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1759-53-1

Basic Information
CAS No.: 1759-53-1
Name: Cyclopropanecarboxylic acid
Article Data: 75
Molecular Structure:
Molecular Structure of 1759-53-1 (Cyclopropanecarboxylic acid)
Formula: C4H6O2
Molecular Weight: 86.0904
Synonyms: Carboxycyclopropane;Cyclopropionic acid;Cyclopropylcarboxylic acid;NSC 1112;Cyclopropyl Carboxylic Acid;
EINECS: 217-162-5
Density: 1.314 g/cm3
Melting Point: 14-17 °C(lit.)
Boiling Point: 183 °C at 760 mmHg
Flash Point: 71.7 °C
Appearance: clear colourless to light yellow liquid
Hazard Symbols: CorrosiveC,IrritantXi
Risk Codes: 22-34
Safety: 26-27-36/37/39-45
Transport Information: UN 3265 8/PG 2
PSA: 37.30000
LogP: 0.48100
Synthetic route
30923-69-4

1‐cyclopropyl‐4,4,4‐trifluorobutane‐1,3‐dione

1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
With oxygen; sodium hydrogencarbonate In acetonitrile for 4h; Molecular sieve; Irradiation;98%
1427519-95-6

(3S,4S)-4-(N-allyl-4-methylphenylsulfonamido)-1,3-diphenylhept-1-yn-3-yl cyclopropanecarboxylate

A

1427520-28-2

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

B

1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
With Echavarren's catalyst; water In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere; stereoselective reaction;A 97%
B n/a
600-05-5

2,3-dibromopropionic acid

75-36-5

acetyl chloride

1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
Stage #1: 2,3-dibromopropionic acid; acetyl chloride With copper(l) chloride; zinc In diethyl ether at 10 - 20℃; for 11h; Inert atmosphere;
Stage #2: With Methylenetriphenylphosphorane In diethyl ether Temperature; Solvent; Concentration;
96%
1427519-96-7

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

A

1427520-27-1

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

B

1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
With Echavarren's catalyst; water In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere; stereoselective reaction;A 94%
B n/a

3,4-dihydronaphthalen-1-yl cyclopropanecarboxylate

A

71019-06-2

2-fluoro-1-tetralone

B

1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
With Selectfluor In water; acetonitrile at 20℃;A 93%
B n/a
5500-21-0

cyclopropropanecarbonitrile

1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
With water; nitrile hydratase SP361 at 30℃; for 24h; in potassium phosphate buffer (pH = 7);92%
With phosphoric acid; phosphorus pentoxide at 140℃;
With sodium hydroxide
With potassium hydroxide
In sodium hydroxide
123-73-9

trans-Crotonaldehyde

1489-69-6

Cyclopropanecarboxaldehyde

1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
90%
1427520-01-1

(3S,4S)-4-(N-allyl-4-methylphenylsulfonamido)-6-(methylsulfonyl)-1,3-diphenylhex-1-yn-3-yl cyclopropanecarboxylate

A

1427520-30-6

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

B

1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
With Echavarren's catalyst; water In 1,2-dichloro-ethane at 80℃; for 24h; Inert atmosphere; stereoselective reaction;A 87%
B n/a
1489-69-6

Cyclopropanecarboxaldehyde

1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
With 2-mesityl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In acetonitrile at 20℃;80%
With Iron(III) nitrate nonahydrate; oxygen In acetonitrile at 25℃; under 760.051 Torr; for 12h; Catalytic behavior; Reagent/catalyst; Schlenk technique;80%
With Oxone; ethylenediaminetetraacetic acid; sodium hydrogencarbonate In water; acetone at 22℃; for 3h; Oxidation;71%
With air at 21℃; for 2h;
85696-55-5

tert-butyl(cyclopropylmethoxy)dimethylsilane

1759-53-1

cyclopropanecarboxylic acid

Conditions
ConditionsYield
With ruthenium(IV) oxide; sodium periodate78%
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Specification

The Cyclopropanecarboxylic acid, with its CAS registry number 1759-53-1, is a kind of clear colourless to light yellow liquid. This is insoluble in water while soluble in ethyl acetate and ether. As to its usage, it is usually applied as the intermediate of plant growth regulator trinexapac-ethyl and also as the pharmaceutic intermediates. Besides, its product categories are including Pharmaceutical Intermediates; Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Cyclopropanes; Simple 3-Membered Ring Compounds.

The characteristics of this chemical are as follows: (1)ACD/LogP: 0.08; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.72; (4)ACD/LogD (pH 7.4): -2.51; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 4.2; (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; (13)Index of Refraction: 1.521; (14)Molar Refractivity: 19.94 cm3; (15)Molar Volume: 65.4 cm3; (16)Polarizability: 7.9×10-24 cm3; (17)Surface Tension: 57.9 dyne/cm; (18)Density: 1.314 g/cm3; (19)Flash Point: 71.7 °C; (20)Enthalpy of Vaporization: 46.22 kJ/mol; (21)Boiling Point: 183 °C at 760 mmHg; (22)Vapour Pressure: 0.362 mmHg at 25°C; (23)Exact Mass: 86.036779; (24)MonoIsotopic Mass: 86.036779; (25)Topological Polar Surface Area: 37.3; (26)Heavy Atom Count: 6; (27)Complexity: 73.6.

Production method of this chemical: Cyclopropanecarbonitrile could react to produce cyclopropanecarboxylic acid. This reaction could happen in the presence of the reagent of aq. NaOH solution.

Use of this chemical: Cyclopropanecarboxylic acid could react to produce cyclopropylmethanol. This reaction could happen in the presence of the reagent of lithium aluminum hydride.

When you are dealing with this chemical, you should be very cautious. For one thing, it is irritant which may cause inflammation to the skin or other mucous membranes. And it may causes burns and it will be dangerous if swallowed. For another thing, it is corrosive which may destroy living tissue on contact. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. If in case of contact with eyes, rinse immediately with plenty of water and seek medical advice, and if in case of accident or if you feel unwell seek medical advice immediately (show the label where possible). Besides, take off immediately all contaminated clothing when contact.

In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: C1CC1C(=O)O
(2)InChI: InChI=1S/C4H6O2/c5-4(6)3-1-2-3/h3H,1-2H2,(H,5,6)
(3)InChIKey: YMGUBTXCNDTFJI-UHFFFAOYSA-N 

Below are the toxicity information of this chemical:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 172mg/kg (172mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 21, Pg. 85, 1969.
 
mouse LD50 intravenous 180mg/kg (180mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#03926,
mouse LD50 subcutaneous 172mg/kg (172mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 21, Pg. 85, 1969.