m-Toluidine supplier | CasNO.108-44-1

Name
m-Toluidine
EINECS 203-583-1
CAS No. 108-44-1
Article Data363
CAS DataBase
Density 0.989 g/cm³
Solubility 0.2 g/100 mL (20 °C) in water
Melting Point -30 ºC
Formula C₇H₉N
Boiling Point 203.4 ºC at 760 mmHg
Molecular Weight 107.155
Flash Point 85.6 ºC
Transport Information UN 1708 6.1/PG 2
Appearance Colorless oily liquid
Safety 53-28-36/37-45-61
Risk Codes 45-23/24/25-33-50
Molecular Structure
Hazard Symbols T,N
Synonyms 3-Aminophenylmethane;3-Aminotoluen;m-Aminotoluene;3-Amino-1-methylbenzene;1-Amino-3-methylbenzene;3-Methylbenzenamine;Meta Toluidine;3-Methylalanine;Meta Toluidine (MT);benzenamine, 3-methyl-;3-Methylaniline;m-Tolylamine;m-Methylaniline;m-Methylbenzenamine;Aniline, 3-methyl-;3-Toluidine;3-Aminotoluene;
PSA 26.02000
LogP 2.15840

Synthetic route

: 99-61-6
3-nitro-benzaldehyde

: 108-44-1
1-amino-3-methylbenzene

Conditions

Conditions	Yield
With triethylsilane; palladium dichloride In ethanol for 1h; Inert atmosphere; Reflux;	98%
With borohydride exchange resin; nickel diacetate In methanol for 5h; Ambient temperature;	97%
With palladium 10% on activated carbon; ammonium formate In ethanol at 100℃; for 24h; Reagent/catalyst;	92%

: 591-17-3
meta-bromotoluene

: 108-44-1
1-amino-3-methylbenzene

Conditions

Conditions	Yield
With ammonium hydroxide; caesium carbonate In water for 3.5h; Reflux; Green chemistry;	90%
With ammonium hydroxide; caesium carbonate In acetonitrile for 7h; Reflux; Green chemistry;	89%
With copper(l) iodide; ammonia; sodium phosphate In water at 100℃; for 24h;	87%

: 99-08-1
1-methyl-3-nitrobenzene

: 108-44-1
1-amino-3-methylbenzene

Conditions

Conditions	Yield
With [1-butyl-2,3-dimethylimidazolium][tppm] stabilized rhodium nanoarticles at 50℃; under 22502.3 Torr; for 5h; Ionic liquid; Autoclave; chemoselective reaction;	100%
With cadmium sulphide; ammonium formate In water at 20℃; for 14h; Inert atmosphere; Irradiation; Sealed tube;	100%
With water; oxalic acid; titanium(IV) oxide for 3h; Wavelength; Irradiation; Inert atmosphere; Sealed tube; Green chemistry; chemoselective reaction;	100%

: 625-95-6
3-Iodotoluene

: 108-44-1
1-amino-3-methylbenzene

Conditions

Conditions	Yield
With ammonium hydroxide; caesium carbonate In acetonitrile for 7h; Reflux; Green chemistry;	90%
With acetamidine hydrochloride; caesium carbonate In N,N-dimethyl-formamide at 140℃; for 20h; Inert atmosphere; Green chemistry;	76%
With ammonium hydroxide; copper(l) iodide; N,N'-bis(3,5-dimethoxyphenyl)cyclopentane-1,1-dicarboxamide; caesium carbonate In dimethyl sulfoxide at 20℃; for 24h; Inert atmosphere; Sealed tube;	75%

: 588-04-5
3,3'-dimethylazobenzene

: 108-44-1
1-amino-3-methylbenzene

Conditions

Conditions	Yield
With formic acid; zinc In methanol at 20℃; for 0.0833333h;	95%
With ammonium formate; nickel In methanol at 20℃; for 0.0833333h;	95%
With zinc In methanol at 25℃; for 0.133333h; Inert atmosphere;	95%

: 7149-70-4
2-bromo-5-nitrotoluene

: 108-44-1
1-amino-3-methylbenzene

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrazine hydrate In methanol at 120℃; for 0.25h; Microwave irradiation;	92%

: 100-80-1
3-methylstyrene

: 108-44-1
1-amino-3-methylbenzene

Conditions

Conditions	Yield
With methanesulfonic acid; trimethylsilylazide In tetrachloromethane at 80℃; for 4h;	80%

: 111-71-7
heptanal

: 99-08-1
1-methyl-3-nitrobenzene

A: N-heptyl-3-methylaniline

B: 108-44-1
1-amino-3-methylbenzene

Conditions

Conditions	Yield
With hydrogen In toluene at 115℃; under 37503.8 Torr; Flow reactor;	A 85 %Chromat. B 15 %Chromat.
With hydrogen In toluene at 100℃; under 22502.3 Torr; Flow reactor;	A 85 %Chromat. B 11 %Chromat.

...Expand

: 7287-81-2
1-(m-methylphenyl)ethanol

: 108-44-1
1-amino-3-methylbenzene

Conditions

Conditions	Yield
With sodium azide; trifluoroacetic acid In hexane at 40℃; for 4h; Sealed tube;	53%
With sodium azide; methanesulfonic acid; trifluoroacetic acid In hexane at 40℃; for 6h;	53%

: 32578-31-7
3-tolyl triflate

: 108-44-1
1-amino-3-methylbenzene

Conditions

Conditions	Yield
Stage #1: 3-tolyl triflate With bis(bis(trimethylsilyl)amido)zinc(II); tri-tert-butyl phosphine; tetrabutylammomium bromide; lithium chloride; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 50℃; for 6h; Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether	91%

: 10335-81-6
3-methylphenylhydroxamic acid

: 108-44-1
1-amino-3-methylbenzene

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 90℃; for 2h; Lossen rearrangement;	99%
With potassium carbonate In dimethyl sulfoxide at 90℃; for 2h; Lossen Rearrangement;	99%
Stage #1: 3-methylphenylhydroxamic acid With potassium carbonate In dimethyl sulfoxide at 90℃; for 3h; Lossen Rearrangement; Stage #2: With hydrogenchloride In water; dimethyl sulfoxide at 20℃; for 0.0833333h;

: 1610-01-1
3-methylcyclohex-2-en-1-one oxime

: 108-44-1
1-amino-3-methylbenzene

Conditions

Conditions	Yield
With hydrogenchloride; acetic anhydride In 3-methylcyclohexenone oxime hydrochloride; acetic acid	81%

: 99-61-6
3-nitro-benzaldehyde

A: 6850-35-7
3-methylcyclohexan-1-amine

B: 108-44-1
1-amino-3-methylbenzene

Conditions

Conditions	Yield
With 5% palladium on Al2O3; hydrogen In tetrahydrofuran at 100℃; under 7500.75 Torr; Flow reactor;

: 108-39-4
3-methyl-phenol

: 108-44-1
1-amino-3-methylbenzene

Conditions

Conditions	Yield
With 5%-palladium/activated carbon; hydrazine hydrate; lithium hydroxide In 1,4-dioxane at 170℃; for 16h; Molecular sieve; Inert atmosphere;	72%
With aluminum oxide; ammonia at 450℃;
With copper-aluminium oxide; nitrogen; ammonia; hydrogen at 470℃; under 147102 Torr;
With aluminum oxide; ammonia at 420℃;
With palladium on activated charcoal; ammonia; hydrogen In toluene at 200℃; under 4500.45 Torr; for 24h; chemoselective reaction;	80 %Chromat.

: 591-24-2, 625-96-7
3-Methylcyclohexanone

: 108-44-1
1-amino-3-methylbenzene

Conditions

Conditions	Yield
With ethene; 5%-palladium/activated carbon; ammonium acetate; potassium carbonate In acetonitrile at 90℃; under 760.051 Torr; for 15h; Reagent/catalyst; Schlenk technique;	78%
Stage #1: 3-Methylcyclohexanone With hydroxylamine hydrochloride; potassium carbonate In N,N-dimethyl acetamide at 20℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: at 130℃; for 5h; Inert atmosphere;	72%
With styrene; ammonium hydroxide In 1-methyl-pyrrolidin-2-one at 120℃; for 20h; Sealed tube; Inert atmosphere;	85 %Chromat.

: 4113-72-8
1-azido-3-methylbenzene

: 108-44-1
1-amino-3-methylbenzene

Conditions

Conditions	Yield
With iron; nickel dichloride In tetrahydrofuran for 1h; ice bath;	80%
With (thermal decomposition) In decalin at 141.3℃; Rate constant;
With sodium tetrahydroborate In methanol; water at 20℃; for 0.233333h; Green chemistry;	> 99 %Chromat.
With sodium tetrahydroborate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In methanol; water at 20℃; for 0.166667h;
With sodium tetrahydroborate In water at 20℃; for 0.1h; Green chemistry;	> 99 %Chromat.

: 99-04-7
m-Toluic acid

: 108-44-1
1-amino-3-methylbenzene

Conditions

Conditions	Yield
Stage #1: m-Toluic acid With trifluorormethanesulfonic acid; trimethylsilylazide In chloroform at 90℃; for 0.0533333h; Schmidt Reaction; Flow reactor; Stage #2: With water In methanol; chloroform at 20℃; Schmidt Reaction; Flow reactor;	79%
With hydrogen azide; chloroform; sulfuric acid
With thionyl chloride; hydroxylamine-O-sulfonic acid 1) 1h, reflux, 2) toluene, 6h, reflux; Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1.1: 1,1'-carbonyldiimidazole / dimethyl sulfoxide / 1 h / 20 °C / Inert atmosphere 1.2: 18 h / 20 °C / Inert atmosphere 2.1: potassium carbonate / dimethyl sulfoxide / 3 h / 90 °C 2.2: 0.08 h / 20 °C View Scheme

: 4-(m-tolyl)-1,2,4-dithiazolidine-3,5-dione

: 108-44-1
1-amino-3-methylbenzene

Conditions

Conditions	Yield
With L-Cysteine In aq. phosphate buffer; dimethyl sulfoxide at 20℃; pH=7.4; Reagent/catalyst;

: 99-08-1
1-methyl-3-nitrobenzene

: 100-51-6
benzyl alcohol

A: 108-44-1
1-amino-3-methylbenzene

B: 65-85-0
benzoic acid

Conditions

Conditions	Yield
With potassium hydroxide In 1,3,5-trimethyl-benzene at 160℃; for 24h; Inert atmosphere; Overall yield = 88 percent;

...Expand

: 99-08-1
1-methyl-3-nitrobenzene

: 98-83-9
isopropenylbenzene

A: 108-44-1
1-amino-3-methylbenzene

B: N-(3-methylphenyl)-N-(3-phenylbutyl)amine

Conditions

Conditions	Yield
With carbon monoxide; hydrogen; chloro(1,5-cyclooctadiene)rhodium(I) dimer at 130℃; under 67505.4 Torr; for 48h; Reduction; alkylation;	A n/a B 66%

...Expand

: 17933-03-8
m-tolylboronic acid

: 108-44-1
1-amino-3-methylbenzene

Conditions

Conditions	Yield
With N-Bromosuccinimide; CYANAMID; bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile at 20℃; for 2h; Reagent/catalyst; Solvent; chemoselective reaction;	89%
With N-Bromosuccinimide; N-methoxylamine hydrochloride; bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile at 20℃;	74%

: 99-08-1
1-methyl-3-nitrobenzene

A: 108-44-1
1-amino-3-methylbenzene

B: 588-04-5
3,3'-dimethylazobenzene

C: 19618-06-5, 71297-97-7, 116723-90-1
3,3'-dimethylazoxybenzene

Conditions

Conditions	Yield
With hydrazine hydrate; nickel(II) nitrate; zinc In tert-butyl alcohol for 0.666667h; Heating;	A 18% B 5 % Chromat. C 54%
With hydrazine hydrate; nickel(II) nitrate; zinc In ethanol for 5h; Heating;	A 30 % Chromat. B 10% C 33%
With carbon monoxide; water; sodium formate; (Ph4C4CO)(CO)3Ru In tetrahydrofuran at 105℃; under 25857.4 Torr; for 4h;	A 96 % Chromat. B 0.5 % Chromat. C 3.5 % Chromat.

...Expand

: {[4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)phenyl]phenylmethylene}-m-tolylamine

: 108-44-1
1-amino-3-methylbenzene

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran at 20℃;	88%

: 537-92-8
3-Methylacetanilide

A: 64-17-5
ethanol

B: 108-44-1
1-amino-3-methylbenzene

C: 102-27-2
N-ethyl-m-toulidine

Conditions

Conditions	Yield
With tris(2,4-pentanedionato)ruthenium(III); ytterbium(III) trifluoromethanesulfonate nonohydrate; hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In tetrahydrofuran at 150℃; under 3750.38 Torr; for 15h; Autoclave;	A n/a B n/a C 82%

...Expand

: 17478-66-9
phenyl-m-tolyl-diazene

A: 62-53-3
aniline

B: 108-44-1
1-amino-3-methylbenzene

Conditions

Conditions	Yield
With potassium hydroxide; nickel-incorporated hexagonal mesoporous aluminophosphate In isopropyl alcohol at 82.84℃; for 2h;	A 54% B 37%

: 537-92-8
3-Methylacetanilide

A: 64-17-5
ethanol

B: 108-44-1
1-amino-3-methylbenzene

Conditions

Conditions	Yield
With hydrogen In toluene at 160℃; under 45004.5 Torr; for 15h; Catalytic behavior; Autoclave;	A 89 %Chromat. B 85%
With {Ru(H)(BH4)(CO)(3-(di-tert-butylphosphino)-N-((1-methyl-1H-imidazol-2-yl)methyl)propylamine)}; hydrogen In isopropyl alcohol at 120℃; under 22502.3 Torr; for 18h; Autoclave;	A 99 %Chromat. B 98 %Chromat.

: 7149-75-9
3-methyl-4-chloroaniline

: 108-67-8
1,3,5-trimethyl-benzene

A: 73728-78-6
4-amino-2,2',4',6'-tetrmethyl-biphenyl

B: 108-44-1
1-amino-3-methylbenzene

Conditions

Conditions	Yield
With triethylamine In 2,2,2-trifluoroethanol for 5h; Photolysis;	A 62% B n/a

...Expand

: 619-25-0
3-Nitrobenzyl alcohol

: 108-44-1
1-amino-3-methylbenzene

Conditions

Conditions	Yield
With triethylsilane; palladium dichloride In ethanol at 20℃; for 2h; Inert atmosphere;	86%

: 696-44-6
N-methyl-m-toluidine

: 108-44-1
1-amino-3-methylbenzene

Conditions

Conditions	Yield
With dichloro(dimethylglyoxime)(dimethylglyoximato)cobalt(III); (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; triethylamine In acetonitrile at -78℃; for 24h; Reagent/catalyst; Sealed tube; Inert atmosphere; Irradiation;	100%

: 99-08-1
1-methyl-3-nitrobenzene

A: 108-44-1
1-amino-3-methylbenzene

B: 621-26-1
3,3'-dimethylhydrazobenzene

Conditions

Conditions	Yield
With potassium hydroxide; aluminium In methanol at 20℃; for 0.25h; Reduction; Reductive coupling;	A 3% B 95%

m-Toluidine Consensus Reports

Reported in EPA TSCA Inventory.

m-Toluidine Standards and Recommendations

OSHA PEL: TWA 2 ppm (skin)
ACGIH TLV: TWA 2 ppm (skin); Not Classifiable as a Human Carcinogen
DOT Classification: 6.1; Label: Poison

m-Toluidine Analytical Methods

For occupational chemical analysis use OSHA: #ID-73.

m-Toluidine Specification

The m-Toluidine, with the CAS registry number 108-44-1, is also known as Benzenamine, 3-methyl-. It belongs to the product categories of Intermediates of Dyes and Pigments; 3-Amino-1-Methylbenzene; Azo dye; Organics. Its EINECS registry number is 203-583-1. This chemical's molecular formula is C₇H₉N and molecular weight is 107.15. What's more, both its IUPAC name and systematic name are the same which is called 3-Methylaniline. This chemical can be obtained by inter-nitrotoluene of reduction with iron powder. It can be used as analytical reagent, but also for the organic and synthetic dyes. In addition, m-Toluidine can be used as cationic dyes, color film reagent intermediates.

Physical properties about m-Toluidine are: (1)ACD/LogP: 1.40; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.33; (4)ACD/LogD (pH 7.4): 1.4; (5)ACD/BCF (pH 5.5): 5.82; (6)ACD/BCF (pH 7.4): 6.77; (7)ACD/KOC (pH 5.5): 117.62; (8)ACD/KOC (pH 7.4): 136.68; (9)#H bond acceptors: 1; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 26.02 Å²; (13)Index of Refraction: 1.567; (14)Molar Refractivity: 35.31 cm³; (15)Molar Volume: 107.9 cm³; (16)Surface Tension: 39.5 dyne/cm; (17)Density: 0.992 g/cm³; (18)Flash Point: 85.6 °C; (19)Enthalpy of Vaporization: 43.96 kJ/mol; (20)Boiling Point: 203.4 °C at 760 mmHg; (21)Vapour Pressure: 0.278 mmHg at 25 °C.

When you are dealing with this chemical, you should be very careful. This chemical may present an immediate or delayed danger to one or more components of the environment. It is toxic by inhalation, in contact with skin and if swallowed. In addition, it is very toxic to aquatic organisms and may cause cancer. Therefore, you should wear suitable protective clothing and gloves. You must avoid exposuring and releasing to the environment. In case of accident or if you feel unwell seek medical advice immediately.

You can still convert the following datas into molecular structure:
(1) SMILES: Cc1cc(N)ccc1
(2) InChI: InChI=1S/C7H9N/c1-6-3-2-4-7(8)5-6/h2-5H,8H2,1H3
(3) InChIKey: JJYPMNFTHPTTDI-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
bird - wild	LD50	oral	242mg/kg (242mg/kg)	Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983. Link to PubMed
cat	LD50	oral	> 50mg/kg (50mg/kg)	National Technical Information Service. Vol. OTS0573041,
mouse	LD50	intraperitoneal	116mg/kg (116mg/kg)	Archivio Italiano di Scienze Farmacologiche. Vol. 1, Pg. 284, 1951.
mouse	LD50	oral	740mg/kg (740mg/kg)	Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 25(8), Pg. 50, 1981.
rabbit	LD50	oral	750mg/kg (750mg/kg)	Vsesoyuznyi Institut Nauchnoi i Tekhnicheskoi Informatsii Vol. #4035-77,
rabbit	LD50	skin	3250mg/kg (3250mg/kg)	National Technical Information Service. Vol. OTS0573041,
rat	LD50	oral	450mg/kg (450mg/kg)	Journal of Pharmacology and Experimental Therapeutics. Vol. 90, Pg. 260, 1947.

Product Name

m-Toluidine

Synthetic route

m-Toluidine Consensus Reports

m-Toluidine Standards and Recommendations

m-Toluidine Analytical Methods

m-Toluidine Specification

Related Products

Hot Products