| Identification | More | [Name]
3,4,5-Trimethoxyaniline | [CAS]
24313-88-0 | [Synonyms]
3,4,5-TRIMETHOXYANILINE
3,4,5-TRIMETHOXYPHENYLAMINE
3,4,5-TRIMOTHOXYANILINE
3,4,5-trimethoxy-benzenamin
3,4,5-Trimethoxy
3,4,5-Trimethoxyaniline 98%
3,4,5-TRIMETHOXYANILINE 98+%
Benzenamine, 3,4,5-trimethoxy- | [EINECS(EC#)]
246-154-4 | [Molecular Formula]
C9H13NO3 | [MDL Number]
MFCD00008393 | [Molecular Weight]
183.2 | [MOL File]
24313-88-0.mol |
| Chemical Properties | Back Directory | [Appearance]
off-white to beige-brown, grey or pink powder | [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 | [form ]
Powder | [pka]
4.35±0.10(Predicted) | [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]
24313-88-0(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R37/38:Irritating to respiratory system and skin .
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S24:Avoid contact with skin .
S36:Wear suitable protective clothing . | [RIDADR ]
2811 | [WGK Germany ]
3
| [Hazard Note ]
Harmful | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29222900 |
| Hazard Information | Back Directory | [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]
[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.
| [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]. | [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 |
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