Indigo

• CAS: 482-89-3
• Catalog Number: ACM482893
• Category: Vat Dyes
• Molecular Weight: 262.26
• Molecular Formula: C16H10N2O2
• Synonyms: Delta(2,2’)-bipseudoindoxyl
• IUPAC Name: 2-(3-Hydroxy-1H-indol-2-yl)indol-3-one
• Canonical SMILES: C1=CC=C2C(=C1)C(=C(N2)C3=NC4=CC=CC=C4C3=O)O
• InChI: InChI=1S/C16H10N2O2/c19-15-9-5-1-3-7-11(9)17-13(15)14-16(20)10-6-2-4-8-12(10)18-14/h1-8,17,19H
• InChI Key: QQILFGKZUJYXGS-UHFFFAOYSA-N
• Boiling Point: 405.51 °C
• Melting Point: >300 °C (lit.)
• Density: 1.01 g/ml
• Appearance: Blue powder
• Active Content: 95%
• Complexity: 448
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 0
• Exact Mass: 262.074227566
• Hazard Statements: Xi,Xn
• Heavy Atom Count: 20
• Hydrogen Bond Acceptor Count: 3
• Hydrogen Bond Donor Count: 2
• Monoisotopic Mass: 262.074227566
• Physical State: Solid
• Rotatable Bond Count: 1
• Safety Description: 26-36
• Supplemental Hazard Statements: H373-H315-H319
• Symbol: GHS08,GHS07
• Topological Polar Surface Area: 65.4 Ų

Custom Q&A

What is the molecular formula of Indigo?

The molecular formula of Indigo is C16H10N2O2.

What is the molecular weight of Indigo?

The molecular weight of Indigo is 262.26 g/mol.

How is the molecular weight of Indigo computed?

The molecular weight of Indigo is computed by PubChem 2.2.

What are some synonyms of Indigo?

Some synonyms of Indigo include INDIGO, Indigotin, Indigo Blue, and Vat blue 1.

In what form does Indigo occur in the solid state?

In the solid state, Indigo occurs in the trans form.

What is the IUPAC name of Indigo?

The IUPAC name of Indigo is 2-(3-hydroxy-1H-indol-2-yl)indol-3-one.

What is the InChIKey of Indigo?

The InChIKey of Indigo is QQILFGKZUJYXGS-UHFFFAOYSA-N.

How many hydrogen bond donor counts does Indigo have?

Indigo has 2 hydrogen bond donor counts.

How many hydrogen bond acceptor counts does Indigo have?

Indigo has 3 hydrogen bond acceptor counts.

What is the exact mass of Indigo?

The exact mass of Indigo is 262.0742275.

Synthetic Use

Upstream Synthesis Route 1

• 120-72-9

• 16990-73-1
• 480-93-3
• 479-41-4
• 482-89-3

Reference: [1] Chemistry - A European Journal, 2000, vol. 6, # 9, p. 1531 - 1536

Upstream Synthesis Route 2

• 2642-37-7

• 482-89-3

Reference: [1]Baumann; Tiemann
[Chemische Berichte, 1879, vol. 12, p. 1101][Chemische Berichte, 1880, vol. 13, p. 413]
Baumann; Brieger
[Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1879, vol. 3, p. 254]

Downstream Synthesis Route 1

• 482-89-3

• 91-56-5

Reference: [1]Yi, Zhi-Qiang; Fang, Xiao-Niu; Cao, Zi-Yi; Wei, Yao; Li, Ya-Jing; Yi, Xiu-Guang
[Journal of Chemical Research, 2019, vol. 43, # 1-2, p. 58 - 62]
[2]Current Patent Assignee: Diez & Co. - DE229815, 1800, C
[Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 10, p. 353][Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 10, p. 353]
[3]Knop
[Journal fur praktische Chemie (Leipzig 1954), 1866, vol. <1>97, p. 81][Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, 1865, p. 584]
Erdmann
[Journal fur praktische Chemie (Leipzig 1954), 1841, vol. <1>24, p. 15]
Laurent
[Annales de Chimie (Cachan, France), 1841, vol. <3>3, p. 383][Journal fuer Praktische Chemie (Leipzig), 1842, vol. <1>25, p. 437]
Forrer
[Chemische Berichte, 1884, vol. 17, p. 976]
Kolbe
[Journal fur praktische Chemie (Leipzig 1954), 1884, vol. <2> 30, p. 474]
Schuetzenberger
[Bulletin de la Societe Chimique de France, 1865, vol. <2> 4, p. 177]
v.Sommaruga
[Justus Liebigs Annalen der Chemie, 1878, vol. 190, p. 369]
Hofmann
[Justus Liebigs Annalen der Chemie, 1845, vol. 53, p. 12;][Journal de pharmacie et de chimie, vol. <3>7, p. 202]
Knape
[Journal fur praktische Chemie (Leipzig 1954), 1891, vol. <2> 43, p. 213,217]
Gericke
[Journal fur praktische Chemie (Leipzig 1954), 1865, vol. <1> 95, p. 180,257][Zeitschrift fuer Chemie, 1865, p. 591]
[4]Knop
[Journal fur praktische Chemie (Leipzig 1954), 1866, vol. <1>97, p. 81][Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, 1865, p. 584]
Erdmann
[Journal fur praktische Chemie (Leipzig 1954), 1841, vol. <1>24, p. 15]
Laurent
[Annales de Chimie (Cachan, France), 1841, vol. <3>3, p. 383][Journal fuer Praktische Chemie (Leipzig), 1842, vol. <1>25, p. 437]
Forrer
[Chemische Berichte, 1884, vol. 17, p. 976]
Kolbe
[Journal fur praktische Chemie (Leipzig 1954), 1884, vol. <2> 30, p. 474]
Schuetzenberger
[Bulletin de la Societe Chimique de France, 1865, vol. <2> 4, p. 177]
v.Sommaruga
[Justus Liebigs Annalen der Chemie, 1878, vol. 190, p. 369]
Hofmann
[Justus Liebigs Annalen der Chemie, 1845, vol. 53, p. 12;][Journal de pharmacie et de chimie, vol. <3>7, p. 202]
Knape
[Journal fur praktische Chemie (Leipzig 1954), 1891, vol. <2> 43, p. 213,217]
Gericke
[Journal fur praktische Chemie (Leipzig 1954), 1865, vol. <1> 95, p. 180,257][Zeitschrift fuer Chemie, 1865, p. 591]
[5]Gandra, Naveen; Frank, Aaron T.; Le Gendre, Onica; Sawwan, Nahed; Aebisher, David; Liebman, Joel F.; Houk; Greer, Alexander; Gao, Ruomei
[Tetrahedron, 2006, vol. 62, # 46, p. 10771 - 10776]

* For details of the synthesis route, please refer to the original source to ensure accuracy.