1-hydroxycyclopropanecarboxylic acid

1-hydroxycyclopropanecarboxylic acid - Names and Identifiers

Name	1-hydroxy-1-cyclopropanecarboxylic acid
Synonyms	SW-66 SWF-66 1-Carboxy-1-hydroxycyclopropane 1-hydroxycyclopropanecarboxylate 1-hydroxycyclopropanecarboxylic acid 1-Hydroxy-cyclopropanecarboxylic acid Cyclopropanecarboxylicacid, 1-hydroxy- 1-HYDROXY-1-CYCLOPROPANECARBOXYLIC ACID 1-hydroxy-1-cyclopropanecarboxylic acid Methyl 3-[dichloro(methyl)silyl]propanoate Propanoic acid, 3-(dichloromethylsilyl)-, methyl ester
CAS	17994-25-1
EINECS	626-105-7
InChI	InChI=1/C4H6O3/c5-3(6)4(7)1-2-4/h7H,1-2H2,(H,5,6)/p-1
InChIKey	GQXURJDNDYACGE-UHFFFAOYSA-N

1-hydroxycyclopropanecarboxylic acid - Physico-chemical Properties

Molecular Formula	C4H6O3
Molar Mass	102.09
Density	1.6760
Melting Point	108-110°C(lit.)
Boling Point	276.57°C
Flash Point	135.3°C
Solubility	Chloroform+DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
Vapor Presure	0.000592mmHg at 25°C
Appearance	Fine Crystalline Powder
Color	Beige
pKa	3.94±0.20(Predicted)
Storage Condition	Keep in dark place,Sealed in dry,Room Temperature
Refractive Index	1.5130 (estimate)

1-hydroxycyclopropanecarboxylic acid - Risk and Safety

Risk Codes	R36/37/38 - Irritating to eyes, respiratory system and skin. R34 - Causes burns R22 - Harmful if swallowed
Safety Description	S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection.
WGK Germany	3
HS Code	29181998

1-hydroxycyclopropanecarboxylic acid - Reference Information

application

1-hydroxycyclopropane carboxylic acid is an important pharmaceutical intermediate. Because many compounds containing cyclopropane substructural units have good biological activity, cyclopropane has a very wide range of applications in drug design, such as many heterocyclic drugs, polypeptide biopharmaceuticals, and pesticides widely used in agriculture All molecules have cyclopropane structural units.

preparation

(1) synthesis of compound 2 compound 1(3.41g,29.6mmol,1.0eq) is dissolved in 40ml of sulfuric acid aqueous solution a (1.62mL of 98% concentrated sulfuric acid is added into water to prepare, and the molar equivalent of sulfuric acid is 1.0eq), and the ice bath is cooled to 0-5 ℃, 10ml of sodium nitrite (2.25g,32.6mmol,1.1eq) aqueous solution was added to the reaction solution and stirred at room temperature for 1 hour. Then the above reaction droplets are added to the refluxed 100ml sulfuric acid aqueous solution B (obtained by adding 1.62mL 98% concentrated sulfuric acid into water, and the molar equivalent of sulfuric acid is 1.0eq). After dropping, stop heating and cool to room temperature. After TLC detection reaction is completed, ethyl acetate (3*100mL) is extracted three times, organic phases are combined, dried with anhydrous magnesium sulfate, filtered and concentrated organic phases to obtain compound 2(2.57g,22.1mmol), colorless oily liquid with 74.8% yield. 1H-NMR(400HZ,DMSO) of compound 2: & 0.951-0.959(t,2h),1.112-1.121(t,2h),3.624(s,3H),6.177(s,1H). In the synthesis process of compound 2, the aqueous sulfuric acid solution used cannot be replaced by hydrochloric acid or nitric acid solution, otherwise it will easily lead to cyclopropane ring opening. The reaction droplets of sulfuric acid aqueous solution A are added to sulfuric acid aqueous solution B to shorten the time of raw materials and products in the reaction system, so that the raw materials can react quickly after being added, because too long reaction time will cause cyclopropane ring opening. (2) Synthesis of Compound 3 Compound 2(113.7mg,0.98mmol,1.0eq) was dissolved in a mixed solution of 7ml tetrahydrofuran and water (5:2), and then lithium hydroxide (240mg,10.02mmol,10eq) was added in batches. The oil bath heats the reaction solution to 30°C, reacts for 12 hours, after the reaction is complete, it is cooled to room temperature, the pH value of the reaction is adjusted to 5-6 with hydrochloric acid (2N) aqueous solution, ethyl acetate (3*20ml) is extracted three times, and the organic phase is combined., Anhydrous magnesium sulfate is dried, filtered, and concentrated in the organic phase to obtain the target compound 3(84.7mg,0.83mmol), a white solid, yield 84.8%

Last Update：2024-04-09 20:48:19