2-Methylbenzyl alcohol

Base Information

• Chemical Name: 2-Methylbenzyl alcohol
• CAS No.: 89-95-2
• Molecular Formula: C8H10O
• Molecular Weight: 122.167
• Hs Code.: 29339990
• European Community (EC) Number: 201-954-2
• NSC Number: 91
• UNII: 7L3M6Y04NC
• DSSTox Substance ID: DTXSID8059001
• Nikkaji Number: J132.821B
• Wikidata: Q27268494
• Metabolomics Workbench ID: 67535
• Mol file: 89-95-2.mol

Synonyms:2-methylbenzyl alcohol;2-methylbenzyl alcohol, 3H-labeled;ortho-methylbenzyl alcohol

Chemical Property of 2-Methylbenzyl alcohol

Chemical Property:

• Appearance/Colour: white crystalline low melting solid
• Vapor Pressure: 0.75 mm Hg ( 86 °C)
• Melting Point: 33-36 °C(lit.)
• Refractive Index: n20/D 1.5408(lit.)
• Boiling Point: 218.4 °C at 760 mmHg
• PKA: 14.37±0.10(Predicted)
• Flash Point: 104.4 °C
• PSA: 20.23000
• Density: 1.022 g/cm³
• LogP: 1.48730
• Storage Temp.: Store below +30°C.
• Solubility.: methanol: 0.1 g/mL, clear
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 122.073164938
• Heavy Atom Count: 9
• Complexity: 80.6

Purity/Quality:

99% ^*data from raw suppliers

2-Methylbenzyl alcohol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-41-22
• Safety Statements: 22-24/25-37/39-26-39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Alcohols and Polyols, Other
• Canonical SMILES: CC1=CC=CC=C1CO
• Uses: 2-Methylbenzyl alcohol is widely used strong mobile phase additive in HPLC. it can be used to produce 2-methyl-benzaldehyde at temperature of 20°C. It will need reagent pyridinium chlorochromate with reaction time of 10 min.

Technology Process of 2-Methylbenzyl alcohol

There total 172 articles about 2-Methylbenzyl alcohol 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: 94.2%

2-methylphenyl aldehyde (529-20-4) + para-methylacetophenone (122-00-9) → CH3C6H4CH(CH3)OH (536-50-5) + 2-methyl-benzyl alcohol (89-95-2)

Guidance literature:

With sodium tetrahydroborate; tin(ll) chloride; In tetrahydrofuran; for 1.5h; Heating; selectivity, absence of SnCl₂, further solvents;

DOI:10.1246/cl.1987.853

Reference yield: 67.0%

2-formylphenyl propanoate (154366-28-6) → 3-methylcoumarine (2445-82-1) + 2-methyl-benzyl alcohol (89-95-2)

Guidance literature:

With 4 A molecular sieve; 2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane 2,8,9-tris(1-methylethyl); In benzene; at 40 ℃; for 3h;

DOI:10.1081/SCC-120003602

Reference yield: 60.0%

o-xylene (95-47-6) → 2-methyl-benzyl alcohol (89-95-2) + 2-methylbenzyl acetate (17373-93-2)

Guidance literature:

With potassium 12-wolframocobalt(III)ate; In water; acetic acid; at 102 ℃; for 49h;

upstream raw materials:

ortho-methylbenzoic acid

ortho-tolylmagnesium bromide

formaldehyd

diethyl ether

Downstream raw materials:

carbamic acid-(2-methyl-benzyl ester)

2-methylphenyl aldehyde

ortho-methylbenzoic acid

2,2'-dimethyl-stilbene

Refernces

2,4-Bis(aryloxy)pyrimidines as Antimicrobial Agents

10.1021/jm00312a036

The study in the literature focuses on the synthesis and antimicrobial activity of 2,4-bis(aryloxy)pyrimidines. The researchers synthesized these compounds by condensing 2,4-dichloropyrimidines with various phenolic compounds in the presence of anhydrous potassium carbonate. The synthesized 2,4-bis(aryloxy)pyrimidines were tested against gram-positive and gram-negative bacteria, as well as a pathogenic strain of yeast. The study found that these compounds exhibited antimicrobial activity, with their effectiveness being largely independent of the substituents in the phenyl ring. The 5-methyl substitution in the pyrimidine ring did not significantly alter the inhibitory activity of the compounds.

An Efficient Route to Pyrimidine Nucleoside Analogues by [4 + 2] Cycloaddition Reaction

10.1021/jo034709a

The research focuses on the development of an efficient synthetic route for pyrimidine nucleoside analogues, which are compounds with significant pharmaceutical value, particularly as antiviral and antitumor agents. The study reports a convergent chemistry approach using [4+2] cycloaddition reactions between glycosyl isothiocyanates (3a-f) and diazadienium salt 5, yielding β-D-uracil analogues (7a-f) with good yields and total regiocontrol. The process involves the preparation of glycosyl isothiocyanates from acetylated or benzoylated glycosyl bromides and the synthesis of diazadienium iodide 5 from vinylthioamide 4. The synthesized compounds were fully characterized using IR, HRMS, and NMR techniques.

Synthesis and in vitro biological evaluation of new pyrimidines as glucagon-like peptide-1 receptor agonists

10.1016/j.bmcl.2017.09.032

The study explores the development of small-molecule GLP-1 receptor agonists for treating type 2 diabetes. The researchers synthesized two series of pyrimidine derivatives. The first series involved substituting positions 2 and 4 of pyrimidines with various groups, while the second series included pyrimidines with urea and Schiff base linkers. These compounds were tested for their ability to increase insulin secretion in cultured βTC6 cells. Key findings include compounds 3a and 10a significantly boosting insulin secretion in both the absence and presence of 2.8 mM glucose, with compound 10a showing effects similar to the potent drug exenatide. The study highlights the potential of these pyrimidine analogs as orally available GLP-1 receptor agonists, providing a foundation for further research into small-molecule therapeutics for diabetes.