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Malachite green hemioxalate

HCID 17093
NotesReactions
Basic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
2437-29-8
Standard SMILES
CN(C)c1ccc(C(=C2C=CC(=[N+](C)C)C=C2)c2ccccc2)cc1.O=C(O)C(=O)O.O=C([O-])C(=O)O
InChIKey
ISCIXAIEDTZJCQ-UHFFFAOYSA-M
Molecular formula
C27H28N2O8
Average molar mass
508.5 g/mol
Monoisotopic mass
508.18456586

Names & identifiers

Preferred name
Malachite green hemioxalate
IUPAC
[4-[[4-(dimethylamino)phenyl]-phenylmethylidene]cyclohexa-2,5-dien-1-ylidene]-dimethylazanium;2-hydroxy-2-oxoacetate;oxalic acid
English name
Malachite green
Molecular formula
C52H54N4O12
Molecular weight
927

Names & synonyms

Oxalate Vert MalachiteOxalato Verde MalaquitaOssalato Verde MalachiteOxalato de verde malaquitaMalachite green hemioxalateoic acid, ethanedioic acidN,N,N',N'-Tetramethyl-4,4'-diaminotriphenylcarbenium oxalateBRILLIANT GREEN OXALATEorb1218299CHEMBL1789985Malachite Green Oxalate(C.I 42000)[4-[[4-(dimethylamino)phenyl]-phenylmethylidene]cyclohexa-2,5-dien-1-ylidene]-dimethylazanium;2-hydroxy-2-oxoacetate;oxalic acid
Show more names
MALACHITE GREENOXALATEMALACHITE GREEN OXALATEBASIC GREENEthanedioateOxalate saltMALACHITE GREEN OXALATE SALTCarboxyformateMalachite green chlorideMalachit Green Oxalate

Properties

Computed structural properties

Topological polar surface area
158 Ų
Hydrogen bond donors
3
Hydrogen bond acceptors
9
Rotatable bonds
4
Heavy atoms
37
Formal charge
0
Complexity
666

Physicochemical properties

Melting point
164 °C · 164°C (dec.)
bulk density
400 · 400-500kg/m3
storage temp.
room temp
solubility
110 g/l · 110g/l
form
Powder/Solid
pka
6.9 · 6.9(at 25℃)
Colour Index
42000 · 42000
color
754 · S. No.: 754
PH Range
0 · 0.0(YELLOW)-2.0(GREEN); 11.0(GREEN)-13.5(CORLORLESS)
PH
2.4 · 2.4 (10g/l, H2O, 24℃)
Water Solubility
60 g/L · 60 g/L (20 ºC)
λmax
614 nm, · 614 nm, 425 nm
Merck
14 · 14,5699
BRN
3644550 · 3644550
Stability
Stable. Substances to be avoided include strong oxidizing agents.
Biological Applications
Detecting bacterial growth; treating fish diseases,malignant neoplasm

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

PPE
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
BQ1190000
ridadr
UN 2811 6.1/PG 3
hs_code
32041300
risk_code
22-41-50/53-63-25-21-40-36/37/38-20/21/22-52/53-51/53-36/38
Signal word
Danger
Symbol(GHS)
GHS05,GHS06,GHS08,GHS09
hazard_code
Xn,N,Xi
safety_code
26-39-45-61-60-46-36/37-2-36/37/39-36-22
hazard_class
6.1(b)
Storage Class
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
packing_group
III
Hazard statements
H301-H318-H361d-H410
Limited Quantities
5.0 kg (11 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Hazard Classifications
Acute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1Eye Dam. 1Repr. 2
Precautionary statements
P201-P202-P273-P280-P301+P310-P305+P351+P338

Chemistry & industry

Applications · 4 items

UsesBasic Green 4 is used in Local, Anti-Infective Agents; Industrial, Fungicides. As an internal antiseptic, it is administered to treat canine dysentery ad calf scours, whereas as an external antiseptic it can be applied to abrasions and infected wounds as a triple dye that consists of gentian violet, brilliant green, and rivanol . Malachite green oxalate (arylmethane dye) is also used as a remedy for mycotic infections in aquaculture. Traditionally, malachite green is used as a dye .

UsesBiological stain, dye reagent, acid base indicator: pH 0.0 yellow, 2.0 green;11.6 green, 14 colorlessMalachite Green oxalate is used as the staining solution for embedded botanical material and as a spore stain. It is also used in studying the photocatalytic degradation with TiO2/WO3. It is employed for determining phosphate in serum and as a reference material in analytical chemistry for the quantification. It is also used as a pH indicator between pH 0.2 - 1.8. It is used as a dye for materials such as silk, leather, and paper.

UsesMalachite Green oxalate salt has been used:in the preparation of Alexander staining solution for cell viability testin malachite green-ammonium molybdate assay for determining the adenosine triphosphatase (ATPase) activity of binding immunoglobulin protein (BiP)as a hydrophobic ion, to study the label-free molecular transport in the living cell membranes of Escherichia coli in real time by second-harmonic generation (SHG) method

General DescriptionMalachite Green is used for bacterial spore staining by Schaeffer and Fulton`s method. It can also be used in place of methyl green in the Pappenheim stain, when combined with the Gram stain.

Preparation methods · 1 item

PreparationTo prepare Basic Green 4, 14 grams of benzaldehyde and 35 grams of dimethylaniline are combined with 31.5 grams of concentrated hydrochloric acid and the contents are heated to 1000 C for a period of 24 hours with the aid of a reflux condenser. The alkalinity of the resulting solution is enhanced by sodium hydroxide, then the reacting mass is distilled over steam to get rid of traces of dimethylaniline and benzaldehyde. The addition of 1 liter of water to the leuco base allows for the separation of hard granules. The granules are then filtered and the compound is unbound from alkali . Notably, the oxidation of the leuco base starts by melting 10g of the base over heat and adding a mixture of 4g of acetic acid and 27g of hydrochloric acid and about 3000ml of water. Nonetheless, 7.5g of a fine paste comprising refined lead oxide is gradually mixed in while stirring should continue for about 2 hours after the initial addition. Moreover, the unreacted lead oxide is obtained through filtration and the resulting filtrate is exposed to heat until it attains its boiling point, after which sodium sulfate is incorporated to separate excess lead. The resulting solution is then placed under heat to bring it to boil for effective precipitation with sodium hydroxide. Upon cooling, it is then filtered, washed, dehydrated, and further broken down in light petroleum, then impurities are filtered off, the resulting solution is evaporated to remove petrol, which yields pure Basic Green 4.

Related reactions

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Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

Database identifiers

CAS
2437-29-8
PubChem CID
17093
ChEMBL
CHEMBL1789985
Major Application
cleaning productscosmeticsfood and beveragespersonal care
InChI
1S/C23H25N2.C2H2O4/c1-24(2)21-14-10-19(11-15-21)23(18-8-6-5-7-9-18)20-12-16-22(17-13-20)25(3)4;3-1(4)2(5)6/h5-17H,1-4H3;(H,3,4)(H,5,6)/q+1;/p-1
InChIKey
CNYGFPPAGUCRIC-UHFFFAOYSA-L
SMILES
C[N+](C)=C1C=CC(C=C1)=C(C2=CC=C(N(C)C)C=C2)C3=CC=CC=C3.[O-]C(C(O)=O)=O
CAS DataBase Reference
2437 · 2437-29-8(CAS DataBase Reference)
EWG's Food Scores
5 · 5-8
FDA UNII
1 H9O33VU · GY1H9O33VU
EPA Substance Registry System
Malachite green oxalate (2437-29-8)
UNSPSC Code
41116130 · 41116130
NACRES
47 · NA.47
Symbol(GHS)
5 · GHS05,GHS06,GHS08,GHS09
Signal word
Danger
Hazard statements
301 · H301-H318-H361d-H410
Precautionary statements
201 · P201-P202-P273-P280-P301+P310-P305+P351+P338
PPE
95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
Hazard Codes
Xn,N,Xi
Risk Statements
22 · 22-41-50/53-63-25-21-40-36/37/38-20/21/22-52/53-51/53-36/38
Safety Statements
26 · 26-39-45-61-60-46-36/37-2-36/37/39-36-22
RIDADR
2811 · UN 2811 6.1/PG 3
WGK Germany
3 · 3
RTECS
1190000 · BQ1190000
TSCA
TSCA listed
HazardClass
6.1 · 6.1(b)
PackingGroup
III
HS Code
32041300 · 32041300
Storage Class
6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
3 OralAquatic · Acute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1Eye Dam. 1Repr. 2
Limited Quantities
5 kg · 5.0 kg (11 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)

Upstream & downstream products

Upstream raw materials

BenzotrichlorideBenzaldehydeN,N-Dimethylaniline

Suppliers100 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
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天津阿尔塔科技有限公司022-65378550-8551 · [email protected]
HBCChem, Inc.+1-510-219-6317 · [email protected]
四川省维克奇生物科技有限公司028-81700200 18116577057 · [email protected]
成都零六生物科技有限公司400-1166-196 13458535857 · [email protected]
雷丁试剂0510-85629785 18013409632 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
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Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
桦特昇生物科技(武汉)有限公司027-59207879 1972026995 18140587686 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
JADECHEM (NINGBO) CO.,LTD.574-89075960 · [email protected]

Additional notes

DefinitionA salt or ester of oxalicacid.