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Home > Encyclopedia > cis-2-Phenylcyclopropanecarboxylicacid

cis-2-Phenylcyclopropanecarboxylicacid

cis-2-Phenylcyclopropanecarboxylicacid structure

cis-2-Phenylcyclopropanecarboxylicacid 

structure
  • CAS No:

    939-89-9

  • Formula:

    C10H10O2

  • Chemical Name:

    cis-2-Phenylcyclopropanecarboxylicacid

  • Synonyms:

    (1R,2S)-rel-2-Phenylcyclopropanecarboxylic acid;(1r,2s)-2-phenylcyclopropanecarboxylic acid;48126-51-8;(1R,2S)-2-phenylcyclopropane-1-carboxylic acid;cis-2-phenylcyclopropane-1-carboxylic acid;CIS-2-PHENYLCYCLOPROPANECARBOXYLIC ACID;cis-2-Phenylcyclopropanecarboxylicacid;SCHEMBL4126470;CTK5H4487;ZINC270483

cis-2-Phenylcyclopropanecarboxylicacid Basic Attributes

162.19

162.068

XTN6536VE6

Characteristics

37.3

1.6

1.250±0.06 g/cm3(Predicted)

105 °C

317.1°C at 760 mmHg

Safety Information

P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501

H302

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 2 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

cis-2-Phenylcyclopropanecarboxylicacid Use and Manufacturing

General procedure: An oven-dried Schlenk tube containing a stirring bar was charged with NiBr2·glyme (0.02 mmol, 10 molpercent), L3 (0.05 mmol, 26 molpercent), Mn (0.52 mmol, 2.60 equiv) and LiCl (0.80 mmol, 4 equiv). The Schlenk tube was evacuated and backfilled under CO2 flow (this procedure was repeated three times). Anhydrous DMA (0.50 mL) and the corresponding cyclopropyl bromide 1 (0.20 mmol, 1 equiv) were then added under CO2 flow. The Schlenk tube was next closed at atmospheric pressure of CO2 (1 atm) and the mixture was stirred for 48 h. The mixture was then carefully quenched with 2M HCl to hydrolyze the resulting carboxylate, and extracted several times with EtOAc and CH2Cl2. The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The products were purified by flash chromatography (hexanes–EtOAc).General procedure: Intermediate U; (Trans)-2-(pyridin-3-yl)cycloA solution of N.aOH (7.116 g in 45 mL of H20, 177.92 mmol) was added to a solution of (frans)-ethy. 2-(pyridin- 3-yl) cyclopropanecarboxylate (Intermediate T, 17 g, 88.96 mmol) in Methanol (170 mL) at 0 °C and stirred at RT for 16 h. After completion, the solvent was evaporated, the residue was diluted with water (50 mL), neutralized with Acetic acid and extracted with EtOAc (4 x 100 mL). The combined extracts were washed with water (100 mL), brine ( 100 mL), dried over anhydrous Na^SO^ filtered and evaporated to afford {trans)-2- (pyridin-3-yl)cyclopropanecarboxylic acid (9 g, 62.06 percent) as off white solid. The crude was carried to next step without further purification

Computed Properties

Molecular Weight:162.18
XLogP3:1.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:162.068079557
Monoisotopic Mass:162.068079557
Topological Polar Surface Area:37.3
Heavy Atom Count:12
Complexity:182
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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