3,4,5-Trimethoxyaniline Chemical Properties

Melting point:

110-113 °C (lit.)

Boiling point:

316.88°C (rough estimate)

Density 

1.1967 (rough estimate)

refractive index 

1.4760 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

4.35±0.10(Predicted)

form 

Powder

color 

Off-white to beige-brown, gray, or pink

BRN 

642919

InChI

InChI=1S/C9H13NO3/c1-11-7-4-6(10)5-8(12-2)9(7)13-3/h4-5H,10H2,1-3H3

InChIKey

XEFRNCLPPFDWAC-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

24313-88-0(CAS DataBase Reference)

EPA Substance Registry System

3,4,5-Trimethoxyaniline (24313-88-0)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

37/38-36/37/38-20/21/22

Safety Statements 

22-24/25-37/39-26-24-36

RIDADR 

2811

WGK Germany 

3

Hazard Note 

Harmful

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29222900

MSDS

• Language:English Provider:3,4,5-Trimethoxyaniline
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3,4,5-Trimethoxyaniline Usage And Synthesis

Chemical Properties

3,4,5-Trimethoxyaniline is off-white to beige-brown, grey or pink powder

Uses

3,4,5-Trimethoxyaniline is a tri-substituted aniline derivative with sympatholytic activity. It is used in the preparation of a novel class of anticancer agents.

Application

3,4,5-Trimethoxyaniline can be used:
(1) As experimental studies, infrared spectra and laser Raman spectra of 3,4,5-trimethoxyaniline were investigated^[1].
(2) Tropanilisation, detropanilisation and Schiff base formation in the reaction of 3,4,5-trimethoxyaniline with tropanilide ions as organic reaction reagents^[2].

Application

[1] BANDANA SHARMA; Shweta P; Munish Kumar Yadav. MOLECULAR STRUCTURE, EXPERIMENTAL AND THEORETICAL (HF, DFT) SPECTRAL ANALYSIS OF 3,4,5- TRIMETHOXYANILINE[J]. Rasayan Journal of Chemistry, 2023. DOI:10.31788/rjc.2023.1628371.
[2] J. TSUNETSUGU; S. E; M SATO. ChemInform Abstract: TROPENYLATION, DETROPENYLATION AND SCHIFF BASE FORMATION IN THE REACTION OF 3,4,5-TRIMETHOXYANILINE WITH TROPENYLIUM ION[J]. ChemInform, 1975. DOI:10.1002/chin.197545221.

Synthesis

Step B / Intermediate B9: Synthesis of 3,4,5-trimethoxyaniline To a solution of 1,2,3-trimethoxy-5-nitrobenzene (6.64 g, 31.2 mmol) in ethanol (250 mL) was added palladium carbon (10%, 300 mg) and hydrazine hydrate (85%, 5.7 mL). The reaction mixture was heated to reflux for 1 hour after gas release ceased. Upon completion of the reaction, the mixture was cooled to room temperature and the catalyst was removed by filtration followed by evaporation of the solvent to afford 3,4,5-trimethoxyaniline (5.5 g, 96.4% yield) as a white solid. The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 5.86 (s, 2H), 4.82 (br, 2H), 3.64 (s, 6H), 3.50 (s, 3H).

References

[1] Patent: WO2012/92880, 2012, A1. Location in patent: Page/Page column 60
[2] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 9, p. 3414 - 3425
[3] Chemische Berichte, 1888, vol. 21, p. 615
[4] Australian Journal of Scientific Research, Series A: Physical Sciences, 1950, vol. 3, p. 467,500
[5] Journal of Pharmacy and Pharmacology, 1958, vol. 10, p. 47,59

3,4,5-Trimethoxyaniline(24313-88-0)Related Product Information

• Trimethyl phosphite
• 4-(Trifluoromethoxy)aniline
• (Trifluoromethoxy)benzene
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• m-Anisidine
• p-Anisidine
• o-Anisidine
• 3,4,5-TRIMETHOXYPHENYL ISOTHIOCYANATE
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• 3,4,5-TRIMETHOXYPHENYL ISOCYANATE
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• 3,4,5-TRIMETHOXY-ACETOACETANILIDE
• 2-CHLORO-N-(3,4,5-TRIMETHOXYPHENYL)ACETAMIDE
• ASISCHEM C66342
• 4-(3,4,5-TRIMETHOXYPHENYL)-3-THIOSEMICARBAZIDE