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375-22-4

Basic Information
CAS No.: 375-22-4
Name: Heptafluorobutyric acid
Article Data: 64
Molecular Structure:
Molecular Structure of 375-22-4 (Heptafluorobutyric acid)
Formula: C4HF7O2
Molecular Weight: 214.04
Synonyms: Butanoicacid, heptafluoro- (9CI);Butyric acid, heptafluoro- (6CI,8CI);Heptafluorobutanoic acid;Perfluorobutanoic acid;Perfluorobutyric acid;Perfluoropropanecarboxylic acid;
EINECS: 206-786-3
Density: 1.679 g/cm3
Melting Point: -17.5 °C
Boiling Point: 120.2 °C at 760 mmHg
Flash Point: 18 °C
Solubility: miscible
Appearance: Clear colorless to faintly yellow liquid
Hazard Symbols: CorrosiveC
Risk Codes: 35
Safety: 26-36/37/39-45
Transport Information: UN 3265 8/PG 2
PSA: 37.30000
LogP: 1.90390
Synthetic route
14154-45-1

6,6,6-Trichlor-perfluor-capronsaeure-chlorid-(1,1-dichlor-heptafluor-butylimid)

A

375-22-4

heptafluorobutyric Acid

B

6,6,6-Trichloro-2,2,3,3,4,4,5,5-octafluoro-hexanoic acid

Conditions
ConditionsYield
With H2SO4 concd. H2SO4;A n/a
B 95%
2218-54-4

sodium heptafluorobutyrate

375-22-4

heptafluorobutyric Acid

Conditions
ConditionsYield
With sulfuric acid at 120℃;92%
868-85-9

Dimethyl phosphite

336-59-4

heptafluorobutyric anhydride

A

375-22-4

heptafluorobutyric Acid

B

[1-(Dimethoxy-phosphoryloxy)-3,3,4,4,5,5,5-heptafluoro-1-heptafluoropropyl-2-oxo-pentyl]-phosphonic acid dimethyl ester

Conditions
ConditionsYield
Ambient temperature;A n/a
B 85%
423-39-2

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane

375-22-4

heptafluorobutyric Acid

Conditions
ConditionsYield
With disodium hydrogenphosphate; potassium dihydrogenphosphate; lipoxygenase; oct-2-yne at 25 - 30℃;83%
With oxygen In N,N-dimethyl-formamide Kinetics; Mechanism; galvanostatic electrolysis; also with perfluoro-octyliodide;
With oxygen In N,N-dimethyl-formamide Rate constant; Mechanism; electrolysis at a carbon cathode;
1606143-50-3

nonafluoro-n-butanesulfenic acid

375-22-4

heptafluorobutyric Acid

Conditions
ConditionsYield
In water; toluene at 20℃; for 2h;75%
With water In toluene at 20℃; for 2h;75%
102061-82-5

sodium 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfinate

106-95-6

allyl bromide

A

375-22-4

heptafluorobutyric Acid

B

129846-67-9

4,4,5,5,6,6,7,7,7-nonafluoro-1-heptene

Conditions
ConditionsYield
With ammonium peroxydisulfate In N,N-dimethyl-formamide at 40℃; for 4h;A 10%
B 72%
762-04-9

phosphonic acid diethyl ester

336-59-4

heptafluorobutyric anhydride

A

375-22-4

heptafluorobutyric Acid

B

1-(diethoxyphosphinyl)heptafluoro-1-(heptafluorobutyryl)butyl diethyl phosphate

Conditions
ConditionsYield
Ambient temperature;A n/a
B 70%
52-68-6

trichlorfon

336-59-4

heptafluorobutyric anhydride

A

375-22-4

heptafluorobutyric Acid

B

169469-22-1

C8H7Cl3F7O5P

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 40℃; for 2h;A n/a
B 68%
2809-67-8

oct-2-yne

423-39-2

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane

A

375-22-4

heptafluorobutyric Acid

B

113999-55-6

2-(perfluorobutyl)-2-octene

Conditions
ConditionsYield
With disodium hydrogenphosphate; potassium dihydrogenphosphate; catalase at 25 - 30℃; for 720h;A 67%
B 10%
124-38-9

carbon dioxide

423-25-6

(heptafluoro n-propyl) magnesiumiodide

375-22-4

heptafluorobutyric Acid

Conditions
ConditionsYield
In diethyl ether introduction of CO2 during formation of the grignard compound at -20°C;;65%
In diethyl ether introduction of CO2 during formation of the grignard compound at -20°C;;65%
In diethyl ether introduction of CO2 after formation of the grignard compound at -20°C;;59%
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The IUPAC name of this chemical is 2,2,3,3,4,4,4-heptafluorobutanoic acid. With the CAS registry number 375-22-4 and EINECS registry number 206-786-3, it is also named as Heptafluorobutyric acid. In addition, the molecular formula is C4HF7O2 and the molecular weight is 214.04. What's more, it is a kind of clear colorless to faintly yellow liquid and belongs to the classes of Pharmaceutical Intermediates; Analytical Chemistry; Ion-Pair Reagents for HPLC; LC/MS Ion-Pair Reagents for Basic Samples; Acylation (GC Derivatizing Reagents); GC Derivatizing Reagents.

Physical properties about this chemical are: (1)ACD/LogP: 3.93; (2)ACD/LogD (pH 5.5): 0.2; (3)ACD/LogD (pH 7.4): 0.18; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 2; (11)Polar Surface Area: 26.3 Å2; (12)Index of Refraction: 1.291; (13)Molar Refractivity: 23.18 cm3; (14)Molar Volume: 127.4 cm3; (15)Polarizability: 9.19 ×10-24cm3; (16)Surface Tension: 18.6 dyne/cm; (17)Density: 1.679 g/cm3; (18)Flash Point: 18 °C; (19)Enthalpy of Vaporization: 39.54 kJ/mol; (20)Boiling Point: 120.2 °C at 760 mmHg; (21)Vapour Pressure: 9.8 mmHg at 25°C.

Preparation of Heptafluorobutyric acid: it can be prepared by 1,1,1,2,2,3,3,4,4-nonafluoro-4-iodo-butane. This reaction will need reagents lipoxygenase, 1/30 M aq. Na2HPO4/KH2PO4 and 2-octyne. The yield is about 83% at reaction temperature of 25-30 °C.

Heptafluorobutyric acid can be prepared by 1,1,1,2,2,3,3,4,4-nonafluoro-4-iodo-butane

Uses of Heptafluorobutyric acid: It can be used an ion pair reagent for reverse-phase HPLC. And it is used in the sequencing, synthesis, and solubilizing of proteins and peptides. In addition, it can be used to get heptafluorobutyryl fluoride. This reaction will need reagents FAR and NaF. The reaction time is 15 minutes at reaction temperature of -78 °C. The yield is about 84%.

Heptafluorobutyric acid can be used to get heptafluorobutyryl fluoride

When you are using this chemical, please be cautious about it as the following:
This chemical can cause severe burns. During using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. And in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.).

You can still convert the following datas into molecular structure:
(1)SMILES: FC(F)(C(F)(F)C(=O)O)C(F)(F)F
(2)InChI: InChI=1/C4HF7O2/c5-2(6,1(12)13)3(7,8)4(9,10)11/h(H,12,13)
(3)InChIKey: YPJUNDFVDDCYIH-UHFFFAOYAI

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 68uL/kg (0.068mL/kg)   "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 2, Pg. 56, 1950.
rabbit LD intravenous > 10uL/kg (0.01mL/kg)   "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 2, Pg. 56, 1950.