3,5-dibromo-4-hydroxybenzonitrile

C7H3Br2NO

CAS1689-84-5
GHS08 Gefahrensymbol: Gesundheitsgefahr – Gesundheitsgefahr
GHS06 Gefahrensymbol: Giftig – Totenkopf mit Knochen
GHS09 Gefahrensymbol: Umweltgefährlich – Umwelt
Danger

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Identification

CAS Number
1689-84-5
EC Number
216-882-7
UN Number
2588
Index Number
608-006-00-0
PubChem CID
15531

Physical-chemical properties

Molecular Formula
C7H3Br2NO
Molar Mass
276.91 g/mol
IUPAC Name
3,5-dibromo-4-hydroxybenzonitrile

Chemical Identifiers

InChI
InChI=1S/C7H3Br2NO/c8-5-1-4(3-10)2-6(9)7(5)11/h1-2,11H
InChI Key
UPMXNNIRAGDFEH-UHFFFAOYSA-N

Overview

3,5-dibromo-4-hydroxybenzonitrile (CAS 1689-84-5) is a halogenated aromatic compound with antimicrobial properties and high aquatic toxicity. This brominated benzonitrile derivative represents an important class of organohalogen compounds widely utilized in industrial applications requiring biocidal activity. The molecular structure features two bromine atoms positioned at the 3 and 5 positions of the benzene ring, along with a hydroxyl group at position 4 and a nitrile functional group, conferring specific chemical reactivity and biological activity profiles. With a molecular weight of 276.91 g/mol and the molecular formula C7H3Br2NO, this compound exhibits characteristics typical of halogenated phenolic derivatives. The substance presents significant safety considerations, classified under multiple hazard categories including reproductive toxicity (Repr. 2), acute toxicity (Acute Tox. 2 and 3), and skin sensitization (Skin Sens. 1). Its environmental impact profile shows high concern with aquatic acute and chronic toxicity classifications, requiring careful handling protocols similar to other toxic aromatic compounds like N-methylaniline. The ADR classification of 6.1 indicates its status as a toxic substance for transportation purposes, necessitating specialized logistics and storage requirements. Primary industrial applications include antimicrobial formulations, chemical synthesis intermediates, and specialized biocide preparations where controlled microbial activity is essential. The compound serves as a building block in pharmaceutical synthesis and agricultural chemical production, leveraging its unique substitution pattern for targeted biological activity. OYSI maintains reliable supply chains for 3,5-dibromo-4-hydroxybenzonitrile, ensuring consistent availability for European industrial customers requiring this specialized chemical intermediate for their manufacturing processes.

Safety & Classification

Danger
Classification:

Repr. 2; Acute Tox. 2 *; Acute Tox. 3 *; Skin Sens. 1; Aquatic Acute 1; Aquatic Chronic 1

HHazard Statements (H-Statements)

Describe the nature and severity of the hazard

H330

Fatal if inhaled.

H301

Toxic if swallowed.

H317

May cause an allergic skin reaction.

H400

Very toxic to aquatic life.

H410

Very toxic to aquatic life with long lasting effects.

Classification according to CLP Regulation (EC) No 1272/2008. The complete list of hazard and precautionary statements can be found in the Safety Data Sheet (SDS).

First Aid Measures

Inhalation

Fatal

Measures if vapours or dust are inhaled

First Aid Actions

  • +P304IF INHALED:
  • +P340Remove person to fresh air and keep comfortable for breathing.
  • +P311Call a POISON CENTER/doctor.

Related hazard statements:

Skin Contact

Irritant

Measures if substance contacts the skin

First Aid Actions

  • +P302IF ON SKIN:
  • +P352Wash with plenty of water.
  • +P361Take off immediately all contaminated clothing.
  • +P313Get medical advice/attention.

Related hazard statements:

Ingestion

Toxic

Measures if substance is accidentally swallowed

First Aid Actions

  • +P301IF SWALLOWED:
  • +P330Rinse mouth.
  • +P331Do NOT induce vomiting.
  • +P310Immediately call a POISON CENTER/doctor.

Related hazard statements:

General Measures

Emergency 112 | Poison Control: +49 30 19240 (DE), +33 1 45 42 59 59 (FR), +31 30 274 88 88 (NL)

First aid measures are based on CLP classification and associated P-statements. They do not replace the Safety Data Sheet (SDS). In case of emergency, always consult the full SDS and a physician.

Transport (ADR)

UN Number2588
ADR Class6.1
Packing GroupII
Tunnel CodeD/E
Proper Shipping NameBromoxynil (ISO)
Marine PollutantNo

Frequently Asked Questions

What is 3,5-dibromo-4-hydroxybenzonitrile?

3,5-dibromo-4-hydroxybenzonitrile is an organobrominated chemical compound with the molecular formula C7H3Br2NO and CAS number 1689-84-5. This substance features a benzene ring substituted with two bromine atoms, one hydroxyl group, and one nitrile group. With a molecular weight of 276.91 g/mol, it belongs to the class of halogenated aromatic compounds and is classified as hazardous due to its toxicity and environmental impact.

What are the physicochemical properties of 3,5-dibromo-4-hydroxybenzonitrile?

3,5-dibromo-4-hydroxybenzonitrile is typically a solid crystalline compound at room temperature due to its aromatic structure and halogen substitutions. The presence of bromine atoms increases the molecular weight and density compared to non-halogenated analogs. The hydroxyl group provides some polarity to the molecule, while the nitrile group contributes to its chemical reactivity. Specific physical parameters like melting point and solubility depend on purity and measurement conditions.

What is 3,5-dibromo-4-hydroxybenzonitrile used for?

3,5-dibromo-4-hydroxybenzonitrile is primarily used as an intermediate in pharmaceutical synthesis and organic chemistry research. Its brominated aromatic structure makes it valuable for developing active pharmaceutical ingredients through various coupling reactions. The compound also serves as a building block in agrochemical synthesis and specialty chemical manufacturing. Due to its hazardous classification, its use is restricted to professional industrial applications with appropriate safety measures.

How to handle 3,5-dibromo-4-hydroxybenzonitrile safely?

3,5-dibromo-4-hydroxybenzonitrile requires strict safety protocols due to its Acute Toxicity 2-3 classification and skin sensitization properties. Personnel must wear appropriate PPE including chemical-resistant gloves, safety goggles, and respiratory protection. Work should be conducted in well-ventilated areas or under fume hoods. Avoid skin and eye contact, inhalation, and ingestion. Emergency washing facilities must be readily accessible, and only trained personnel should handle this substance in controlled professional environments.

How to store 3,5-dibromo-4-hydroxybenzonitrile correctly?

3,5-dibromo-4-hydroxybenzonitrile must be stored in tightly sealed containers in a cool, dry, well-ventilated area away from heat sources and incompatible materials. Storage areas should be secured and accessible only to authorized personnel due to its hazardous classification. The containers should be properly labeled with GHS pictograms (GHS06, GHS08, GHS09) and hazard information. Regular inspection of storage conditions and container integrity is essential to prevent leaks or degradation.

What to do in case of contact with 3,5-dibromo-4-hydroxybenzonitrile?

Immediate action is required due to the acute toxicity of 3,5-dibromo-4-hydroxybenzonitrile. For skin contact, remove contaminated clothing and wash affected area thoroughly with soap and water. In case of eye contact, rinse immediately with clean water for at least 15 minutes. If inhaled, move person to fresh air immediately. For ingestion, do not induce vomiting and seek medical attention immediately. Always consult the safety data sheet and contact poison control or emergency services when exposure occurs.

How to dispose of 3,5-dibromo-4-hydroxybenzonitrile properly?

3,5-dibromo-4-hydroxybenzonitrile disposal must comply with local and European waste regulations due to its hazardous classification. The substance cannot be disposed of as regular waste and requires treatment as hazardous chemical waste. Contact authorized waste management companies specializing in hazardous materials for proper disposal. Containers must be properly labeled and documented throughout the disposal process. Incineration at licensed facilities under controlled conditions is typically the preferred disposal method for such organic compounds.

How to transport 3,5-dibromo-4-hydroxybenzonitrile?

3,5-dibromo-4-hydroxybenzonitrile is classified as ADR Class 6.1 (toxic substances), Packing Group II, requiring strict transport regulations compliance. Packages must be properly labeled with hazard symbols and shipping documentation must include all required safety information. Only authorized carriers trained in hazardous materials transport can handle shipments. Vehicles must carry appropriate emergency equipment and spill containment materials. Transport containers must meet UN specification standards for toxic substances.

Is 3,5-dibromo-4-hydroxybenzonitrile subject to specific regulations?

3,5-dibromo-4-hydroxybenzonitrile is subject to European REACH and CLP regulations due to its hazardous classification. While not currently listed as SVHC (Substance of Very High Concern), its reproductive toxicity (Repr. 2) and acute toxicity classifications require compliance with strict handling, labeling, and safety data sheet requirements. Companies using this substance must ensure proper risk assessments, worker protection measures, and environmental safeguards are implemented according to European chemical safety legislation.

Where to buy 3,5-dibromo-4-hydroxybenzonitrile in Europe?

3,5-dibromo-4-hydroxybenzonitrile is available through OYSI, a specialized European distributor of chemical products. As a professional chemical supplier, OYSI ensures compliance with European regulations including proper documentation, safety data sheets, and transport requirements. The compound is restricted to professional use only due to its hazardous classification. Customers must demonstrate legitimate industrial or research purposes and appropriate safety handling capabilities when requesting quotations for this controlled substance.

Data Sources

Classification per CLP Regulation (EC) No 1272/2008. Data from ECHA and PubChem.