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3,5-Dimethylaniline
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Name

3,5-Dimethylaniline

 EINECS 203-607-0
CAS No. 108-69-0 Density 0.972 g/cm3
PSA 26.02000 LogP 2.46680
Solubility <0.1 g/100 mL at 19 °C in water Melting Point 7-9 °C
Formula C8H11N Boiling Point 218.5 °C at 760 mmHg
Molecular Weight 121.182 Flash Point 93.3 °C
Transport Information UN 1711 6.1/PG 2 Appearance clear yellow-brown to brown liquid
Safety 28-36/37-45-61-28A Risk Codes 23/24/25-33-51/53
Molecular Structure Molecular Structure of 108-69-0 (3,5-Dimethylaniline) Hazard Symbols ToxicT,DangerousN
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;

Article Data 71

3,5-Dimethylaniline Synthetic route

556-96-7

5-bromo-1,3-xylene

108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
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%
99-12-7

5-nitro-m-xylene

108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
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
ConditionsYield
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%
556-97-8

1-chloro-3,5-dimethylbenzene

108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
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
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 90℃; for 4h; Lossen Rearrangement;97%
108-68-9

3,5-Dimethylphenol

108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
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
ConditionsYield
With Pd(OH)x/LDH In N,N-dimethyl acetamide at 130℃; for 11h; Schlenk technique; Inert atmosphere;91%

5-[(3,5-dimethylphenyl)imino]-5H-5γ4-dibenzo[b,d]thiophene-5-oxide

108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane In toluene at 100℃; Sealed tube;88%
635-46-1

1,2,3,4-tetrahydroisoquinoline

99-12-7

5-nitro-m-xylene

A

91-22-5

quinoline

B

108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
With nickel-nitrogen-doped carbon framework In water at 145℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry;A 73%
B 76%
99-12-7

5-nitro-m-xylene

6872-06-6

2-methyl indoline

A

95-20-5

2-methyl-1H-indole

B

108-69-0

3,5-dimethylaminoaniline

Conditions
ConditionsYield
With nickel-nitrogen-doped carbon framework In water at 145℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry;A 74%
B 76%

3,5-Dimethylaniline Chemical Properties

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

3,5-Dimethylaniline Uses

3,5-Dimethylaniline(108-69-0) is used for production of pesticides, dyes, and other chemicals.

3,5-Dimethylaniline 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 .
4.   Carcinogenicity:3,5-Dimethylaniline(108-69-0)- Not listed as a carcinogen by  NTP, IARC,ACGIH, or CA Prop 65. 
Other: See actual entry in RTECS for complete information.

3,5-Dimethylaniline Consensus Reports

Reported in EPA TSCA Inventory.

3,5-Dimethylaniline 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

3,5-Dimethylaniline Standards and Recommendations

DFG MAK: (all isomers except 2,4-xylidene) Confirmed Animal Carcinogen with Unknown Relevance to Humans

3,5-Dimethylaniline 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.
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