2-Bromomalonaldehyde Chemical Properties

Melting point:

132-136 °C(lit.)

Boiling point:

134.8±25.0 °C(Predicted)

Density 

1.750±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

Acetonitrile (Slightly), DMSO (Slightly)

form 

Solid

pka

1.70±0.10(Predicted)

color 

Pale Beige to Pale Yellow

Sensitive 

Air Sensitive

InChI

InChI=1S/C3H3BrO2/c4-3(1-5)2-6/h1-3H

InChIKey

SURMYNZXHKLDFO-UHFFFAOYSA-N

SMILES

C(=O)C(Br)C=O

CAS DataBase Reference

2065-75-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant/Keep Cold

HS Code 

29130000

MSDS

• Language:English Provider:SigmaAldrich

2-Bromomalonaldehyde Usage And Synthesis

Chemical Properties

Light Yellow Solid

Uses

Used in the formation of glyoxal-derived adducts from substituted guanines

Synthesis

1,1,3,3-tetramethoxypropane (23) (10 g) was used as a raw material, and a solution of water (H2O, 11 mL) with concentrated HCl (0.43 mL) was stirred at room temperature for 10 minutes. Subsequently, Br2 (3.1 mL) was slowly added dropwise to the above solution at room temperature for a controlled time of 50 minutes or more. After the dropwise addition was completed, the reaction mixture was continued to be stirred at room temperature for 20 minutes. After completion of the reaction, the mixture was concentrated under vacuum. The resulting residual solid was washed with water (H2O) to give the final target product 2-bromomalonaldehyde (24) (3.6 g, 39%) as a yellow solid. The melting point of the product was 147-148 °C; 1H NMR (CDCl3) δ 4.73-4.80 (1H,m),8.47 (2H,br s); FAB MS m/e (M-H)-149.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 235 - 238
[2] Patent: US2005/85492, 2005, A1. Location in patent: Page/Page column 25
[3] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 5, p. 1219 - 1233
[4] Organic and Biomolecular Chemistry, 2005, vol. 3, # 18, p. 3388 - 3398
[5] Patent: WO2004/67521, 2004, A1. Location in patent: Page 68

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