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

Name
2-Amino-4-chloro-5-methylbenzenesulfonic acid
EINECS 201-837-6
CAS No. 88-51-7
Article Data11
CAS DataBase
Density 1.553 g/cm³
Solubility
Melting Point 180.5oC
Formula C₇H₈ClNO₃S
Boiling Point 356oC
Molecular Weight 221.664
Flash Point
Transport Information UN 3261
Appearance white to light gray powder
Safety 26-36/37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols
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;
PSA 88.77000
LogP 3.13930

Synthetic route

: 95-74-9
3-chloro-p-toluidine

: 88-51-7
6-amino-4-chloro-meta-toluenesulfonic acid

Conditions

Conditions	Yield
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

...Expand

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

: 88-51-7
6-amino-4-chloro-meta-toluenesulfonic acid

Conditions

Conditions	Yield
at 199.84℃;

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

: 88-51-7
6-amino-4-chloro-meta-toluenesulfonic acid

Conditions

Conditions	Yield
at 219.84℃;

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

: 88-51-7
6-amino-4-chloro-meta-toluenesulfonic acid

Conditions

Conditions	Yield
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

Conditions	Yield
Heating;

: 67-52-7
BARBITURIC ACID

: 88-51-7
6-amino-4-chloro-meta-toluenesulfonic acid

: C11H9ClN4O6S

Conditions

Conditions	Yield
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

Conditions	Yield
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

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

: 88-51-7
6-amino-4-chloro-meta-toluenesulfonic acid

: 23138-55-8
3-Bromophenyl isocyanate

: 697278-42-5
2-[3-(3-bromo-phenyl)-ureido]-4-chloro-5-methyl-benzenesulfonic acid

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃;	65%

: 88-51-7
6-amino-4-chloro-meta-toluenesulfonic acid

: 697278-51-6
4-chloro-2-[3-(1H-indol-2-yl)-ureido]-5-methyl-benzenesulphonic acid

Conditions

Conditions	Yield
Stage #1: Indole-2-carboxylic acid With diphenyl phosphoryl azide; triethylamine In toluene at 20℃; for 0.5h; Stage #2: 6-amino-4-chloro-meta-toluenesulfonic acid With triethylamine at 80℃; for 3h; Stage #3: With hydrogenchloride In water; ethyl acetate	53%

: 88-51-7
6-amino-4-chloro-meta-toluenesulfonic acid

: 104613-64-1
2-amino-4-chloro-5-methyl benzenesulfonyl chloride

Conditions

Conditions	Yield
With chlorosulphuric acid
Stage #1: 6-amino-4-chloro-meta-toluenesulfonic acid With sulfuryl dichloride In dichloromethane at 60℃; for 1h; Stage #2: With thionyl chloride In dichloromethane at 100℃; for 7h;	2.2 g
With chlorosulphuric acid

: 88-51-7
6-amino-4-chloro-meta-toluenesulfonic acid

: 4,6-dichloro-toluene-3-sulfonic acid

Conditions

Conditions	Yield
ueber die Diazonium-Verbindung;

: 88-51-7
6-amino-4-chloro-meta-toluenesulfonic acid

: 2-chloro-5-sulfo-toluene-4-diazonium-betaine

Conditions

Conditions	Yield
Diazotization;

: 88-51-7
6-amino-4-chloro-meta-toluenesulfonic acid

: 55825-29-1
2-amino-4-chloro-5-methyl-benzenesulfonamide

Conditions

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

: 88-51-7
6-amino-4-chloro-meta-toluenesulfonic acid

: 871832-00-7
2-azido-4-chloro-5-methylbenzenesulfonic acid

Conditions

Conditions	Yield
Stage #1: 6-amino-4-chloro-meta-toluenesulfonic acid With sulfuric acid; sodium nitrite In water at 0℃; for 0.5h; Stage #2: With sodium azide In water at 0 - 20℃; for 12h;

: 88-51-7
6-amino-4-chloro-meta-toluenesulfonic acid

: 895917-83-6
(S)-methyl 1-(2-amino-4-chloro-5-methylphenylsulfonyl)pyrrolidine-2-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sulfuryl chloride / CH2Cl2 / 1 h / 60 °C 1.2: 2.2 g / thionyl chloride / CH2Cl2 / 7 h / 100 °C 2.1: 75 percent / pyridine / 4 h / 20 °C View Scheme

: 88-51-7
6-amino-4-chloro-meta-toluenesulfonic acid

: (S)-1-(2-Amino-4-chloro-5-methyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sulfuryl chloride / CH2Cl2 / 1 h / 60 °C 1.2: 2.2 g / thionyl chloride / CH2Cl2 / 7 h / 100 °C 2.1: 75 percent / pyridine / 4 h / 20 °C 3.1: 88 percent / aq. NaOH / ethanol View Scheme

: 88-51-7
6-amino-4-chloro-meta-toluenesulfonic acid

: 871832-22-3
2-azido-4-chloro-5-methylbenzenesulfonamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: NaNO2; H2SO4 / H2O / 0.5 h / 0 °C 1.2: NaN3 / H2O / 12 h / 0 - 20 °C 2.1: oxalyl chloride / CH2Cl2; dimethylformamide / 3 h / Heating 3.1: 75 percent / NH3 / dioxane; CH2Cl2 / 3 h / 25 °C View Scheme

: 88-51-7
6-amino-4-chloro-meta-toluenesulfonic acid

: 871832-21-2
2-azido-4-chloro-5-methyl-benzenesulfonyl chloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaNO2; H2SO4 / H2O / 0.5 h / 0 °C 1.2: NaN3 / H2O / 12 h / 0 - 20 °C 2.1: oxalyl chloride / CH2Cl2; dimethylformamide / 3 h / Heating View Scheme

: 88-51-7
6-amino-4-chloro-meta-toluenesulfonic acid

: 871832-04-1
2-azido-4-chloro-N-(2-methoxyethyl)-5-methylbenzenesulfonamide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: NaNO2; H2SO4 / H2O / 0.5 h / 0 °C 1.2: NaN3 / H2O / 12 h / 0 - 20 °C 2.1: oxalyl chloride / CH2Cl2; dimethylformamide / 3 h / Heating 3.1: ethyldiisopropylamine / CH2Cl2 / 6 h / 25 °C View Scheme

: 88-51-7
6-amino-4-chloro-meta-toluenesulfonic acid

: 3-n-butylamino-6-chloro-7-methyl-2H-1,2,4-benzothiadiazine 1,1-dioxide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: NaNO2; H2SO4 / H2O / 0.5 h / 0 °C 1.2: NaN3 / H2O / 12 h / 0 - 20 °C 2.1: oxalyl chloride / CH2Cl2; dimethylformamide / 3 h / Heating 3.1: 75 percent / NH3 / dioxane; CH2Cl2 / 3 h / 25 °C 4.1: triphenylphosphine resin / CH2Cl2; tetrahydrofuran / 16 h / 25 °C 4.2: 55 percent / 1,2-dichloro-ethane; tetrahydrofuran / 24 h / 80 °C View Scheme

: 88-51-7
6-amino-4-chloro-meta-toluenesulfonic acid

: 6-chloro-7-methyl-3-(4-fluorophenylsulfonylamino)-2H-1,2,4-benzothiadiazine 1,1-dioxide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: NaNO2; H2SO4 / H2O / 0.5 h / 0 °C 1.2: NaN3 / H2O / 12 h / 0 - 20 °C 2.1: oxalyl chloride / CH2Cl2; dimethylformamide / 3 h / Heating 3.1: 75 percent / NH3 / dioxane; CH2Cl2 / 3 h / 25 °C 4.1: triphenylphosphine resin / CH2Cl2; tetrahydrofuran / 16 h / 25 °C 4.2: 45 percent / 1,2-dichloro-ethane; tetrahydrofuran / 24 h / 80 °C View Scheme

: 88-51-7
6-amino-4-chloro-meta-toluenesulfonic acid

: 2-N-(2-methoxyethyl)-3-(3-fluoro-4-methylphenylamino)-6-chloro-7-methyl-2H-1,2,4-benzothiadiazine 1,1-dioxide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: NaNO2; H2SO4 / H2O / 0.5 h / 0 °C 1.2: NaN3 / H2O / 12 h / 0 - 20 °C 2.1: oxalyl chloride / CH2Cl2; dimethylformamide / 3 h / Heating 3.1: ethyldiisopropylamine / CH2Cl2 / 6 h / 25 °C 4.1: triphenylphosphine resin / CH2Cl2 / 16 h / 25 °C 4.2: 45 percent / 1,2-dichloro-ethane / 24 h / 80 °C View Scheme

: 88-51-7
6-amino-4-chloro-meta-toluenesulfonic acid

: 2-N-(2-methoxyethyl)-3-(4-fluorophenylsulfonylamino)-6-chloro-7-methyl-2H-1,2,4-benzothiadiazine 1,1-dioxide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: NaNO2; H2SO4 / H2O / 0.5 h / 0 °C 1.2: NaN3 / H2O / 12 h / 0 - 20 °C 2.1: oxalyl chloride / CH2Cl2; dimethylformamide / 3 h / Heating 3.1: ethyldiisopropylamine / CH2Cl2 / 6 h / 25 °C 4.1: triphenylphosphine resin / CH2Cl2 / 16 h / 25 °C 4.2: 80 percent / 1,2-dichloro-ethane / 24 h / 80 °C View Scheme

: 88-51-7
6-amino-4-chloro-meta-toluenesulfonic acid

: 65151-15-7
C7H6ClN2O3S(1+)*Cl(1-)

Conditions

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

: 88-51-7
6-amino-4-chloro-meta-toluenesulfonic acid

: 119-17-5
1-(3'-sulfophenyl)-3-methyl-5-pyrazolone

: Pigment Yellow 191 monohydrate

Conditions

Conditions	Yield
Stage #1: 6-amino-4-chloro-meta-toluenesulfonic acid With hydrogenchloride; sodium nitrite Stage #2: 1-(3'-sulfophenyl)-3-methyl-5-pyrazolone With sodium hydroxide Stage #3: With water; calcium chloride at 80℃;

: 88-51-7
6-amino-4-chloro-meta-toluenesulfonic acid

: 92-70-6
3-Hydroxy-2-naphthoic acid

: 16013-44-8
4-[(5-chloro-4-methyl-2-sulfophenyl)azo]-3-hydroxy-2-naphthoic acid

Conditions

Conditions	Yield
Stage #1: 6-amino-4-chloro-meta-toluenesulfonic acid With sodium hydroxide In water Stage #2: With hydrogenchloride; sodium acetate; sodium nitrite In water at 10℃; pH=3 - 4; Stage #3: 3-Hydroxy-2-naphthoic acid In water at 15 - 60℃; for 3.5h;
Stage #1: 6-amino-4-chloro-meta-toluenesulfonic acid With hydrogenchloride; sodium nitrite In water at 0℃; for 1h; Stage #2: 3-Hydroxy-2-naphthoic acid With stearic acid; sodium hydroxide In water at 12℃; for 1.5h; Reagent/catalyst; Temperature;

: 88-51-7
6-amino-4-chloro-meta-toluenesulfonic acid

: 89-36-1
4-(4,5-dihydro-3-methyl-5-oxo-1H-pyrazol-1-yl)benzenesulfonic acid

: C17H13ClN4O7S2(2-)*Ca(2+)

Conditions

Conditions	Yield
Stage #1: 6-amino-4-chloro-meta-toluenesulfonic acid; 4-(4,5-dihydro-3-methyl-5-oxo-1H-pyrazol-1-yl)benzenesulfonic acid With hydrogenchloride; sodium hydroxide; sodium nitrite In water at 40 - 80℃; pH=6 - 6.5; Stage #2: With calcium chloride In water at 80℃; for 2h;

: 88-51-7
6-amino-4-chloro-meta-toluenesulfonic acid

: 89-36-1
4-(4,5-dihydro-3-methyl-5-oxo-1H-pyrazol-1-yl)benzenesulfonic acid

: C17H13ClN4O7S2(2-)*Sr(2+)

Conditions

Conditions	Yield
Stage #1: 6-amino-4-chloro-meta-toluenesulfonic acid; 4-(4,5-dihydro-3-methyl-5-oxo-1H-pyrazol-1-yl)benzenesulfonic acid With hydrogenchloride; sodium hydroxide; sodium nitrite In water at 40 - 80℃; pH=6 - 6.5; Stage #2: With strontium chloride In water at 80℃; for 2h;

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.

Product Name

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

Synthetic route

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

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