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2-Bromomalonaldehyde

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CAS:2065-75-0
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2-Bromomalonaldehyde Basic information
Product Name:2-Bromomalonaldehyde
Synonyms:2-BroMo-1,3-propanedialdehyde;2-broMo-1,3-propanedial;2-bromomalondialdehyde;Propanedial, 2-broMo-;Bromomalonaldehyde 97%;2-Bromomaloldehyde;2-Bromomalondialdehyd for synthesis;BROMOMALONALDEHYDE
CAS:2065-75-0
MF:C3H3BrO2
MW:150.96
EINECS:
Product Categories:Aldehydes;blocks;Bromides;Aldehyde Labeling Reagents;C1 to C6;Carbonyl Compounds;bc0001
Mol File:2065-75-0.mol
2-Bromomalonaldehyde Structure
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
pka1.70±0.10(Predicted)
color Pale Beige to Pale Yellow
Sensitive Air Sensitive
InChIInChI=1S/C3H3BrO2/c4-3(1-5)2-6/h1-3H
InChIKeySURMYNZXHKLDFO-UHFFFAOYSA-N
SMILESC(=O)C(Br)C=O
CAS DataBase Reference2065-75-0(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
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
Eye Dam. 1
MSDS Information
ProviderLanguage
SigmaAldrich English
2-Bromomalonaldehyde Usage And Synthesis
Chemical PropertiesLight Yellow Solid
UsesUsed in the formation of glyoxal-derived adducts from substituted guanines
Synthesis
1,1,3,3-Tetramethoxypropane

102-52-3

2-Bromomalonaldehyde

2065-75-0

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
Tag:2-Bromomalonaldehyde(2065-75-0) Related Product Information
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