DIMETHYL IMINODIACETATE HYDROCHLORIDE Chemical Properties

Melting point:

~170 °C (dec.)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

color 

White to Off-White

BRN 

3703236

Stability:

Hygroscopic

CAS DataBase Reference

39987-25-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2922.49.8000

MSDS

• Language:English Provider:SigmaAldrich

DIMETHYL IMINODIACETATE HYDROCHLORIDE Usage And Synthesis

Synthesis

Methanol (500 mL) was cooled to -20 °C and SOCl2 (36 mL, 0.5 mol) was added slowly and dropwise under vigorous stirring while controlling the temperature of the reaction mixture below -10 °C. Subsequently, iminodiacetic acid (13.3 g, 0.1 mol) was added all at once. The reaction mixture was stirred continuously at room temperature for 24 hours. After completion of the reaction, the volatiles were evaporated under reduced pressure at room temperature and the residue was crystallized with methanol. The product aminobisacetic acid dimethyl hydrochloride 16 g (81% yield) was obtained as a white crystalline solid. The product was characterized as follows: 1H NMR (300 MHz, D2O) δ=4.13 (s, 4H), 3.85 (s, 6H); 13C NMR (75 MHz, D2O) δ=168.08, 54.12, 47.66. Elemental analysis results (C6H12ClNO4): calculated values C 36.47%, H 6.12%, N 7.09%; measured values C 36.52%, H 6.01%, N 6.98%.

References

[1] Organic Preparations and Procedures International, 2002, vol. 34, # 1, p. 87 - 94
[2] Heterocycles, 2008, vol. 76, # 2, p. 1237 - 1248
[3] Molecules, 2008, vol. 13, # 5, p. 1111 - 1119
[4] Synthesis (Germany), 2016, vol. 48, # 24, p. 4580 - 4588
[5] Inorganic Chemistry, 2018, vol. 57, # 15, p. 8964 - 8977

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