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2-Amino-4-chloro-5-methylbenzenesulfonic acid
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Name

2-Amino-4-chloro-5-methylbenzenesulfonic acid

 EINECS 201-837-6
CAS No. 88-51-7 Density 1.553 g/cm3
PSA 88.77000 LogP 3.13930
Solubility N/A Melting Point 180.5oC
Formula C7H8ClNO3S Boiling Point 356oC
Molecular Weight 221.664 Flash Point N/A
Transport Information UN 3261 Appearance white to light gray powder
Safety 26-36/37/39 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 88-51-7 (2-Amino-4-chloro-5-methylbenzenesulfonic acid) Hazard Symbols N/A
Synonyms

m-Toluenesulfonicacid, 6-amino-4-chloro- (7CI,8CI);1-Amino-3-chloro-4-methylbenzene-6-sulfonicacid;1-Amino-4-methyl-5-chlorobenzene-2-sulfonic acid;2-Amino-4-chloro-5-methyl-1-benzenesulfonic acid;2-Chloro-p-toluidine-5-sulfonic acid;2-Chloro-4-aminotoluene-5-sulfonic acid;2-Chloro-4-toluidine-5-sulfonic acid;3-Chloro-4-methylaniline-6-sulfonic acid;4-Amino-2-chlorotoluene-5-sulfonicacid;6-Amino-4-chloro-m-toluenesulfonic acid;Brilliant Toning Red Amine;

Article Data 11

2-Amino-4-chloro-5-methylbenzenesulfonic acid Synthetic route

95-74-9

3-chloro-p-toluidine

88-51-7

6-amino-4-chloro-meta-toluenesulfonic acid

Conditions
ConditionsYield
With sulfuric acid In 1,2-dichloro-benzene at 240℃; for 8h; Autoclave;99.1%
With sulfuric acid In 1,2-dichloro-benzene at 240℃; for 8.5h; Temperature; Dean-Stark;99.2%
durch Sulfurierung;
6-chloro-4-nitro-toluene-sulfonic acid-(3)

6-chloro-4-nitro-toluene-sulfonic acid-(3)

88-51-7

6-amino-4-chloro-meta-toluenesulfonic acid

110-01-0

thiophene

7664-93-9

sulfuric acid

95-74-9

3-chloro-p-toluidine

88-51-7

6-amino-4-chloro-meta-toluenesulfonic acid

2-picolinium 2-amino-4-chloro-5-methylbenzenesulfonate monohydrate

88-51-7

6-amino-4-chloro-meta-toluenesulfonic acid

Conditions
ConditionsYield
at 199.84℃;

quinolinium 2-amino-4-chloro-5-methylbenzenesulfonate quinoline

88-51-7

6-amino-4-chloro-meta-toluenesulfonic acid

Conditions
ConditionsYield
at 219.84℃;

bis(1-ammonio-3-chloro-4-methylbenzene)sulfate

88-51-7

6-amino-4-chloro-meta-toluenesulfonic acid

Conditions
ConditionsYield
at 239.84℃;

bis(1-ammonio-3-chloro-4-methylbenzene)sulfate

A

88-51-7

6-amino-4-chloro-meta-toluenesulfonic acid

B

95-74-9

3-chloro-p-toluidine

Conditions
ConditionsYield
Heating;
67-52-7

BARBITURIC ACID

88-51-7

6-amino-4-chloro-meta-toluenesulfonic acid

C11H9ClN4O6S

Conditions
ConditionsYield
Stage #1: 6-amino-4-chloro-meta-toluenesulfonic acid With sulfuric acid; potassium hydroxide In water at 20℃; pH=1-2; Cooling with ice;
Stage #2: With nitrosylsulfuric acid In water at 10℃; for 0.833333h; pH=1;
Stage #3: BARBITURIC ACID With potassium hydroxide In water at 25 - 30℃; for 1h; pH=3;		98%
Stage #1: 6-amino-4-chloro-meta-toluenesulfonic acid With potassium hydroxide In water
Stage #2: With nitrosylsulfuric acid; sulfuric acid In water at 10℃; for 0.833333h; pH=1;
Stage #3: BARBITURIC ACID With potassium hydroxide In water at 25 - 30℃; for 1h; pH=2 - 3;
88-51-7

6-amino-4-chloro-meta-toluenesulfonic acid

92-70-6

3-Hydroxy-2-naphthoic acid

Pigment Red 48

Conditions
ConditionsYield
Stage #1: 6-amino-4-chloro-meta-toluenesulfonic acid With hydrogenchloride; sodium hydroxide; sodium nitrite In water at 20.84℃; for 0.5h;
Stage #2: 3-Hydroxy-2-naphthoic acid With aminosulfonic acid; sodium hydroxide In water for 2h;		95%
28920-43-6

(fluorenylmethoxy)carbonyl chloride

88-51-7

6-amino-4-chloro-meta-toluenesulfonic acid

895917-82-5

4-chloro-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-methylbenzenesulfonic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In 1,4-dioxane; water89%

2-Amino-4-chloro-5-methylbenzenesulfonic acid Specification

The IUPAC name of 2-Chloro-p-toluidine-5-sulfonic acid is 2-amino-4-chloro-5-methylbenzenesulfonic acid. With the CAS registry number 88-51-7, it is also named as Benzenesulfonic acid, 2-amino-4-chloro-5-methyl-; m-Toluenesulfonic acid, 6-amino-4-chloro-. This product is intermediates of dyes and pigments. It is off-white paste which is important intermediate of organic pigments that can synthesize Fast Scarlet BBN, Fast Red F5R, Fast Red BBS, Fast Red 2BL, Fast Red MGP and so on.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.69; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.81; (4)ACD/LogD (pH 7.4): -1.81; (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: 1.62; (13)Molar Refractivity: 50.17 cm3; (14)Molar Volume: 142.7 cm3; (15)Polarizability: 19.88×10-24 cm3; (16)Surface Tension: 63.9 dyne/cm; (17)Rotatable Bond Count: 1; (18)Exact Mass: 220.991342; (19)MonoIsotopic Mass: 220.991342; (20)Topological Polar Surface Area: 88.8; (21)Heavy Atom Count: 13.

The 2-Chloro-p-toluidine-5-sulfonic acid can be obtained by the raw material p-nitrotoluene which can generate the mixture of toluene o-chlorine nitrate and toluene p-chlorine nitrate by chlorination. o-Chlorophenol is isolated by the crystallization, and then by reducing, refining, sulfonation to obtain the product. Consumption of raw materials fixed: p-nitrotoluene (98.5%) 780kg / t, sulfuric acid (98) 485kg / t, chlorine (99%) 589kg / t, sulfur (99%) 273kg / t, sodium sulfide (63.5%) 1051kg / t, hydrochloric acid (32.5%) 391kg / t.

When you are using this chemical, please be cautious about it as the following. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. 

People can use the following data to convert to the molecule structure. 
1.SMILES: Clc1cc(c(cc1C)S(=O)(=O)O)N;
2.InChI: InChI=1/C7H8ClNO3S/c1-4-2-7(13(10,11)12)6(9)3-5(4)8/h2-3H,9H2,1H3,(H,10,11,12).

The following is the toxicity data which has been tested. 

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LC inhalation > 13gm/m3/4H (13000mg/m3)   Acute Toxicity Data. Journal of the American College of Toxicology, Part B. Vol. 1, Pg. 746, 1992.
rat LD50 oral 12300mg/kg (12300mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1055, 1986.

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