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Cyclobutanecarboxylic acid

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Name

Cyclobutanecarboxylic acid

EINECS 223-072-7
CAS No. 3721-95-7 Density 1.202 g/cm3
PSA 37.30000 LogP 0.87110
Solubility Slightly soluble in water. Melting Point -7.5 ºC(lit.)
Formula C5H8O2 Boiling Point 195.3 ºC at 760 mmHg
Molecular Weight 100.117 Flash Point 85.4 ºC
Transport Information UN 3265 Appearance Clear colourless to slightly amber liquid
Safety 23-24/25-36-26 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 3721-95-7 (Cyclobutanecarboxylic acid) Hazard Symbols IrritantXi
Synonyms

Cyclobutane-1-carboxylicacid;NSC 4535;Cyclobutance carboxylic acid;

Article Data 40

Cyclobutanecarboxylic acid Synthetic route

74-85-1

ethene

79-10-7

acrylic acid

3721-95-7

Cyclobutanecarboxylic acid

Conditions
ConditionsYield
In dichloromethane at -30 - -20℃; for 3h; Temperature; UV-irradiation;97%
In cyclohexane at 10 - 16℃; Solvent; Diels-Alder Cycloaddition;95%
1427519-99-0

(3S,4S)-4-(N-allyl-4-methylphenylsulfonamido)-6-methyl-1,3-diphenylhept-1-yn-3-yl cyclobutanecarboxylate

A

3721-95-7

Cyclobutanecarboxylic acid

B

1427520-27-1

((3R,6S)-6-isobutyl-3-methyl-5-phenyl-1-tosyl-1,2,3,6-tetrahydropyridin-4-yl)(phenyl)methanone

Conditions
ConditionsYield
With Echavarren's catalyst; water In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere; stereoselective reaction;A n/a
B 96%
4415-82-1

cyclobutanemethanol

3721-95-7

Cyclobutanecarboxylic acid

Conditions
ConditionsYield
With C15H27Br2CoN3; potassium hydroxide In toluene at 140℃; for 16h; Cannizzaro Reaction; Inert atmosphere; Sealed tube;73%
With lead(IV) acetate; calcium carbonate In benzene
124-38-9

carbon dioxide

4399-47-7

Bromocyclobutane

584-08-7

potassium carbonate

3721-95-7

Cyclobutanecarboxylic acid

Conditions
ConditionsYield
With nickel(II) bromide dimethoxyethane; 2.9-dimethyl-1,10-phenanthroline; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; C60H36N2 In N,N-dimethyl-formamide at 20℃; for 24h; Molecular sieve; Irradiation;41%
120-92-3

cyclopentanone

3721-95-7

Cyclobutanecarboxylic acid

Conditions
ConditionsYield
With poly(bisanthracenyl) diselenide; dihydrogen peroxide In tert-butyl alcohol for 5h; Heating;15%
With selenium(IV) oxide; dihydrogen peroxide; tert-butyl alcohol
With dihydrogen peroxide In tert-butyl alcohol
2987-17-9

cyclobutylaldehyde

3721-95-7

Cyclobutanecarboxylic acid

Conditions
ConditionsYield
With silver(l) oxide
With sodium hydroxide at 80℃; for 42h;
4426-11-3

cyclobutanecarbonitrile

3721-95-7

Cyclobutanecarboxylic acid

Conditions
ConditionsYield
With sodium hydroxide
durch Verseifung;
beim Verseifen;
5445-51-2

cyclobutane-1,1'-dicarboxylic acid

3721-95-7

Cyclobutanecarboxylic acid

Conditions
ConditionsYield
at 210 - 220℃;
98431-45-9

ethyl 3-iodocyclobutane-1-carboxylate

3721-95-7

Cyclobutanecarboxylic acid

Conditions
ConditionsYield
With sodium amalgam; ethanol
124-38-9

carbon dioxide

53213-06-2, 99503-19-2

cyclobutyltriphenylphosphonium ylide

3721-95-7

Cyclobutanecarboxylic acid

Conditions
ConditionsYield
(i) , (ii) (alkaline hydrolysis); Multistep reaction;

Cyclobutanecarboxylic acid Specification

The Cyclobutanecarboxylic acid, with the CAS registry number 3721-95-7, is also known as Cyclo-butyl formic acid. It belongs to the product categories of Acids and Derivatives; Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Cyclobutanes & Cyclobutenes; Simple 4-Membered Ring Compounds; Cycloalkanes; C1 to C5; Carbonyl Compounds; Carboxylic Acids. Its EINECS registry number is 223-072-7. This chemical's molecular formula is C5H8O2 and molecular weight is 100.12. What's more, its IUPAC name is the same with its product name. This chemical can be prepared by Cyclobutane-1, 1-dicarboxylic acid. This reaction needs the temperature of 160 °C. The yield is 86-91 %.

Physical properties about Cyclobutanecarboxylic acid are: (1)ACD/LogP: 0.65; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.14; (4)ACD/LogD (pH 7.4): -1.93; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 8.84; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 26.3 Å2; (13)Index of Refraction: 1.501; (14)Molar Refractivity: 24.55 cm3; (15)Molar Volume: 83.2 cm3; (16)Surface Tension: 49.5 dyne/cm; (17)Density: 1.202 g/cm3; (18)Flash Point: 85.4 °C; (19)Enthalpy of Vaporization: 47.56 kJ/mol; (20)Boiling Point: 195.3 °C at 760 mmHg; (21)Vapour Pressure: 0.182 mmHg at 25 °C.

Uses of Cyclobutanecarboxylic acid: (1) it is used in organic synthesis; (2) it is used to produce other chemicals. For example, it can react with Methanol to get Cyclobutanecarboxylic acid methyl ester. The reaction occurs with reagent H2SO4 and other condition of heating for 8 hours. The yield is 75 %.

Cyclobutanecarboxylic acid can react with Methanol to get Cyclobutanecarboxylic acid methyl ester.

When you are dealing with this chemical, you should be very careful. This chemical is inflammation to the skin, eyes and respiratory system or other mucous membranes. Therefore, you should avoid contacting with skin, eyes and wear suitable protective clothing. You can not breathe the gas/fumes/vapour/spray. And in case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(O)C1CCC1
(2) InChI: InChI=1S/C5H8O2/c6-5(7)4-2-1-3-4/h4H,1-3H2,(H,6,7)
(3) InChIKey: TXWOGHSRPAYOML-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1270mg/kg (1270mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 21, Pg. 85, 1969.
Link to PubMed
mouse LD50 subcutaneous 1270mg/kg (1270mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 21, Pg. 85, 1969.
Link to PubMed

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