3-Methylmandelic acid

Base Information

• Chemical Name: 3-Methylmandelic acid
• CAS No.: 65148-70-1
• Molecular Formula: C9H10O3
• Molecular Weight: 166.177
• Hs Code.: 2918199090
• European Community (EC) Number: 673-651-7
• NSC Number: 126597
• DSSTox Substance ID: DTXSID40298863
• Nikkaji Number: J570.428F
• ChEMBL ID: CHEMBL3546299
• Mol file: 65148-70-1.mol

Synonyms:3-Methylmandelic acid;65148-70-1;2-hydroxy-2-(3-methylphenyl)acetic acid;2-Hydroxy-2-(m-tolyl)acetic acid;MFCD03789128;3-METHYLMANDELICACID;NSC126597;SCHEMBL698995;2-hydroxy-2-m-tolylacetic acid;CHEMBL3546299;hydroxy-3-methylphenylacetic acid;DTXSID40298863;2-Hydroxy-2-(m-tolyl)aceticacid;3-methylmandelic acid, AldrichCPR;AKOS005266062;FS-1579;NSC-126597;SB83958;SY314616;CS-0231982;F79163;EN300-1260417;J-509622;J-509650;Z788000614

Chemical Property of 3-Methylmandelic acid

Chemical Property:

• Vapor Pressure: 5.75E-05mmHg at 25°C
• Melting Point: 95-96°C
• Boiling Point: 332.6°Cat760mmHg
• Flash Point: 169.1°C
• PSA: 57.53000
• Density: 1.264g/cm³
• LogP: 1.11300
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 166.062994177
• Heavy Atom Count: 12
• Complexity: 167

Purity/Quality:

98%min ^*data from raw suppliers

3-Methylmandelicacid 98% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC=C1)C(C(=O)O)O

Technology Process of 3-Methylmandelic acid

There total 18 articles about 3-Methylmandelic acid 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: 81.0%

chloroform (67-66-3,8013-54-5) + m-tolyl aldehyde (620-23-5) → 3-methylmandelic acid (65148-70-1)

Guidance literature:

With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; β‐cyclodextrin; at 50 ℃; for 8h;

DOI:10.1080/00397919408012623

Reference yield: 71.0%

Bromoform (75-25-2) + m-tolyl aldehyde (620-23-5) → 3-methylmandelic acid (65148-70-1)

Guidance literature:

With lithium chloride; potassium hydroxide; In 1,4-dioxane; at 0 - 35 ℃; for 60h; Reagent/catalyst; Solvent;

DOI:10.1002/ejoc.201700161

Reference yield: 51.0%

N-benzyl-N,N,N-triethylammonium chloride (56-37-1) + m-tolyl aldehyde (620-23-5) → 3-methylmandelic acid (65148-70-1)

Guidance literature:

With sodium hydroxide; In chloroform; water; at 56 ℃; for 1h;

upstream raw materials:

5-methyl-benzo[b]thiophene-2,3-dione

1-methyl-4-nitrosobenzene

2-oxo-2-(m-tolyl)acetaldehyde

potassium cyanide

Downstream raw materials:

3-methylphenyloxoacetic acid

methyl 2-hydroxy-2-m-tolylacetate

methyl 2-hydroxy-2-(3-methylphenyl)acetate

benzyl 2-bromo-2-(m-tolyl)acetate

Refernces

• 1、 Potera?a, Marcin,Dranka, Maciej,Borowiecki, Pawe?. "Chemoenzymatic Preparation of Enantiomerically Enriched (R)-(–)-Mandelic Acid Derivatives: Application in the Synthesis of the Active Agent Pemoline". . p. 2290 - 2304. Retrieved 2017/05/01.
• 2、 Coles,Ellis,Leung,Sarson,Threlfall,Tizzard. "Relationships between the racemic structures of substituted mandelic acids containing 8- and 10-membered hydrogen bonded dimer rings". . p. 10816 - 10823. Retrieved 2015/02/19.