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22348-32-9

22348-32-9

Identification

  • Product Name:2-Pyrrolidinemethanol,a,a-diphenyl-, (2R)-

  • CAS Number: 22348-32-9

  • EINECS:606-992-7

  • Molecular Weight:253.344

  • Molecular Formula: C17H19NO

  • HS Code:29221990

  • Mol File:22348-32-9.mol

Synonyms:2-Pyrrolidinemethanol,a,a-diphenyl-, (R)- (8CI);(+)-2-(Diphenylhydroxymethyl)pyrrolidine;(+)-a,a-Diphenyl-2-pyrrolidinemethanol;(R)-(+)-a,a-Diphenyl-2-pyrrolidinemethanol;(R)-2-(diphenylhydroxymethylpyrrolidine);(R)-a,a-Diphenyl-2-pyrrolidinemethanol;(R)-a,a-Diphenylprolinol;a,a-Diphenyl-D-prolinol;α,α-Diphenyl-D-prolinol;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:Warning

  • Hazard Statement:H315 Causes skin irritationH319 Causes serious eye irritation H335 May cause respiratory irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:TCI Chemical
  • Product Description:(R)-(+)-alpha,alpha-Diphenyl-2-pyrrolidinemethanol >98.0%(GC)(T)
  • Packaging:5g
  • Price:$ 466
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  • Manufacture/Brand:TCI Chemical
  • Product Description:(R)-(+)-alpha,alpha-Diphenyl-2-pyrrolidinemethanol >98.0%(GC)(T)
  • Packaging:1g
  • Price:$ 135
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:(R)-(+)-α,α-Diphenyl-2-pyrrolidinemethanol 98%
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:(R)-(+)-α,α-Diphenyl-2-pyrrolidinemethanol 98%
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  • Manufacture/Brand:Sigma-Aldrich
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  • Manufacture/Brand:Medical Isotopes, Inc.
  • Product Description:(R)-Diphenyl(pyrrolidin-2-yl)methanol
  • Packaging:5 g
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:5-(4-Chlorophenyl)-3-methyl-1H-pyrazole 95%
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  • Manufacture/Brand:Matrix Scientific
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:(R)-(+)-Alpha,alpha-Diphenyl-2-pyrrolidinemethanol 95+%
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  • Manufacture/Brand:Matrix Scientific
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Relevant articles and documentsAll total 54 Articles be found

London Dispersion Interactions Rather than Steric Hindrance Determine the Enantioselectivity of the Corey–Bakshi–Shibata Reduction

Eschmann, Christian,Song, Lijuan,Schreiner, Peter R.

supporting information, p. 4823 - 4832 (2021/02/01)

The well-known Corey–Bakshi–Shibata (CBS) reduction is a powerful method for the asymmetric synthesis of alcohols from prochiral ketones, often featuring high yields and excellent selectivities. While steric repulsion has been regarded as the key director of the observed high enantioselectivity for many years, we show that London dispersion (LD) interactions are at least as important for enantiodiscrimination. We exemplify this through a combination of detailed computational and experimental studies for a series of modified CBS catalysts equipped with dispersion energy donors (DEDs) in the catalysts and the substrates. Our results demonstrate that attractive LD interactions between the catalyst and the substrate, rather than steric repulsion, determine the selectivity. As a key outcome of our study, we were able to improve the catalyst design for some challenging CBS reductions.

Preparation method of duloxetine

-

Paragraph 0054-0059, (2021/09/26)

To the method, 1 - naphthol and 3 - (2 - thienyl) -2 - acrolein serve as starting materials, and (S)-3 - (1 - naphthyloxy) -3 - (2 - thienyl) propanal is obtained through addition reaction under the action of a catalyst. The raw materials are cheap and easily available, and 1 - fluoronaphthalene which is expensive is not needed. Sodium hydride and operation are tedious, the cost is low, the process operation is safe and convenient, the three wastes are small in generation amount, and green and environment-friendly. The reaction atom economy is high, the reaction selectivity of each step is high, the side reaction is small, the optical purity and yield of the target product are high, and the green industrial production is facilitated.

Basicities and Nucleophilicities of Pyrrolidines and Imidazolidinones Used as Organocatalysts

An, Feng,Maji, Biplab,Min, Elizabeth,Ofial, Armin R.,Mayr, Herbert

supporting information, p. 1526 - 1547 (2020/02/04)

The Br?nsted basicities pKaH (i.e., pKa of the conjugate acids) of 32 pyrrolidines and imidazolidinones, commonly used in organocatalytic reactions, have been determined photometrically in acetonitrile solution using CH acids as indicators. Most investigated pyrrolidines have basicities in the range 16 aH aH aH 12.6) and the 2-imidazoliummethyl-substituted pyrrolidine A21 (pKaH 11.1) are outside the typical range for pyrrolidines with basicities comparable to those of imidazolidinones. Kinetics of the reactions of these 32 organocatalysts with benzhydrylium ions (Ar2CH+) and structurally related quinone methides, common reference electrophiles for quantifying nucleophilic reactivities, have been measured photometrically. Most reactions followed second-order kinetics, first order in amine and first order in electrophile. More complex kinetics were observed for the reactions of imidazolidinones and several pyrrolidines carrying bulky 2-substituents, due to reversibility of the initial attack of the amines at the electrophiles followed by rate-determining deprotonation of the intermediate ammonium ions. In the presence of 2,4,6-collidine or 2,6-di-tert-butyl-4-methyl-pyridine, the deprotonation of the initial adducts became faster, which allowed the rate of the attack of the amines at the electrophiles to be determined. The resulting second-order rate constants k2 followed the correlation log?k2(20 °C) = sN(N + E), where electrophiles are characterized by one parameter (E) and nucleophiles are characterized by the two solvent-dependent parameters N and sN. In this way, the organocatalysts A1-A32 were integrated in our comprehensive nucleophilicity scale, which compares n-, -, and σ-nucleophiles. The nucleophilic reactivities of the title compounds correlate only poorly with their Br?nsted basicities.

Synthesis process of chiral catalyst

-

Paragraph 0077; 0078; 0081-0084; 0085; 0088; 0089, (2019/02/17)

The invention relates to a low-cost efficient synthesis process of both a chiral catalyst chiral (R)-(+)-2-(Diphenylhydroxymethyl)pyrrolidine and a hydrochloride thereof. According to the process, rawmaterials which can be commercially obtained easily and are environmentally friendly are used; a one-kettle method is used for operation; through esterification reaction, Boc protecting group addition on amino group, Grignard reaction and Boc protecting group removal, high-optical-purity (R)-(+)-2-(Diphenylhydroxymethyl)pyrrolidine hydrochloride is obtained. The process is simplified; the production cost is reduced; the requirements of green chemistry at present are met. The content of (R)-(+)-2-(Diphenylhydroxymethyl)pyrrolidine and the hydrochloride thereof, prepared by the process, is higher than 99.0 percent; the optical purity is not smaller than 99.5 percent; the total yield is higher than 80 percent.

Isosteric expansion of the structural diversity of chiral ligands: Design and application of proline-based N,N′-dioxide ligands for copper-catalyzed enantioselective Henry reactions

Gao, En,Li, Meng,Duan, Lili,Li, Lin,Li, Yue-Ming

, (2019/08/16)

Chiral N,N′-dioxide catalysts were designed based on isosteric approach. Using L-Proline as the starting material, a variety of chiral N,N′-dioxide ligands were obtained via conventional functional group transformations and were utilized in asymmetric Henry reactions between nitromethane and aromatic aldehydes. Using the N,N′-dioxide-copper(II) complexes as the catalysts, asymmetric Henry reaction produced the corresponding β-nitroalcohols in up to 66% yields and up to 83% ee's under mild conditions. The reactions were easy to carry out, and special care such as air or moisture-free conditions was not required.

Process route upstream and downstream products

Process route

2-[hydroxy(diphenyl)methyl]pyrrolidine-1-carboxylic acid tert-butyl ester
137496-68-5

2-[hydroxy(diphenyl)methyl]pyrrolidine-1-carboxylic acid tert-butyl ester

Conditions
Conditions Yield
With trifluoroacetic acid;
91%
With potassium hydroxide; In methanol; dimethyl sulfoxide; at 65 ℃; for 4h;
78%
With potassium hydroxide; In methanol; dimethyl sulfoxide; at 65 ℃; for 4h;
73%
With hydrogenchloride; In ethyl acetate; at 20 ℃; for 2h;
60.16%
With potassium hydroxide; In methanol; dimethyl sulfoxide;
With potassium hydroxide; In methanol; dimethyl sulfoxide; at 65 ℃;
With sodium hydroxide; In ethanol; for 1h; Reflux;
With sodium hydroxide; In ethanol; for 1h; Reflux;
With hydrogenchloride; In 1,4-dioxane; at 0 - 20 ℃; for 2h;
phenylmagnesium chloride
100-59-4

phenylmagnesium chloride

L-proline methyl ester monohydrochloride
2133-40-6

L-proline methyl ester monohydrochloride

Conditions
Conditions Yield
phenylmagnesium chloride; L-proline methyl ester monohydrochloride; In tetrahydrofuran; at 0 - 15 ℃; for 7h;
With water; ammonium chloride; In tetrahydrofuran; pH=5 - 6;
86.6%
ethyl (S)-(-)-2-<hydroxy(diphenyl)methyl>-1-pyrrolidinecarboxylate
152326-82-4

ethyl (S)-(-)-2--1-pyrrolidinecarboxylate

Conditions
Conditions Yield
With potassium hydroxide; In methanol; for 4h; Heating;
92%
With potassium hydroxide; In methanol; for 4h; Heating;
90%
With potassium hydroxide; In methanol; Reflux;
87%
With potassium hydroxide; In methanol; for 12h; Reflux; Inert atmosphere;
85%
With potassium hydroxide; In methanol;
80%
With potassium hydroxide; In methanol; for 36h; Reflux;
78%
With potassium hydroxide; In methanol; at 25 ℃; for 4h; Reflux;
48%
With potassium hydroxide; In methanol; for 4h; Heating;
15%
With potassium hydroxide; In methanol; for 4h;
Multi-step reaction with 2 steps
1: 94 percent / KOH / methanol / 2 h / Ambient temperature
2: 99 percent / KOH / methanol / 4 h / Heating
With potassium hydroxide; In methanol;
ethyl (S)-(-)-2--1-pyrrolidinecarboxylate; With potassium hydroxide; In methanol; toluene; at 60 ℃; for 1h;
With water; In methanol; toluene; at 60 ℃; for 1h;
Conditions
Conditions Yield
With sodium tetrahydroborate; In methanol; at 0 - 25 ℃; for 0.583333h;
85%
phenylmagnesium bromide

phenylmagnesium bromide

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: tetrahydrofuran / 20 h / 20 °C
2: 92 percent / H2; acetic acid / Pd(OH)2/C / CH2Cl2; methanol / 47 h / 20 °C / 760 Torr
With hydrogen; acetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane;
Multi-step reaction with 2 steps
1: KOH / methanol; dimethylsulfoxide
With potassium hydroxide; In methanol; dimethyl sulfoxide;
Multi-step reaction with 2 steps
1: tetrahydrofuran / Heating
2: 90 percent / KOH / methanol / 4 h / Heating
With potassium hydroxide; In tetrahydrofuran; methanol;
phenylmagnesium chloride
100-59-4

phenylmagnesium chloride

(S)-N-(tert-butoxycarbonyl)proline methyl ester
59936-29-7

(S)-N-(tert-butoxycarbonyl)proline methyl ester

Conditions
Conditions Yield
phenylmagnesium chloride; (S)-N-(tert-butoxycarbonyl)proline methyl ester; In tetrahydrofuran; at 10 - 60 ℃; Industrial scale;
With hydrogenchloride; In water; at 45 ℃; for 9h; Industrial scale;
With sodium hydroxide; Temperature; Industrial scale;
99.9 % ee
(S)-proline-N-ethyl carbamate methyl ester
77581-28-3,93423-88-2

(S)-proline-N-ethyl carbamate methyl ester

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

Conditions
Conditions Yield
(S)-proline-N-ethyl carbamate methyl ester; phenylmagnesium bromide; In tetrahydrofuran; at 20 ℃; Inert atmosphere;
With potassium hydroxide; In methanol; for 16h; Reflux; Inert atmosphere;
96%
N-benzyl-(S)-proline methyl ester
113304-84-0,127986-89-4

N-benzyl-(S)-proline methyl ester

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: tetrahydrofuran / 20 h / 20 °C
2: 92 percent / H2; acetic acid / Pd(OH)2/C / CH2Cl2; methanol / 47 h / 20 °C / 760 Torr
With hydrogen; acetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane;
(S)-diphenylprolinol sulfate

(S)-diphenylprolinol sulfate

Conditions
Conditions Yield
With sodium hydroxide; In tetrahydrofuran; water; at 20 - 25 ℃; for 0.5h;
99%
(S)-proline-N-ethyl carbamate methyl ester
77581-28-3,93423-88-2

(S)-proline-N-ethyl carbamate methyl ester

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1.1: Mg; iodine / tetrahydrofuran / Heating
1.2: 45 percent / tetrahydrofuran / Heating
2.1: 15 percent / KOH / methanol / 4 h / Heating
With potassium hydroxide; iodine; magnesium; In tetrahydrofuran; methanol; 1.2: Grignard reaction;
Multi-step reaction with 2 steps
1: 79 percent / tetrahydrofuran
2: 80 percent / potassium hydroxide / methanol
With potassium hydroxide; In tetrahydrofuran; methanol;
Multi-step reaction with 2 steps
1: tetrahydrofuran / 20 °C
2: KOH / methanol / 4 h
With potassium hydroxide; In tetrahydrofuran; methanol; 1: Grignard reaction;
Multi-step reaction with 2 steps
1: tetrahydrofuran / Heating
2: 90 percent / KOH / methanol / 4 h / Heating
With potassium hydroxide; In tetrahydrofuran; methanol;
Multi-step reaction with 2 steps
1: 1) Mg / 1) THF, 30 min, r.t., 2) THF, 0 deg C, 3 h
2: 92 percent / KOH / methanol / 4 h / Heating
With potassium hydroxide; magnesium; In methanol;

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