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Basic Information
| CAS No.: | 108-69-0 |
|---|---|
| Name: | 3,5-Dimethylaniline |
| Molecular Structure: | |
|
|
|
| Formula: | C8H11N |
| Molecular Weight: | 121.182 |
| Synonyms: | 3,5-Dimethylbenzeneamine;3,5-Xylidine;3,5-Dimethy Iani line;3,5-Dimethyl aniline;Product Name: 3,5-dimethylaniline;3,5-Xylidene;3,5-Xylylamine;5-Amino-1,3-xylene;3, 5-Dimethylbenzeneamine;benzenamine, 3,5-dimethyl-;1-Amino-3,5-dimethylbenzene;5-Amino-1,3-dimethylbenzene;Benzene, 1-amino-3,5-dimethyl-;3,5-Xylidine;3, 5-Xylylamine;3,5-Dimethylphenylamine;3,5-Dimethylbenzenamine; |
| EINECS: | 203-607-0 |
| Density: | 0.972 g/cm3 |
| Melting Point: | 7-9 °C |
| Boiling Point: | 218.5 °C at 760 mmHg |
| Flash Point: | 93.3 °C |
| Solubility: | <0.1 g/100 mL at 19 °C in water |
| Appearance: | clear yellow-brown to brown liquid |
| Hazard Symbols: |
 T, N
|
| Risk Codes: | 23/24/25-33-51/53 |
| Safety: | 28-36/37-45-61-28A |
| Transport Information: | UN 1711 6.1/PG 2 |
| PSA: | 26.02000 |
| LogP: | 2.46680 |
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Synthetic route
Conditions
| Conditions | Yield |
|---|---|
| With copper(I) oxide; ammonium hydroxide In 1-methyl-pyrrolidin-2-one at 80℃; for 15h; | 100% |
| With copper(l) iodide; 2-carboxyquinoline N-oxide; potassium carbonate; ammonium hydroxide In dimethyl sulfoxide at 80℃; for 23h; Inert atmosphere; | 91% |
| With copper(l) iodide; ammonia; sodium phosphate In water at 100℃; for 24h; | 86% |
| With diethylenetriaminopentaacetic acid; ammonia; copper(II) oxide; potassium hydroxide In water at 100℃; for 6h; | 74% |
| Stage #1: 5-bromo-1,3-xylene With magnesium In tetrahydrofuran Inert atmosphere; Stage #2: With C10H17NO In tetrahydrofuran; toluene at -78℃; for 2h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; water; toluene Inert atmosphere; | 74% |
Conditions
| Conditions | Yield |
|---|---|
| With borane-ammonia complex In methanol; water at 49.84℃; for 0.166667h; Catalytic behavior; | 99% |
| With sodium tetrahydroborate In water at 60℃; for 0.0166667h; | 96% |
| Stage #1: 5-nitro-m-xylene With Cu(OH)x impregnated on Fe3O4 In water for 0.0833333h; Green chemistry; Stage #2: With sodium tetrahydroborate In water at 55 - 60℃; for 0.116667h; Green chemistry; | 95% |
- 22445-41-6
3,5-dimethylphenyl iodide
- 108-69-0
3,5-dimethylaminoaniline
Conditions
| Conditions | Yield |
|---|---|
| With copper(I) oxide; ammonium hydroxide In 1-methyl-pyrrolidin-2-one at 80℃; for 15h; | 99% |
| With potassium phosphate; copper(l) iodide; N-((1-oxy-pyridin-2-yl)methyl)oxalamic acid; ammonia In water; dimethyl sulfoxide at 25℃; Schlenk technique; Inert atmosphere; Sealed tube; chemoselective reaction; | 95% |
| With copper(l) iodide; 2-carboxyquinoline N-oxide; potassium carbonate; ammonium hydroxide In dimethyl sulfoxide at 50℃; for 23h; Inert atmosphere; | 92% |
Conditions
| Conditions | Yield |
|---|---|
| With ammonium hydroxide; potassium phosphate In dimethyl sulfoxide at 80℃; UV-irradiation; | 99% |
| Multi-step reaction with 2 steps 1.1: sulfuric acid; nitric acid / 30 °C / Cooling with ice 2.1: palladium on activated charcoal / ethanol / 0.5 h / 50 °C / Autoclave 2.2: 0.83 h / 65 °C / 2250.23 Torr / Autoclave View Scheme |
- 62034-72-4
N-hydroxy-3,5-dimethylbenzamide
- 108-69-0
3,5-dimethylaminoaniline
Conditions
| Conditions | Yield |
|---|---|
| With potassium carbonate In dimethyl sulfoxide at 90℃; for 4h; Lossen Rearrangement; | 97% |
Conditions
| Conditions | Yield |
|---|---|
| With palladium/alumina; ammonia; hydrogen In toluene at 250℃; under 2250.23 Torr; Temperature; Pressure; Solvent; | 95% |
| With 5%-palladium/activated carbon; hydrazine hydrate; lithium hydroxide In 1,4-dioxane at 170℃; for 16h; Molecular sieve; Inert atmosphere; | 71% |
| With ammonia at 350℃; under 117681 - 183877 Torr; | |
| With aluminum oxide; nitrogen; ammonia; hydrogen at 450℃; under 147102 Torr; |
- 101252-04-4
3,5-dimethyl-cyclohexanone oxime
- 108-69-0
3,5-dimethylaminoaniline
Conditions
| Conditions | Yield |
|---|---|
| With Pd(OH)x/LDH In N,N-dimethyl acetamide at 130℃; for 11h; Schlenk technique; Inert atmosphere; | 91% |
- 108-69-0
3,5-dimethylaminoaniline
Conditions
| Conditions | Yield |
|---|---|
| With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane In toluene at 100℃; Sealed tube; | 88% |
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3,5-Dimethylaniline
Chemistry
Molecular Formula:C8H11N
Molar mass:121.17964g/mol
Structure:
Synonyms :3,5-Xylidene;3,5-Dimethylbenzenamine;Benzenamine, 3,5-dimethyl-;5-Amino-1,3-xylene;3,5-Xylylamine;5-Amino-m-xylene;m-Xylidine
Density:0.975 g/cm3
Flash Point:93.3 °C
Boiling Point:218.5 °C at 760 mmHg
Index of Refraction:1.559
Vapour Pressure:0.126 mmHg at 25°C
Melting point:7-9°C
Solubility: Not dissolve in water
Water solubility:<0.1 g/100 mL at 19°C
Molar mass:121.17964g/mol
Structure:
Synonyms :3,5-Xylidene;3,5-Dimethylbenzenamine;Benzenamine, 3,5-dimethyl-;5-Amino-1,3-xylene;3,5-Xylylamine;5-Amino-m-xylene;m-Xylidine
Density:0.975 g/cm3
Flash Point:93.3 °C
Boiling Point:218.5 °C at 760 mmHg
Index of Refraction:1.559
Vapour Pressure:0.126 mmHg at 25°C
Melting point:7-9°C
Solubility: Not dissolve in water
Water solubility:<0.1 g/100 mL at 19°C
Uses
3,5-Dimethylaniline(108-69-0) is used for production of pesticides, dyes, and other chemicals.
Toxicity Data With Reference
| 1. | mmo-sat 1 mg/plate | EMMUEG Environmental and Molecular Mutagenesis. 11 (Suppl 12)(1988),1. | ||
| 2. | orl-rat LD50:707 mg/kg | NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) PB214-270 . | ||
| 3. | orl-mus LD50:421 mg/kg | NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) PB214-270 . |
Other: See actual entry in RTECS for complete information.
Consensus Reports
Reported in EPA TSCA Inventory.
Safety Profile
Suspected carcinogen. Moderately toxic by ingestion. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also XYLIDINE; 2,3-XYLIDINE; 2,4-XYLIDINE; 2,5-XYLIDINE; 2,6-XYLIDINE; 3,4-XYLIDINE; 2,4-XYLIDINE HYDROCHLORIDE; 2,5-XYLIDINE HYDROCHLORIDE.
Hazard Codes:T
,N
Risk Statements:
23: Toxic by inhalation
24: Toxic in contact with skin
25: Toxic if swallowed
33: Danger of cumulative effects
51: Toxic to aquatic organisms
53: May cause long-term adverse effects in the aquatic environment
28: After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer)
37: Wear suitable gloves
39: Wear eye/face protection
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
61: Avoid release to the environment. Refer to special instructions safety data sheet
Standards and Recommendations
DFG MAK: (all isomers except 2,4-xylidene) Confirmed Animal Carcinogen with Unknown Relevance to Humans
Specification
Stability and Reactivity of 3,5-Dimethylaniline(108-69-0):
Conditions to Avoid:Incompatible materials, light, exposure to air, excess heat.
Chemical Stability:Stable under normal pressures and temperatures. Darkens on exposure to light and air.
Incompatibilities with Other Materials: Excess heat, chloroformates, acids, acid chlorides,acid anhydrides,halogens,coatings, plastics, rubber, hypochlorite.
Hazardous Decomposition Products: carbon dioxide,nitrogen oxides,Carbon monoxide.
Conditions to Avoid:Incompatible materials, light, exposure to air, excess heat.
Chemical Stability:Stable under normal pressures and temperatures. Darkens on exposure to light and air.
Incompatibilities with Other Materials: Excess heat, chloroformates, acids, acid chlorides,acid anhydrides,halogens,coatings, plastics, rubber, hypochlorite.
Hazardous Decomposition Products: carbon dioxide,nitrogen oxides,Carbon monoxide.