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Undecafluorohexanoic acid

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Name

Undecafluorohexanoic acid

EINECS 206-196-6
CAS No. 307-24-4 Density 1.722 g/cm3
PSA 37.30000 LogP 3.17450
Solubility N/A Melting Point 14 °C
Formula C6HF11O2 Boiling Point 143 °C at 760 mmHg
Molecular Weight 314.055 Flash Point 40.3 °C
Transport Information UN 3265 8/PG 2 Appearance colourless liquid
Safety 26-36/37/39-45 Risk Codes 34-37
Molecular Structure Molecular Structure of 307-24-4 (PERFLUOROHEXANOIC ACID) Hazard Symbols CorrosiveC; ToxicT
Synonyms

Hexanoicacid, undecafluoro- (6CI,7CI,8CI,9CI);NSC 5213;Perfluoro-1-pentanecarboxylicacid;Perfluorohexanoic acid;Undecafluorocaproic acid;Undecafluorohexanoicacid;

Article Data 25

Undecafluorohexanoic acid 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%

Undecafluorohexanoic acid 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

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