(1S,2S)-2-Fluorocyclopropanecarboxylic acid CAS#: 127199-14-8; ChemWhat Code: 1411675

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

Product Name(1S,2S)-2-Fluorocyclopropanecarboxylic acid
IUPAC Name(1S,2S)-2-fluorocyclopropane-1-carboxylic acid 
Molecular Structurestructure of (1S,2S)-2-Fluorocyclopropanecarboxylic acid CAS 127199-14-8
CAS Registry Number 127199-14-8
Synonyms(1S,2S)-2-fluorocyclopropanecarboxylic acid
127199-14-8
105919-34-4
cis-2-fluorocyclopropanecarboxylic acid
(1s,2s)-2-fluorocyclopropane-1-carboxylic acid
cis-2-Fluorocyclopropane-1-carboxylic acid
cis-2-Fluoro-cyclopropanecarboxylic acid
(1S,2S)-rel-2-Fluorocyclopropanecarboxylic acid
Cyclopropanecarboxylic acid, 2-fluoro-, (1S-cis)-
MFCD19237459
(cis)-2-fluorocyclopropanecarboxylic acid
Cyclopropanecarboxylic acid, 2-fluoro-, (1S,2S)-
(1S,2S)-2-fluorocyclopropanecarboxylicacid
MFCD04972869
SCHEMBL1463730
AMY5475
DTXSID901262266
CFA19914
CS1221
AKOS006294678
Molecular FormulaC4H5FO2
Molecular Weight104.08
InChIInChI=1S/C4H5FO2/c5-3-1-2(3)4(6)7/h2-3H,1H2,(H,6,7)/t2-,3+/m1/s1  
InChI KeyHZQKMZGKYVDMCT-GBXIJSLDSA-N
Canonical SMILESC1[C@H]([C@H]1F)C(=O)O

Physical Data

AppearanceWhite solid
Melting Point, °C Solvent (Melting Point)
55 – 56
62 – 63toluene

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Frequency (NMR Spectroscopy), MHz
Chemical shifts1Hchloroform-d6400
Chemical shifts, Spectrum1Hchloroform-d1400
Chemical shifts, Spectrum1Hchloroform-d1
100
Chemical shifts1HCDCl3
Chemical shifts19FCDCl3
Description (IR Spectroscopy)Solvent (IR Spectroscopy)Temperature (IR Spectroscopy), °C
ATR (attenuated total reflectance), Bands
BandsKBr3210 – 1190 cm**(-1)

Route of Synthesis (ROS)

Route of Synthesis (ROS) of (1S,2S)-2-Fluorocyclopropanecarboxylic acid

Route of Synthesis (ROS) of (1S,2S)-2-Fluorocyclopropanecarboxylic acid

ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 10 – 30℃; for 5h;83.4%
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;1.1 g
Experimental Procedure
DMF (50 mL), (1S,2S)-2-fluorocyclopropanecarboxylic acid (425 mg, 4.1 mmol), HATU (2.1 g, 5.58 mmol) and DIEA (1.44 g, 11.16 mmol) were successively added to compound 4a (1.0 g, 3.71 mmol), and the mixture was stirred at room temperature for 5 h. The reaction was quenched by adding water, extracted 3 times with ethyl acetate and washed twice with saturated brine. The organic phase was dried and concentrated, and the residue was separated and purified by silica gel column chromatography (eluent: EA/PE=1/2) to obtain 117E (1.1 g, 83.4%). LC-MS (ESI): m/z=356.3 [M+H]+.

Safety and Hazards

Pictogram(s)
SignalDanger
GHS Hazard StatementsH314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
Precautionary Statement CodesP260, P261, P264, P271, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P319, P321, P363, P403+P233, P405, and P501
(The corresponding statement to each P-code can be found at the GHS Classification page.)

Other Data

TransportationStore in room temperature for long time and dry place; in container tightly sealed; Protect from light.
HS Code
StorageStore in room temperature for long time and dry place; in container tightly sealed; Protect from light.
Shelf Life2 years
Market Price
Druglikeness
Lipinski rules component
Molecular Weight104.081
logP0.27
HBA2
HBD1
Matching Lipinski Rules4
Veber rules component
Polar Surface Area (PSA)37.3
Rotatable Bond (RotB)1
Matching Veber Rules2
Use Pattern
(1S,2S)-2-Fluorocyclopropanecarboxylic acid CAS#: 127199-14-8 and its derivatives can act as chiral catalysts in asymmetric synthesis reactions. They can guide the reaction selectively to produce chiral products, thereby enhancing the stereo-selectivity and efficiency of the reaction.

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