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4-Bromo-1,8-naphthalic anhydride
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CAS No. 81-86-7
- Cat. No. CS-0015910
- Purity≥95%
- MDL No.MFCD00006927
*For research and further manufacturing use only, not for direct human use.
Structure of 81-86-7
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General Information
- CAS No. 81-86-7
- Cat. No. CS-0015910
- Purity ≥95%
- MDL No. MFCD00006927
- Storage Store at room temperature
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₂H₅BrO₃
- Molecular Weight 277.07
- Synonym(s) 4-Bromo-1,8-naphthalenedicarboxylic Anhydride
- SMILES O=C1C2=CC=CC3=C2C(C(O1)=O)=CC=C3Br
Description
4-Bromo-1,8-naphthalic anhydride features a sterically accessible anhydride moiety flanked by a bromine substituent at the 4-position. This electron-deficient naphthalene core enables efficient coupling in Diels-Alder reactions and serves as a direct handle for functionalization via nucleophilic substitution. Bench-stable under inert conditions, it facilitates streamlined access to complex polycyclic architectures in synthetic organic chemistry.
Application
4-Bromo-1,8-naphthalic anhydride serves as a versatile building block for the synthesis of functionalized naphthalene derivatives. Its anhydride functionality enables facile acylation and amidation reactions, while the bromine substituent provides a site for palladium-catalyzed cross-coupling. The compound exhibits good bench stability and facilitates straightforward purification, making it well-suited for use in medicinal chemistry and materials science applications.
Synthesis
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Route1
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81-84-5 - ~92%
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In-stock
81-86-7
References
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Rotstein, Benjamin H.; Mourtada, Rida; Kelley, Shana O.; Yudin, Andrei K. Chemistry - A European Journal, 2011 , vol. 17, # 44 p. 12257 - 12261
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Route2
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In-stock
2051-98-1 - ~82%
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In-stock
81-86-7
References
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Alaei, Parvaneh; Rouhani, Shohre; Gharanjig, Kamaladin; Ghasemi, Jahanbakhsh Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2012 , vol. 90, p. 85 - 92
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Route3
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75839-72-4
- ~12%
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In-stock
81-86-7
References
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Solodar', S. L.; Vinogradov, L. M. Journal of Organic Chemistry USSR (English Translation), 1980 , vol. 16, p. 1102 - 1104 Zhurnal Organicheskoi Khimii, 1980 , vol. 16, # 6 p. 1275 - 1277
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS07
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Signal Word : Warning
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UN#: N/A
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Class : N/A
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Packing Group : N/A
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Hazard Statements : H315-H319-H335
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Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501
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Quality Control
Computational Chemistry Data
- TPSA 43.37
- LogP 2.9129
- H_Acceptors 3
- H_Donors 0
- Rotatable_Bonds 0
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Key Words
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