METHYL 5-METHYLNICOTINATE Chemical Properties

Melting point:

46-48°C

Boiling point:

90°C 3mm

Density 

1.104±0.06 g/cm3(Predicted)

Flash point:

90°C/3mm

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Soluble in Chloroform and Methanol.

pka

3.49±0.20(Predicted)

form 

Solid

color 

White

BRN 

472498

InChI

InChI=1S/C8H9NO2/c1-6-3-7(5-9-4-6)8(10)11-2/h3-5H,1-2H3

InChIKey

KQILMMLAGGFMCM-UHFFFAOYSA-N

SMILES

C1=NC=C(C)C=C1C(OC)=O

CAS DataBase Reference

29681-45-6

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/38

Safety Statements 

26-36

HazardClass 

IRRITANT

HS Code 

2933399990

MSDS

• Language:English Provider:ALFA

METHYL 5-METHYLNICOTINATE Usage And Synthesis

Chemical Properties

METHYL 5-METHYLNICOTINATE is White Crystalline Solid

Uses

METHYL 5-METHYLNICOTINATE is a metabolite of Nicotine. Used for the synthesis of (5-methylpyridin-3-yl)methanol, a key intermediate of Rupatadine fumarate.

Uses

5-Methyl-N?-nitrosonornicotine (5-MeNNN) was synthesized from methyl 5-methylnicotinate. 5-Methyl-N?-nitrosonornicotine is used as the starting material in organic compound synthesis.

Synthesis

S1, Preparation of methyl 5-methylnicotinate: Depending on the molar amount of 5-methylnicotinate, 16 equivalents of methanol were slowly added dropwise over a period of 20 minutes, followed by 3 equivalents of thionyl chloride. The reaction mixture was warmed up to 82°C and held at this temperature for 6 hours. Continuous stirring was required during the dropwise addition and during the holding phase. Upon completion of the reaction, the temperature was lowered to 55 °C and the excess methanol and thionyl chloride were removed by distillation under reduced pressure. The reaction mixture was cooled to room temperature and ice water was added to obtain solution A. The pH of solution A was adjusted with ammonia under ice bath conditions to 8. Subsequently, ethyl acetate was added for extraction. The separated ethyl acetate phase was dried by adding anhydrous sodium sulfate until the moisture content was reduced to 0.3% by weight. The dried solution was filtered and the ethyl acetate was removed by rotary evaporator to finally obtain methyl 5-methylnicotinate.

References

[1] Patent: EP2824103, 2015, A1. Location in patent: Paragraph 0039
[2] Patent: CN106560471, 2017, A. Location in patent: Paragraph 0054; 0060; 0066; 0072; 0078; 0084; 0090; 0096
[3] Heterocyclic Communications, 2015, vol. 21, # 4, p. 203 - 205
[4] Journal of Organic Chemistry, 1988, vol. 53, # 15, p. 3513 - 3521
[5] Biochemistry, 2010, vol. 49, # 49, p. 10421 - 10439

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