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133-74-4

Basic Information
CAS No.: 133-74-4
Name: 5-Chloroorthanilic acid
Article Data: 15
Molecular Structure:
Molecular Structure of 133-74-4 (5-Chloroorthanilic acid)
Formula: C6H6ClNO3S
Molecular Weight: 207.638
Synonyms: 1-Amino-4-chloro-2-benzenesulfonicacid;2-Amino-5-chlorobenzenesulfonic acid;4-Chloroaniline-2-sulfonic acid;p-Chloroaniline-o-sulfonic acid;
EINECS: 205-119-3
Density: 1.642 g/cm3
Melting Point: >300 °C
Solubility: 3130 mg/L at 0 °C in water
Hazard Symbols: T,N
Risk Codes: R23/24/25; R33; R51/53
PSA: 88.77000
LogP: 2.83090
Synthetic route
2942-10-1

6-chloro-1,3-benzothiazole

133-74-4

2-amino-5-chlorobenzenesulfonic acid

Conditions
ConditionsYield
With [RuCl(P(C6H5)3)2(O(C6H4)NCH(C4H3N))]; bromamine B; sodium hydroxide In water; acetonitrile at 39.84℃; for 5.5h;95%
106-47-8

4-chloro-aniline

133-74-4

2-amino-5-chlorobenzenesulfonic acid

Conditions
ConditionsYield
With sulfuric acid for 0.05h; microwave irradiation;87%
With sulfuric acid at 170 - 180℃; for 5h;60%
With diphenyl sulphone; sulfuric acid
19063-16-2

(4-chloro-phenyl)-amidosulfuric acid

133-74-4

2-amino-5-chlorobenzenesulfonic acid

Conditions
ConditionsYield
at 200℃; Beim Erhitzen der N-<4-chlor-phenyl>-sulfamidsauren Salze;
106-47-8

4-chloro-aniline

A

88-43-7

4-chloroaniline-3-sulfonic acid

B

133-74-4

2-amino-5-chlorobenzenesulfonic acid

Conditions
ConditionsYield
With sulfuric acid
539-03-7

N-(4-chlorophenyl)acetamide

133-74-4

2-amino-5-chlorobenzenesulfonic acid

Conditions
ConditionsYield
With sulfuric acid at 180℃;
With sulfuric acid at 140 - 170℃;
7664-93-9

sulfuric acid

539-03-7

N-(4-chlorophenyl)acetamide

133-74-4

2-amino-5-chlorobenzenesulfonic acid

Conditions
ConditionsYield
at 180℃;
7647-01-0

hydrogenchloride

5-chloro-2-ureido-benzenesulfonic acid

133-74-4

2-amino-5-chlorobenzenesulfonic acid

Conditions
ConditionsYield
Hydrolysis;
5329-14-6

aminosulfonic acid

106-47-8

4-chloro-aniline

133-74-4

2-amino-5-chlorobenzenesulfonic acid

Conditions
ConditionsYield
at 230℃;
110-01-0

thiophene

7664-93-9

sulfuric acid

106-47-8

4-chloro-aniline

133-74-4

2-amino-5-chlorobenzenesulfonic acid

133-74-4

2-amino-5-chlorobenzenesulfonic acid

disodium 4,4'-dichlorobiphenyl-2,2'-disulfonate

Conditions
ConditionsYield
Stage #1: 2-amino-5-chlorobenzenesulfonic acid With hydrogenchloride; sodium nitrite In water at 5℃; for 0.25h; Cooling with ice;
Stage #2: With hydrogenchloride; copper; sodium carbonate In water at 0 - 25℃; for 0.5h; Reagent/catalyst; Solvent; Cooling with ice;
77%
Downstream Products
88-45-9
874-17-9
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Specification

This chemical is called 5-Chloroorthanilic acid, and its systematic name is 2-Amino-5-chlorobenzenesulphonic acid. With the molecular formula of C6H6ClNO3S, its molecular weight is 207.63. The CAS registry number of this chemical is 133-74-4, and its product categories are Amines; Phenyls & Phenyl-Het; Phenyls & Phenyl-Het.

Other characteristics of the 5-Chloroorthanilic acid can be summarised as followings: (1)ACD/LogP: 1.28; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.22; (4)ACD/LogD (pH 7.4): -2.22; (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)Polar Surface Area: 54.99 Å2; (13)Index of Refraction: 1.639; (14)Molar Refractivity: 45.54 cm3; (15)Molar Volume: 126.4 cm3; (16)Polarizability: 18.05×10-24cm3; (17)Surface Tension: 69.7 dyne/cm; (18)Density: 1.642 g/cm3.

Preparation of this chemcial: The 5-Chloroorthanilic acid could be obtained the reactant of 4-chloro-aniline, the reagent of aq. H2SO4, and the yield is 87 %. In addition, this reaction should be taken for 3 minutes with the microwave irradiation.

You can still convert the following datas into molecular structure: 
1.SMILES: Clc1cc(c(N)cc1)S(=O)(=O)O
2.InChI: InChI=1/C6H6ClNO3S/c7-4-1-2-5(8)6(3-4)12(9,10)11/h1-3H,8H2,(H,9,10,11)
3.InChIKey: ZCGVPUAAMCMLTM-UHFFFAOYAY
4.Std. InChI: InChI=1S/C6H6ClNO3S/c7-4-1-2-5(8)6(3-4)12(9,10)11/h1-3H,8H2,(H,9,10,11)
5.Std. InChIKey: ZCGVPUAAMCMLTM-UHFFFAOYSA-N