HuagongsheHuagongshe Chemistry Print Report · For research reference only
N-bromobutanimide
NBS · bromosuccinimide · N-BROMOBUTANIMIDE · 1-BROMO-2,5-PYRROLIDINEDIONE · N-Bromsuccinimid · N-BROMOSUCINIMIDE · N-Bromsuccinimide · N-Brom-succinimid
Identifiers & Physical Properties
| CAS No. | 128-08-5 |
|---|---|
| Molecular formula | C4H4BrNO2 |
| Average molar mass | 177.98 g/mol |
| Monoisotopic mass | 176.94254 g/mol |
| SMILES | O=C1CCC(=O)N1Br |
| InChIKey | PCLIMKBDDGJMGD-UHFFFAOYSA-N |
| PubChem CID | 67184 |
| ChEBI | CHEBI:53174 |
| EC No. | 204-877-2 |
| DTXSID | DTXSID2038738 |
Chemical & Physical Properties
| XLogP | -0.1 |
|---|---|
| Topological polar surface area | 37.4 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 0 |
| Heavy atoms | 8 |
| Formal charge | 0 |
| Complexity | 129 |
| Odor | Faint odor of brominecharacteristic odour of bromine |
| Density | 2.098 g/cu cm at 25 °C2.098 @25 °C |
| Color/Form | Orthorhombic bisphenoidal crystalsCrystals from benzeneSolid at 20 °C and 1031 hPapowder |
| Solubility | In water, 1.47 g/100 g water at 25 °CSlightly soluble in waterSlightly soluble in ethyl acetate, diethyl ethervery soluble in acetoneinsoluble in hexaneIn tert-butanol 0.73acetone 14.40carbon tetrachloride 0.02hexane 0.006glacial acetic acid 3.10 (all in g/100 g of solvent, 25 °C)14.8g/l (decomposition)Soluble in acetone, tetrahydrofuran, dimethyl formamide, dimethyl sulfoxide and acetonitrile. Slightly soluble in water and acetic acid. Insoluble in ether, hexane and carbon tetrachloride. |
| Boiling point | 338.9 °C at 101.325 kPa221.4°C (rough estimate) |
| Decomposition | Melting range 172-178 °C (decomposes).When heated to decomposition it emits toxic fumes of Br- and NOx. |
| Melting point | 173-175 °C (slight decomposition)MP: 174 °C175-180 °C (dec.)(lit.) |
| Vapor pressure | 11.0 [mmHg]VP: 0.001 Pa at 25 °C14.8 hPa (20 °C) |
| Physical Description | Solid with a mild odor of bromine[Merck Index] White, pale yellow, or cream-colored powder[Alfa Aesar MSDS] |
| Stability/Shelf Life | Stable under recommended storage conditions. |
| Bulk density | 750kg/m3 |
| Refractive index | 1.6060 (estimate) |
| Storage conditions | Store at +2°C to +8°C. |
| Physical state | Crystalline Powder |
| pKa (acidity coefficient) | -2.78±0.20(Predicted) |
| Color | White to light yellow |
| Biological source | rabbit |
| Sensitivity | Moisture Sensitive |
| Merck | 14,1438 |
| BRN | 113916 |
| Stability | Stable. Incompatible with strong oxidizing agents, halogenated hydrocarbons. |
| Major applications | peptide synthesis |
| InChI | 1S/C4H4BrNO2/c5-6-3(7)1-2-4(6)8/h1-2H2 |
| InChIKey | PCLIMKBDDGJMGD-UHFFFAOYSA-N |
| SMILES | BrN1C(=O)CCC1=O |
| LogP (partition coefficient) | -1.19 |
| CAS DataBase Reference | 128-08-5(CAS DataBase Reference) |
| FDA UNII | K8G1F2UCJF |
| NIST Chemistry Reference | 2,5-Pyrrolidinedione, 1-bromo-(128-08-5) |
| EPA Substance Registry System | N-Bromosuccinimide (128-08-5) |
| UNSPSC Code | 12352203 |
| NACRES | NA.41 |
| GHS pictogram | GHS03,GHS05,GHS07,GHS08,GHS09 |
| Signal word | Warning |
| GHS hazard statements | H272-H290-H315-H317-H319-H341-H400 |
| GHS precautionary statements | P210-P273-P280-P302+P352-P305+P351+P338-P308+P313 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges |
| Hazard symbols | C,Xn |
| Risk statements (R) | 22-34-36/37/38 |
| Safety statements (S) | 26-36/37/39-45-37/39 |
| UN transport number | UN 3261 8/PG 2 |
| Water hazard class (WGK) | 3 |
| Hazard Note | Harmful |
| TSCA inventory status | TSCA listed |
| Hazard class | 8Aquatic Acute 1Eye Irrit. 2Met. Corr. 1Muta. 2Ox. Sol. 3Skin Irrit. 2Skin Sens. 1B |
| Packing group | III |
| Customs code | 29251995 |
| Storage class | 5.1B - Oxidizing hazardous materials |
| Hazardous substances data | 128-08-5(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: > 2000 mg/kg |
| REACH registrations | Active |
| Limited quantities | 1 Kg (2.2 lbs) (solid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml) |
Safety & Regulations
| GHS classification | DangerH272 (38.7%): May intensify fireoxidizer [Danger Oxidizing liquidsOxidizing solids]H290 (38.7%): May be corrosive to metals [Warning Corrosive to Metals]H302 (55.8%): Harmful if swallowed [Warning Acute toxicity, oral]H314 (35.2%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]H315 (46.2%): Causes skin irritation [Warning Skin corrosion/irritation]H317 (21.6%): May cause an allergic skin reaction [Warning Sensitization, Skin]H319 (65.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (26.6%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]H341 (15.1%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]H400 (43.2%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]P203, P210, P220, P234, P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P318, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P363, P370+P378, P390, P391, P403+P233, P405, P406, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 199 reports by companies from 25 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatory information | Chemical: 2,5-Pyrrolidinedione, 1-bromo-Status: Active Update: 02-04-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/5434Status: Active Update: 20-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/20333Succinibromimide: Does not have an individual approval but may be used under an appropriate group standard |
| Hazards summary | A strong skin, eye, and mucous membrane irritant[Merck Index] Causes burnsInhalation may cause corrosive injuries to upper respiratory tract and lungsHarmful by ingestion[Alfa Aesar MSDS] See N-Chlorosuccinimide. |
| Other Hazardous Reactions | Conditions to avoid: Exposure to light. Exposure to moisture. |
| Hazard Classes and Categories | Ox. Sol. 3 (38.7%)Met. Corr. 1 (38.7%)Acute Tox. 4 (55.8%)Skin Corr. 1B (35.2%)Skin Irrit. 2 (46.2%)Skin Sens. 1 (21.6%)Eye Irrit. 2 (65.3%)STOT SE 3 (26.6%)Muta. 2 (15.1%)Aquatic Acute 1 (43.2%) |
| Skin, Eye, and Respiratory Irritations | N-bromosuccinimide is classified as irritating to skin: Causes skin irritation. Red skin on arms.Highly irritating to eyes, skin, mucous membranes.Strong irritant to eyes and skin.An irritating poison to skin, eyes and mucous membranes. |
| Hazardous Reactivities and Incompatibilities | Violent reaction with dibenzoyl peroxide + 4-toluic acid.Explosive reaction with propiononitrile after heating to 105 °C for 24 hr.Reacts explosively with aniline, diallyl sulfide, and hydrazine hydrate.Incompatible materials: Strong oxidizing agents, Strong acids, Strong bases, Iron and iron salts. |
| CSL Reaction Information | CSL00039N-BROMOSUCCINIMIDE + 1-METHYL-2-PYRROLIDINONE + 1-METHYLPYRROLIDINEThermal runaway from ambient to >100°CExplosiveBrominationUser-Reported |
| Firefighting Hazards | Carbon oxides, nitrogen oxides (NOx), Hydrogen bromide gas |
| Fire fighting procedures | Wear self contained breathing apparatus for fire fighting if necessary.Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. |
| Storage conditions | Keep container tightly closed in a dry and well-ventilated place. Recommended storage temperature: 2 - 8 °C. Light sensitive. Moisture sensitive. Store under inert gas. |
| Cleanup methods | ACCIDENTAL RELEASE MEASURESPersonal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Do not let product enter drains. Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal. |
| Disposal methods | SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in air, soil or watereffects on animal, aquatic and plant lifeand conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. Contaminated packaging: Dispose of as unused product. |
| Preventive Measures | ACCIDENTAL RELEASE MEASURESPersonal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Do not let product enter drains.Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.For more Preventive Measures (Complete) data for N-Bromosuccinimide (6 total), please visit the HSDB record page. |
| Protective Action Criteria (PAC) | 6.0 [mg/m3]66 [mg/m3]400 [mg/m3] |
| Personal Protective Equipment (PPE) | Eye/face protection: Face shield and safety glasses. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).Skin protection: Handle with gloves.Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.Respiratory protection Where risk assessment shows air-purifying respirators are appropriate use a full-face particle respirator type N100 (US) or type P3 (EN 143) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).Use a repirator when handling dry material, which evolves toxic fumes of bromine. |
| Treatment | 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 | N-Bromosuccinimide (NBS) is a known protein reagent able to modify amino acids and proteins, resulting in oxidation of tryptophan, tyrosine and histidine residues, as well as sulfhydryl, alcohol and phenol groups. These properties make NBS a suitable reagent to selectively block certain amino acid residues in biochemistry, and also permit the histochemical detection of proteins by oxidative deamination followed by the Schiff reaction. In this paper we show that, under ultraviolet excitation, NBS selectively reveals the cytoplasmic granules of mammalian eosinophils and chicken heterophils, rendering considerable white--blue fluorescence, in a remarkable fluorogenic reaction which rapidly increases at the beginning of the observation. This emission slightly decays afterwards and then remains almost stable still yielding a high level of emission after 10 min of continuous excitation. Possible mechanisms underlying these results are discussed and we propose NBS as a very suitable fluorogenic reagent for the microscopical detection and analysis of proteins. |
| Health effects | Strong lachrymator. Strong irritant to eyes, skin and soft tissues. Toxic if inhaled, swallowed or absorbed through skin. It is extremely destructive to the tissue of the mucous membranes and upper respiratory tract. |
| Environmental fate | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 3(SRC), determined from a structure estimation method(2), indicates that N-bromosuccinimide is expected to have very high mobility in soil(SRC). Volatilization of N-bromosuccinimide from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.9X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(3). N-bromosuccinimide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.9X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). A 93% biodegradation using activated sludge in the OECD Die Away Test(4) suggests that biodegradation is an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 3(SRC), determined from a structure estimation method(2), indicates that N-bromosuccinimide is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 3.9X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of -1.19(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A 93% biodegradation using activated sludge in the OECD Die Away Test(6) suggests that biodegradation is an important environmental fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), N-bromosuccinimide, which has an estimated vapor pressure of 6.9X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase N-bromosuccinimide is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 0.9 days(SRC), calculated from its rate constant of 1.9X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase N-bromosuccinimide may be removed from the air by wet and dry deposition(SRC). N-Bromosuccinimide contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC). |
| Adverse effects | Dermatotoxin - Skin burns.Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors. |
| Exposure routes | Oral (L626)inhalation (L626)dermal (L626) |
| Toxicity summary | IDENTIFICATION AND USE: N-Bromosuccinimide is a versatile brominating agent. It is a known protein reagent able to modify amino acids and proteins, resulting in oxidation of tryptophan, tyrosine and histidine residues, as well as sulfhydryl, alcohol and phenol groups. These properties make it a suitable reagent to selectively block certain amino acid residues in biochemistry, and also permit the histochemical detection of proteins by oxidative deamination followed by the Schiff reaction. HUMAN STUDIES: N-bromosuccinimide causes skin irritation (red skin on arms). ANIMAL STUDIES: N-bromosuccinimide was sensitizing in mice treated with concentrations of 2.5, 5 or 10% w/w on three consecutive days, by open application on the ears. N-bromosuccinimide was tested in a mouse lymphoma L5178Y TK+/- assay with and without metabolic activation at a concentration range of 20 to 210 ug/mL. The results without metabolic activation were equivocal and those with metabolic activation were negative.Organobromide compounds such as n-Bromosuccinimide are strong alkylating agents. Consequently they can readily modify free thiols (cysteines), methionines as well as tryptophan and histidine residues on the surfaces of proteins leading to the disruption of enzyme, transporter or membrane functions. One of the most probable protein targets is the TRPA1 ion channel that is expressed in sensory nerves (trigeminal nerve) of the eyes, nose, mouth and lungs |
| Signs and Symptoms | Causes severe eye and skin burns. Irritating to eyes, skin, and respiratory system. Acute exposure (ingestion or inhalation) can lead to nausea, vomiting and coma. |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of N-bromosuccinimide can be estimated to be 3(SRC). According to a classification scheme(2), this estimated Koc value suggests that N-bromosuccinimide is expected to have very high mobility in soil(SRC). |
| Human Toxicity Excerpts | /OTHER TOXICITY INFORMATION/ N-bromosuccinimide is classified as irritating to skin: Causes skin irritation. Red skin on arms. |
| Artificial Pollution Sources | N-Bromosuccinimide's production and use as a chemical reagent(1) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | AEROBIC: N-Bromosuccinimide, present at 40 mg/L, was 93% biodegraded using an activated sludge incubated at 22.2 °C for 35 days in the OECD DOC Die Away Test. The abiotic degradation measured as DOC (mg/L) was 7% after 28 days and 3% at the end of the test(1). |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| UN transport number | UN 3261 8/PG 2 |
| Customs code | 29251995 |
| Toxicity | LD50 orally in Rabbit: > 2000 mg/kg |
| Risk statements (R) | 22-34-36/37/38 |
| Signal word | Warning |
| GHS pictogram | GHS03,GHS05,GHS07,GHS08,GHS09 |
| Hazard symbols | C,Xn |
| hazard_note | Harmful |
| Safety statements (S) | 26-36/37/39-45-37/39 |
| Hazard class | 8Aquatic Acute 1Eye Irrit. 2Met. Corr. 1Muta. 2Ox. Sol. 3Skin Irrit. 2Skin Sens. 1B |
| Storage class | 5.1B - Oxidizing hazardous materials |
| Packing group | III |
| GHS hazard statements | H272-H290-H315-H317-H319-H341-H400 |
| Limited quantities | 1 Kg (2.2 lbs) (solid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml) |
| REACH registrations | Active |
| GHS precautionary statements | P210-P273-P280-P302+P352-P305+P351+P338-P308+P313 |
| Hazardous substances data | 128-08-5(Hazardous Substances Data) |
Applications & Uses
Uses
N-Bromosuccinimide is a brominated succinimide used as a chemical reagent in radical substitution and electrophilic addition reactions in organic synthesis. In bromination of olefins; in oxidation of alcohols to aldehydes and ketones and of aldehydes to acid bromides.
Preparation & Synthesis
Preparation
N-Bromosuccinimide is prepared by addition of bromine to a cold aqueous solution of succinimide or by reaction of succinimide with NaBrO2 in the presence of HBr.1.62mol (160g) succinimide is dissolved in a mixture of 1.60mol (64g) NaOH, 300g crushed ice and 400ml water. Cool the mixture in an ice bath, and add 85ml (1.65 mol, 264g) Br2 at once while stirring violently. Stir for two more minutes, then filter the precipitated product and wash with ice water. Dry in a desiccator. Yield 75-81%.Don't clean up NBS too much, the stinky yellow stuff still containing a bit of Br2 works best. N-Bromosuccinimide is a brominating agent that replaces hydrogen atoms in benzylic or allylic positions. It is used in the oxidation of secondary alcohols to ketones and in controlled low-energy brominations.