88-53-9

Basic information

• Product Name: 2-Amino-5-chloro-4-methylbenzenesulfonic acid
• Synonyms: 2-AMINO 4-METHYL 5-CHLORO BENZENE SULFONIC ACID;2-AMINO-5-CHLORO-4-METHYBENZENESULFONIC ACID;2-AMINO-5-CHLORO-4-METHYLBENZENESULFONIC ACID;2-AMINO-5-CHLORO-P-TOLUENESULFONIC ACID;2-Amino-5-Chlorotoluene-4-sulfonic acid;LAKE RED C AMINE 97%;C Acid, High Isomer;C Acid, Sambo Grade SC2
• CAS NO: 88-53-9
• Molecular Formula: C₇H₈ClNO₃S
• Molecular Weight: 221.66
• EINECS: 205-020-5
• Product Categories: Intermediates of Dyes and Pigments;Organics;API Intermediate
• Mol File: 88-53-9.mol

Chemical Properties

• Boiling Point: 394oC
• Appearance: /
• Density: 1.553 g/cm³
• PKA: -1.59±0.50(Predicted)
• Water Solubility: Practically insoluble in water
• CAS DataBase Reference: 2-Amino-5-chloro-4-methylbenzenesulfonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-5-chloro-4-methylbenzenesulfonic acid(88-53-9)
• EPA Substance Registry System: 2-Amino-5-chloro-4-methylbenzenesulfonic acid(88-53-9)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RTECS: DB4807000
• Hazardous Substances Data: 88-53-9(Hazardous Substances Data)

Usage

Chemical Properties

White to pink powder. Essentially insoluble as free acid; soluble as sodium or ammonium salt.

Uses

Intermediate for azo pigments.

InChI:InChI=1/C7H8ClNO3S/c1-4-2-6(9)7(3-5(4)8)13(10,11)12/h2-3H,9H2,1H3,(H,10,11,12)

Synthetic route

3-chloro-4-methylbenzenesulfonic acid (98-34-0) → 5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9)

Conditions	Yield
man nitriert und reduziert;

6-chloro-3-nitro-toluene-sulfonic acid-(4) → 5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9)

Conditions	Yield
With iron; acetic acid

sulfuric acid (7664-93-9) + 3-methyl-4-chloroaniline (7149-75-9) → 5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9)

Conditions	Yield
In thiophene

toluene-4-sulfonic acid (104-15-4) → 5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: chlorine / 70 - 80 °C / Large scale 2: nitric acid / 65 - 75 °C / Large scale 3: iron View Scheme

toluene (108-88-3) → 5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: sulfuric acid / 100 - 125 °C / Large scale 2: chlorine / 70 - 80 °C / Large scale 3: nitric acid / 65 - 75 °C / Large scale 4: iron View Scheme

2-nitro-4-methyl-5-chlorobenzenesulfonic acid (6973-13-3) → 5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9)

Conditions	Yield
With iron
With 41 % nickel on carbon; hydrogen In water at 60 - 65℃; under 15001.5 Torr; for 2h;

1-amino-3-methylbenzene (108-44-1) → 5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.33 h / 20 - 85 °C / Inert atmosphere 2: dihydrogen peroxide; acetic acid; hydrogenchloride / 6 h / 15 - 25 °C 3: sulfuric acid / 2 h / 105 °C 4: 1,2-dichloro-benzene / 8 h / 135 - 190 °C View Scheme

3-Methylacetanilide (537-92-8) → 5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: dihydrogen peroxide; acetic acid; hydrogenchloride / 6 h / 15 - 25 °C 2: sulfuric acid / 2 h / 105 °C 3: 1,2-dichloro-benzene / 8 h / 135 - 190 °C View Scheme

C7H8ClN*H2O4S → 5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9)

Conditions	Yield
In 1,2-dichloro-benzene at 135 - 190℃; for 8h;

BARBITURIC ACID (67-52-7) + 5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9) → C11H9ClN4O6S

Conditions	Yield
Stage #1: 5-amino-2-chloro-toluene-4-sulfonic acid With sulfuric acid; potassium hydroxide In water at 10℃; pH=1-2; Stage #2: With nitrosylsulfuric acid In water at 10℃; for 0.833333h; Stage #3: BARBITURIC ACID With potassium hydroxide In water at 25 - 30℃; for 1h; pH=2 - 3;	98%
Stage #1: 5-amino-2-chloro-toluene-4-sulfonic acid With potassium hydroxide In water pH=10; 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;

5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9) → 4-chloro-2-iodo-5-methylbenzenesulfonic acid

Conditions	Yield
Stage #1: 5-amino-2-chloro-toluene-4-sulfonic acid With sodium carbonate In water Stage #2: With sodium nitrite In water at 0℃; for 0.75h; Further stages;	90%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + 5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9) → 5-chloro-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methyl-benzenesulfonic acid (946066-41-7)

Conditions	Yield
With sodium hydrogencarbonate In 1,4-dioxane; water at 0℃;	89%
With sodium hydrogencarbonate In 1,4-dioxane

5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9) + aminosulfonic acid (5329-14-6) → 2-chloro-5-hydroxy-toluene-4-sulfonic acid ; sodium-compound (133685-26-4)

Conditions	Yield
With sodium nitrite In sulfuric acid	83%

5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9) → 1-amino-3-methylbenzene-6-sulfonic acid (88-62-0)

Conditions	Yield
With ethanol; nickel Hydrogenation;

5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9) → 2,6-dibromo-4-chloro-3-methyl-aniline

Conditions	Yield
With water; bromine

5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9) → 3-methyl-4-chloroaniline (7149-75-9)

Conditions	Yield
With sulfuric acid

5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9) → 2-amino-5-chloro-4-methyl-benzenesulfonamide (102074-13-5)

Conditions	Yield
(i) ClSO3H, NaCl, (heating), (ii) aq. NH3; Multistep reaction;

5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9) + water (7732-18-5) + bromine water → 2,6-dibromo-4-chloro-3-methyl-aniline

sulfuric acid (7664-93-9) + 5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9) → 3-methyl-4-chloroaniline (7149-75-9)

5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9) → 2-amino-5-chloro-4-methyl-benzenesulfonyl chloride (104613-63-0)

Conditions	Yield
Stage #1: 5-amino-2-chloro-toluene-4-sulfonic acid With sulfuryl dichloride In 1,1-dichloroethane at 60℃; for 1h; Stage #2: With thionyl chloride In 1,1-dichloroethane at 100℃; for 7h;

5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9) → 6-chloro-4-sulfo-toluene-3-diazonium ; chloride

Conditions	Yield
With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 2h; Product distribution / selectivity;
With hydrogenchloride; potassium hydroxide; sodium nitrite In water at 20 - 60℃; for 0.75h; Product distribution / selectivity;

aqueous sodium nitrite + aqueous sulfamic acid + 5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9) → 2-chloro-5-hydroxy-toluene-4-sulfonic acid ; sodium-compound (133685-26-4)

Conditions	Yield
In hydrogenchloride

5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9) → 2-amino-5-chloro-4-ethylbenzene-1-sulfonic acid (88-56-2)

5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9) + N-phenylacetoacetamide (102-01-2) → C17H16ClN3O5S (768320-71-4)

2-hydroxy-3-phenyl-carbamoylnaphthalene + 5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9) → C24H18ClN3O5S (1023357-45-0)

4-acetoacetylaminonaphtholsulfonic acid sodium salt (40842-93-1) + 5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9) → 2C21H16ClN3O8S2(2-)*Ca(2+)*2K(1+)

Conditions	Yield
Stage #1: 5-amino-2-chloro-toluene-4-sulfonic acid With hydrogenchloride; potassium hydroxide; sodium nitrite In water at 20 - 60℃; for 0.75h; Stage #2: With calcium chloride In water for 0.0833333h; Stage #3: 4-acetoacetylaminonaphtholsulfonic acid sodium salt With acetic acid In water at 20 - 93℃; for 2h; pH=5 - 9;

1-methyl-pyrrolidin-2-one (872-50-4) + 5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9) → 2-ammonio-5-chloro-4-methylbenzenesulfonate 1-methyl-2-pyrrolidone monosolvate (1367347-88-3)

Conditions	Yield
at 20℃; for 0.5h; Sonication;

5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9) + dimethyl sulfoxide (67-68-5) → 2-ammonio-5-chloro-4-methylbenzenesulfonate dimethyl sulfoxide monosolvate

Conditions	Yield
at 20℃; for 0.5h; Sonication;

5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9) + C15H16N2O5 → C22H21ClN4O8S

Conditions	Yield
Stage #1: 5-amino-2-chloro-toluene-4-sulfonic acid With hydrogenchloride; sodium hydroxide; sodium nitrite In water at 0 - 10℃; for 1.5h; pH=7; Stage #2: C15H16N2O5 With sodium carbonate; sodium hydroxide In water for 3h; pH=8 - 9;

trifluoro-[1,3,5]triazine (675-14-9) + 4-amino-5-hydroxy-2,7-naphthalenedisulfonic acid (90-20-0) + 5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9) + 4-amino-benzoic acid (150-13-0) → C27H15ClFN7O12S3(4-)*4Na(1+)

Conditions	Yield
Stage #1: trifluoro-[1,3,5]triazine; 5-amino-2-chloro-toluene-4-sulfonic acid With sodium hydroxide In water for 2h; pH=3 - 3.5; Stage #2: 4-amino-5-hydroxy-2,7-naphthalenedisulfonic acid With sodium hydroxide In water at 40℃; for 3h; pH=3 - 3.5; Stage #3: 4-amino-benzoic acid Further stages;

1,3,5-trichloro-2,4,6-triazine (108-77-0) + 4-amino-5-hydroxy-2,7-naphthalenedisulfonic acid (90-20-0) + 5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9) + 4-amino-benzoic acid (150-13-0) → C27H15Cl2N7O12S3(4-)*4Na(1+)

Conditions	Yield
Stage #1: 1,3,5-trichloro-2,4,6-triazine; 5-amino-2-chloro-toluene-4-sulfonic acid With sodium hydroxide In water at 5 - 10℃; for 2h; pH=3 - 3.5; Stage #2: 4-amino-5-hydroxy-2,7-naphthalenedisulfonic acid With sodium hydroxide In water at 40℃; for 3h; pH=3 - 3.5; Stage #3: 4-amino-benzoic acid Further stages;

1,3,5-trichloro-2,4,6-triazine (108-77-0) + 2-amino-1-benzenesulfonic acid (88-21-1) + 4-amino-5-hydroxy-2,7-naphthalenedisulfonic acid (90-20-0) + 5-amino-2-chloro-toluene-4-sulfonic acid (88-53-9) → C26H15Cl2N7O13S4(4-)*4Na(1+)

Conditions	Yield
Stage #1: 1,3,5-trichloro-2,4,6-triazine; 5-amino-2-chloro-toluene-4-sulfonic acid With sodium hydroxide In water at 5℃; for 2h; pH=3 - 3.5; Stage #2: 4-amino-5-hydroxy-2,7-naphthalenedisulfonic acid With sodium hydroxide In water at 40℃; for 3h; pH=3 - 3.5; Stage #3: 2-amino-1-benzenesulfonic acid Further stages;

Upstream product

• 98-34-0 3-chloro-4-methylbenzenesulfonic acid 
• 7664-93-9 sulfuric acid 
• 7149-75-9 3-methyl-4-chloroaniline 
• 104-15-4 toluene-4-sulfonic acid 
• 108-88-3 toluene 
• 6973-13-3 2-nitro-4-methyl-5-chlorobenzenesulfonic acid 
• 537-92-8 3-Methylacetanilide 
• 108-44-1 1-amino-3-methylbenzene 

Downstream Products

• 88-62-0 1-amino-3-methylbenzene-6-sulfonic acid 
• 861559-78-6 2,6-dibromo-4-chloro-3-methyl-aniline 
• 7149-75-9 3-methyl-4-chloroaniline 
• 946066-41-7 5-chloro-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methyl-benzenesulfonic acid 
• 104613-63-0 2-amino-5-chloro-4-methyl-benzenesulfonyl chloride 
• 133685-26-4 2-chloro-5-hydroxy-toluene-4-sulfonic acid ; sodium-compound 
• 88-56-2 2-amino-5-chloro-4-ethylbenzene-1-sulfonic acid 
• 1367347-88-3 2-ammonio-5-chloro-4-methylbenzenesulfonate 1-methyl-2-pyrrolidone monosolvate 
• 102074-13-5 2-amino-5-chloro-4-methyl-benzenesulfonamide 

Relevant articles and documents

Method for preparing CLT acid by taking m-toluidine as raw material

The invention discloses a method for preparing CLT acid by taking m-toluidine as a raw material, and belongs to the field of chemical synthesis. The method solves the problems that existing CLT acid production is low in yield, not environmentally friendly and the like. The method comprises: S01) an acylation step, namely a step of reacting m-toluidine and acetic anhydride to obtain acylation reaction solution; S02) a chlorination step, namely a step of adding acetic acid and concentrated hydrochloric acid into the acylation reaction solution, then adding hydrogen peroxide, and finally adding an aqueous solution containing sodium sulfite to obtain a chlorination reaction solution; S03) a hydrolyzing step to form salt, namely a step of adding concentrated sulfuric acid into the chlorinationreaction solution, and removing the solvent after reaction; S04) a transposition sulfonation step, namely a step of adding chlorobenzene into the solvent-removed reaction solution obtained in the stepS03, heating the mixture, adding dichlorobenzene, heating the mixture again, reacting the mixture for 7-10 hours with the temperature of the system being maintained at a temperature higher than 170 DEG C, and stopping heating; and S05) a step of post-treatment to obtain a finished product that is the CLT acid. The method has the advantages of environmental protection and the like.

A continuous catalytic hydrogenation reduction for preparing CLT acid

The invention discloses a method for preparing CLT acid through continuous catalytic hydrogenation reduction. The method is performed in a set of ejecting circuit continuous reactor, adopts the ejecting circuit continuous reactor to simplify the catalytic hydrogenation reduction process flow and improve the hydrogenation reduction efficiency. Meanwhile, the method can effectively reduce spillage and loss of a catalyst, caused by frequent filtering during intermittent catalytic hydrogenation reduction to realize internal recycling of the catalyst so as to prolong the service life of the catalyst. In addition, when the method is used for preparing CLT acid through continuous catalytic hydrogenation reduction, a reaction kettle is relatively small in size, good in reaction stability, relatively low in dechlorination products in a reaction product, high in selectivity, less in by-products and relatively low in content of residual main nitro compounds, and the nitro conversion rate can be higher than 99.80%.

Method for achieving pipe-type continuous production of CLT acid nitride

The invention discloses a method for achieving pipe-type continuous production of CLT acid nitride. The method comprises the steps that 1, methylbenzene and sulfuric acid conduct a sulfonation reaction in a sulfonation pipe reactor; 2, thth sulfonation reaction solution obtained in the first step and chlorine are continuously fed into a chlorination pipe reactor for a chlorination reaction; 3, the chlorination reaction solution obtained in the second step and nitric acid are continuously fed into a nitrification pipe reactor for a nitrification reaction, and then the CLT acid nitride is prepared. According to the method for achieving pipe-type continuous production of the CLT acid nitride, purification treatment does not need to be conducted on an intermediate in the reaction process, operation is easy, the reaction efficiency is high, and the objective product selectivity is high.

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