137-17-7

Basic information

• Product Name: 2,4,5-TRIMETHYLANILINE
• Synonyms: 2,4,5-Trimethylaniline 100mg [137-17-7];2,4,5-Trimethylaniline, tech;TriMethylaniline solutio;2.4.5-TriMethy;2,4,5-Trimethylaniline Solution, 100ppm;TIMTEC-BB SBB008592;PSI-CUMIDINE;PSEUDOCUMIDINE
• CAS NO: 137-17-7
• Molecular Formula: C₉H₁₃N
• Molecular Weight: 135.21
• EINECS: 205-282-0
• Product Categories: TP - TZMethod Specific;2002/61/EC;Alpha Sort;Amines;Analytical Standards;AromaticsChemical Class;AromaticsVolatiles/ Semivolatiles;Chemical Class;European Community: ISO and DIN;T-ZAlphabetic
• Mol File: 137-17-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 62 °C
• Boiling Point: 232 °C
• Flash Point: -5 °C
• Appearance: Colorless to reddish yellow liquid
• Density: 0.78 g/mL
• Vapor Pressure: 0.0527mmHg at 25°C
• Refractive Index: 1.5130 (estimate)
• Storage Temp.: 2-8°C
• PKA: 5.01±0.10(Predicted)
• Water Solubility: 1.5g/L(28.70 oC)
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• BRN: 2352436
• CAS DataBase Reference: 2,4,5-TRIMETHYLANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,5-TRIMETHYLANILINE(137-17-7)
• EPA Substance Registry System: 2,4,5-TRIMETHYLANILINE(137-17-7)

Safety Data

• Hazard Codes: F,Xn,N,T
• Statements: 11-20/21/22-36-51/53-23/24/25-45
• Safety Statements: 16-36/37-61-45-53
• RIDADR: UN1648 3/PG 2
• WGK Germany: 2
• RTECS: BZ0520000
• Hazardous Substances Data: 137-17-7(Hazardous Substances Data)

Usage

Chemical Properties

white to light tan crystalline solid

Uses

Manufacture of dyes, organic synthesis.

General Description

White crystals or beige powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2,4,5-TRIMETHYLANILINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Hazard

Questionable carcinogen.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition 2,4,5-TRIMETHYLANILINE emits toxic fumes of nitrogen oxides.

Fire Hazard

Flash point data for 2,4,5-TRIMETHYLANILINE are not available; however, 2,4,5-TRIMETHYLANILINE is probably combustible.

Safety Profile

Confirmed carcinogen with experimental carcinogenic and tumorigenic data. Moderately toxic by ingestion. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. Used as a dye, pigment, and printing ink. See also ANILINE DYES.

InChI:InChI=1/C9H13N/c1-6-4-8(3)9(10)5-7(6)2/h4-5H,10H2,1-3H3

Synthetic route

5-nitropseudocumene (610-91-3) → 2,4,5-trimethylaniline (137-17-7)

Conditions	Yield
With hydrogenchloride; hydrogen; palladium on activated charcoal under 22800 Torr; Ambient temperature;	97%
With sodium dithionite
With iron
palladium In methanol
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 35℃; for 2h;

methanol (67-56-1) + m-toluidine hydrochloride (638-03-9) → 2,4,5-trimethylaniline (137-17-7)

Conditions	Yield
at 235℃;

methanol (67-56-1) + m-toluidine hydrochloride (638-03-9) → 2,3,4,6-tetramethylaniline (488-71-1) + isodurenol (3238-38-8) + 2,4,5-trimethylaniline (137-17-7) + 4-amino-o-xylene (95-64-7)

Conditions	Yield
je nach Mengenverhaeltnis und Temperatur; Produkt 5:Pentamethylphenol;

methanol (67-56-1) + 3,4-dimethylaniline hydrochloride (7356-54-9) → 2,4,5-trimethylaniline (137-17-7)

Conditions	Yield
at 300 - 320℃;

N,N-dimethyl-m-toluidine (121-72-2) + (E)-3-Ureido-but-2-enoic acid ethyl ester (5435-44-9, 22243-66-9) → 2,4,5-trimethylaniline (137-17-7)

Conditions	Yield
at 300℃;

N,N-dimethyl-m-toluidine (121-72-2) → 2,4,5-trimethylaniline (137-17-7)

Conditions	Yield
With zinc(II) chloride at 300℃;

ethanol (64-17-5) + acetic anhydride (108-24-7) + acetic acid (64-19-7) + 1-(2,4,5-Trimethyl-phenylazo)-[2]naphthol (94378-05-9) + zinc → 2,4,5-trimethylaniline (137-17-7) + 2,4,5-trimethylacetanilide (88166-77-2) + 1-acetylamino-naphthalen-2-ol (117-93-1) + 1-amino-2-naphthol (2834-92-6)

...Expand

hydrogenchloride (7647-01-0) + methanol (67-56-1) + 2,5-Dimethylaniline (95-78-3) → 2,4,5-trimethylaniline (137-17-7)

Conditions	Yield
at 300 - 320℃;

hydrogenchloride (7647-01-0) + formaldehyd (50-00-0) + 2,5-Dimethylaniline (95-78-3) → 2,4,5-trimethylaniline (137-17-7) + bis-(4-amino-2,5-dimethyl-phenyl)-methane (5339-30-0)

Conditions	Yield
Erhitzen des Reaktionsprodukts mit Calciumhydroxid;
Erhitzen des Reaktionsprodukts mit Natriumcarbonat;

5-nitro-pseudocumene → 2,4,5-trimethylaniline (137-17-7)

Conditions	Yield
With hydrogenchloride; tin

methanol (67-56-1) + hydrochloride of asymm.o-xylidine → 2,4,5-trimethylaniline (137-17-7)

Conditions	Yield
at 300 - 320℃;

methanol (67-56-1) + hydrochloride of p-xylidine → 2,4,5-trimethylaniline (137-17-7)

Conditions	Yield
at 300 - 320℃;

xylidine → 2,4,5-trimethylaniline (137-17-7)

Conditions	Yield
Darstellung;

hydrogenchloride (7647-01-0) + 1,3-bis-(2,4,5-trimethyl-phenyl)-triazene → 2,4,5-trimethylphenol (496-78-6) + 2,4,5-trimethylaniline (137-17-7)

3,4,6-trimethyl-2-(2,4,5-trimethyl-phenylazo)-aniline + hydrogen trichloro-stannate(II) → 2,4,5-trimethylaniline (137-17-7) + 3,4,6-trimethyl-o-phenylenediamine (4846-22-4)

1-(2,4,5-trimethyl-phenylazo)-[2]naphthylamine + copper → 2,4,5-trimethylaniline (137-17-7) + 1,2-diaminonaphthalene (938-25-0) + 2-<2.4.5-trimethyl-phenyl>-

Conditions	Yield
in verschiedenen Loesungsmitteln;

1,2,4-Trimethylbenzene (95-63-6) → 2,4,5-trimethylaniline (137-17-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 38 percent / HNO3 (d= 1,40), H2SO4 (d = 1,83) 2: 97 percent / H2, aq. HCl / 10percent Pd/C / 22800 Torr / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: nitric acid; sulfuric acid 2: Na2S2O4 View Scheme

2,4,5-trimethylaniline (137-17-7) + acetylacetone (123-54-6) → 2,4,5,6,8-pentamethyl-quinoline (50519-33-0)

Conditions	Yield
	90%
With sulfuric acid

cycl-isopropylidene malonate (2033-24-1) + 2,4,5-trimethylaniline (137-17-7) + trimethyl orthoformate (149-73-5) → 2,2-dimethyl-5-{[(2,4,5-trimethylphenyl)amino]methylene}-1,3-dioxane-4,6-dione (1129400-01-6)

Conditions	Yield
Stage #1: cycl-isopropylidene malonate; trimethyl orthoformate for 2h; Inert atmosphere; Reflux; Stage #2: 2,4,5-trimethylaniline for 2h; Inert atmosphere; Reflux;	82%

2,4,5-trimethylaniline (137-17-7) + Nitrosobenzene (586-96-9) → 1-phenyl-2-(2,4,5-trimethylphenyl)diazene

Conditions	Yield
With acetic acid at 20℃; Cooling;	79%

formaldehyd (50-00-0) + 2,4,5-trimethylaniline (137-17-7) → 1,2,4,7,8,10-hexamethyl-6H,12H-5,11-methanodibenzo<1,5>diazocine (111437-12-8)

Conditions	Yield
With hydrogenchloride In ethanol for 24h; Ambient temperature;	78%

(R)-3,5-dichloro-1-(1-cyclopropylpropyl)pyrazin-2(1H)-one (475158-80-6) + 2,4,5-trimethylaniline (137-17-7) → (R)-5-chloro-1-(1-cyclopropylpropyl)-3-(2,4,5-trimethylphenylamino)pyrazin-2(1H)-one (1173523-71-1)

Conditions	Yield
With palladium diacetate; potassium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene for 5h; Inert atmosphere; Reflux;	71%

2,4,5-trimethylaniline (137-17-7) + Benzoyl isothiocyanate (532-55-8) → 1-Benzoyl-3-(2,4,5-trimethyl-phenyl)-thiourea (117174-81-9)

Conditions	Yield
In acetone for 0.5h; Heating;	70%

methyl 3-pyridinecarboxylate (93-60-7) + 2,4,5-trimethylaniline (137-17-7) → N-mesitylnicotinamide

Conditions	Yield
With C18H15IMnN3O3; sodium t-butanolate In toluene at 120℃; for 18h; Inert atmosphere; Schlenk technique;	56%

(R)-3,5-dichloro-1-(1-cyclopropylethyl)pyrazin-2(1H)-one (1173435-13-6) + 2,4,5-trimethylaniline (137-17-7) → (R)-5-chloro-1-(1-cyclopropylethyl)-3-(2,4,5-trimethylphenylamino)pyrazin-2(1H)-one (1173435-75-0)

Conditions	Yield
Stage #1: (R)-3,5-dichloro-1-(1-cyclopropylethyl)pyrazin-2(1H)-one; 2,4,5-trimethylaniline With sodium hexamethyldisilazane In tetrahydrofuran at 0 - 10℃; Inert atmosphere; Stage #2: With water; sodium hydrogencarbonate In tetrahydrofuran	41%

4-chloro-2-(3-pyridyl)-6-(trifluoromethyl)pyrimidine (204394-69-4) + 2,4,5-trimethylaniline (137-17-7) → 4-(2,4,5-Trimethylanilino)-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine (438249-55-9)

Conditions	Yield
	30%

2,4,5-trimethylaniline (137-17-7) + phenylpropynoic acid methyl ester (4891-38-7) → (E)-methyl 3-(2-amino-3,5,6-trimethylphenyl)-3-phenylpropenoate (1041644-10-3) + (E)-methyl 3-(3-amino-2,5,6-trimethylphenyl)-3-phenylpropenoate (1041644-09-0)

Conditions	Yield
With fluorosulphonic acid at -30℃; for 1h;	A 18% B 30%
With fluorosulphonic acid at -30℃;	A 18% B 30%

2,4,5-trimethylaniline (137-17-7) + N,N-bis(2-Chloroethyl)-3-methoxypropylamine Hydrochloride (30824-26-1) → 1-(3-Methoxypropyl)-4-(2,4,5-trimethylphenyl)piperazine (76088-51-2)

Conditions	Yield
With sodium hydroxide; N-ethyl-N,N-diisopropylamine; benzenesulfonyl chloride 1) ethanol, reflux, 5.5 h; 2) tetrahydrofurane, reflux, 15 min;;	28%

2,4,5-trimethylaniline (137-17-7) + methyl 3-(4-methylphenyl)prop-2-ynoate (7515-16-4) → (E)-methyl 3-(2-amino-3,5,6-trimethylphenyl)-3-(4-methylphenyl)acrylate (1139721-55-3) + (E)-methyl 3-(3-amino-2,5,6-trimethylphenyl)-3-(4-methylphenyl)acrylate (1139719-59-7)

Conditions	Yield
With fluorosulphonic acid at -75℃;	A 19% B 11%

methyl 3-(4-methoxyphenyl)propynoate (7515-17-5) + 2,4,5-trimethylaniline (137-17-7) → (Z)-methyl 3-(3-amino-2,5,6-trimethylphenyl)-3-(4-methoxyphenyl)acrylate + (E)-methyl 3-(3-amino-2,5,6-trimethylphenyl)-3-(4-methoxyphenyl)acrylate (1139719-60-0)

Conditions	Yield
With fluorosulphonic acid at -75℃;	A 9% B 17%

2,4,5-trimethylaniline (137-17-7) + 4-(p-tolyl)but-3-yn-2-one (80221-02-9) → (Z)-4-(3-amino-2,5,6-trimethylphenyl)-4-(4-methylphenyl)but-3-en-2-one (1139719-64-4)

Conditions	Yield
With fluorosulphonic acid at -30℃;	16%

Dimethyl oxalate (553-90-2) + 2,4,5-trimethylaniline (137-17-7) → (2,4,5-trimethyl-phenyl)-oxalamic acid methyl ester + N,N'-bis-(2,4,5-trimethyl-phenyl)-oxalamide (778595-30-5)

methanol (67-56-1) + 2,4,5-trimethylaniline (137-17-7) → 1,2,4,5,7,8-hexamethyl-acridine (40505-10-0)

Conditions	Yield
With hydrogenchloride at 252℃;

methanol (67-56-1) + 2,4,5-trimethylaniline (137-17-7) → 2,3,4,6-tetramethylaniline (488-71-1) + 1,2,4,5,7,8-hexamethyl-acridine (40505-10-0)

Conditions	Yield
at 252℃; im Autoklaven;

1-bromo-butane (109-65-9) + 2,4,5-trimethylaniline (137-17-7) → N,N-dibutyl-2,4,5-trimethyl-aniline

carbon disulfide (75-15-0) + 2,4,5-trimethylaniline (137-17-7) → 5-(4-methoxy-benzylidene)-2-thioxo-3-(2,4,5-trimethyl-phenyl)-thiazolidin-4-one

Conditions	Yield
With ammonium hydroxide Behandeln des Reaktionsprodukts mit Chloressigester in Alkohol und Kochen mit Anisaldehyd in Eisessig;

phosgene (75-44-5) + 2,4,5-trimethylaniline (137-17-7) → 2,4,5-trimethylphenyl isocyanate (85324-94-3)

phthalic anhydride (85-44-9) + 2,4,5-trimethylaniline (137-17-7) → N-(2,4,5-trimethyl-phenyl)-phthalimide (40101-46-0)

phthalic anhydride (85-44-9) + 2,4,5-trimethylaniline (137-17-7) → N-(2,4,5-trimethyl-phenyl)-phthalamic acid

Conditions	Yield
man spaltet das hierbei entstandene N-<2.4.5-Trimethyl-phenyl>-phthalimid durch 1/2-stdg. Kochen mit alkoh. Kali;

formaldehyd (50-00-0) + α-naphthol (90-15-3) + 2,4,5-trimethylaniline (137-17-7) → 8,9,11-trimethyl-benz[c]acridine

Conditions	Yield
und Eingiessen der Fluessigkeit in Kalilauge;

formaldehyd (50-00-0) + 2-methyl-6-hydroxynaphthalene (17579-79-2) + 2,4,5-trimethylaniline (137-17-7) → 3,8,10,11-tetramethyl-benz[a]acridine (111584-57-7)

1,5-dibromo-pentane (111-24-0) + 2,4,5-trimethylaniline (137-17-7) → N,N'-bis-(2,4,5-trimethyl-phenyl)-pentanediyldiamine

formic acid (64-18-6) + 2,4,5-trimethylaniline (137-17-7) → N-(2,4,5-trimethylphenyl)formamide (858244-30-1)

Upstream product

• 7647-01-0 hydrogenchloride 
• 67-56-1 methanol 
• 95-78-3 2,5-Dimethylaniline 
• 95-63-6 1,2,4-Trimethylbenzene 
• 50-00-0 formaldehyd 
• 64-17-5 ethanol 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 94378-05-9 1-(2,4,5-Trimethyl-phenylazo)-[2]naphthol 
• 610-91-3 5-nitropseudocumene 
• 121-72-2 N,N-dimethyl-m-toluidine 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 7356-54-9 3,4-dimethylaniline hydrochloride 
• 638-03-9 m-toluidine hydrochloride 

Downstream Products

• 778595-30-5 N,N'-bis-(2,4,5-trimethyl-phenyl)-oxalamide 
• 488-71-1 2,3,4,6-tetramethylaniline 
• 40505-10-0 1,2,4,5,7,8-hexamethyl-acridine 
• 858244-30-1 N-(2,4,5-trimethylphenyl)formamide 
• 19241-18-0 2,4,5-trimethyl-phenyl isothiocyanate 
• 860763-34-4 (2,4,5-trimethyl-phenyl)-carbamonitrile 
• 16596-06-8 N,N'-bis-(2,4,5-trimethyl-phenyl)-formamidine 
• 95-63-6 1,2,4-Trimethylbenzene 

Relevant articles and documents

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4. Synthese von Plectranthonen, diterpenoiden Phenanthren-1,4-chinonen

The following phenanthrene-1,4-diones have been synthesized by using the photocyclization of the corresponding highly substituted stilbenes as the key step: 3-hydroxy-5,7,8-trimethyl-2-(prop-2-enyl)phenanthrene-1,4-dione (1), (RS)-, (R)-, and (S)-2--1-methylethyl)acetate (2, 31, and 32, resp.), 3-hydroxy-7,8-dimethyl-2-(prop-2-enyl)phenanthrene-1,4-dione (3), 3-hydroxy-7,8,10-trimethyl-2-(prop-2-enyl)phenanthrene-1,4-dione (4), 5,7,8-trimethyl-2-(prop-2-enyl)phenanthrene-1,4-dione (17) and 3-hydroxy-2-methylphenanthrene-1,4-dione (42).The quinones 1 and 3 proved to be identical with recently isolated plectranthons A and C.Compounds 2, 31, and 32 exhibited the same UV/VIS, IR, 1H-NMR and mass spectra as natural plectranthon B, but had different melting points.This might be due either to crystal modifications or to diastereoisomerism caused by the helical structure of the phenanthrene-1,4-dione skeleton.The spectral data of synthetic 4 were not compatible with those of natural plectranthon D for which structure 4 had been proposed based mainly on 1H-NMR arguments concerning the chemical shifts of H-C(9) and H-C(10) in 1-3.Extensive 1H-NMR investigations have now revealed that the currently stated assignments of the H-C(9)/H-C(10) AB system have to be reversed for highly substituted phenanthrene-1,4-diones: in the model compounds 2-methylphenanthrene-1,4-dione (41) and 2, H-C(10) resonates at lower field as expected (peri-position), whereas in the highly substituted congeners 1, 2, 3, 31, and 32, H-C(9) is shifted paramagnetically, a fact which had lead to the erroneous assignment of structure 4 for natural plectranthon D.