Sudan black B

Structural formula
General
Surname	Sudan black B
other names	2,3-Dihydro-2,2-dimethyl-6 - {[1-naphthyl-4- (phenylazo)] azo} -1 H -perimidine; Solvent Black 3; Fat black BN; CI 26150;
Molecular formula	C 29 H 24 N 6
Brief description	dark brown to black odorless solid
External identifiers / databases
EC number	224-087-1
ECHA InfoCard	100,021,898
PubChem	61336
Wikidata	Q10861380
properties
Molar mass	456.55 g mol −1
Physical state	firmly
density	1.49 g cm −3
Melting point	120-124 ° C
solubility	practically insoluble in water; soluble in oils, fats, warm petrolatum, paraffin, phenol, ethanol, acetone, benzene, toluene and hydrocarbons;
Refractive index	1.457
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Sudan black B is a synthetically produced chemical compound from the group of azo and Sudan dyes .

Extraction and presentation

Sudan Black B can be prepared by coupling diazotized 4-Phenylazonaphthalenamin-1 with 2,3-dihydro-2,2-dimethyl-1 H are obtained -perimidin.

It can be obtained by diazotizing aniline , coupling with 1-naphthylamine , diazotizing again, coupling with 1,8-diaminonaphthalene and reacting with acetone .

properties

Sudan black B is a flammable, hardly ignitable, dark brown to black odorless solid that is practically insoluble in water. In a large number of fat solvents it changes its color character from blue-black to red. Many aliphatic and aromatic hydrocarbons as well as oxy derivatives of aromatic hydrocarbons including their halogen derivatives and the halogenated paraffins cause the hue to lighten from blue-black to red, while the large group of aliphatic alcohols , aldehydes and ketones with the exception of chloroacetone and saturated aliphatic carboxylic acids have no effect the color character. Sudan black B was also dissolved in lecithin , sphingomyelin and ganglioside of some lipoids in a metachromatic red solution. The metachromatic effect depends on the solvent in the sense of a polar alignment of the charges within the dye molecule determined by the solvent.

use

Sudan black B is used to stain chromosomes and bacterial lipids (λ _max = 596–605 nm, extinction coefficient: E 1% = 575–630 (596–605 nm, ethanol)). It is a basic black dye that is also used to color the triglycerides and lipids of some lipoproteins . It is also used in fingerprint enhancement and in the investigation of haematological diseases. Sudan black B is often used in cytochemistry to color neutral fats , phospholipids and cerebrosides . In hematology it gives easily reproducible reactions with cells of the blood and bone marrow. The method stains the lipid membrane that surrounds the azurophilic granules. The staining result largely resembles the peroxidase staining , but is judged to be somewhat more sensitive compared to the representation of myeloperoxidase (MPO) in myeloblasts . Another advantage mentioned is that it is simpler to carry out in contrast to MPO staining. The reaction should also be positive in lymphoblasts . According to another statement, lymphatic progenitor cells should be negative.

Trade names

BASF: Sudan Jet Black B, ~ BB
Bayer: Ceres Black BN
Hoechst: Bold Black HB, ~ HBN
Wolfen: Sudan Black B

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g Entry on Sudanschwarz B in the GESTIS substance database of the IFA , accessed on November 8, 2016(JavaScript required) .
^ ^A ^b Carl L. Yaws: The Yaws Handbook of Physical Properties for Hydrocarbons and Chemicals Physical Properties for More Than 54,000 Organic and Inorganic Chemical Compounds, Coverage for C1 to C100 Organics and Ac to Zr Inorganics . Gulf Professional Publishing, 2015, ISBN 978-0-12-801146-1 , pp. 661 ( limited preview in Google Book search).
↑ ^a ^b Datasheet Sudan Black B at AlfaAesar, accessed on November 8, 2016 ( PDF )(JavaScript required) .
↑ U. Pfüller, H. Franz, A. Preiß: Sudan Black B: Chemical structure and histochemistry of the blue main components. In: Histochemistry. 54, 1977, p. 237, doi : 10.1007 / BF00492246 .
↑ ^a ^b German Statutory Accident Insurance BK Report Aromatic Amine - A Work Aid in Occupational Disease Determination Procedures - Report of the Accident Insurance Institutions and the IFA - ( Memento of November 12, 2016 in the Internet Archive ), accessed on November 11, 2016.
↑ Paul B. Diezel, Gundega Neimanis: About the metachromatic effect of Sudanschwarz B. In: Virchow's archive for pathological anatomy and physiology and for clinical medicine. 330, 1957, p. 619, doi: 10.1007 / BF00954946 .
↑ PB Diezel: The Metabolic Disorders of Sphingolipoids A Histochemical Study of Primary Lipoidoses and Demyelinating Diseases of the Nervous System . Springer-Verlag, 2013, ISBN 978-3-642-86371-4 , p. 157 ( limited preview in Google Book search).
↑ Datasheet Sudan Black B, certified by the Biological Stain Commission at Sigma-Aldrich , accessed on November 8, 2016 ( PDF ).
↑ G. Soldani, P. Losi, C. Milioni, A. Raffi: Light microscopy evaluation of polyurethane vascular grafts porosity by Sudan Black B staining. In: Journal of Microscopy. 206, 2002, p. 139, doi: 10.1046 / j.1365-2818.2002.01021.x .
↑ hemato-images.eu: Sudanschwarz B-staining , accessed on November 8, 2016.
^ Microscopic technique: Romeis - microscopic technique . Springer-Verlag, 2015, ISBN 978-3-642-55190-1 , p. 226 ( limited preview in Google Book search).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on Sudanschwarz B in the GESTIS substance database of the IFA , accessed on November 8, 2016(JavaScript required) .

[Carl_L._Yaws-2] A ^b Carl L. Yaws: The Yaws Handbook of Physical Properties for Hydrocarbons and Chemicals Physical Properties for More Than 54,000 Organic and Inorganic Chemical Compounds, Coverage for C1 to C100 Organics and Ac to Zr Inorganics . Gulf Professional Publishing, 2015, ISBN 978-0-12-801146-1 , pp. 661 ( limited preview in Google Book search).

[Alfa-3] Datasheet Sudan Black B at AlfaAesar, accessed on November 8, 2016 ( PDF )(JavaScript required) .

[4] U. Pfüller, H. Franz, A. Preiß: Sudan Black B: Chemical structure and histochemistry of the blue main components. In: Histochemistry. 54, 1977, p. 237, doi : 10.1007 / BF00492246 .

[DGUV-5] German Statutory Accident Insurance BK Report Aromatic Amine - A Work Aid in Occupational Disease Determination Procedures - Report of the Accident Insurance Institutions and the IFA - ( Memento of November 12, 2016 in the Internet Archive ), accessed on November 11, 2016.

[DOI10.1007/BF00954946-6] Paul B. Diezel, Gundega Neimanis: About the metachromatic effect of Sudanschwarz B. In: Virchow's archive for pathological anatomy and physiology and for clinical medicine. 330, 1957, p. 619, doi: 10.1007 / BF00954946 .

[P._B._Diezel-7] PB Diezel: The Metabolic Disorders of Sphingolipoids A Histochemical Study of Primary Lipoidoses and Demyelinating Diseases of the Nervous System . Springer-Verlag, 2013, ISBN 978-3-642-86371-4 , p. 157 ( limited preview in Google Book search).

[Sigma-8] Datasheet Sudan Black B, certified by the Biological Stain Commission at Sigma-Aldrich , accessed on November 8, 2016 ( PDF ).

[DOI10.1046/j.1365-2818.2002.01021.x-9] G. Soldani, P. Losi, C. Milioni, A. Raffi: Light microscopy evaluation of polyurethane vascular grafts porosity by Sudan Black B staining. In: Journal of Microscopy. 206, 2002, p. 139, doi: 10.1046 / j.1365-2818.2002.01021.x .

[hemato-images.eu-10] to-images.eu: Sudanschwarz B-staining , accessed on November 8, 2016.

[Mikroskopische_Technik-11] Microscopic technique: Romeis - microscopic technique . Springer-Verlag, 2015, ISBN 978-3-642-55190-1 , p. 226 ( limited preview in Google Book search).