35691-65-7

Basic information

• Product Name: DBDCB
• Synonyms: 2-bromo-2-(bromomethyl)-glutaronitril;2-bromo-2-(bromomethyl)-pentanedinitril;methyldibromoglutaronitrile;tektamer38;dbdcb;2-bromo-(2-bromomethyl)glutaronitrile;2-Bromo-2-(bromomethyl)pentanedinitrile;1,2-DIBROMO-2,4-DICYANOBUTANE
• CAS NO: 35691-65-7
• Molecular Formula: C₆H₆Br₂N₂
• Molecular Weight: 265.93
• EINECS: 252-681-0
• Product Categories: Industrial/Fine Chemicals;FUNGICIDE;Building Blocks;C6 to C7;Chemical Synthesis;Cyanides/Nitriles;Nitrogen Compounds;Organic Building Blocks
• Mol File: 35691-65-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 48-50°C
• Boiling Point: 338.6 °C at 760 mmHg
• Flash Point: 158.6 °C
• Appearance: Crystals with a pungent odor
• Density: 1.9436 (rough estimate)
• Vapor Pressure: 9.71E-05mmHg at 25°C
• Refractive Index: 1.6300 (estimate)
• Storage Temp.: 2-8°C
• Water Solubility: Insoluble in water
• Merck: 14,3021
• BRN: 1930600
• CAS DataBase Reference: DBDCB(CAS DataBase Reference)
• NIST Chemistry Reference: DBDCB(35691-65-7)
• EPA Substance Registry System: DBDCB(35691-65-7)

Safety Data

• Hazard Codes: Xn
• Statements: 20/22-37/38-41-34-22
• Safety Statements: 26-36/37/39-45
• RIDADR: 3439
• WGK Germany: 2
• RTECS: MA5599000
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 35691-65-7(Hazardous Substances Data)

Usage

Description

1,2-Dibromo-2,4-dicyanobutane (DBDCB) is an organobromine compound that consists of pentanedinitrile bearing bromo and bromomethyl substituents at position 2. It is a light yellow crystalline solid or powder with a pungent odor and is insoluble in water. DBDCB is the main sensitizer of Euxyl K400, a widely used preservative agent in cosmetics, toiletries, or metalwork fluids.

Uses

Used in Metalworking Fluids:
DBDCB is used as a preservative for metalworking fluids to prevent the growth of bacteria and fungi, ensuring the proper functioning and longevity of the fluids.
Used in Cosmetics and Toiletries:
DBDCB is used as an active ingredient in Euxyl K 400, a broad-spectrum preservative with activity against fungi and bacteria, providing protection to cosmetics and toiletries from microbial contamination.
Used in Adhesives:
DBDCB is used as a preservative in adhesives to prevent the growth of microorganisms that can spoil the product and affect its performance.
Used in Latex Emulsions and Paints:
DBDCB is used as a preservative in latex paint and adhesives to prevent microbial growth, which can cause spoilage and affect the quality of the final product.
Used in Dispersed Pigments and Detergents:
DBDCB is used as a preservative in dispersed pigments and detergents to prevent microbial contamination and ensure the stability of these products.
Used in Agricultural Applications:
DBDCB is used as a microbiocide in the manufacture of food-grade paper and paperboard, as well as in recirculating water cooling systems, oil-recovery drilling mud systems, paper mill and pulp mill water systems, and similar industrial processing and chemical systems. It helps control slime-forming bacteria and fungi, maintaining the efficiency and cleanliness of these systems.
Used in the European and BSCA Baseline Series:
Despite the EU ban on MDBGN, its inclusion in products used in the workplace, such as barrier creams and after-work creams, makes its inclusion in the European and BSCA baseline series still relevant at the current time.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

DBDCB may polymerize in the presence of metals and some metal compounds. Incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents.

Trade name

BIOCHEK?; BIOCLEAR?; MERCK? 48051; METACIDE? 38; METASOL; TEKTAMER

Contact allergens

Methyldibromo glutaronitrile is a biocide widely used as a preservative agent in cosmetics, toiletries, and metalworking fluids. It is a potent allergen, banned in all cosmetics in the EU since 2007.

Safety Profile

Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NO, and Br-.

Potential Exposure

Nitrile microbiocide used as a preser- vative in food grade adhesives and as a slimicide in the manufacture of food grade paper and paperboard; used to control slime-forming bacteria and fungi in recirculating water cooling system; oil recovery drilling mud systems; paper mill and pulp mill water systems and similar indus- trial processing and chemical systems.

Shipping

UN3261 Corrosive solid, acidic, organic, n.o.s., Hazard class: 8; Labels: 8-Corrosive material, Technical Name Required. UN3439 Nitriles, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

Incompatibilities

Corrosive. Strong oxidizers and reducing agents, strong acids and bases. Reacts with acids, steam, warm water producing toxic and flammable hydrogen cya- nide fumes. Hydrogen cyanide is produced when propioni- trile is heated to decomposition. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give car- boxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids .

InChI:InChI=1/C6H6Br2N2/c7-4-6(8,5-10)2-1-3-9/h1-2,4H2

Synthetic route

2,4-dicyano-1-butene (1572-52-7) → 1,2-Dibromo-2,4-dicyanobutane (35691-65-7)

Conditions	Yield
With bromine Irradiation;

acrylonitrile (107-13-1) → 1,2-Dibromo-2,4-dicyanobutane (35691-65-7)

Conditions	Yield
Stage #1: acrylonitrile With triethylamine; zinc(II) chloride for 1h; Autoclave; Green chemistry; Large scale; Stage #2: With bromine In water at 50 - 100℃; for 2h; Green chemistry; Large scale;	510 kg

1,2-Dibromo-2,4-dicyanobutane (35691-65-7) → 2,4-dicyano-1-butene (1572-52-7)

Conditions	Yield
In acetonitrile Product distribution; Mechanism; other solvents;

Upstream product

• 107-13-1 acrylonitrile 
• 1572-52-7 2,4-dicyano-1-butene 

Downstream Products

• 1572-52-7 2,4-dicyano-1-butene 

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