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4-Aminotoluene-3-sulfonic acid

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Name

4-Aminotoluene-3-sulfonic acid

EINECS 201-831-3
CAS No. 88-44-8 Density 1.431 g/cm3
PSA 88.77000 LogP 2.48590
Solubility 32g/L(19 oC) Melting Point 300 °C
Formula C7H9NO3S Boiling Point 375oC
Molecular Weight 187.219 Flash Point N/A
Transport Information UN 2585 8/PG 3 Appearance beige crystalline powder
Safety 53-26-27-28-36/37/39-45-28A Risk Codes 45-34
Molecular Structure Molecular Structure of 88-44-8 (4-Aminotoluene-3-sulfonic acid) Hazard Symbols ToxicT, CorrosiveC
Synonyms

m-Toluenesulfonicacid, 6-amino- (6CI,7CI,8CI);1-Amino-4-methylbenzene-2-sulfonic acid;2-Amino-5-methyl-1-benzenesulfonic acid;2-Amino-5-methylbenzenesulfonic acid;4-Amino-1-methylbenzene-3-sulfonic acid;4-Aminotoluene-3-sulphonic acid;4-Methyl-2-sulfoaniline;4-Methylaniline-2-sulfonic acid;6-Amino-m-toluenesulfonic acid;Benzenesulfonic acid,2-amino-5-methyl-;PTMS;PTMSA;p-Toluidine-2-sulfonic acid;p-Toluidine-m-sulfonic acid;

Article Data 42

4-Aminotoluene-3-sulfonic acid Synthetic route

2942-15-6

6-methylbenzothiazole

88-44-8

2-Amino-5-methylbenzenesulfonic acid

Conditions
ConditionsYield
With [RuCl(P(C6H5)3)2(O(C6H4)NCH(C4H3N))]; bromamine B; sodium hydroxide In water; acetonitrile at 39.84℃; for 4h;96%
106-49-0

p-toluidine

88-44-8

2-Amino-5-methylbenzenesulfonic acid

Conditions
ConditionsYield
With sulfuric acid for 0.0416667h; microwave irradiation;84%
With sulfuric acid at 170 - 180℃; for 3h;70%
With sulfuric acid at 210 - 230℃;
540-25-0

4-toluidinium hydrogen sulfate

88-44-8

2-Amino-5-methylbenzenesulfonic acid

Conditions
ConditionsYield
for 0.00833333h; microwave irradiation;78%
99-99-0

1-methyl-4-nitrobenzene

A

19063-15-1

4-methylphenylsulfamic acid

B

88-44-8

2-Amino-5-methylbenzenesulfonic acid

Conditions
ConditionsYield
With sodium disulfite
118-88-7

4-amino-toluene-2-sulfonic acid

A

68734-90-7

4-amino-toluene-3,5-disulfonic acid

B

88-44-8

2-Amino-5-methylbenzenesulfonic acid

Conditions
ConditionsYield
With sulfuric acid at 180 - 200℃;
599-86-0

4-methyl-N-(4-methylphenyl)benzenesulfonamide

88-44-8

2-Amino-5-methylbenzenesulfonic acid

Conditions
ConditionsYield
With sulfuric acid
623-10-9

N-(4-methylphenyl)hydroxylamine

88-44-8

2-Amino-5-methylbenzenesulfonic acid

Conditions
ConditionsYield
With ethanol; sulfur dioxide

N,N-di-p-tolyl urea

A

118-88-7

4-amino-toluene-2-sulfonic acid

B

88-44-8

2-Amino-5-methylbenzenesulfonic acid

Conditions
ConditionsYield
With sulfuric acid at 150 - 160℃;

4-(4-dimethylamino-phenylazo)-toluene-3-sulfonic acid

A

88-44-8

2-Amino-5-methylbenzenesulfonic acid

B

99-98-9

4-amino-N,N-dimethylaniline

Conditions
ConditionsYield
durch Reduktion;
861519-01-9

4-ureido-toluene-3-sulfonic acid

108-24-7

acetic anhydride

88-44-8

2-Amino-5-methylbenzenesulfonic acid

4-Aminotoluene-3-sulfonic acid Consensus Reports

Reported in EPA TSCA Inventory.

4-Aminotoluene-3-sulfonic acid Specification

The IUPAC name of 4-Aminotoluene-3-sulfonic acid is 2-amino-5-methylbenzenesulfonic acid. With the CAS registry number 88-44-8, it is also named as 6-Amino-m-toluenesulfonic acid; Kyselina 4-toluidin-3-sulfonova. The product's categories are intermediates of dyes and pigments and organics. It is beige crystalline powder.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.55; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.94; (4)ACD/LogD (pH 7.4): -2.95; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 4; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.61; (13)Molar Refractivity: 45.34 cm3; (14)Molar Volume: 130.7 cm3; (15)Polarizability: 17.97×10-24 cm3; (16)Surface Tension: 61.7 dyne/cm; (17)Rotatable Bond Count: 1; (18)Exact Mass: 187.030314; (19)MonoIsotopic Mass: 187.030314; (20)Topological Polar Surface Area: 88.8; (21)Heavy Atom Count: 12.

The 4-Aminotoluene-3-sulfonic acid can be obtained by p-toluidine which reacts with sulfuric acid, then translocation by high-temperature baking to get crude product. Or translocation sulfonation in the presence of organic solvents to obtain the product. Solvent process route is reasonable, high solvent recovery, and good product quality (purity 98.5%). The yield is above 90%.

The 4-Aminotoluene-3-sulfonic acid can be used as ntermediates of dyes and pigments and in the production of pigment C.I.57: 1. It also can used in many organic synthesis. For example: It reacts with formaldehyde to get 2-dimethylamino-5-methyl-benzenesulfonic acid. This reaction needs reagent H2, catalytic agent Pd/C, and solvent methanol H2O at pressure of 2068.6. The yield is 78%.

When you are using this chemical, please be cautious about it as the following. It may cause burns and cancer. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. After contact with skin, wash immediately with plenty of soap-suds. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 

People can use the following data to convert to the molecule structure. 
1.SMILES: O=S(=O)(O)c1cc(ccc1N)C;
2.InChI: InChI=1/C7H9NO3S/c1-5-2-3-6(8)7(4-5)12(9,10)11/h2-4H,8H2,1H3,(H,9,10,11).

The following is the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LD50 oral 11700mg/kg (11700mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1054, 1986.

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