Methyl N-(4-methylpyridin-3-yl)carbamate

Base Information

• Chemical Name: Methyl N-(4-methylpyridin-3-yl)carbamate
• CAS No.: 694495-63-1
• Molecular Formula: C8H10N2O2
• Molecular Weight: 166.18
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID20470362
• Wikidata: Q82298430
• Mol file: 694495-63-1.mol

Synonyms:Methyl N-(4-methylpyridin-3-yl)carbamate;694495-63-1;3-Methoxycarbonylamino-4-methylpyridine;methyl (4-methylpyridin-3-yl)carbamate;Methyl 4-methylpyridin-3-ylcarbamate;MFCD09030045;methyl(4-methylpyridin-3-yl)carbamate;Methyl (4-Methyl-3-pyridyl)carbamate;Carbamic acid, (4-methyl-3-pyridinyl)-, methyl ester;SCHEMBL692100;DTXSID20470362;FTEFYIXMXZZAGN-UHFFFAOYSA-N;BCP13436;CS-M3531;AKOS006283447;ME-0097;Methyl (4-methyl-3-pyridinyl)carbamate;SY060891;FT-0764222;EN300-189034;A914570;(4-Methyl-pyridin-3-yl)-carbamic Acid Methyl Ester;J-521709

Chemical Property of Methyl N-(4-methylpyridin-3-yl)carbamate

Chemical Property:

• Vapor Pressure: 0.076mmHg at 25°C
• Melting Point: 117～118℃
• Boiling Point: 227.812oC at 760 mmHg
• PKA: 12.94±0.70(Predicted)
• Flash Point: 91.578oC
• PSA: 51.22000
• Density: 1.201g/cm3
• LogP: 1.64130
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 166.074227566
• Heavy Atom Count: 12
• Complexity: 161

Purity/Quality:

99% ^*data from raw suppliers

Methyl4-Methylpyridin-3-ylcarbamate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=NC=C1)NC(=O)OC
• Uses: Methyl 4-Methylpyridin-3-ylcarbamate can be used as JAK3 inhibitors for its immunosuppressant properties.

Technology Process of Methyl N-(4-methylpyridin-3-yl)carbamate

There total 2 articles about Methyl N-(4-methylpyridin-3-yl)carbamate 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: 98.0%

3-amino-4-methylpyridine (3430-27-1) + methyl chloroformate (79-22-1) → O-methyl-N-(4-methylpyridin-3-yl)carbamate (694495-63-1)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 48h; Cooling with ice;

DOI:10.1002/cmdc.201300520

Reference yield: 92.0%

3-amino-4-methylpyridine (3430-27-1) + carbonic acid dimethyl ester (616-38-6) → O-methyl-N-(4-methylpyridin-3-yl)carbamate (694495-63-1)

Guidance literature:

With potassium tert-butylate; In 2-methyltetrahydrofuran; at 25 ℃; for 4h; Cooling with ice;

Reference yield: 97.0%

O-methyl-N-(4-methylpyridin-3-yl)carbamate (694495-63-1) + benzyl bromide (100-39-0) → 1-benzyl-3-methoxycarbonylamino-4-methyl-pyridinium bromide (923036-27-5)

Guidance literature:

In toluene; at 100 ℃; for 16h;

upstream raw materials:

3-amino-4-methylpyridine

carbonic acid dimethyl ester

methyl chloroformate

Downstream raw materials:

cis-(4-methyl-piperidin-3-yl)-carbamic acid methyl ester

trans-(4-methyl-piperidin-3-yl)-carbamic acid methyl ester

1-benzyl-3-methoxycarbonylamino-4-methyl-pyridinium bromide

1-benzyl-3-methoxycarbonylamino-4-methylpyridinium chloride

Refernces

• 1、 Zhi, Shuang,Liu, Dengke,Liu, Ying,Liu, Bingni,Wang, Donghua,Chen, Ligong. "An Efficient Method for Synthesis of Tofacitinib Citrate". . p. 1259 - 1263. Retrieved 2016/07/29.
• 2、 Gehringer, Matthias,Pfaffenrot, Ellen,Bauer, Silke,Laufer, Stefan A.. "Design and synthesis of tricyclic jak3 inhibitors with picomolar affinities as novel molecular probes". supporting information. p. 277 - 281. Retrieved 2014/04/03.