39-45
Transport Information: UN 3265 8/PG 2
PSA: 37.30000
LogP: 3.17450
Synthetic route
355-43-1

n-perfluorohexyl iodide

A

307-24-4

undecafluorohexanoic acid

B

perfluorohexyl sulfinic acid

Conditions
ConditionsYield
With sulfur dioxide In water; N,N-dimethyl-formamide at 20℃; Product distribution; effect of water content of the solvent, role of allyl alcohol, Faradic yield;A 3%
B 95%
2923-26-4

sodium undecafluorohexanoate

307-24-4

undecafluorohexanoic acid

Conditions
ConditionsYield
With sulfuric acid at 120℃;94%
65500-50-7

perfluoro-2-octene

307-24-4

undecafluorohexanoic acid

Conditions
ConditionsYield
With bis(acetylacetonate)oxovanadium; dihydrogen peroxide92%
With bis(acetylacetonate)oxovanadium; dihydrogen peroxide Product distribution; various reaction conditions;92%
355-43-1

n-perfluorohexyl iodide

106-95-6

allyl bromide

A

355-37-3

1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorohexane

B

307-24-4

undecafluorohexanoic acid

C

80793-18-6

3-(perfluorohexyl)prop-1-ene

Conditions
ConditionsYield
With potassium hydroxide; 2,2'-azobis(isobutyronitrile) at 80℃; for 56h; Substitution;A n/a
B n/a
C 88%
355-43-1

n-perfluorohexyl iodide

307-24-4

undecafluorohexanoic acid

Conditions
ConditionsYield
With disodium hydrogenphosphate; potassium dihydrogenphosphate; lipoxygenase; oct-2-yne at 25 - 30℃;84%
With ammonium peroxydisulfate; sodium formate In N,N-dimethyl-formamide at 55℃; for 12h;83.9%
Multi-step reaction with 2 steps
1: 79 percent / sodium formaldehyde sulfoxylate, NaHCO3 / dimethylformamide; H2O / 17 h / 80 - 85 °C
2: 94 percent / concentrated sulfuric acid / 120 °C
View Scheme
31143-13-2

(E)-perfluorooct-2-ene

307-24-4

undecafluorohexanoic acid

Conditions
ConditionsYield
With hydrogen; oxygen; lead(II) oxide; ozone; calcium carbonate; palladium In 1,1,2-Trichloro-1,2,2-trifluoroethane 1.) 5 deg C to 10 deg C, 2 h, 2.) 20 deg C;80%
556-56-9

allyl iodid

355-43-1

n-perfluorohexyl iodide

A

355-37-3

1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorohexane

B

307-24-4

undecafluorohexanoic acid

C

80793-18-6

3-(perfluorohexyl)prop-1-ene

Conditions
ConditionsYield
With potassium hydroxide; 2,2'-azobis(isobutyronitrile) at 80℃; for 56h; Substitution;A n/a
B n/a
C 77%
102061-83-6

sodium 1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane-1-sulfinate

307-24-4

undecafluorohexanoic acid

Conditions
ConditionsYield
With 2,2'-azobis(2-methylpropionamidine) dihydrochloride; water at 55℃; for 6.5h;75%
102061-83-6

sodium 1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane-1-sulfinate

762-72-1

allyl-trimethyl-silane

A

307-24-4

undecafluorohexanoic acid

B

132673-95-1

4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-1-(trimethylsilyl)nonane

Conditions
ConditionsYield
With ammonium peroxydisulfate In N,N-dimethyl-formamide at 40℃; for 4h;A 13%
B 74%
102061-83-6

sodium 1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane-1-sulfinate

106-95-6

allyl bromide

A

307-24-4

undecafluorohexanoic acid

B

80793-18-6

3-(perfluorohexyl)prop-1-ene

Conditions
ConditionsYield
With ammonium peroxydisulfate In N,N-dimethyl-formamide at 40℃; for 4h;A 12%
B 67%
673-32-5

1-Phenylprop-1-yne

355-43-1

n-perfluorohexyl iodide

A

307-24-4

undecafluorohexanoic acid

B

113999-57-8

1-phenyl-2-(perfluorohexyl)propene

Conditions
ConditionsYield
With disodium hydrogenphosphate; potassium dihydrogenphosphate; catalase at 25 - 30℃; for 504h;A 66%
B 28%
355-43-1

n-perfluorohexyl iodide

536-74-3

phenylacetylene

A

307-24-4

undecafluorohexanoic acid

B

55009-92-2, 113999-56-7

(E)-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-octen-1-yl)benzene

Conditions
ConditionsYield
With disodium hydrogenphosphate; potassium dihydrogenphosphate; urease at 25 - 30℃; for 264h;A 2%
B 66%
591-87-7

Allyl acetate

102061-83-6

sodium 1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane-1-sulfinate

A

307-24-4

undecafluorohexanoic acid

B

83311-03-9

4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononyl acetate

Conditions
ConditionsYield
With ammonium peroxydisulfate In N,N-dimethyl-formamide at 40℃; for 4h;A 24%
B 63%
629-05-0

n-octyne

355-43-1

n-perfluorohexyl iodide

A

307-24-4

undecafluorohexanoic acid

B

113999-58-9

(E)-1-(perfluorohexyl)-1-octene

Conditions
ConditionsYield
With disodium hydrogenphosphate; potassium dihydrogenphosphate; catalase at 25 - 30℃; for 312h;A 14%
B 61%
102061-83-6

sodium 1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane-1-sulfinate

106-96-7

propargyl bromide

A

307-24-4

undecafluorohexanoic acid

B

130716-18-6

4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-1,2-nonadiene

Conditions
ConditionsYield
With ammonium peroxydisulfate In N,N-dimethyl-formamide at 40℃; for 4h;A 17%
B 54%
2809-67-8

oct-2-yne

355-43-1

n-perfluorohexyl iodide

A

307-24-4

undecafluorohexanoic acid

B

113999-59-0

2-(perfluorohexyl)-2-octene

Conditions
ConditionsYield
With disodium hydrogenphosphate; potassium dihydrogenphosphate; urease at 25 - 30℃; for 720h;A 53%
B 18%
764-93-2

1-decyne

355-43-1

n-perfluorohexyl iodide

A

307-24-4

undecafluorohexanoic acid

B

120464-27-9

1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-7-hexadecene

Conditions
ConditionsYield
With disodium hydrogenphosphate; potassium dihydrogenphosphate; urease at 25 - 30℃;A 39%
B 42%
2051-49-2

n-hexanoic anhydride

307-24-4

undecafluorohexanoic acid

Conditions
ConditionsYield
With hydrogen fluoride anschliessend Behandeln mit Wasser;
335-53-5

undecafluorohexanoyl chloride

506-64-9

silver(I) cyanide

A

307-24-4

undecafluorohexanoic acid

B

595-06-2

hydroxy-undecafluoropentyl-malonic acid diamide

Conditions
ConditionsYield
Behandeln des als ein Dimeres des Undecafluor-2-oxo-hexannitrils angesehenen Reaktionsprodukts mit konz.wss.Salzsaeure;
142-62-1

hexanoic acid

307-24-4

undecafluorohexanoic acid

Conditions
ConditionsYield
anodische Fluorierung;
67097-65-8

perfluorohexyl fluorosulfate

307-24-4

undecafluorohexanoic acid

Conditions
ConditionsYield
(hydrolysis);

(E)-1,1,1,2,2,3,3,4,5,6,6,7,7,8,8,9,9,9-Octadecafluoro-non-4-ene

A

375-22-4

heptafluorobutyric Acid

B

422-64-0

pentafluoropropionic acid

C

2706-90-3

Perfluoropentanoic acid

D

307-24-4

undecafluorohexanoic acid

E

375-85-9

perfluoroheptanoic acid

F

76-05-1

trifluoroacetic acid

Conditions
ConditionsYield
With ruthenium(IV) oxide; sodium hypochlorite; ruthenium tetroxide In 1,1,2-Trichloro-1,2,2-trifluoroethane for 1h; Product distribution; other times, other reagents, other times, further products;
53826-12-3

3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctanoic acid

68-12-2, 33513-42-7

N,N-dimethyl-formamide

A

307-24-4

undecafluorohexanoic acid

B

45084-94-4

2-Dimethylamino-methylen-1,3-bis-dimethyl-immonio-propan

C

38571-88-9, 52950-91-1, 80077-94-7

Dimethyl-<3-dimethylamino-prop-2t-en-yliden>ammonium

Conditions
ConditionsYield
With trichlorophosphate at 60 - 85℃; Vilsmeier reaction;
335-67-1

Perfluorooctanoic acid

A

375-22-4

heptafluorobutyric Acid

B

2706-90-3

Perfluoropentanoic acid

C

307-24-4

undecafluorohexanoic acid

D

375-85-9

perfluoroheptanoic acid

Conditions
ConditionsYield
With sodium sulfate; Ni-Cu photocatalyst; titanium(IV) oxide In water for 2h; Kinetics; UV-irradiation; Electrochemical reaction;
With sulfuric acid; LaNi0.8Sr0.2O3; iron(II) sulfate; sodium sulfate In water for 2.5h; pH=5; Catalytic behavior; Kinetics; Mechanism; Reagent/catalyst; pH-value; Electrolysis;
335-56-8

1-bromo-1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexane

307-24-4

undecafluorohexanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 84 percent / sodium formaldehyde sulfoxylate, NaHCO3 / dimethylformamide; H2O / 20 h / 80 - 85 °C
2: 94 percent / concentrated sulfuric acid / 120 °C
View Scheme
355-37-3

1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorohexane

307-24-4

undecafluorohexanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: KSO3F / fluorosulfonic acid / (electrolysis)
2: (hydrolysis)
View Scheme

perfluorohexanoyl cyanide dimer

307-24-4

undecafluorohexanoic acid

Conditions
ConditionsYield
hydrolysis;
375-85-9

perfluoroheptanoic acid

A

307-24-4

undecafluorohexanoic acid

B

124-38-9

carbon dioxide

Conditions
ConditionsYield
With dipotassium peroxodisulfate; water at 60℃; under 4875.49 Torr; for 3h; Kinetics; Temperature; Reagent/catalyst;
335-67-1

Perfluorooctanoic acid

A

307-24-4

undecafluorohexanoic acid

B

375-85-9

perfluoroheptanoic acid

Conditions
ConditionsYield
for 4h; Electrolysis;
335-67-1

Perfluorooctanoic acid

A

375-61-1

1H-perfluoropentane

B

355-37-3

1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorohexane

C

2706-90-3

Perfluoropentanoic acid

D

375-83-7

perfluoro-1H-heptane

E

307-24-4

undecafluorohexanoic acid

F

375-85-9

perfluoroheptanoic acid

Conditions
ConditionsYield
With water at 23 - 51℃; for 0.025h; Microwave irradiation; Sonication;
307-24-4

undecafluorohexanoic acid

111-40-0

1,5-diamino-3-azapentane

N-aminoethyl(perfluoropentyl)formylamine

Conditions
ConditionsYield
at 30 - 132℃; for 0.5h;96.7%
307-24-4

undecafluorohexanoic acid

67-63-0

isopropyl alcohol

isopropyl 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexanoate

Conditions
ConditionsYield
for 3h; Reflux;90%
307-24-4

undecafluorohexanoic acid

355-41-9

perfluoro-n-hexyl chloride

Conditions
ConditionsYield
With trichlorophosphate at 5 - 110℃;90%
307-24-4

undecafluorohexanoic acid

5001-18-3

1,3-adamantandiol

1005454-12-5

3-hydroxy-1-adamantyl perfluorohexanoate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 4h; Heating / reflux;88%
307-24-4

undecafluorohexanoic acid

75-16-1

methylmagnesium bromide

2708-07-8

3,3,4,4,5,5,6,6,7,7,7-undecafluoroheptan-2-one

Conditions
ConditionsYield
Stage #1: undecafluorohexanoic acid; methylmagnesium bromide In diethyl ether at -8 - 20℃; for 2h; Inert atmosphere;
Stage #2: With hydrogenchloride In water
64%
307-24-4

undecafluorohexanoic acid

3375-31-3

palladium diacetate

palladium perfluorohexanoate

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one at 60℃; for 24h; Inert atmosphere;61%
75-91-2

tert.-butylhydroperoxide

307-24-4

undecafluorohexanoic acid

3375-31-3

palladium diacetate

palladium (II) tert-butyl peroxide perfluorohexanoate

Conditions
ConditionsYield
In neat (no solvent) byproducts: C5F11CO2H; mixed with stirring at room temp.; filtered, washed (n-pentane), dried (vac.), elem. anal.;60%

palladium (II) nitrate

307-24-4

undecafluorohexanoic acid

palladium perfluorohexanoate

Conditions
ConditionsYield
at 80℃; for 12h; Inert atmosphere;57%
861675-46-9

3-methanesulfonyloxy-1-adamantyl methacrylate

307-24-4

undecafluorohexanoic acid

1005454-11-4

3-[(perfluoropentyl)carbonyloxy]-1-adamantyl methacrylate

Conditions
ConditionsYield
With sodium dihydrogenphosphate; 4-methoxy-phenol In 4-butanolide at 120℃; for 6h; Product distribution / selectivity;51.5%
66-71-7

1,10-Phenanthroline

307-24-4

undecafluorohexanoic acid

35342-67-7, 35342-68-8

copper (I) tert-butoxide

[(1,10-phenanthroline)2Cu][n-C5F11CO2]

Conditions
ConditionsYield
Stage #1: 1,10-Phenanthroline; copper (I) tert-butoxide In tetrahydrofuran at 20℃; for 0.0833333h;
Stage #2: undecafluorohexanoic acid In tetrahydrofuran at 20℃; for 0.333333h;
51%
307-24-4

undecafluorohexanoic acid

palladium dichloride

palladium perfluorohexanoate

Conditions
ConditionsYield
at 100℃; for 2h; Inert atmosphere;46%
307-24-4

undecafluorohexanoic acid

palladium(II) hydroxide

palladium perfluorohexanoate

Conditions
ConditionsYield
at 80℃; for 12h; Inert atmosphere;42%
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Specification

The Undecafluorohexanoic acid, with the CAS registry number 307-24-4 and EINECS registry number 206-196-6, has the systematic name of undecafluorohexanoic acid. It is a kind of colourless liquid which is incompatible with oxidizing agents. And the molecular formula of the chemical is C6HF11O2.

The characteristics of Undecafluorohexanoic acid are as followings: (1)ACD/LogP: 5.97; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 2.23; (4)ACD/LogD (pH 7.4): 2.22; (5)ACD/BCF (pH 5.5): 3.71; (6)ACD/BCF (pH 7.4): 3.61; (7)ACD/KOC (pH 5.5): 7.71; (8)ACD/KOC (pH 7.4): 7.5; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 26.3 Å2; (13)Index of Refraction: 1.289; (14)Molar Refractivity: 33.04 cm3; (15)Molar Volume: 182.3 cm3; (16)Polarizability: 13.09×10-24cm3; (17)Surface Tension: 17.4 dyne/cm; (18)Density: 1.722 g/cm3; (19)Flash Point: 40.3 °C; (20)Enthalpy of Vaporization: 41.93 kJ/mol; (21)Boiling Point: 143 °C at 760 mmHg; (22)Vapour Pressure: 3.09 mmHg at 25°C.  

Preparation of Undecafluorohexanoic acid: This chemical can be prepared by hexadecafluoro-oct-2-ene. And the yield is about 92%.      

You should be cautious while dealing with this chemical. It irritates to respiratory system, and may cause burns. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection, and if in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice; In case of accident or if you feel unwell, seek medical advice immediately (show label where possible). 

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: FC(F)(C(F)(F)C(=O)O)C(F)(F)C(F)(F)C(F)(F)F
(2)InChI: InChI=1/C6HF11O2/c7-2(8,1(18)19)3(9,10)4(11,12)5(13,14)6(15,16)17/h(H,18,19)
(3)InChIKey: PXUULQAPEKKVAH-UHFFFAOYAH