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; |
Conditions | Yield |
---|---|
at 235℃; |
methanol
m-toluidine hydrochloride
A
2,3,4,6-tetramethylaniline
B
isodurenol
C
2,4,5-trimethylaniline
D
4-amino-o-xylene
Conditions | Yield |
---|---|
je nach Mengenverhaeltnis und Temperatur; Produkt 5:Pentamethylphenol; |
Conditions | Yield |
---|---|
at 300 - 320℃; |
N,N-dimethyl-m-toluidine
(E)-3-Ureido-but-2-enoic acid ethyl ester
2,4,5-trimethylaniline
Conditions | Yield |
---|---|
at 300℃; |
Conditions | Yield |
---|---|
With zinc(II) chloride at 300℃; |
ethanol
acetic anhydride
acetic acid
1-(2,4,5-Trimethyl-phenylazo)-[2]naphthol
A
2,4,5-trimethylaniline
B
2,4,5-trimethylacetanilide
C
1-acetylamino-naphthalen-2-ol
D
1-amino-2-naphthol
hydrogenchloride
methanol
2,5-Dimethylaniline
2,4,5-trimethylaniline
Conditions | Yield |
---|---|
at 300 - 320℃; |
hydrogenchloride
formaldehyd
2,5-Dimethylaniline
A
2,4,5-trimethylaniline
B
bis-(4-amino-2,5-dimethyl-phenyl)-methane
Conditions | Yield |
---|---|
Erhitzen des Reaktionsprodukts mit Calciumhydroxid; | |
Erhitzen des Reaktionsprodukts mit Natriumcarbonat; |
2,4,5-trimethylaniline
Conditions | Yield |
---|---|
With hydrogenchloride; tin |
Conditions | Yield |
---|---|
at 300 - 320℃; |
Conditions | Yield |
---|---|
at 300 - 320℃; |
2,4,5-trimethylaniline
Conditions | Yield |
---|---|
Darstellung; |
Conditions | Yield |
---|---|
in verschiedenen Loesungsmitteln; |
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 |
Conditions | Yield |
---|---|
90% | |
With sulfuric acid |
cycl-isopropylidene malonate
2,4,5-trimethylaniline
trimethyl orthoformate
2,2-dimethyl-5-{[(2,4,5-trimethylphenyl)amino]methylene}-1,3-dioxane-4,6-dione
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% |
Conditions | Yield |
---|---|
With acetic acid at 20℃; Cooling; | 79% |
formaldehyd
2,4,5-trimethylaniline
1,2,4,7,8,10-hexamethyl-6H,12H-5,11-methanodibenzo<1,5>diazocine
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 24h; Ambient temperature; | 78% |
(R)-3,5-dichloro-1-(1-cyclopropylpropyl)pyrazin-2(1H)-one
2,4,5-trimethylaniline
(R)-5-chloro-1-(1-cyclopropylpropyl)-3-(2,4,5-trimethylphenylamino)pyrazin-2(1H)-one
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
Benzoyl isothiocyanate
1-Benzoyl-3-(2,4,5-trimethyl-phenyl)-thiourea
Conditions | Yield |
---|---|
In acetone for 0.5h; Heating; | 70% |
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
2,4,5-trimethylaniline
(R)-5-chloro-1-(1-cyclopropylethyl)-3-(2,4,5-trimethylphenylamino)pyrazin-2(1H)-one
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
2,4,5-trimethylaniline
4-(2,4,5-Trimethylanilino)-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine
Conditions | Yield |
---|---|
30% |
2,4,5-trimethylaniline
phenylpropynoic acid methyl ester
A
(E)-methyl 3-(2-amino-3,5,6-trimethylphenyl)-3-phenylpropenoate
B
(E)-methyl 3-(3-amino-2,5,6-trimethylphenyl)-3-phenylpropenoate
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
N,N-bis(2-Chloroethyl)-3-methoxypropylamine Hydrochloride
1-(3-Methoxypropyl)-4-(2,4,5-trimethylphenyl)piperazine
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
methyl 3-(4-methylphenyl)prop-2-ynoate
A
(E)-methyl 3-(2-amino-3,5,6-trimethylphenyl)-3-(4-methylphenyl)acrylate
B
(E)-methyl 3-(3-amino-2,5,6-trimethylphenyl)-3-(4-methylphenyl)acrylate
Conditions | Yield |
---|---|
With fluorosulphonic acid at -75℃; | A 19% B 11% |
methyl 3-(4-methoxyphenyl)propynoate
2,4,5-trimethylaniline
B
(E)-methyl 3-(3-amino-2,5,6-trimethylphenyl)-3-(4-methoxyphenyl)acrylate
Conditions | Yield |
---|---|
With fluorosulphonic acid at -75℃; | A 9% B 17% |
2,4,5-trimethylaniline
4-(p-tolyl)but-3-yn-2-one
(Z)-4-(3-amino-2,5,6-trimethylphenyl)-4-(4-methylphenyl)but-3-en-2-one
Conditions | Yield |
---|---|
With fluorosulphonic acid at -30℃; | 16% |
Dimethyl oxalate
2,4,5-trimethylaniline
B
N,N'-bis-(2,4,5-trimethyl-phenyl)-oxalamide
Conditions | Yield |
---|---|
With hydrogenchloride at 252℃; |
methanol
2,4,5-trimethylaniline
A
2,3,4,6-tetramethylaniline
B
1,2,4,5,7,8-hexamethyl-acridine
Conditions | Yield |
---|---|
at 252℃; im Autoklaven; |
Conditions | Yield |
---|---|
With ammonium hydroxide Behandeln des Reaktionsprodukts mit Chloressigester in Alkohol und Kochen mit Anisaldehyd in Eisessig; |
phthalic anhydride
2,4,5-trimethylaniline
N-(2,4,5-trimethyl-phenyl)-phthalimide
Conditions | Yield |
---|---|
man spaltet das hierbei entstandene N-<2.4.5-Trimethyl-phenyl>-phthalimid durch 1/2-stdg. Kochen mit alkoh. Kali; |
Conditions | Yield |
---|---|
und Eingiessen der Fluessigkeit in Kalilauge; |
formaldehyd
2-methyl-6-hydroxynaphthalene
2,4,5-trimethylaniline
3,8,10,11-tetramethyl-benz[a]acridine
Molecular Structure of 2,4,5-Trimethylaniline (CAS NO.137-17-7):
EINECS: 205-282-0
IUPAC Name: 2,4,5-Trimethylaniline
Molecular Formula: C9H13N
Molecular Weight: 135.206220 g/mol
XLogP3-AA: 2.3
H-Bond Donor: 1
H-Bond Acceptor: 1
Canonical SMILES: CC1=CC(=C(C=C1C)N)C
InChI: InChI=1S/C9H13N/c1-6-4-8(3)9(10)5-7(6)2/h4-5H,10H2,1-3H3
InChIKey: BMIPMKQAAJKBKP-UHFFFAOYSA-N
Index of Refraction: 1.552
Molar Refractivity: 44.96 cm3
Molar Volume: 140.5 cm3
Surface Tension: 36.7 dyne/cm
Density: 0.962 g/cm3
Flash Point: 102.9 °C
Enthalpy of Vaporization: 47.12 kJ/mol
Boiling Point: 234.5 °C at 760 mmHg
Vapour Pressure: 0.0527 mmHg at 25 °C
Melting Point: 62 °C
Water Solubility: 1009 mg/L at 25 °C
Storage Temp.: 2-8 °C
1. | mma-sat 10 µg/plate | ENMUDM Environmental Mutagenesis. 8 (Suppl 7)(1986),1. | ||
2. | dnd-ham:lng 10 mmol/L | MUREAV Mutation Research. 77 (1980),317. | ||
3. | orl-rat LD50:1250 mg/kg | MarJV# Personal Communication from Josef V. Marhold, VUOS, 539-18, Pardubice, Czechoslovakia, to the Editor of RTECS, Cincinnati, OH, March 29, 1977 29MAR77 . |
IARC Cancer Review: Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 27 ,1982,p. 177.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . NCI Carcinogenesis Bioassay (feed); Clear Evidence: mouse, rat NCITR* National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-160 ,1979. .
Safety Information of 2,4,5-Trimethylaniline (CAS NO.137-17-7):
Hazard Codes: F ,Xn ,N ,T
Hazard Note: Harmful
Risk Statements: 11-20/21/22-36-51/53-23/24/25-45
R11:Highly flammable
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed
R36:Irritating to eyes
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed
R45:May cause cancer
Safety Statements: 16-36/37-61-45-53
S16:Keep away from sources of ignition
S36/37:Wear suitable protective clothing and gloves
S61:Avoid release to the environment. Refer to special instructions / safety data sheets
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S53:Avoid exposure - obtain special instructions before use
RIDADR: UN1648 3/PG 2
RTECS: BZ0520000
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.
DFG MAK: Animal Carcinogen, Suspected Human Carcinogen
2,4,5-Trimethylaniline with CAS Registry Number of 137-17-7 is white crystals or beige powder. It is also called for 1,2,4-Trimethyl-5-aminobenzene ; 1-Amino-2,4,5-trimethylbenzene ; 2,4,5-Trimethylanilin ; 2,4,5-Trimethylanilin [Czech] ; 2,4,5-Trimethylbenzenamine ; Benzenamine, 2,4,5-trimethyl- ; CCRIS 608 ; HSDB 2908 ; NCI-C02299 ; NSC 37004 ; Pseudocumidine ; Pseudokumidin ; Pseudokumidin [Czech] ; Psi-cumidine ; psi-Cumidine ; Aniline, 2,4,5-trimethyl- ; Benzenamine, 2,4,5-trimethyl- (9CI) . 2,4,5-Trimethylaniline may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides.
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