2,5-DIMETHOXYTEREPHTHALALDEHYDE Chemical Properties

Melting point:

209-213 °C

Boiling point:

371℃

Density 

1.207

Flash point:

168℃

storage temp. 

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

form 

solid

color 

Light yellow to yellow

InChI

InChI=1S/C10H10O4/c1-13-9-3-8(6-12)10(14-2)4-7(9)5-11/h3-6H,1-2H3

InChIKey

YSIIHTHHMPYKFP-UHFFFAOYSA-N

SMILES

C1(C=O)=CC(OC)=C(C=O)C=C1OC

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

HS Code 

2912490090

2,5-DIMETHOXYTEREPHTHALALDEHYDE Usage And Synthesis

Uses

1. Synthesis of bis(N-salicylidene-aniline)s BSANs 2. COF applications

Synthesis

1. To a solution of 1,4-dimethoxybenzene (10.0 g, 72.3 mmol) in 1,4-dioxane (30 mL), 38% aqueous formaldehyde (5 mL) and paraformaldehyde (3.0 g, 99.0 mmol) were added sequentially. The reaction mixture was heated to 90°C and concentrated hydrochloric acid (5 mL each) was added in two portions over 30 minutes. The reaction mixture was continued to be heated for 1 hour and then 30 mL of concentrated hydrochloric acid was added. Cooled to room temperature, a white precipitate was precipitated, collected by filtration and dried under vacuum. The crude product was recrystallized from acetone to give 1,4-bis(chloromethyl)-2,5-dimethoxybenzene (4.5 g, 26% yield) as a white solid. 2. 1,4-bis(chloromethyl)-2,5-dimethoxybenzene (15.0 g, 63.8 mmol) and hexamethylenetetetramine (18.0 g, 127.6 mmol) were dissolved in chloroform (50 mL) and refluxed and stirred for 24 hours. After the reaction was completed, it was cooled to room temperature and the light yellow precipitate was collected by filtration. The precipitate was dissolved in water (30 mL), acidified by the addition of acetic acid (10 mL) and stirred at 90 °C for 24 hours. After cooling to room temperature, it was extracted with dichloromethane (200 mL). The organic phase was washed three times with water (200 mL) and dried over anhydrous sodium sulfate. After evaporating the solvent, the residue was recrystallized from ethanol to give 2,5-dimethoxybenzene-1,4-dicarboxaldehyde (5.5 g, 45% yield) as a bright yellow solid. 1H NMR (300 MHz, CDCl3) δ 10.50 (s, 2H), 7.26 (s, 2H), 3.95 (s, 6H). 13C NMR (101 MHz, CDCl3) δ 189.19, 155.73, 129.15, 110.92, 77.33, 77.01, 76.70, 56.23. FTMS for C10H10O4: calcd. m/z 195.1 [M + 1]+; found 194.1.

References

[1] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 10, p. 2755 - 2756
[2] Science China Chemistry, 2018, vol. 61, # 7, p. 857 - 862
[3] Journal of the American Chemical Society, 2018, vol. 140, # 3, p. 984 - 992
[4] Journal of Molecular Structure, 2016, vol. 1106, p. 121 - 129
[5] Journal of the American Chemical Society, 1950, vol. 72, p. 2992

2,5-DIMETHOXYTEREPHTHALALDEHYDE(7310-97-6)Related Product Information

• 2,5-DIAMINO-3-PICOLINE,
• Ethyl 2,5-dichloro-1,3-thiazole-4-carboxylate
• 2,5-Dichloro-quinazoline
• 2,5-diMethylH-iMidazo[1,2-a]pyridine-3-carboxylic acid
• 2,5-DIMETHOXYTEREPHTHALALDEHYDE
• 2 5-BIS(3' 7'-DIMETHYLOCTYLOXY)TEREPHTA&
• 2 5-BIS(HEXYLOXY)TEREPHTHALALDEHYDE 98
• 2 5-BIS(OCTYLOXY)TEREPHTHALALDEHYDE 98
• 2-METHOXY-5-(2-ETHYLHEXYLOXY)TEREPHTHALALDEHYDE
• 2,5-DIMETHOXYTEREPHTHALALDEHYDE, TECH
• 2-METHOXY-5-(3',7'-DIMETHYLOCTYLOXY)TEREPHTHALALDEHYDE
• RARECHEM AL BI 0865
• RARECHEM AL BF 0934
• RARECHEM AL BE 0934
• ALPHA,ALPHA'-DIBROMO-2,5-DIMETHOXY-1,4-DIACETYLBENZENE
• 1,4-DIMETHOXY-2,5-DIACETYLBENZENE
• RARECHEM AL BE 0910
• RARECHEM AL BI 0934