Vat Orange 3

• CAS: 4378-61-4
• Catalog Number: ACM4378614
• Category: Main Products
• Molecular Weight: 464.12
• Molecular Formula: C₂₂H₈Br₂O₂
• Synonyms: 4,10-Dibrom-dibenzo[def,mno]chrysen-6,12-dion; Indazin Scarlet GL; Lionogen Red GD; Helanthrene Orange RK; Hostaperm Scarlet GO; 4,10-dibromoanthanthrone; Monolite Red 2Y; Indanthrenbrillantorange RK; Lake Fast Red G; 4,10-dibromo-dibenzo[def,MnO]chrysene-6,12-dione; golden yellow KX; Sumitone Fast Red G; Brilliant Orange KKh; Brilliant Orange RK; 4.10-Dibrom-anthanthron
• IUPAC Name: Helio Brilliant Orange RK
• SMILES: C1=CC2=C3C(=C1)C(=CC4=C3C5=C(C2=O)C=C(C6=CC=CC(=C65)C4=O)Br)Br
• InChI Key: HTENFZMEHKCNMD-UHFFFAOYSA-N
• Boiling Point: 689.9ºC at 760 mmHg
• Flash Point: 229.6ºC
• Density: 1.97
• Appearance: solid
• EC Number: 224-481-3
• Exact Mass: 461.88900

Case Study

Transforming Vat Orange 3 into a Multifunctional Phosphorus-Hybrid Nanocarbon Platform

Dadgaryeganeh, Reza, et al. Chemical Science 16.8 (2025): 3680-3692.

Vat dyes such as Vat Orange 3 (VO3) are inexpensive, widely available, and possess extended π-conjugation - attractive starting points for high-value organic materials. A synthetic route was developed to first functionalize VO3 with bromoaryl units, followed by the key step of incorporating phosphorus via reaction with PhPCl2. This yielded two new target compounds as mixtures of cis- and trans- isomers. This methodology successfully converted the flat, planar dye into a twisted, phosphorus-modified nanocarbon structure. The chemistry delivers a versatile platform for sensor materials, responsive thin films and as a precursor family for engineered 2D organic nanocarbons.
Synthetic Routes:
VO3 → intermediate S1 (improved solubility) in 85% yield to break strong stacking. Install 2-bromoaryl groups via Miyaura borylation sequence to access S3 (76% yield) and S4 (58% yield). Introduce phosphoryl groups by metal-halogen exchange (n-BuLi) then PhPCl2, followed by controlled hydrolysis and Michaelis-Arbuzov rearrangement to give intermediates S5/S6. Final cyclization/oxidation (AgNO3-catalysed) produced two target families (termed 1-O and 2-O), isolated as separable cis/trans isomers in overall yields of 25% and 19%, respectively.
A subsequent step reduces P=O to trivalent phosphorus (using trichlorosilane under microwave heating at 150 °C), giving P(III) species (compounds 1 and 2) as isomeric mixtures (31P ~ -27 to -26 ppm); these are air-sensitive and handled/purified under inert atmosphere.

Vat Orange 3 as a Stable and Cost-Effective n-Type Semiconductor for Organic Electronics

Kahraman, Bilge, et al. Journal of Materials Chemistry C 12.11 (2024): 3838-3853.

Purified Vat Orange 3 (VO3) was evaluated as the active semiconductor layer in OFETs with a staggered bottom-gate, top-contact architecture. Thin films (~80 nm) were deposited via vacuum sublimation (at ~225-235°C) onto a dielectric stack.
Key Findings:
· Clear n-Type Semiconductor Behavior: VO3 functions as an n-type organic semiconductor in OFETs. Electrochemical data indicate a deep LUMO (below -4.0 eV), which explains the need to measure devices in an inert atmosphere (ambient injection/measurement compromised).
· Exceptional Material Stability: Measured field-effect mobilities were modest relative to state-of-the-art organic semiconductors. However, purified VO3 demonstrated very good stability against degradation when stored in air. OFETs fabricated with material stored for several years showed reproducible results, highlighting its robustness. VO3 sublimes reproducibly at ~225-235 °C under vacuum and shows good thermal handling for vacuum deposition.
· Chemical Handle for Tuning: VO3 has reactive bromine sites that allow relatively facile routes to chemical modification (cross-coupling, etc.) to tune the electronic structure, as well as polymerize/ create networks.
· Limitations for Hole Transport: Devices are n-type current, not p-type, even with Au contacts; deep HOMO/LUMO energetics imply that different contact metals (with different work functions) or chemical doping may be necessary to access hole transport.

Custom Q&A

What is the molecular formula of Vat Orange 3 according to the reference?

The molecular formula of Vat Orange 3 is C22H8Br2O2.

When was Vat Orange 3 created and modified according to the reference?

Vat Orange 3 was created on 2005-08-08 and modified on 2023-12-23.

What is the IUPAC name of Vat Orange 3 according to the reference?

The IUPAC name of Vat Orange 3 is 9,18-dibromohexacyclo[11.7.1.1 4,20 .0 2,11 .0 3,8 .0 17,21 ]docosa-1(21),2,4,6,8,10,13,15,17,19-decaene-12,22-dione.

What is the InChI of Vat Orange 3 according to the reference?

The InChI of Vat Orange 3 is InChI=1S/C22H8Br2O2/c23-15-7-14-19-17-9(15)3-1-5-11(17)21(25)13-8-16(24)10-4-2-6-12(22(14)26)18(10)20(13)19/h1-8H.

What is the Canonical SMILES of Vat Orange 3 according to the reference?

The Canonical SMILES of Vat Orange 3 is C1=CC2=C(C=C3C4=C2C(=C1)C(=O)C5=CC(=C6C=CC=C(C6=C54)C3=O)Br)Br.

What is the molecular weight of Vat Orange 3 according to the reference?

The molecular weight of Vat Orange 3 is 464.1 g/mol.

What is the XLogP3-AA value of Vat Orange 3 according to the reference?

The XLogP3-AA value of Vat Orange 3 is 6.5.

How many hydrogen bond donor counts does Vat Orange 3 have according to the reference?

Vat Orange 3 has 0 hydrogen bond donor counts.

What is the topological polar surface area of Vat Orange 3 according to the reference?

The topological polar surface area of Vat Orange 3 is 34.1 Ų.

How many heavy atom counts does Vat Orange 3 have according to the reference?

Vat Orange 3 has 26 heavy atom counts.