(5-Amino-2-methylphenyl)methanol

Base Information

• Chemical Name: (5-Amino-2-methylphenyl)methanol
• CAS No.: 111437-10-6
• Molecular Formula: C8H11NO
• Molecular Weight: 137.181
• Hs Code.: 2922199090
• NSC Number: 157709
• DSSTox Substance ID: DTXSID60303286
• Wikidata: Q82048478
• Mol file: 111437-10-6.mol

Synonyms:(5-amino-2-methylphenyl)methanol;111437-10-6;NSC157709;SCHEMBL792457;3-Hydroxymethyl-4-methylaniline;5-Amino-2-methylbenzyl alcohol;DTXSID60303286;XLPOTCGMVRSMDN-UHFFFAOYSA-N;AKOS006337446;NSC-157709;CS-0210622;EN300-314417;Z1203578809

Chemical Property of (5-Amino-2-methylphenyl)methanol

Chemical Property:

• PSA: 46.25000
• LogP: 1.65070
• Solubility.: Dichloromethane, Ethyl Alcohol, Methanol
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 137.084063974
• Heavy Atom Count: 10
• Complexity: 105

Purity/Quality:

≥95% ^*data from raw suppliers

5-Amino-2-methylbenzenemethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=C(C=C1)N)CO
• Uses: 5-Amino-2-methylbenzenemethanol is an intermediate in the synthesis of 8-Hydroxymethyl Riboflavin which is an impurity of Riboflavin (R414995), a nutritional factor found in milk, eggs, malted barley, liver, kidney, heart, leafy vegetables. Richest natural source is yeast. Minute amounts present in all plant and animal cells. Vitamin (enzyme cofactor).

Technology Process of (5-Amino-2-methylphenyl)methanol

There total 7 articles about (5-Amino-2-methylphenyl)methanol 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: 87.0%

(2-methyl-5-nitro-7-phenyl)methanol (22474-47-1) → 3-(hydroxymethyl)-4-methylaniline (111437-10-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 24h; under 760 Torr;

DOI:10.1021/jm960153q

Reference yield: 71.0%

methyl 5-amino-2-methylbenzoate (18595-12-5) → 3-(hydroxymethyl)-4-methylaniline (111437-10-6)

Guidance literature:

methyl 5-amino-2-methylbenzoate; With lithium aluminium tetrahydride; In tetrahydrofuran; at 65 ℃; for 1h;

With Glauber's salt; In tetrahydrofuran; at 20 ℃;

Reference yield:

5-nitro-o-toluic acid (1975-52-6) → 3-(hydroxymethyl)-4-methylaniline (111437-10-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) B₂H₆ / 1.) THF, from 0 to 20 deg C

2: 87 percent / H₂ / 5percent Pd/C / ethyl acetate / 24 h / 760 Torr

With hydrogen; diborane; palladium on activated charcoal; In ethyl acetate;

DOI:10.1021/jm960153q

upstream raw materials:

2-(chloromethyl)-4-nitrotoluene

(2-methyl-5-nitro-7-phenyl)methanol

5-amino-2-methylbenzoic acid

methanol

Downstream raw materials:

4-amino-o-xylene

6-(3-Hydroxymethyl-4-methyl-phenylamino)-1H-pyrimidine-2,4-dione

6-(3-hydroxymethyl-4-methyl-phenylamino)-3-(4-methoxy-butyl)-1H-pyrimidine-2,4-dione

Refernces

• 1、 Ashton, Michael J.,Brown, Thomas J.,Fenton, Garry,Halley, Frank,Harper, Mark F.,Lockey, Peter M.,Porter, Barry,Roach, Alan G.,Stuttle, Keith A. J.,Vicker, Nigel,Walsh, Roger J. A.. "New low-density lipoprotein receptor upregulators acting via a novel mechanism". . p. 3343 - 3356. Retrieved 2007/10/03.
• 2、 Sucholeiki, Irving,Lynch, Vincent,Phan, Ly,Wilcox, Craig S.. "Molecular Armatures. Synthesis and Structure of Troegers Base Analogues Derived from 4-, 2,4-, 3,4-, and 2,4,5-Substituted Aniline Derivatives". . p. 98 - 104. Retrieved 2007/10/02.