Methyl 2-(dimethylamino)benzoate

Base Information

• Chemical Name: Methyl 2-(dimethylamino)benzoate
• CAS No.: 10072-05-6
• Molecular Formula: C10H13 N O2
• Molecular Weight: 179.219
• Hs Code.: 2922499990
• European Community (EC) Number: 233-202-4
• NSC Number: 97545
• UNII: 77LQP0681T
• DSSTox Substance ID: DTXSID10143477
• Nikkaji Number: J113.552J
• Wikidata: Q27266593
• Mol file: 10072-05-6.mol

Synonyms:Methyl 2-(dimethylamino)benzoate;10072-05-6;Methyl N,N-dimethylanthranilate;N,N-Dimethylanthranilic acid methyl ester;METHYL 2-DIMETHYLAMINOBENZOATE;Benzoic acid, 2-(dimethylamino)-, methyl ester;UNII-77LQP0681T;Anthranilic acid, N,N-dimethyl-, methyl ester;77LQP0681T;EINECS 233-202-4;NSC-97545;AI3-05573;methyl dimethyl anthranilate;SCHEMBL43644;methyl 2-dimethylamino-benzoate;FEMA NO. 4169;methyl N,N-dimethyl anthranilate;DTXSID10143477;NSC97545;MFCD00025858;NSC 97545;AKOS005207048;METHYL O-(DIMETHYLAMINO)BENZOATE;AS-66959;2-(Dimethylamino)benzoic acid methyl ester;Anthranilic acid,N-dimethyl-, methyl ester;CS-0313334;D0675;FT-0628453;METHYL N,N-DIMETHYLANTHRANILATE [FHFI];D89698;J-000201;Q27266593;sodium(6R-trans)-7-[[(3,5-dichloro-4-oxo-1(4H)-pyridyl)acetyl]amino]-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Chemical Property of Methyl 2-(dimethylamino)benzoate

Chemical Property:

• Refractive Index: 1.5555
• Boiling Point: 264°Cat760mmHg
• PKA: 3.77±0.18(Predicted)
• Flash Point: 103.6°C
• PSA: 29.54000
• Density: 1.084g/cm³
• LogP: 1.53920
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 179.094628657
• Heavy Atom Count: 13
• Complexity: 180

Purity/Quality:

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

Methyl2-(Dimethylamino)benzoate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)C1=CC=CC=C1C(=O)OC

Technology Process of Methyl 2-(dimethylamino)benzoate

There total 18 articles about Methyl 2-(dimethylamino)benzoate 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: 76.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 2-carbomethoxyaniline (134-20-3) → methyl 2-(dimethylamino)benzoate (10072-05-6) + Methyl N-methylanthranilate (85-91-6)

Guidance literature:

With acetic acid; zinc; In 1,4-dioxane; water; at 50 ℃; for 4h;

DOI:10.1016/j.jep.2011.03.035

Reference yield: 45.0%

methanol (67-56-1) + carbon monoxide (201230-82-2) + N,N-dimethyl-aniline (121-69-7,77733-26-7) → methyl 2-(dimethylamino)benzoate (10072-05-6)

Guidance literature:

With dichloro bis(acetonitrile) palladium(II); In N,N-dimethyl-formamide; toluene; at 100 ℃;

DOI:10.1021/acs.joc.9b02771

Reference yield: 29.0%

anthranilic acid (118-92-3,159201-01-1,50816-84-7,80206-34-4,104809-47-4) + methyl iodide (74-88-4) → methyl 2-(dimethylamino)benzoate (10072-05-6) + 2-carbomethoxyaniline (134-20-3) + Methyl N-methylanthranilate (85-91-6)

Guidance literature:

With potassium phosphate; In acetone; at 60 ℃; for 2h;

upstream raw materials:

diazomethane

diethyl ether

N,N-dimethylanthranilic acid

2-carboxy-tri-N-methyl-anilinium betaine

Downstream raw materials:

Methyl-5-acetyl-2-dimethylaminobenzoat

2-methoxycarbonyl-tri-N-methyl-anilinium; iodide

2-dimethylamino-cyclohexanecarboxylic acid methyl ester

N,N-dimethylanthranilic acid hydrazide

Refernces

• 1、 Selva, Maurizio,Tundo, Pietro,Foccardi, Tommaso. "Mono-N-methylation of functionalized anilines with alkyl methyl carbonates over NaY faujasites. 4. Kinetics and selectivity". . p. 2476 - 2485. Retrieved 2005.
• 2、 Kugler,E.,Kovats,E.. "-". . p. 1480 - 1513. Retrieved 1963.
• 3、 Wang, Shoucai,Li, Xuan,Zang, Jiawang,Liu, Meichen,Zhang, Siyu,Jiang, Guangbin,Ji, Fanghua. "Palladium-Catalyzed Multistep Tandem Carbonylation/N-Dealkylation/Carbonylation Reaction: Access to Isatoic Anhydrides". . p. 2672 - 2679. Retrieved 2020/02/04.