Dimethyl 5-aminoisophthalate Chemical Properties

Melting point:

178-181 °C (lit.)

Boiling point:

178-180 °C

Density 

1.248±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

Soluble in Chloroform.

pka

2.31±0.10(Predicted)

form 

powder to crystal

color 

White to Light yellow to Light orange

BRN 

2116565

InChI

InChI=1S/C10H11NO4/c1-14-9(12)6-3-7(10(13)15-2)5-8(11)4-6/h3-5H,11H2,1-2H3

InChIKey

DEKPYXUDJRABNK-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

99-27-4(CAS DataBase Reference)

NIST Chemistry Reference

5-Aminoisophthalic acid, dimethyl ester(99-27-4)

EPA Substance Registry System

1,3-Benzenedicarboxylic acid, 5-amino-, dimethyl ester (99-27-4)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

TSCA 

Yes

HS Code 

29224999

MSDS

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

Dimethyl 5-aminoisophthalate Usage And Synthesis

Chemical Properties

Solid

Uses

Dimethyl 5-aminoisophthalate is a important organic intermediate. It can be used in agrochemical, pharmaceutical and dyestuff field. Hexagonal assembly of double helices of luminescent calcium 5-aminoisophthalate coordination polymer leaves enough room for the formation of loosely held water pipes, which could be dehydrated at very low temperatures.

Synthesis

The general procedure for the synthesis of dimethyl 5-aminoisophthalate from dimethyl 5-nitroisophthalate was as follows: the hydrogenation of nitroaromatics was carried out in a PTFE-lined stainless steel autoclave equipped with a manometer and a magnetic stirrer. The procedure was as follows: 0.5 mmol of dimethyl 5-nitroisophthalate, 15 mol% of Co/C-N-X catalyst, 100 μL of n-hexadecane, and 2 mL of solvent were mixed and added to the reactor at room temperature. The autoclave was purged several times using hydrogen to remove air. After the preset reaction temperature was reached, the hydrogen pressure was adjusted to 1 MPa and a magnetic stirrer (600 r/min) was activated to start the reaction. Upon completion of the reaction, the solid catalyst in the reaction solution was separated by centrifugation. The products in the reaction solution were quantitatively analyzed and structurally identified by gas chromatography-mass spectrometry (Shimadzu GCMS-QP5050A, equipped with a 0.25 mm × 30 m DB-WAX capillary column). Nuclear magnetic resonance hydrogen (1H NMR) and carbon (13C NMR) spectral data were acquired on a Bruker Avance III 400 spectrometer using CDCl3 or DMSO-d6 as solvents and tetramethylsilane (TMS) as an internal standard. Pure products from amplification experiments were obtained by fast column chromatography (eluent was a solvent mixture of petroleum ether and ethyl acetate) purification.

References

[1] ACS Catalysis, 2015, vol. 5, # 3, p. 1526 - 1529
[2] Journal of the Chemical Society, 1905, vol. 87, p. 1265
[3] Journal fuer Praktische Chemie (Leipzig), 1882, vol. <2> 25, p. 505,515
[4] Australian Journal of Chemistry, 1997, vol. 50, # 12, p. 1159 - 1182
[5] Patent: US2004/82811, 2004, A1

Dimethyl 5-aminoisophthalate (99-27-4)Related Product Information

• Dimethyl sulfide
• Dimethyl sulfoxide
• Dimethyl ether
• S,S'-Dimethyl dithiocarbonate
• Methyl anthranilate
• Biphenyl dimethyl dicarboxylate
• Dimethyl malate
• Dimethyl isophthalate
• Dimethyl terephthalate
• 4-Aminobenzoic acid
• 5-Aminoisophthalic acid
• ETHANE
• Dimethyl fumarate
• Dacthal
• N,N-Dimethylformamide
• Mono-methyl isophthalate
• Dimethyl phthalate
• Dimethyl succinate