Lot numbers can be found on the outside label of a product:
3-(3-Bromophenyl)-3-oxopropanenitrile
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CAS No. 70591-86-5
- Cat. No. CS-0094689
- Purity≥98%
- MDL No.MFCD02260778
*For research and further manufacturing use only, not for direct human use.
Structure of 70591-86-5
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General Information
- CAS No. 70591-86-5
- Cat. No. CS-0094689
- Purity ≥98%
- MDL No. MFCD02260778
- Storage 4°C
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₉H₆BrNO
- Molecular Weight 224.05
- Synonym(s) Benzenepropanenitrile, 3-bromo-beta-oxo-
- SMILES N#CCC(C1=CC=CC(Br)=C1)=O
Description
3-(3-Bromophenyl)-3-oxopropanenitrile features a brominated phenyl ring coupled to a β-ketonitrile motif, enabling direct integration into Suzuki-Miyaura and Ullmann coupling cascades. The electron-deficient nitrile group facilitates nucleophilic addition, while the ketone offers coordination sites for transition metals. This bifunctional architecture supports rapid assembly of complex heterocycles under mild conditions.
Application
3-(3-Bromophenyl)-3-oxopropanenitrile serves as a versatile building block for heterocyclic synthesis, enabling efficient access to substituted quinoline and benzothiazole scaffolds via cyclization reactions. Its α,β-unsaturated nitrile functionality exhibits robust reactivity in nucleophilic addition and transition-metal-catalyzed coupling processes. The bromo substituent provides a handle for further diversification through cross-coupling chemistry. Bench-stable and readily purified by recrystallization, it functions effectively in standard synthetic workflows requiring functional group tolerance and predictable reactivity.
Synthesis
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Route1
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In-stock
618-89-3 -
75-05-8 - ~90%
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In-stock
70591-86-5
References
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BRISTOL-MYERS SQUIBB COMPANY; NAIDU, B. Narasimhulu; PATEL, Manoj; D'ANDREA, Stanley; ZHENG, Zhizhen Barbara; CONNOLLY, Timothy P.; LANGLEY, David R.; PEESE, Kevin; WANG, Zhongyu; WALKER, Michael A.; KADOW, John F. Patent: WO2014/28384 A1, 2014 ; Location in patent: Page/Page column 24; 25 ;
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Route2
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In-stock
6952-59-6 -
75-05-8
- ~76%
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In-stock
70591-86-5
References
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Takayama, Kazuhisa; Iwata, Masahiro; Hisamichi, Hiroyuki; Okamoto, Yoshinori; Aoki, Motonori; Niwa, Akira Chemical and pharmaceutical bulletin, 2002 , vol. 50, # 8 p. 1050 - 1059
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Route3
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151-50-8
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In-stock
18523-22-3 - ~66%
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In-stock
70591-86-5
References
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Gavrin, Lori K.; Lee, Arthur; Provencher, Brian A.; Massefski, Walter W.; Huhn, Stephen D.; Ciszewski, Gregory M.; Cole, Derek C.; McKew, John C. Journal of Organic Chemistry, 2007 , vol. 72, # 3 p. 1043 - 1046
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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 : H302-H315-H319-H335
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Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501
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Quality Control
Computational Chemistry Data
- TPSA 40.86
- LogP 2.54548
- H_Acceptors 2
- H_Donors 0
- Rotatable_Bonds 2
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Key Words
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