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  • 76-60-8 Structure
  • Basic information

    1. Product Name: Bromocresol green
    2. Synonyms: Phenol,4,4’-(3H-2,1-benzoxathiol-3-ylidene)bis(2,6-dibromo-3-methyl-,S,S-dioxide;tetrabromo-m-cresolphthaleinsulfone;vertdebromocresol;BACILLUS OF CALMETTE AND GUERIN;BCG;BROMCRESOL GREEN;BROMOCRESOL GREEN SULTONE FORM;BROMOCRESOL BLUE
    3. CAS NO:76-60-8
    4. Molecular Formula: C21H14Br4O5S
    5. Molecular Weight: 698.01
    6. EINECS: 200-972-8
    7. Product Categories: Organics;Analytical Chemistry;Indicator (pH);pH Indicators;TLC Stains;B;Stains and Dyes;Stains&Dyes, A to;Flavones, Flavonoids, FoodstuffsDerivatization Reagents TLC;Organic Acids, Carboxylic AcidsDerivatization Reagents;Derivatization Reagents TLC;TLC Reagents, A-C;TLC ReagentsDerivatization Reagents TLC;TLC Visualization Reagents (alphabetic sort);TLC Visualization Reagents (by application);Sulfonephthalein
    8. Mol File: 76-60-8.mol
    9. Article Data: 5
  • Chemical Properties

    1. Melting Point: 225 °C
    2. Boiling Point: 626 °C at 760 mmHg
    3. Flash Point: 12 °C
    4. Appearance: Pale orange/Powder/Solid
    5. Density: 0.79 g/mL at 20 °C
    6. Refractive Index: N/A
    7. Storage Temp.: Store at RT.
    8. Solubility: Solubility Sparingly soluble in water; soluble in ethanol, ether
    9. PKA: 4.7(at 25℃)
    10. Water Solubility: slightly soluble
    11. Stability: Stable. Incompatible with strong oxidizing agents.
    12. Merck: 14,1386
    13. BRN: 372527
    14. CAS DataBase Reference: Bromocresol green(CAS DataBase Reference)
    15. NIST Chemistry Reference: Bromocresol green(76-60-8)
    16. EPA Substance Registry System: Bromocresol green(76-60-8)
  • Safety Data

    1. Hazard Codes: F,Xi,Xn
    2. Statements: 11-36-67-36/37/38-20/21/22
    3. Safety Statements: 7-16-24/25-26-37/39-36
    4. RIDADR: UN 1219 3/PG 2
    5. WGK Germany: 3
    6. RTECS: SJ7456000
    7. TSCA: Yes
    8. HazardClass: 3
    9. PackingGroup: II
    10. Hazardous Substances Data: 76-60-8(Hazardous Substances Data)

76-60-8 Usage

Chemical Properties

tan to yellow crystals

Uses

Different sources of media describe the Uses of 76-60-8 differently. You can refer to the following data:
1. As indicator, pH 3.8 yellow; pH 5.4 blue-green.
2. Bromocresol Green is a pH sensitive indicator used in the growth medium for microorganisms and titrations. It is useful in various colorimetric detection studies and as an actively tracking dye for DNA agarose gel electrophoresis. It acts as an inhibitor of prostaglandin E2 transport protein. It is also used in TLC for visualizing compounds containing functional groups having pKa less than 5.
3. Bromocresol Green (BCG) is a pH sensitive triphenylmethane dye useful in a variety of colorimetric detection technologies. BCG is used as a tracking dye for DNA agarose gel electrophoresis, in protein determinations and in charge-transfer complexation processes. In TLC BCG is used for visualisation of the compounds with functional groups whose pKa is below 5.0.

Hazard

Moderately toxic.

Purification Methods

Crystallise the dye from glacial acetic acid or dissolve it in aqueous 5% NaHCO3 solution and precipitate it from the hot solution by dropwise addition of aqueous HCl. Repeat this until the UV/VIS-extinction did not increase 423nm. It is an indicator: at pH 3.81 at max (yellow) and pH 5.4 (blue-green). [Beilstein 19/3 V 460.]

Check Digit Verification of cas no

The CAS Registry Mumber 76-60-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 6 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 76-60:
(4*7)+(3*6)+(2*6)+(1*0)=58
58 % 10 = 8
So 76-60-8 is a valid CAS Registry Number.
InChI:InChI=1/C21H14Br4O5S/c1-9-12(7-14(22)19(26)17(9)24)21(13-8-15(23)20(27)18(25)10(13)2)11-5-3-4-6-16(11)31(28,29)30-21/h3-8,26-27H,1-2H3

76-60-8 Well-known Company Product Price

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

  • (A17090)  Bromocresol Green   

  • 76-60-8

  • 5g

  • 300.0CNY

  • Detail
  • Alfa Aesar

  • (A17090)  Bromocresol Green   

  • 76-60-8

  • 25g

  • 1129.0CNY

  • Detail
  • Fluka

  • (02559)  BromocresolGreensolution  indicator, ready-to-use

  • 76-60-8

  • 02559-500ML

  • 1,334.97CNY

  • Detail
  • Fluka

  • (32742)  BromocresolGreenSultoneForm  Reag. Ph. Eur., indicator

  • 76-60-8

  • 32742-5G

  • 628.29CNY

  • Detail
  • Fluka

  • (32742)  BromocresolGreenSultoneForm  Reag. Ph. Eur., indicator

  • 76-60-8

  • 32742-25G

  • 2,323.62CNY

  • Detail
  • Sigma

  • (17470)  BromocresolGreenSultoneForm  for microscopy (Bot., Hist., Vit.), indicator (pH 3.8-5.4)

  • 76-60-8

  • 17470-5G

  • 450.45CNY

  • Detail
  • Sigma

  • (17470)  BromocresolGreenSultoneForm  for microscopy (Bot., Hist., Vit.), indicator (pH 3.8-5.4)

  • 76-60-8

  • 17470-25G

  • 1,674.27CNY

  • Detail

76-60-8SDS

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 Bromocresol green

1.2 Other means of identification

Product number -
Other names bromcresol green spray

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:76-60-8 SDS

76-60-8Synthetic route

2-sulfobenzoic acid cyclic anhydride
81-08-3

2-sulfobenzoic acid cyclic anhydride

3-methyl-phenol
108-39-4

3-methyl-phenol

bromocresol green
76-60-8

bromocresol green

Conditions
ConditionsYield
With phosphorus pentoxide Behandeln des Reaktionsgemisches mit Wasser und mit Brom in Essigsaeure;
Conditions
ConditionsYield
In dichloromethane Equilibrium constant;
2-[Bis-(3,5-dibromo-4-hydroxy-2-methyl-phenyl)-methyl]-benzenesulfonic acid; compound with triethyl-amine

2-[Bis-(3,5-dibromo-4-hydroxy-2-methyl-phenyl)-methyl]-benzenesulfonic acid; compound with triethyl-amine

A

bromocresol green
76-60-8

bromocresol green

B

triethylamine
121-44-8

triethylamine

Conditions
ConditionsYield
In acetonitrile at 25℃; Equilibrium constant; other solvents;
C21H14Br4O5S*2C17H23NO3

C21H14Br4O5S*2C17H23NO3

A

bromocresol green
76-60-8

bromocresol green

atropine
51-55-8

atropine

Conditions
ConditionsYield
In dichloromethane at 20℃; Equilibrium constant; Thermodynamic data; other temperatures; ΔH0, ΔS0, ΔG0;
m-cresolsulfonphthalein

m-cresolsulfonphthalein

bromocresol green
76-60-8

bromocresol green

Conditions
ConditionsYield
With bromine; acetic acid
Conditions
ConditionsYield
In dichloromethane Equilibrium constant; Thermodynamic data; ΔH0, ΔS0, ΔG0;
bromocresol green
76-60-8

bromocresol green

A

2-{(3,5-Dibromo-4-hydroxy-2-methyl-phenyl)-[3,5-dibromo-2-methyl-4-oxo-cyclohexa-2,5-dien-(Z)-ylidene]-methyl}-benzenesulfonic acid; compound with (2S,3R,4S,6R,7R,8R,8aS,13aR,13bR)-3-ethyl-13-methyl-1,3,4,7,8,13,13a,13b-octahydro-2H,6H-2,7-cyclo-6,8a-methano-pyrido[1',2':1,2]azepino[3,4-b]indole-4,8-diol

2-{(3,5-Dibromo-4-hydroxy-2-methyl-phenyl)-[3,5-dibromo-2-methyl-4-oxo-cyclohexa-2,5-dien-(Z)-ylidene]-methyl}-benzenesulfonic acid; compound with (2S,3R,4S,6R,7R,8R,8aS,13aR,13bR)-3-ethyl-13-methyl-1,3,4,7,8,13,13a,13b-octahydro-2H,6H-2,7-cyclo-6,8a-methano-pyrido[1',2':1,2]azepino[3,4-b]indole-4,8-diol

B

2-{(3,5-Dibromo-4-hydroxy-2-methyl-phenyl)-[3,5-dibromo-2-methyl-4-oxo-cyclohexa-2,5-dien-(Z)-ylidene]-methyl}-benzenesulfonic acid; compound with (2S,3R,4S,6R,7R,8R,8aS,13aR,13bR)-3-ethyl-13-methyl-1,3,4,7,8,13,13a,13b-octahydro-2H,6H-2,7-cyclo-6,8a-methano-pyrido[1',2':1,2]azepino[3,4-b]indole-4,8-diol

2-{(3,5-Dibromo-4-hydroxy-2-methyl-phenyl)-[3,5-dibromo-2-methyl-4-oxo-cyclohexa-2,5-dien-(Z)-ylidene]-methyl}-benzenesulfonic acid; compound with (2S,3R,4S,6R,7R,8R,8aS,13aR,13bR)-3-ethyl-13-methyl-1,3,4,7,8,13,13a,13b-octahydro-2H,6H-2,7-cyclo-6,8a-methano-pyrido[1',2':1,2]azepino[3,4-b]indole-4,8-diol

Conditions
ConditionsYield
at 15℃; Equilibrium constant; ΔH, ΔS, ΔG (excit.), variation of temperature;
bromocresol green
76-60-8

bromocresol green

triethylamine
121-44-8

triethylamine

2-[Bis-(3,5-dibromo-4-hydroxy-2-methyl-phenyl)-methyl]-benzenesulfonic acid; compound with triethyl-amine

2-[Bis-(3,5-dibromo-4-hydroxy-2-methyl-phenyl)-methyl]-benzenesulfonic acid; compound with triethyl-amine

Conditions
ConditionsYield
In acetonitrile at 25℃; Equilibrium constant; other solvents;
bromocresol green
76-60-8

bromocresol green

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine
738-70-5

5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine

C21H14Br4O5S*C14H18N4O3
74152-32-2

C21H14Br4O5S*C14H18N4O3

Conditions
ConditionsYield
In methanol Ambient temperature;0.022 g
bromocresol green
76-60-8

bromocresol green

homatropine
114173-36-3

homatropine

A

2-{(3,5-Dibromo-4-hydroxy-2-methyl-phenyl)-[3,5-dibromo-2-methyl-4-oxo-cyclohexa-2,5-dien-(Z)-ylidene]-methyl}-benzenesulfonic acid; compound with hydroxy-phenyl-acetic acid 8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester

2-{(3,5-Dibromo-4-hydroxy-2-methyl-phenyl)-[3,5-dibromo-2-methyl-4-oxo-cyclohexa-2,5-dien-(Z)-ylidene]-methyl}-benzenesulfonic acid; compound with hydroxy-phenyl-acetic acid 8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester

B

2-{(3,5-Dibromo-4-hydroxy-2-methyl-phenyl)-[3,5-dibromo-2-methyl-4-oxo-cyclohexa-2,5-dien-(Z)-ylidene]-methyl}-benzenesulfonic acid; compound with hydroxy-phenyl-acetic acid 8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester

2-{(3,5-Dibromo-4-hydroxy-2-methyl-phenyl)-[3,5-dibromo-2-methyl-4-oxo-cyclohexa-2,5-dien-(Z)-ylidene]-methyl}-benzenesulfonic acid; compound with hydroxy-phenyl-acetic acid 8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl ester

Conditions
ConditionsYield
at 16℃; Kinetics; Equilibrium constant; ΔH, ΔS, ΔG (excit.), variation of temperature;
bromocresol green
76-60-8

bromocresol green

clidinium bromide
3485-62-9

clidinium bromide

Br(1-)*C21H14Br4O5S*C22H26NO3(1+)

Br(1-)*C21H14Br4O5S*C22H26NO3(1+)

Conditions
ConditionsYield
pH=3; aq. buffer;
bromocresol green
76-60-8

bromocresol green

dequalinium chloride
522-51-0

dequalinium chloride

C21H14Br4O5S*C30H40N4(2+)*2Cl(1-)

C21H14Br4O5S*C30H40N4(2+)*2Cl(1-)

Conditions
ConditionsYield
pH=6; aq. buffer;
ciprofloxacin
85721-33-1

ciprofloxacin

bromocresol green
76-60-8

bromocresol green

C17H18FN3O3*C21H14Br4O5S

C17H18FN3O3*C21H14Br4O5S

Conditions
ConditionsYield
With acetic acid In ethanol; chloroform; water
ofloxacin
82419-36-1

ofloxacin

bromocresol green
76-60-8

bromocresol green

C18H20FN3O4*C21H14Br4O5S

C18H20FN3O4*C21H14Br4O5S

Conditions
ConditionsYield
With acetic acid In ethanol; chloroform; water
bromocresol green
76-60-8

bromocresol green

1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid
70458-96-7

1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

C16H18FN3O3*C21H14Br4O5S

C16H18FN3O3*C21H14Br4O5S

Conditions
ConditionsYield
With acetic acid In ethanol; chloroform; water
bromocresol green
76-60-8

bromocresol green

moxifloxacin
151096-09-2

moxifloxacin

C21H14Br4O5S*C21H24FN3O4

C21H14Br4O5S*C21H24FN3O4

Conditions
ConditionsYield
In ethanol; chloroform aq. acetate buffer;
5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione hydrochloride
112529-15-4

5-{4-[2-(5-ethyl-2-pyridyl)ethoxy]benzyl}-2,4-thiazolidinedione hydrochloride

bromocresol green
76-60-8

bromocresol green

pioglitazone-BCG ion-pair complex

pioglitazone-BCG ion-pair complex

Conditions
ConditionsYield
pH=2.4; aq. buffer;
bromocresol green
76-60-8

bromocresol green

eszopiclone
138729-47-2

eszopiclone

C17H17ClN6O3*C21H14Br4O5S

C17H17ClN6O3*C21H14Br4O5S

Conditions
ConditionsYield
In aq. buffer Acidic conditions;
4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-methylpiperidine hydrochloride

4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-methylpiperidine hydrochloride

bromocresol green
76-60-8

bromocresol green

C21H14Br4O5S*C21H21N

C21H14Br4O5S*C21H21N

Conditions
ConditionsYield
In aq. acetate buffer
bromocresol green
76-60-8

bromocresol green

aprepitant

aprepitant

C23H21F7N4O3*C21H14Br4O5S

C23H21F7N4O3*C21H14Br4O5S

Conditions
ConditionsYield
Stage #1: bromocresol green With sodium hydroxide In water
Stage #2: aprepitant In aq. phosphate buffer pH=4; pH-value;
bromocresol green
76-60-8

bromocresol green

carbetapentane citrate
23142-01-0

carbetapentane citrate

C20H31NO3*C21H14Br4O5S

C20H31NO3*C21H14Br4O5S

Conditions
ConditionsYield
In chloroform; cyclohexane

76-60-8Relevant articles and documents

Detection and identification of side reactions of halogenated hydrocarbon solvents with amines of pharmaceutical interest by secondary processes to the neutralizations of sulphonphthaleinic dyes with these amines

Gainza,Konyeaso,Asenjo

, p. 226 - 232 (2007/10/02)

The neutralization reactions between amines and diprotic acid dyes in organic solvents generate {dye-, amineH+} and {dye2-, (amineH+)2} ion associates that show two absorption bands in the visible spectrum. An unidentified third absorption band; which appears with a high amine concentration, proves that halogenated hydrocarbon solvents (dichloromethane, chloroform, 1,2-dichloroethane, and carbon tetrachloride) give side reactions with amines (atropine, tropine, quinine, ephedrine, and ajmaline) that generate a quaternary ammonium salt, N-halogenalkylammonium halide ({N+- RX,X-}). The molecular weight of the quaternary ammonium salt is the sum of the amine and that of the solvent. The {N+-RX,X-} ion associated reacts with {dye2-, (amineH+)2} by substitution reactions, forming {dye2-, amineH+, N+-RX} and {dye2-, (N+-RX)2} ion associates that justify the third absorption band. The amine-solvent side reactions are of first order with respect to the amine, being very slow processes with rate constant values from 399.4 h-1 (tropine-dichloromethane reaction) to 15.8 h-1 (atropine-1,2-dichloroethane reaction). Rate constants increase with the basicity of the amine measured in the halogenated hydrocarbons employed. Rate constants also increase with a reduction in the number of the halogen atoms present in the halogenated solvent. The new visible absorption band that appears in the amine-dye neutralization gives a quick colorimetric test to bring to light this kind of side reaction in these solvents.

Substitution reactions of benzethonium chloride with ion associates of bromocresol green - quinine and bromophenol blue - quinine in dichlormethane

Gainza, Alberto Hernandez,Konyeaso, Roy Ikemefula

, p. 937 - 944 (2007/10/02)

An excess concentration of base quinine (Q) reacts with a sulphonphthalein diacidic dye XH2, (bromocresol green, BCGH2, or bromophenol blue, BPBH2) in dichlormethane solution to form an ion associate (X(2-)(QH21+)2) of stoichiometry 1:2 (dye:amine).Benzethonium chloride (CIB) reacts with the 1:2 ion associate to form an ion associate (QH1+,X2-,B1+) and quinine hydrochloride ClQH(1+).This substitution reaction is a chemical equilibrium with formation constants of 1.50+/-0.67, 1.64+/-0.54, 1.07+/-0.29, 1.04+/-0.20, and 0.84+/-0.26 for BCG and 1.86+/-0.59, 1.47+/-0.23, 1.40+/-0.65, 1.13+/-0.37, and 1.11+/-0.27 for BPB at 283.16, 288.16, 293.16, 298.16, and 303.16 K respectively.The thermodynamic parameters determined by van't Hoff's equation are ΔH0 = -21.766+/-7.482 kJmol-1, ΔS0 = -73+/-51 Jmol-1K-1, and ΔG0 = -1.134+/-0.972 kJmol-1 for BCG and ΔH0 = -18.678+/-7.482 kJmol-1, ΔS0 = -61+/-26 Jmol-1K-1, ΔG0 = -0.916+/-0.401 kJmol-1 for BPB (ΔG0 at 293.16K; and ΔH0 and ΔS0 determined in the range 283-303K). Key words: bromocresol green-quinine-benzetonium, ion associate mixture, bromophenol blue-quinine-benzethonium, equilibrium constants, thermodynamic parameters.

Antiglaucoma agents

-

, (2008/06/13)

Pharmaceutical compositions and a method for reducing intraocular pressure by topically applying a carboxyalkyl dipeptide are disclosed.

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