Ethyl N-(diphenylmethylene)glycinate Chemical Properties

Melting point:

51-53 °C(lit.)

Boiling point:

195°C/2mmHg(lit.)

Density 

1.0690 (rough estimate)

refractive index 

1.5400 (estimate)

Flash point:

>110°C

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

2.22±0.50(Predicted)

form 

Crystalline Powder or Crystals

color 

White to light yellow

Sensitive 

Moisture Sensitive

λmax

247nm(Hexane)(lit.)

BRN 

1979922

Stability:

Moisture Sensitive

InChIKey

QUGJYNGNUBHTNS-UHFFFAOYSA-N

LogP

1.35-3.18 at 25℃ and pH0-14

Dissociation constant

2.3 at 25℃

CAS DataBase Reference

69555-14-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-36/37-26

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

3

F 

10-21

HS Code 

29224999

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Ethyl N-(diphenylmethylene)glycinate Usage And Synthesis

Chemical Properties

white to light yellow crystalline powder or

Uses

N-(Diphenylmethylene)glycine Ethyl Ester is used as a reagent in the synthesis of pyrazolopyrrolyl tetrahydropyran DPP-4 inhibitors.

Application

Ethyl N-(diphenylmethylene)glycinate features a diphenylmethylene group that enhances its reactivity and stability, making it particularly useful in organic synthesis and pharmaceutical development.

Reactions

Ethyl N-(diphenylmethylene)glycinate undergoes monoalkylations, dialkylations and Michael additions to ethylenic and acetylenic acceptors under appropriate solid-liquid phase transfer catalysis conditions. Further transformations of the α-disubstituted ketimines lead to α-alkylated aspartic and glutamic acid derivatives.

Synthesis

Ethyl N-(diphenylmethylene)glycinate is prepared by transimination of Benzophenone Imine with alkyl glycinate hydrochloride (room temperature/CH2Cl2).

References

[1] Patent: EP1422220, 2004, A1. Location in patent: Page 5
[2] Patent: CN104557684, 2017, B. Location in patent: Paragraph 0021-0026; 0027; 0028; 0029; 0030-0033
[3] Tetrahedron Letters, 2005, vol. 46, # 16, p. 2795 - 2797
[4] Patent: US2010/173777, 2010, A1. Location in patent: Page/Page column 23
[5] Patent: WO2016/27285, 2016, A2. Location in patent: Page/Page column 50; 51

Ethyl N-(diphenylmethylene)glycinate(69555-14-2)Related Product Information

• Ethyl acetate
• Ethanol
• Ethyl vanillin
• Tris(trimethylsilyl)phosphate
• Ethyl formate
• Ethyl acrylate
• Ethyl propionate
• Ethylbenzene
• D-2-Phenylglycine
• Ethylparaben
• 4-Hydroxy-D-(-)-2-phenylglycine
• Glycine
• Betaine
• N-(DIPHENYLMETHYLENE)GLYCINE METHYL ESTER
• DIETHYL(DIPHENYLMETHYL) PHOSPHATE
• Benzophenone imine
• Sodium hydroxymethylglycinate
• BENZYL N-(DIPHENYLMETHYLENE)-L-SERINATE