Bromcyan

Cyanogen Bromide

HCID 10476CAS 506-68-3

Grundinformationen

Standard-SMILES
N#CBr
InChIKey
ATDGTVJJHBUTRL-UHFFFAOYSA-N
Summenformel
CBrN
Durchschnittliche Molmasse
105,92 g/mol
Monoisotopische Masse
104,9214111

Überblick

Cyanogen bromide is a colorless to white crystalline solid with a penetrating odor. It is slightly soluble in water. It is gradually decomposed by water and very rapidly by acids to give off hydrogen bromide, a flammable and poisonous gas. Contamination with many materials can cause rapid decomposition of the material. It is toxic by inhalation of its vapors or by the hydrogen cyanide from decomposition or by ingestion. Toxic oxides of nitrogen are produced in fire involving this material. It is used in gold extraction, to make other chemicals, and as a fumigant.

Namen und Bezeichner

Bevorzugter Name
Cyanogen Bromide
IUPAC
carbononitridic bromide
Lokaler Name
Bromcyan
Englischer Name
Cyanogen bromide
Summenformel
CBrN
Molmasse
105.92

Namen und Synonyme

CYANOGEN BROMIDE506-68-3Bromine cyanideCyanobromideBromocyanideBromocyanogencarbononitridic bromideBromocyanCampilitCyanogen monobromideBromure de cyanogenBromocyane
Weitere Namen anzeigen
BrCNCyanic bromideCyanogens bromidetl822(CN)Br
Cyanogen bromide (BrCN)Cyanogen bromide ((CN)Br)TL 822Bromine monocyanideDTXSID9021550OS382OHJ8PBromine cyanide (BrCN)NSC-89684

Datenbank-Bezeichner

CAS
506-68-3
PubChem CID
10476
DTXSID
DTXSID9021550
ChEMBL
CHEMBL3561885
UNII
OS382OHJ8P
EC Number
208-051-2
Nikkaji
J2.608E

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,1
Polarare Oberfläche (TPSA)
23,8 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
0
Schwere Atome
3

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Toxic Gases & Vapors -> Cyanides

Reactive agents - 1st degree

SpringerMaterials PropertiesDunham energy parameter
PesticidesPesticide -> EPA IRIS
OdorPenetrating
TasteBitter
Density · 6 Einträge

2.015 at 68 °F (EPA, 1998) - Denser than water; will sink

2.015 g/cu cm at 20 °C

Percent in saturated air: 12.1% (20 °C); density of saturated air: 1.32 (20 °C)

2.0 g/cm³

Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.53

2.015 @ 20°C

Physikochemische Eigenschaften

Schmelzpunkt
50 · 50-53 °C (lit.)
Siedepunkt
61 · 61-62 °C (lit.)
Dichte
1.443 g/mL · 1.443 g/mL at 25 °C
Dampfdichte
3.65 · 3.65 (vs air)
Dampfdruck
100 mm · 100 mm Hg ( 22.6 °C)
Brechungsindex
1.467 · 1.4670 (estimate)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H300+H310+H330 (60.5%): Fatal if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

P260, P262, P264, P264+P265, P270, P271, P273, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P320, P321, P330, P361+P364, P363, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 177 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: Cyanogen bromide

Status: Active Update: 06-11-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/25751

Cyanogen bromide: HSNO Approval: HSR004413 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - Cyanogen bromide: Human health tier I assessment
DOT LabelPoison Corrosive
Fire Hazards · 3 Einträge

Cyanogen bromide is not combustible itself, but impure cyanogen bromide decomposes rapidly and tends to explode. A violent reaction may take place on contact with large quantities of acid. Vapors are highly irritating. When material is heated to decomposition, it emits very toxic fumes of cyanide and bromide. Avoid water, acids. Avoid physical damage, contact with acids or water, and store away from a location where water may be needed for fire control. (EPA, 1998)

· Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes.

Not combustible but forms flammable gas on contact with water or damp air. Gives off irritating or toxic fumes (or gases) in a fire.

Fire PotentialNoncombustible
Health Hazards · 2 Einträge

Super toxic; probable oral lethal dose in humans is less than 5 mg/kg or a taste (less than 7 drops) for a 70 kg (150 lb.) person. Vapors are highly irritant and very poisonous. Individuals with chronic diseases of the kidneys, respiratory tract, skin, or thyroid are at greater risk of developing toxic cyanide effects. (EPA, 1998)

· TOXIC and/or CORROSIVE; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death.

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Wear full protective clothing. Avoid direct water contact as it will cause cyanogen bromide to decompose, releasing toxic gases. Avoid breathing vapors or dusts; keep upwind; wear self-contained breathing apparatus.

In case of fire in the surroundings, use appropriate extinguishing media.

First Aid Measures · 4 Einträge

Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Refer for medical attention . Rinse mouth. Induce vomiting (ONLY IN CONSCIOUS PERSONS!).

Accidental Release Measures · 2 Einträge

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 2 Einträge

Warning: Cyanogen bromide may be fatal if inhaled, swallowed, or absorbed through skin or mucous membranes. Caution is advised.

General First Aid:

Safe StorageSeparated from food and feedstuffs. See Chemical Dangers. Dry. Well closed.
Exposure Control and Personal Protection · 2 Einträge

· Wear positive pressure self-contained breathing apparatus (SCBA).

2.0 [mg/m3], as CN, inhalable fraction, as CN[German Research Foundation (DFG)]

Toxikologische Informationen

Treatment · 1 Eintrag

EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

Interactions · 1 Eintrag

An approach to antidote therapy for cyanide poisoning by using Stroma-Free Methemoglobin Solution was investigated. Rats injected with an LD100 intravenous dose of cyanide were treated with Stroma-Free Methemoglobin Solution equal to 1.5% of their total body hemoglobin. There was a highly significant increase in the survival rate of the treated group compared to saline controls. The potential advantages of Stroma-Free Methemoglobin Solution over current antidotes include an immediate onset of action, rapid elimination of cyanide from the body and a mode of action that doesn't compromise any of the patients' oxygen carrying capacity. Stroma-Free Methemoglobin Solution shows promise as a significant adjunct in the treatment of cyanide poisoning. /Stroma-free methemoglobin solution is prepared from outdated red blood cells by the removal of all cellular membranes (stroma) and induction of methemoglobinemia equivalent to 90% of the total hemoglobin with potassium ferricyanide. Any excess potassium ferricyanide is then removed by dialysis against saline. The resultant preparation does not contain the antigenic components that have been previously reported to cause renal failure and coagulopathies./

Target OrgansEndocrine
Health Effects · 1 Eintrag

Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. Bromine vapour causes irritation and direct damage to the mucous membranes. Elemental bromine also burns the skin. The bromide ion is a central nervous system depressant and chronic exposure produces neuronal effects. This is called bromism and can result in central reactions reaching from somnolence to coma, cachexia, exicosis, loss of reflexes or pathologic reflexes, clonic seizures, tremor, ataxia, loss of neural sensitivity, paresis, papillar edema of the eyes, abnormal speech, cerebral edema, delirium, aggressiveness, and psychoses. (L625, L626, L627, L96, L97)

Ecotoxicity Values · 2 Einträge

LC50; Species: Lepomis macrochirus (Bluegill) length 33-75 mm; Conditions: freshwater, static, 23 °C, pH 7.6-7.9, hardness 55 mg/L CaCO3; Concentration: 240 ug/L for 96 hr /formulated product/

LC50; Species: Menidia beryllina (Inland silverside) length 40-100 mm; Conditions: saltwater, static, 20 °C, pH 7.6-7.9, hardness 55 mg/L CaCO3; Concentration: 470 ug/L for 96 hr /formulated product/

Adverse EffectsOther Poison - Chemical Asphyxiant

Regulatorische Informationen

RCRA Requirements · 2 Einträge

U246; As stipulated in 40 CFR 261.33, when cyanogen bromide, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

D003; A solid waste containing cyanogen bromide may become characterized as a hazardous waste when subjected to testing for reactivity as stipulated in 40 CFR 261.23, and if so characterized, must be managed as a hazardous waste.

CERCLA Reportable Quantities · 2 Einträge

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1000 lb or 454 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Cyanogen bromide is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500 or 10,000 lbs. Extremely hazardous substances that are solids are subject to either of two threshold planning quantities ... The lower quantity applies only if the solid exists in powdered form and has a particle size less than 100 microns; or is handled in solution or in molten form; or meets the criteria for a National Fire Protection Association (NFPA) rating of 2, 3 or 4 for reactivity. If the solid does not meet any of these criteria, it is subject to the upper ... threshold planning quantity ... .

Clean Water Act Requirements · 3 Einträge

Toxic pollutant designated pursuant to section 307(a)(1) of the Federal Water Pollution Control Act and is subject to effluent limitations. /Cyanides/

The procedures described in the "Guidelines for Deriving Numerical National Water Quality Criteria for the Protection of Aquatic Organisms and Their Uses" indicate that, except possibly where a locally important species is very sensitive, freshwater aquatic organisms and their uses should not be affected unacceptably if the four day average concentration of cyanide does not exceed 5.2 ug/L more than once every three years on the average and if the one hour average concentration does not exceed 22 ug/L more than once every three years on the average. /Cyanide/

The procedures described in the "Guidelines for Deriving Numerical National Water Quality Criteria for the Protection of Aquatic Organisms and Their Uses" indicate that, except posssibly where a locally important species is very sensitive, saltwater aquatic organisms and their uses should not be affected unacceptably if the one hour average concentration of cyanide does not exceed 1.0 ug/L more than once every three years on the average. /Cyanide/

Sicherheitsdaten

F
8-17-19-21
wgk
3
tsca
TSCA listed
ridadr
UN 1889
hs_code
28530090
RTECS-Nr.
GT2100000

Chemie und Industrie

Pharmakologische Informationen

Bionecessity · 1 Eintrag

The spatial organization of biofilms is strongly regulated by chemical cues released by settling organisms. However, the exact nature of these interactions and the repertoire of chemical cues and signals that micro-organisms produce and exude in response to the presence of competitors remain largely unexplored. Biofilms dominated by microalgae often show remarkable, yet unexplained fine-scale patchy variation in species composition. Because this occurs even in absence of abiotic heterogeneity, antagonistic interactions might play a key role. Here /the authors/ show that a marine benthic diatom produces chemical cues that cause chloroplast bleaching, a reduced photosynthetic efficiency, growth inhibition and massive cell death in naturally co-occurring competing microalgae. Using headspace solid phase microextraction (HS-SPME)-GC-MS, we demonstrate that this diatom exudes a diverse mixture of volatile iodinated and brominated metabolites including the natural product cyanogen bromide (BrCN), which exhibits pronounced allelopathic activity. Toxin production is light-dependent with a short BrCN burst after sunrise. BrCN acts as a short-term signal, leading to daily "cleaning" events around the algae. /Investigators/ show that allelopathic effects are H2O2 dependent and link BrCN production to haloperoxidase activity. This strategy is a highly effective means of biofilm control and may provide an explanation for the poorly understood role of volatile halocarbons from marine algae, which contribute significantly to the atmospheric halocarbon budget.

Mechanism of Action · 1 Eintrag

Cyanide has a very high affinity for iron in the ferric state. When absorbed /cyanide/ ... reacts readily with trivalent iron of cytochrome oxidase in mitochondria; cellular respiration is thus inhibited & cytotoxic hypoxia results. Since utilization of oxygen is blocked, venous blood is oxygenated and is almost as bright red as arterial blood. Respiration is stimulated because chemoreceptive cells respond as they do to decreased oxygen. A transient stage of CNS stimulation with hyperpnea and headache is observed; finally there are hypoxic convulsions and death due to respiratory arrest. /Cyanide/

Biological Half-LifeHalf-life for the conversion of cyanide to thiocyanate from a non-lethal dose in man is between 20 min and 1 hr. /Cyanide/
Metabolism/Metabolites · 4 Einträge

The small quantity of cyanide always present in human tissues is metabolized at the approximate rate of 17 ug/kg x min, primarily by the hepatic enzyme rhodanese, which catalyzes the irreversible reaction of cyanide and a sulfane to produce thiocyanate, a relatively nontoxic compound excreted in the urine. ... The limiting factor under normal conditions is the availability of a sulfane as a substrate for rhodanese, and sulfur is administered therapeutically as sodium thiosulfate to accelerate this reaction. The lethal dose of cyanide is time dependent because of the ability of the body to detoxify small amounts of cyanide via the rhodanese-catalyzed reaction with sulfane. A given amount of cyanide absorbed slowly may cause no biological effects even though the same amount administered over a very short period of time may be lethal. /Hydrogen cyanide and cyanogen chloride/

... Cyanide ion is conjugated with sulfur to form thiocyanate. ... conjugation is catalyzed by the enzyme rhodanese which is widely distributed in most animal tissues except blood, liver being particularly active. ... the rhodanese mechanism is capable of detoxicating only limited amt of cyanide, such as are formed during normal metab. /another sulfur donor is 3-mercaptopyruvate. The enzyme, mercaptosulfur transferase is localized in cytosol./ /Cyanide/

/One of/ the major mechanism/s/ for removing cyanide from the body is its enzymatic conversion, by the mitochondrial enzyme rhodanese (transsulfurase), to thiocyanate, which is relatively ... /less toxic/. /Cyanide/

Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. Bromine is mainly absorbed via inhalation, but may also enter the body through dermal contact. Bromine salts can be ingested. Due to its reactivity, bromine quickly forms bromide and may be deposited in the tissues, displacing other halogens. (L626, L96)

Absorption, Distribution and Excretion · 4 Einträge

Cyanide is distributed to all organs and tissues via the blood, where its concn in red cells is greater than that in plasma by a factor of two or three. Presumably, the accumulation of cyanide in erythrocytes is a reflection of its binding to methemoglobin. /Cyanide/

The cyanide ion is readily absorbed after oral or parenteral admin. Prolonged local contact with cyanide soln ... may result in absorption of toxic amt through skin. Part of absorbed cyanide is excreted unchanged by the lung. Larger portion ... is converted by sulfurtransferase to relatively nontoxic thiocyanate ion. /Cyanide/

Once absorbed into the body, cyanide can form complexes with heavy metal ions. /Cyanide/

Presumably, the accumulation of cyanide in erythrocytes is a reflection of its binding to methemoglobin. /Cyanide/

Verwendung und Herstellung

Uses · 6 Einträge

Used as a parasiticide, a fumigant, a cyaniding reagent to extract gold, and an intermediate in the synthesis of organic chemicals; also used in cellulose technology and textile treatment; [HSDB]

Textiles (Fiber & Fabric Manufacturing) [Category: Industry]

It is used in organic synthesis as a fumigant and pesticide and in gold-extraction processes. It has also been used in connection with cellulose technology.

In bioseparation procedures ... widely used to activate agarose and dextran gels

Organic synthesis, parasiticide, fumigating compositions, rat exterminants, cyaniding reagent in fold extraction processes

in organic synthesis or as a fumigant; In textile treatment; in gold cyaniding...

U.S. ProductionProduction volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#2013]
Methods of Manufacturing · 4 Einträge

Cyanogen bromide can be prepared from bromine and cyanide salts or hydrogen cyanide.

Prepared from potassium or sodium cyanide and bromine.

Industrial prepn from sodium bromide, sodium chlorate, and sodium cyanide in 30% H2SO4.

Cyanogen bromide may be prepared by either the action of bromine on potassium cyanide or the interaction of sodium bromide, sodium cyanide, sodium chlorate, and sulfuric acid.

Formulations/Preparations · 4 Einträge

97% Purity product and 5.0 M solution in acetonitrile

... 97% min grade /is available/ ...

A 50 wt% soln of the bromide in chloroform is a stable and convenient form for use.

Commercial products are generally solutions in chloroform.

General Manufacturing Information · 3 Einträge

Cyanogen bromide ((CN)Br): ACTIVE

Co[-]distillation with chloroform prevents condenser blockage during cyanogen bromide manufacture as well as improving ease of handling.

A recent designer drug "ICE" or "U4EA" was found to be produced from cyanogen bromide and an over the counter decongestant.

Anwendungen

VerwendenCyanogen bromide is used in organic synthesis and as a reagent in bioanalysis.

Anbieter50 Anbieter

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