Isopropyl mandelate

Base Information

• Chemical Name: Isopropyl mandelate
• CAS No.: 4118-51-8
• Molecular Formula: C11H13O2
• Molecular Weight: 194.23
• Hs Code.: 2918199090
• NSC Number: 6582
• DSSTox Substance ID: DTXSID201285542
• Nikkaji Number: J41.635E
• Mol file: 4118-51-8.mol

Synonyms:4118-51-8;Isopropyl mandelate;propan-2-yl 2-hydroxy-2-phenylacetate;Isopropyl 2-hydroxy-2-phenylacetate;Isopropyl DL-Mandelate;MANDELIC ACID, ISOPROPYL ESTER;NSC 6582;AI3-01788;2-Hydroxy-2-phenylacetic acid isopropyl ester;Benzeneacetic acid, alpha-hydroxy-, 1-methylethyl ester;Propan-2-yl (2RS)-2-Hydroxy-2-phenylacetate (Isopropyl Mandelate);Mandelic acid isopropyl;Pregabalin EP Impurity D;WLN: QYR&VOY1&1;mandelic acid isopropyl ester;SCHEMBL4485794;NSC6582;DTXSID201285542;Isopropyl2-hydroxy-2-phenylacetate;NSC-6582;AKOS008952421;1-Methylethyl alpha-hydroxybenzeneacetate;BS-50525;LS-89135;CS-0166145;E76331;EN300-220268;Z54683128;Isopropyl 2-hydroxy-2-phenylacetate (Pregabalin Impurity;Benzeneacetic acid, .alpha.-hydroxy-, 1-methylethyl ester;Benzeneacetic acid, alpha-hydroxy-, 1-methylethyl ester (9CI);(+/-)-Isopropyl Mandelate;(+/-)-Mandelic Acid Isopropyl Ester;Isopropyl 2-Hydroxy-2-phenylacetate;Isopropyl Mandelate

Chemical Property of Isopropyl mandelate

Chemical Property:

• Vapor Pressure: 0.000875mmHg at 25°C
• Refractive Index: 1.5600 (estimate)
• Boiling Point: 291.8°C at 760 mmHg
• PKA: 12.39±0.20(Predicted)
• Flash Point: 119.4°C
• PSA: 46.53000
• Density: 1.117g/cm³
• LogP: 1.67160
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 194.094294304
• Heavy Atom Count: 14
• Complexity: 183

Purity/Quality:

98%,99%, ^*data from raw suppliers

Isopropyl 2-hydroxy-2-phenylacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)OC(=O)C(C1=CC=CC=C1)O
• Uses: Isopropyl DL-Mandelate is used in nonporous silica/alumina amorphous material. Pregabalin (P704800) impurity.

Technology Process of Isopropyl mandelate

There total 19 articles about Isopropyl mandelate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

phenylglyoxal hydrate (1074-12-0) + isopropyl alcohol (67-63-0,8013-70-5) → isopropyl mandelate (4118-51-8)

Guidance literature:

With yttrium(III) chloride; triethylamine; at 60 ℃; for 20h;

Reference yield: 93.0%

MANDELIC ACID (611-71-2,611-72-3,17199-29-0,90-64-2) + isopropyl alcohol (67-63-0,8013-70-5) → isopropyl mandelate (4118-51-8)

Guidance literature:

With boric acid; at 20 ℃; for 18h;

DOI:10.1021/ol036123g

Reference yield: 90.0%

isopropyl benzoylformate (31197-66-7) → isopropyl mandelate (4118-51-8)

Guidance literature:

With methanol; benzaldehyde; 1,3-bis(mesityl)imidazolium chloride; triethylamine; at 25 ℃; for 5h; regioselective reaction; Inert atmosphere;

DOI:10.1016/j.tetlet.2010.12.022

upstream raw materials:

MANDELIC ACID

isopropyl alcohol

phenylglyoxal hydrate

2-Hydroxy-2-phenyl-1,1,1-tris-(phenylmercapto)-aethan

Downstream raw materials:

(R)-α-hydroxyphenylacetic acid iso-propyl ester

(S)-α-hydroxyphenylacetic acid iso-propyl ester

Refernces

• 1、 Rao, Santhosh,Kapanaiah, Raja,Prabhu, Kandikere Ramaiah. "Boron-Catalyzed C?C Functionalization of Allyl Alcohols". supporting information. . Retrieved 2019/02/14.
• 2、 Rao, Santhosh,Kapanaiah, Raja,Prabhu, Kandikere Ramaiah. "Boron-catalyzed CC functionalization of allyl alcohols". supporting information. p. 1301 - 1306. Retrieved 2019/10/28.