2,2-Dibromo-2-cyanoacetamide
[CAS# 10222-01-2]

Identification

• Classification: Organic raw materials >> Amino compound >> Amide compound
• Name: 2,2-Dibromo-2-cyanoacetamide
• Synonyms: 2,2-Dibromo-2-carbamoylacetonitrile; 2,2-Dibromo-3-nitrilopropionamide; DBNPA
• Molecular Formula: C₃H₂Br₂N₂O
• Molecular Weight: 241.87
• CAS Registry Number: 10222-01-2
• EC Number: 233-539-7
• SMILES: C(#N)C(C(=O)N)(Br)Br

Properties

• Density: 2.5±0.1 g/cm³, Calc.^*
• Melting point: 122-125 °C (Expl.)
• Index of Refraction: 1.625, Calc.^*
• Boiling Point: 221.5±40.0 °C (760 mmHg), Calc.^*
• Flash Point: 87.8±27.3 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS06;GHS07;GHS08;GHS05;GHS09 Danger
• Risk Statements: H301-H314-H315-H317-H318-H330-H331-H372-H400-H410
• Safety Statements: P260-P261-P264-P264+P265-P270-P271-P272-P273-P280-P284-P301+P316-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P319-P320-P321-P330-P332+P317-P333+P317-P362+P364-P363-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Serious eye damage	Eye Dam.	1	H318
Skin irritation	Skin Irrit.	2	H315
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	2	H330
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Acute toxicity	Acute Tox.	3	H331
Skin corrosion	Skin Corr.	1B	H314
Skin sensitization	Skin Sens.	1B	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	2	H300
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Acute toxicity	Acute Tox.	1	H330
Skin corrosion	Skin Corr.	1	H314
Skin corrosion	Skin Corr.	1C	H314
Specific target organ toxicity - single exposure	STOT SE	3	H335
Specific target organ toxicity - single exposure	STOT SE	3	H336

Discovery and Applications

2,2-Dibromo-2-cyanoacetamide is an organic compound that has found applications primarily in the field of synthetic chemistry. It is known for its role as an intermediate in the synthesis of other chemical compounds, particularly in the preparation of bioactive molecules. The structure of 2,2-Dibromo-2-cyanoacetamide consists of a cyanoacetamide group with two bromine atoms attached to the carbon atom, making it a reactive compound with important applications in organic synthesis.

The discovery of 2,2-Dibromo-2-cyanoacetamide can be traced to efforts in the mid-20th century to develop reagents that could participate in a variety of chemical reactions. This compound is part of a class of compounds known for their reactivity, particularly in nucleophilic substitution reactions. The bromine atoms attached to the molecule are electrophilic, making the compound an effective halogenating agent in synthetic processes.

2,2-Dibromo-2-cyanoacetamide is mainly used in the synthesis of other organic compounds. It serves as an important intermediate in the preparation of various heterocyclic compounds, which are crucial in pharmaceuticals, agrochemicals, and materials science. It is commonly involved in the creation of molecules with biological activity, including potential antimicrobial, anticancer, and antiviral agents. The cyano group and the amide functionality in the structure of 2,2-Dibromo-2-cyanoacetamide contribute to its reactivity and its ability to form stable intermediates with various nucleophiles.

Additionally, this compound has been used in the development of certain types of pesticides and herbicides. Its ability to interact with biological systems at the molecular level has made it valuable for the design of agrochemicals that can target specific biochemical pathways in pests and plants. The reactivity of the compound, combined with its functional groups, allows for the creation of molecules that can selectively inhibit enzymes or interfere with cell processes, making it useful in the development of crop protection agents.

In summary, 2,2-Dibromo-2-cyanoacetamide is a versatile and reactive compound that plays an important role in synthetic organic chemistry. Its applications are diverse, ranging from the development of bioactive molecules in pharmaceutical research to its use in the synthesis of agrochemicals.

References

1973. Rates and products of decomposition of 2,2-dibromo-3-nitrilopropionamide. Journal of Agricultural and Food Chemistry, 21(3).
DOI: 10.1021/jf60189a012

2020. Non-target screening reveals the mechanisms responsible for the antagonistic inhibiting effect of the biocides DBNPA and glutaraldehyde on benzoic acid biodegradation. Journal of Hazardous Materials, 386.
DOI: 10.1016/j.jhazmat.2019.121661

2022. Quantification and Degradation of 2,2-Dibromo-3-Nitrilopropionamide (DBNPA) in Bioethanol Fermentation Coproducts. World Journal of Microbiology and Biotechnology, 38(5).
DOI: 10.1007/s11274-022-03253-0