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alpha-Cyclopentylmandelic acid

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Name

alpha-Cyclopentylmandelic acid

EINECS 207-047-8
CAS No. 427-49-6 Density 1.247 g/cm3
PSA 57.53000 LogP 2.14900
Solubility N/A Melting Point 144-150 °C
Formula C13H16O3 Boiling Point 395.6 °C at 760 mmHg
Molecular Weight 220.268 Flash Point 207.2 °C
Transport Information N/A Appearance white to beige powder
Safety 45-36/37/39-26 Risk Codes 34
Molecular Structure Molecular Structure of 427-49-6 (alpha-Cyclopentylmandelic acid) Hazard Symbols CorrosiveC,IrritantXi
Synonyms

Mandelicacid, a-cyclopentyl- (6CI,7CI,8CI);Mandelic acid, α-cyclopentyl;2-Cyclopentyl-2-hydroxy-2-(phenyl)acetic acid;Cyclopentylphenylglycolic acid;NSC 96637;a-Cyclopentylmandelic acid;Cyclopentyl-hydroxy-phenyl-acetic acid;α-Cyclopentyl-DL-mandelic Acid;

Article Data 15

alpha-Cyclopentylmandelic acid Synthetic route

596-51-0

glycopyrronium bromide

A

3-hydroxy-1,1-dimethyl pyrrolidinium bromide

B

427-49-6

2-cyclopentyl-2-hydroxy-2-phenylacetic acid

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃;A 3.87 g
B 92%
611-73-4

Benzoylformic acid

33240-34-5

cyclopentylmagnesium bromide

427-49-6

2-cyclopentyl-2-hydroxy-2-phenylacetic acid

Conditions
ConditionsYield
In diethyl ether at 0 - 20℃; for 24.5h;36.4%
Stage #1: Benzoylformic acid; cyclopentylmagnesium bromide In diethyl ether at 0 - 20℃; for 24.5h;
Stage #2: With hydrogenchloride In diethyl ether; water
36.4%
19833-96-6

2-Cyclopentyl-2-hydroxy-2-phenylacetic acid methyl ester

427-49-6

2-cyclopentyl-2-hydroxy-2-phenylacetic acid

Conditions
ConditionsYield
With sodium hydroxide In methanol; water at 20℃; Inert atmosphere;25%
16098-80-9

2-cyclopentyl-2-hydroxy-2-phenylacetic acid ethyl ester

427-49-6

2-cyclopentyl-2-hydroxy-2-phenylacetic acid

Conditions
ConditionsYield
With potassium hydroxide In methanol at 20℃;
1603-79-8

phenylglyoxylic acid ethyl ester

427-49-6

2-cyclopentyl-2-hydroxy-2-phenylacetic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrahydrofuran / 0 - 20 °C
2: KOH / methanol / 20 °C
View Scheme
33240-34-5

cyclopentylmagnesium bromide

427-49-6

2-cyclopentyl-2-hydroxy-2-phenylacetic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrahydrofuran / 0 - 20 °C
2: KOH / methanol / 20 °C
View Scheme
15206-55-0

methyl 2-oxo-2-phenylacetate

427-49-6

2-cyclopentyl-2-hydroxy-2-phenylacetic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: iodine; magnesium / tetrahydrofuran / 0 °C / Reflux; Inert atmosphere
1.2: 10 - 20 °C / Inert atmosphere
2.1: sodium hydroxide / water; methanol / 20 °C / Inert atmosphere
View Scheme
74240-38-3

Cyclozil chloromethacryloyloxymethylate

A

50-00-0

formaldehyd

B

108-01-0

2-(N,N-dimethylamino)ethanol

C

79-41-4

poly(methacrylic acid)

D

427-49-6

2-cyclopentyl-2-hydroxy-2-phenylacetic acid

Conditions
ConditionsYield
With potassium chloride In methanol at 24.9℃; Rate constant; Kinetics; Mechanism; different pH values from 298-323 K, different ion strength of KCl solution;
427-49-6

2-cyclopentyl-2-hydroxy-2-phenylacetic acid

64471-45-0

(2R)-2-cyclopentyl-2-hydroxy-2-phenylacetic acid

Conditions
ConditionsYield
Stage #1: 2-cyclopentyl-2-hydroxy-2-phenylacetic acid With D-tyrosine methyl ester In water; acetonitrile at 0℃; for 4h; Reflux;
Stage #2: With hydrogenchloride In water; toluene at 40℃;
83.4%
With L-Tyr-OMe In acetonitrile Reflux;71%
Stage #1: 2-cyclopentyl-2-hydroxy-2-phenylacetic acid With 12-epi-strychnine In methanol at 20℃;
Stage #2: With (+)-1-phenylethylamine In ethyl acetate
33.3%
91189-05-8

N-{[1-(Benzyl)-3-pyrrolidinyl]methyl}-N-methylamine

427-49-6

2-cyclopentyl-2-hydroxy-2-phenylacetic acid

N-(l-benzyl-pvrrolidin-3-vlmethvf)-2-cvclopentvl-2-hvdroxv-N-methyl-2-phenyl-acetamide

Conditions
ConditionsYield
Stage #1: 2-cyclopentyl-2-hydroxy-2-phenylacetic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap In N,N-dimethyl-formamide at 15 - 20℃; for 2h;
Stage #2: N-{[1-(Benzyl)-3-pyrrolidinyl]methyl}-N-methylamine With 4-methyl-morpholine In N,N-dimethyl-formamide at 15 - 20℃; for 1 - 14h;
Stage #3: With water for 0.25h;
75.34%

alpha-Cyclopentylmandelic acid Specification

The Benzeneacetic acid, a-cyclopentyl-a-hydroxy-, with the CAS registry number 427-49-6, is also known as α-Cyclopentylmandelic acid. Its EINECS number is 207-047-8. This chemical's molecular formula is C13H16O3 and formula weight is 220.26. What's more, its IUPAC name is 2-cyclopentyl-2-hydroxy-2-phenylacetic acid. Its systematic name is Cyclopentylphenylglycolic acid.

Physical properties of Benzeneacetic acid, a-cyclopentyl-a-hydroxy- are: (1)ACD/LogP: 2.77 ; (2)ACD/LogD (pH 5.5): 0.34; (3)ACD/LogD (pH 7.4): -0.89; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 2.84; (7)ACD/KOC (pH 7.4): 1; (8)#H bond acceptors: 3; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 4; (11)Polar Surface Area: 35.53 Å2; (12)Index of Refraction: 1.589; (13)Molar Refractivity: 59.52 cm3; (14)Molar Volume: 176.5 cm3; (15)Surface Tension: 55.3 dyne/cm; (16)Density: 1.247 g/cm3; (17)Flash Point: 207.2 °C; (18)Enthalpy of Vaporization: 68.11 kJ/mol; (19)Boiling Point: 395.6 °C at 760 mmHg; (20)Vapour Pressure: 5.73E-07 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
It can cause burns. In case of contact with eyes, you need rinse immediately with plenty of water and seek medical advice. When using it, you should wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1CCC(C1)C(C2=CC=CC=C2)(C(=O)O)O
(2)InChI: InChI=1S/C13H16O3/c14-12(15)13(16,11-8-4-5-9-11)10-6-2-1-3-7-10/h1-3,6-7,11,16H,4-5,8-9H2,(H,14,15)
(3)InChIKey: WFLUEQCOAQCQLP-UHFFFAOYSA-N

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