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547-58-0 Usage

Description

Methyl orange is an orange, azoic dye. It has a transition range from 3.1 to 4.4. Methyl orange does not have a full spectrum of color change, but has a sharper end point. Methyl orange shows red color in acidic medium (pH < 3.1) and yellow color in basic medium (pH > 4.4). It is used as a pH-indicator in 0.1% aqueous solution for the titration of mineral acids (not organic acids) and strong bases. Methyl orange is also used in dyeing and printing textiles as a dyestuff.

References

[1] https://en.wikipedia.org/wiki/Methyl_orange [2] Mohammed Bassim Alqaragully (2014) International Journal of Advanced Research in Chemical Science, 1, 48-59

Chemical Properties

Orange-yellow powder. Soluble in hotwater; insoluble in alcohol.

Uses

Different sources of media describe the Uses of 547-58-0 differently. You can refer to the following data:
1. As indicator in 0.1% aqueous solution. pH: 3.1 red, 4.4 yellow. Employed for titrating most mineral acids, strong bases, estimating alkalinity of waters; useless for organic acids. In dyeing and printing of textiles.
2. Methyl orange is a pH indicator frequently used in titrations, also used for histological microscopy.

Definition

Different sources of media describe the Definition of 547-58-0 differently. You can refer to the following data:
1. An acid–base indicator that is red in solutions below a pH of 3 and yellow above a pH of 4.4. As the transition range is clearly on the acid side, methyl orange is suitable for the titration of an acid with a moderately weak base, such as sodium carbonate.
2. methyl orange: An organic dyeused as an acid–base indicator. Itchanges from red below pH 3.1 toyellow above pH 4.4 (at 25°C) and isused for titrations involving weakbases.

Preparation

4-Aminobenzenesulfonic acid diazo, and N,N-dimethylaniline coupling.

Air & Water Reactions

Azo dyes can be explosive when suspended in air at specific concentrations. Insoluble in water.

Reactivity Profile

Methyl Orange is an azo compound. Azo, diazo, azido compounds can detonate. This applies in particular to organic azides that have been sensitized by the addition of metal salts or strong acids. Toxic gases are formed by mixing materials of this class with acids, aldehydes, amides, carbamates, cyanides, inorganic fluorides, halogenated organics, isocyanates, ketones, metals, nitrides, peroxides, phenols, epoxides, acyl halides, and strong oxidizing or reducing agents. Flammable gases are formed by mixing materials in this group with alkali metals. Explosive combination can occur with strong oxidizing agents, metal salts, peroxides, and sulfides.

Properties and Applications

orange. The strong sulfuric acid for green light yellow, diluted into red orange. The dye solution to join strong hydrochloric acid for orange red; Add thick sodium hydroxide solution for green light yellow. Standard Light Fastness Soaping Persperation Fastness Oxygen bleaching Fastness to seawater Fading Stain Fading Stain Fading Stain ISO AATCC

Standard

Light Fastness

Fading

Stain

Purification Methods

Recrystallise it twice from hot water, then wash it with a little EtOH followed by diethyl ether. It is an indicator: pH 3.1 (red) and pH 4.4 (yellow). [Beilstein 16 IV 510.]

Check Digit Verification of cas no

The CAS Registry Mumber 547-58-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,4 and 7 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 547-58:
(5*5)+(4*4)+(3*7)+(2*5)+(1*8)=80
80 % 10 = 0
So 547-58-0 is a valid CAS Registry Number.
InChI:InChI=1/C14H15N3O3S.Na/c1-17(2)13-7-3-11(4-8-13)15-16-12-5-9-14(10-6-12)21(18,19)20;/h3-10H,1-2H3,(H,18,19,20);/q;+1/p-1/b16-15-;

547-58-0 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
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  • Detail
  • Alfa Aesar

  • (A17604)  Methyl Orange   

  • 547-58-0

  • 25g

  • 223.0CNY

  • Detail
  • Alfa Aesar

  • (A17604)  Methyl Orange   

  • 547-58-0

  • 100g

  • 304.0CNY

  • Detail
  • Alfa Aesar

  • (A17604)  Methyl Orange   

  • 547-58-0

  • 500g

  • 1158.0CNY

  • Detail
  • Alfa Aesar

  • (38695)  Methyl Orange, 0.1% w/v aq. soln.   

  • 547-58-0

  • 500ml

  • 216.0CNY

  • Detail
  • Alfa Aesar

  • (17874)  Methyl Orange, ACS   

  • 547-58-0

  • 5g

  • 101.0CNY

  • Detail
  • Alfa Aesar

  • (17874)  Methyl Orange, ACS   

  • 547-58-0

  • 25g

  • 181.0CNY

  • Detail
  • Alfa Aesar

  • (17874)  Methyl Orange, ACS   

  • 547-58-0

  • 100g

  • 567.0CNY

  • Detail
  • Fluka

  • (34576)  MethylOrangesolution  0.1%, indicator, Reag. Ph. Eur.

  • 547-58-0

  • 34576-500ML

  • 575.64CNY

  • Detail
  • Fluka

  • (34576)  MethylOrangesolution  0.1%, indicator, Reag. Ph. Eur.

  • 547-58-0

  • 34576-1L

  • 746.46CNY

  • Detail
  • Fluka

  • (32624)  MethylOrange  indicator, Reag. Ph. Eur.

  • 547-58-0

  • 32624-100G

  • 374.40CNY

  • Detail
  • Fluka

  • (32624)  MethylOrange  indicator, Reag. Ph. Eur.

  • 547-58-0

  • 32624-250G

  • 817.83CNY

  • Detail
  • Sigma-Aldrich

  • (68250)  MethylOrange  for microscopy (Hist.), indicator (pH 3.0-4.4)

  • 547-58-0

  • 68250-25G

  • 211.77CNY

  • Detail

547-58-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Methyl Orange

1.2 Other means of identification

Product number -
Other names Acid Orange 52

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:547-58-0 SDS

547-58-0Synthetic route

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

methyl orange
547-58-0

methyl orange

Conditions
ConditionsYield
Stage #1: N,N-dimethyl-aniline With hydrogenchloride In water; N,N-dimethyl-formamide at 25℃;
Stage #2: With sodium nitrite In water; N,N-dimethyl-formamide
Stage #3: 4-aminobenzene sulfonic acid In water; N,N-dimethyl-formamide at 25℃; for 0.00333333h;
95.01%
diethyl ether
60-29-7

diethyl ether

4'-aminoazobenzene-4-sulfonic acid
104-23-4

4'-aminoazobenzene-4-sulfonic acid

A

4-(4-dimethylamino-phenylazo)-benzenesulfonic acid methyl ester
111915-50-5

4-(4-dimethylamino-phenylazo)-benzenesulfonic acid methyl ester

B

methyl orange
547-58-0

methyl orange

4-sulfobenzenediazonium
2154-66-7

4-sulfobenzenediazonium

4,4'-methylene-bis(N,N-dimethylaniline)
101-61-1

4,4'-methylene-bis(N,N-dimethylaniline)

A

formaldehyd
50-00-0

formaldehyd

B

methyl orange
547-58-0

methyl orange

Methyl Orange anion
70735-00-1

Methyl Orange anion

methyl orange
547-58-0

methyl orange

Conditions
ConditionsYield
With sodium hydroxide; sodium cation In water Thermodynamic data; pH 12, 6 h; partition coefficient also investigated; ΔH0, ΔS0, ΔG0;
α-cyclodextrin-Methyl Orange complex
64887-49-6

α-cyclodextrin-Methyl Orange complex

A

methyl orange
547-58-0

methyl orange

B

alpha cyclodextrin
10016-20-3

alpha cyclodextrin

Conditions
ConditionsYield
In water at 25℃; Equilibrium constant;
In methanol; water at 25℃; Equilibrium constant;
In water; dimethyl sulfoxide at 25℃; Equilibrium constant;
4-(4-Dimethylamino-phenylazo)-benzenesulfonatehexadecyl-trimethyl-ammonium;
99023-50-4

4-(4-Dimethylamino-phenylazo)-benzenesulfonatehexadecyl-trimethyl-ammonium;

A

methyl orange
547-58-0

methyl orange

B

cetyltrimethylammonim bromide
57-09-0

cetyltrimethylammonim bromide

Conditions
ConditionsYield
With sodium bromide at 19.9℃; Equilibrium constant; var. temps.;
4-(4-Dimethylamino-phenylazo)-benzenesulfonatedodecyl-trimethyl-ammonium;

4-(4-Dimethylamino-phenylazo)-benzenesulfonatedodecyl-trimethyl-ammonium;

A

methyl orange
547-58-0

methyl orange

B

dodecyltrimethylammonium bromide
1119-94-4

dodecyltrimethylammonium bromide

Conditions
ConditionsYield
With sodium bromide at 19.9℃; Equilibrium constant; var. temps.;
4-(4-Dimethylamino-phenylazo)-benzenesulfonatetrimethyl-tetradecyl-ammonium;

4-(4-Dimethylamino-phenylazo)-benzenesulfonatetrimethyl-tetradecyl-ammonium;

A

methyl orange
547-58-0

methyl orange

B

cetyltrimethylammonium bromide
1119-97-7

cetyltrimethylammonium bromide

Conditions
ConditionsYield
With sodium bromide at 19.9℃; Equilibrium constant; var. temps.;
4-(4-Dimethylamino-phenylazo)-benzenesulfonate1-hexadecyl-pyridinium;

4-(4-Dimethylamino-phenylazo)-benzenesulfonate1-hexadecyl-pyridinium;

A

cetylpyridinium chloride
123-03-5

cetylpyridinium chloride

B

methyl orange
547-58-0

methyl orange

Conditions
ConditionsYield
With sodium chloride at 19.9℃; Equilibrium constant; var. temps.;
4-(4-Dimethylamino-phenylazo)-benzenesulfonate1-hexadecyl-pyridinium;

4-(4-Dimethylamino-phenylazo)-benzenesulfonate1-hexadecyl-pyridinium;

A

methyl orange
547-58-0

methyl orange

B

cetylpyridinium bromide
140-72-7

cetylpyridinium bromide

Conditions
ConditionsYield
With sodium bromide at 19.9℃; Equilibrium constant; var. temps.;
sodium sulfanilate
515-74-2

sodium sulfanilate

4-amino-N,N-dimethylaniline
99-98-9

4-amino-N,N-dimethylaniline

methyl orange
547-58-0

methyl orange

Conditions
ConditionsYield
With oxygen; 1.5% Au/TiO2 In toluene at 100℃; under 2250.23 - 3750.38 Torr; for 40h;92 %Chromat.
p-sulfobenzenediazonium chloride
6118-33-8

p-sulfobenzenediazonium chloride

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

methyl orange
547-58-0

methyl orange

Conditions
ConditionsYield
With hydrogenchloride In water at 0℃; for 0.25h;71 %Spectr.
methyl orange
547-58-0

methyl orange

N,N'-dihydromethylorange
26363-66-6

N,N'-dihydromethylorange

Conditions
ConditionsYield
With sodium tetrahydroborate In water for 0.0333333h; Kinetics;98.58%
With titanium(IV) oxide Rate constant; Irradiation; anaerobe, buffered soln., effect of the pH, TiO2 concn., effect of the oxygen;
titanium(IV) oxide for 1.33333h; Quantum yield; Irradiation; photooxidation at pH=11.2;
trihexyl(tetradecyl)phosphonium chloride
258864-54-9

trihexyl(tetradecyl)phosphonium chloride

methyl orange
547-58-0

methyl orange

[P(6,6,6,14)][MO]
1198363-83-5

[P(6,6,6,14)][MO]

Conditions
ConditionsYield
In acetone at 20℃; for 48h;94%
In dichloromethane; water
methyl orange
547-58-0

methyl orange

A

sodium sulfanilate
515-74-2

sodium sulfanilate

B

4-amino-N,N-dimethylaniline
99-98-9

4-amino-N,N-dimethylaniline

Conditions
ConditionsYield
With formic acid; zinc In methanol at 20℃; for 0.216667h;A 55%
B 92%
With sodium tetrahydroborate; water; fullerene-C60; sodium hydroxide at 20℃; for 5h; pH=11; UV-irradiation;
With hydrogenchloride; copper In water at 18.84 - 20.84℃; under 3000.3 Torr; pH=3; Reagent/catalyst; pH-value; Pressure; Concentration;
lanthanum(III) nitrate hexahydrate

lanthanum(III) nitrate hexahydrate

methyl orange
547-58-0

methyl orange

water
7732-18-5

water

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

[La(methyl orange)3(DMF)3(H2O)2]

[La(methyl orange)3(DMF)3(H2O)2]

Conditions
ConditionsYield
at 80℃; for 5h;92%
C10H23O2S(1+)*Cl(1-)

C10H23O2S(1+)*Cl(1-)

methyl orange
547-58-0

methyl orange

bis-ethanol hexylsulfonium methyl orange
1198363-82-4

bis-ethanol hexylsulfonium methyl orange

Conditions
ConditionsYield
In acetone at 20℃; for 48h;89%
methyl orange
547-58-0

methyl orange

1-butyl-3-methylimidazolium chloride
79917-90-1

1-butyl-3-methylimidazolium chloride

1-butyl-3-methylimidazolium methyl orange
1297245-59-0

1-butyl-3-methylimidazolium methyl orange

Conditions
ConditionsYield
In acetone at 20℃; for 48h;86%
In acetone at 20℃; for 72h;85%
N,N,N',N''-tetrahexyl-N'',N''-dimethylguanidinium chloride
672953-05-8

N,N,N',N''-tetrahexyl-N'',N''-dimethylguanidinium chloride

methyl orange
547-58-0

methyl orange

tetrahexyldimethylguanidinium methyl orange
1198363-79-9

tetrahexyldimethylguanidinium methyl orange

Conditions
ConditionsYield
In acetone at 20℃; for 48h;81%
methyl orange
547-58-0

methyl orange

sodium sulfanilate
515-74-2

sodium sulfanilate

Conditions
ConditionsYield
With ammonium formate; nickel In methanol at 20℃; for 0.216667h;55%
potassium tetrachloropalladate(II)
10025-98-6

potassium tetrachloropalladate(II)

methyl orange
547-58-0

methyl orange

[(KSO3C6H4NNC6H3(NMe2))Pd(μ-Cl)]2

[(KSO3C6H4NNC6H3(NMe2))Pd(μ-Cl)]2

Conditions
ConditionsYield
In 1,4-dioxane; water slow addn. of aq. soln. of palladium compd. to soln. of methyl orange indioxane/water (1:1), stirring at room temp. for one week; according to S.-H. Li, C.-W. Yu and J.-G. Xu, Chem. Commun., 2005, 250; concn. under vacuum, isolation of ppt., washing with ethanol and diethylether, drying under vacuum;52%
dichloro bis(acetonitrile) palladium(II)
21264-30-2, 90243-59-7, 14592-56-4

dichloro bis(acetonitrile) palladium(II)

methyl orange
547-58-0

methyl orange

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

{(N,N-dimethylformamide)PdCl(μ-Me2NC6H3N=NC6H3SO3Na)PdCl(N,N-dimethylformamide)}

{(N,N-dimethylformamide)PdCl(μ-Me2NC6H3N=NC6H3SO3Na)PdCl(N,N-dimethylformamide)}

Conditions
ConditionsYield
at 25℃; Kinetics;50%
methyl orange
547-58-0

methyl orange

dabsyl chloride
56512-49-3

dabsyl chloride

Conditions
ConditionsYield
With phosphorus pentachloride for 0.133333h;20%
With phosphorus pentachloride for 0.133333h;
With trichlorophosphate at 110℃;
methyl orange
547-58-0

methyl orange

N-methyl-2,4-dinitroaniline
2044-88-4

N-methyl-2,4-dinitroaniline

Conditions
ConditionsYield
With nitric acid
methyl orange
547-58-0

methyl orange

4-(4-dimethylamino-3-nitro-phenylazo)-benzenesulfonic acid

4-(4-dimethylamino-3-nitro-phenylazo)-benzenesulfonic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite
methyl orange
547-58-0

methyl orange

4-(4-dimethylamino-phenylazo)-benzenesulfonic acid ; hydrochloride

4-(4-dimethylamino-phenylazo)-benzenesulfonic acid ; hydrochloride

Conditions
ConditionsYield
With hydrogenchloride
methyl orange
547-58-0

methyl orange

4-aminobenzene sulfonic acid
121-57-3

4-aminobenzene sulfonic acid

Conditions
ConditionsYield
With Pd-BaSO4; sodium acetate; acetic acid Hydrogenation;
With sodium dithionite; water
With sodium dithionite; ethanol
With hydrogen iodide
With sodium carbonate at 95℃; bei der elektrolytischen Reduktion;
cetylpyridinium chloride
123-03-5

cetylpyridinium chloride

methyl orange
547-58-0

methyl orange

4-(4-Dimethylamino-phenylazo)-benzenesulfonate1-hexadecyl-pyridinium;

4-(4-Dimethylamino-phenylazo)-benzenesulfonate1-hexadecyl-pyridinium;

Conditions
ConditionsYield
In water at 19.9℃; Equilibrium constant; Thermodynamic data; ΔH, ΔG, ΔS; var. temps.;
methyl orange
547-58-0

methyl orange

dodecyltrimethylammonium bromide
1119-94-4

dodecyltrimethylammonium bromide

4-(4-Dimethylamino-phenylazo)-benzenesulfonatedodecyl-trimethyl-ammonium;

4-(4-Dimethylamino-phenylazo)-benzenesulfonatedodecyl-trimethyl-ammonium;

Conditions
ConditionsYield
In water at 19.9℃; Equilibrium constant; Thermodynamic data; ΔH, ΔG, ΔS; var. temps.;
methyl orange
547-58-0

methyl orange

cetyltrimethylammonim bromide
57-09-0

cetyltrimethylammonim bromide

4-(4-Dimethylamino-phenylazo)-benzenesulfonatehexadecyl-trimethyl-ammonium;
99023-50-4

4-(4-Dimethylamino-phenylazo)-benzenesulfonatehexadecyl-trimethyl-ammonium;

Conditions
ConditionsYield
In water at 19.9℃; Equilibrium constant; Thermodynamic data; ΔH, ΔG, ΔS; var. temps.;
methyl orange
547-58-0

methyl orange

cetyltrimethylammonium bromide
1119-97-7

cetyltrimethylammonium bromide

4-(4-Dimethylamino-phenylazo)-benzenesulfonatetrimethyl-tetradecyl-ammonium;

4-(4-Dimethylamino-phenylazo)-benzenesulfonatetrimethyl-tetradecyl-ammonium;

Conditions
ConditionsYield
In water at 19.9℃; Equilibrium constant; Thermodynamic data; ΔH, ΔG, ΔS; var. temps.;
methyl orange
547-58-0

methyl orange

cetylpyridinium bromide
140-72-7

cetylpyridinium bromide

4-(4-Dimethylamino-phenylazo)-benzenesulfonate1-hexadecyl-pyridinium;

4-(4-Dimethylamino-phenylazo)-benzenesulfonate1-hexadecyl-pyridinium;

Conditions
ConditionsYield
In water at 19.9℃; Equilibrium constant; Thermodynamic data; ΔH, ΔG, ΔS; var. temps.;
methyl orange
547-58-0

methyl orange

C48H80O40*C14H14N3O3S(1-)*Na(1+)
98928-66-6

C48H80O40*C14H14N3O3S(1-)*Na(1+)

C48H80O40*2C14H14N3O3S(1-)*2Na(1+)
97130-86-4, 98928-66-6

C48H80O40*2C14H14N3O3S(1-)*2Na(1+)

Conditions
ConditionsYield
In water at 15 - 35℃; Equilibrium constant; Kinetics; Thermodynamic data;
methyl orange
547-58-0

methyl orange

hyoscine-N-butyl bromide
149-64-4

hyoscine-N-butyl bromide

L-hyoscine butyl bromide, complex with methyl orange

L-hyoscine butyl bromide, complex with methyl orange

Conditions
ConditionsYield
With CH3COONa buffer; acetic acid In water pH 4.20;

547-58-0Relevant articles and documents

Molecular Assemblies Offering Hydrogen-Bonding Cavities: Influence of Macrocyclic Cavity and Hydrogen Bonding on Dye Adsorption

Gupta, Rajeev,Gupta, Ruchika,Pachisia, Sanya

supporting information, p. 3616 - 3630 (2022/03/02)

This work presents a set of Hg macrocycles of amide-phosphine-based ligands offering H-bonding cavities of different dimensions. Such macrocycles are shown to selectively adsorb anionic dyes followed by neutral dyes as well as Prontosil, a biologically relevant antibiotic, within their cavities with the aid of H-bonding-assisted encapsulation. Kinetic experiments supported by spectroscopic and docking studies illustrate the importance of the cavity structure as well as H-bonds for the selective adsorption of dyes.

PROCESS FOR THE SYNTHESIS OF ARYLDIAZONIUM SALTS USING NITROGEN OXIDES IN OXYGEN-CONTAINING GAS STREAMS, ESPECIALLY FROM INDUSTRIAL WASTE GASES

-

Page/Page column 43, (2017/06/30)

The present invention relates to a process for the synthesis of aryldiazonium salts using nitrogen oxides in oxygen-containing gas streams, especially from industrial waste gases.

Interaction of Methyl Orange with Submicellar Cationic Surfactants

Dutta, Robin K.,Bhat, Subray N.

, p. 2457 - 2460 (2007/10/02)

The interaction of aqueous Methyl Orange (MO), an azo dye, with alkyltrimethylammonium and N-hexadecylpyridinium halide surfactants in submicellar concentration ranges has been investigated.The interaction gives rise to a new absorption band of MO with a maximum at ca. 370 nm, and the appearance of the new band has been attributed to change in the chromophore microenvironment in water structure enforced closely packed ion pairs of the dye with submicellar cationic surfactant.The strength of the interaction depends on the alkyl chain length of the surfactant, the surfactant head group and the counter ions.

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