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Merck
CN

N4876

Ninhydrin

powder, suitable for amino acid detection

Synonym(s):

1,2,3-Indantrione monohydrate, 2,2-Dihydroxy-1,3-indanedione, Trioxohydrindene monohydrate

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About This Item

Empirical Formula (Hill Notation):
C9H6O4
CAS Number:
485-47-2
Molecular Weight:
178.14
Beilstein:
1910963
EC Number:
207-618-1
MDL number:
MFCD00003791
UNSPSC Code:
12352100
PubChem Substance ID:
24897715
NACRES:
NA.21

Key Documents

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Product Name

Ninhydrin, suitable for amino acid detection

form

powder

Quality Level

200

mp

250 °C (dec.) (lit.)

solubility

ethanol: 100 mg/mL
H2O: 50 mg/mL (with sonication)

suitability

suitable for amino acid detection

functional group

hydroxyl
ketone

SMILES string

OC1(O)C(=O)c2ccccc2C1=O

InChI

1S/C9H6O4/c10-7-5-3-1-2-4-6(5)8(11)9(7,12)13/h1-4,12-13H

InChI key

FEMOMIGRRWSMCU-UHFFFAOYSA-N

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General description

Ninhydrin is an important building block in organic synthesis and has been employed to prepare a variety of chemicals for complexing and/or sensing metal ions. It is an amino acid-sensitive reagent used for the preparation of Ruhemann′s purple.

Application

Ninhydrin can be used:
  • For the detection of free amino groups in amino acids, peptides, and proteins.
  • As a ligand for the Cu-catalyzed N-arylation of nitrogen-containing heterocycles with aryl and heteroaryl halides to synthesize N-arylheterocycles.
  • As a reactant to synthesize aldols by reacting with active methylene compounds.
Used for the detection of free amino groups in amino acids, peptides and proteins.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000485019
0000485019
0000428374
0000428374
BCCN6105

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Isolation and activation of collagenase from fish processing waste.
Daboor SM, et al.
Advances in Bioscience and Biotechnology, 3(3) (2012)
Vibrational spectroscopy and density functional theory study of ninhydrin.
Li R, et al.
Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 136, 1642-1648 (2015)
Reaction of diaminofurazane with ninhydrin.
Pirogov SV, et al.
Chemistry of Heterocyclic Compounds, 33(12), 1473-1474 (1997)
Quantitative determination of chitosans by ninhydrin.
Prochazkova S, et al.
Carbohydrate Polymers, 38(2), 115-122 (1999)
Substituted naphthoquinones as novel amino acid sensitive reagents for the detection of latent fingermarks on paper surfaces
Jelly R, et al.
Talanta, 82, 1717-1724 (2010)
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