HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Butyne-1,4-diol
BOZ · BYD · But-2-yne-1,4-diol · 1,4-BUTYNEDIOL · Butynediol · 2-BUTYN-1,4-DIOL · 2-Butin-1,4-diol · Dihydroxydimethylacetylene
Identifiers & Physical Properties
| CAS No. | 110-65-6 |
|---|---|
| Molecular formula | C4H6O2 |
| Average molar mass | 86.09 g/mol |
| Monoisotopic mass | 86.03677943 g/mol |
| SMILES | OCC#CCO |
| InChIKey | DLDJFQGPPSQZKI-UHFFFAOYSA-N |
| PubChem CID | 8066 |
| ChEMBL | CHEMBL3187551 |
| ChEBI | CHEBI:16413 |
| EC No. | 203-788-6 |
| DTXSID | DTXSID4021921 |
Chemical & Physical Properties
| XLogP | -1.1 |
|---|---|
| Topological polar surface area | 40.5 |
| Hydrogen bond donors | 2 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 0 |
| Heavy atoms | 6 |
| Formal charge | 0 |
| Complexity | 66 |
| Chemical classes | Other Classes -> Other Organic CompoundsReactive agents - 1st degree |
| SpringerMaterials Properties | Boiling point |
| LogP (partition coefficient) | -0.73 |
| Density | 1.07 at 68 °F (USCG, 1999) - Denser than waterwill sinkRelative density = 1.115 at 20 °CRelative density (water = 1): 1.11.115 @ 20°C1.2 |
| Color/Form | Plates from benzene and ethyl acetateWhite, orthorhombic crystalsWHITE TO LIGHT YELLOWYellow scaley solid at 20 °C and 1,013 hPa |
| Solubility | Insoluble in benzeneslightly soluble in ethyl ether, choroformvery soluble in ethanol, acetone, methanolSoluble in aqueous acids.In water, 3.74X10+6 mg/L at 25 °CSolubility in water, g/100ml at 20 °C: 75 (good)3740g/l3740 g/L (20 ºC) |
| Flash point | 263 °F (USCG, 1999)128 °C263 °F (OPEN CUP)152 °C306 °F |
| Boiling point | 460 °F at 760 mmHg (USCG, 1999)238 °CNo boiling point at normal pressuredecomposes at >160 °C238 °C @760 [mm Hg]238 °C(lit.) |
| Decomposition | When heated to decomposition it emits acrid smoke and fumes and may explode. |
| Melting point | 50 °C58 °C54 °C |
| Vapor density | Relative vapor density (air = 1): 3.0 |
| Vapor pressure | 0.000556 [mmHg]5.56X10-4 mm Hg at 25 °CVapor pressure, Pa at 20 °C: 0.2<0.1 mm Hg ( 55 °C) |
| Bulk density | 500kg/m3 |
| Refractive index | 1.4804 |
| Storage conditions | Store below +30°C. |
| Physical state | Crystalline Platelets or Flakes |
| pKa (acidity coefficient) | 12.72±0.10(Predicted) |
| Color | slightly brown |
| pH | 4-7.5 (100g/l, H2O, 23℃) |
| BRN | 1071237 |
| Henry's law constant | 2.0×103 mol/(m3Pa) at 25℃, Altschuh et al. (1999) |
| Exposure limits | EU LTEL:0.5 mg/m3 |
| Stability | Stable. Highly flammable solid. Incompatible with strong oxidizing agents, acid chlorides, acid anhydrides, strong acids, strong bases. |
| InChI | 1S/C4H6O2/c5-3-1-2-4-6/h5-6H,3-4H2 |
| InChIKey | DLDJFQGPPSQZKI-UHFFFAOYSA-N |
| SMILES | OCC#CCO |
| LogP (partition coefficient) | -0.73 at 25℃ |
| CAS DataBase Reference | 110-65-6(CAS DataBase Reference) |
| EWG's Food Scores | 1-2 |
| FDA UNII | AXH202FPQM |
| NIST Chemistry Reference | 2-Butyne-1,4-diol(110-65-6) |
| EPA Substance Registry System | 2-Butyne-1,4-diol (110-65-6) |
| UNSPSC Code | 12352104 |
| NACRES | NA.22 |
| GHS pictogram | GHS05,GHS06,GHS08 |
| Signal word | Danger |
| GHS hazard statements | H301+H311+H331-H314-H372-H370-H317-H402 |
| GHS precautionary statements | P501-P273-P272-P260-P270-P271-P264-P280-P308+P311-P361+P364-P303+P361+P353-P333+P313-P301+P330+P331-P301+P310+P330-P304+P340+P310-P305+P351+P338+P310-P403+P233-P405 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges |
| Hazard symbols | T,C |
| Risk statements (R) | 21-23/25-34-43-48/22 |
| Safety statements (S) | 25-26-36/37/39-45-46 |
| UN transport number | UN 2716 |
| Water hazard class (WGK) | 2 |
| RTECS number | ES0525000 |
| F | 23-10 |
| Autoignition temperature | 410 °C |
| TSCA inventory status | TSCA listed |
| Hazard class | 6.1Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralEye Dam. 1Skin Corr. 1BSkin Sens. 1STOT RE 2 |
| Packing group | III |
| Customs code | 29053980 |
| Storage class | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Hazardous substances data | 110-65-6(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: 100 mg/kg |
| REACH registrations | Active |
| Limited quantities | 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) |
Safety & Regulations
| GHS classification | DangerH301: Toxic if swallowed [Danger Acute toxicity, oral]P260, P261, P264, P270, P271, P272, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P333+P317, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]P260, P261, P262, P264, P264+P265, P270, P271, P272, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P333+P317, P361+P364, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatory information | Chemical: 2-Butyne-1,4-diol2-Butyne-1,4-diol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Butyne-1,4-diol are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 30-08-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/132242-Butyne-1,4-diol: Does not have an individual approval but may be used under an appropriate group standardThe 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.) |
| DOT label | Poison |
| Fire hazards | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:· Combustible material: may burn but does not ignite readily.Combustible. Risk of explosion on contact with bases, oxidizing agents or halogens. |
| Health hazards | May cause dermatitis. (USCG, 1999)· TOXIC and/or CORROSIVEinhalation, ingestion or skin contact with material may cause severe injury or death. |
| Hazards summary | A severe skin and eye irritant[HSDB] Toxic by inhalation, ingestion, and skin contact[CAMEO] May cause skin burns and sensitization[eChemPortal: ESIS] A corrosive substance that can cause injury to the skin, eyes, and respiratory tractInhalation may cause chemical pneumonitisMay cause skin sensitizationCauses liver, brain, and reproductive injury in high-dose animal studies[MSDSonline] Danger of cutaneous absorptionDanger of skin sensitization[MAK] |
| DOT ID and guide | 2716 153 |
| Reactive group | Alcohols and Polyols |
| EC classification | Symbol: C, TR: 21-23/25-34-43-48/22S: (1/2)-25-26-36/37/39-45-46 |
| UN classification | UN Hazard Class: 6.1UN Pack Group: III |
| Special Reports | European Chemicals BureauIUCLID Dataset, But-2-yne-1,4-diol (110-65-6) (2000 CD-ROM edition). Provides information on usage patterns, toxicity, and environmental effects supplied by industry to the European Union. Available from the database query page: http://ecb.jrc.it/esis/esis.php as of September 09, 2006. |
| Reactivity Profile | Pure 1,4-BUTYNEDIOL is non-explosive. Small amounts of certain impurities-alkali hydroxides, alkaline earth hydroxides, halides-may cause explosive decomposition upon distillation. Butynediol should not be treated with basic catalysts in the absence of a solvent at room temperature, and its stability is less with elevated temperatures. In strong acids, contamination with mercury salts can also result in violent decomposition. [NFPA 491M 1991]. |
| Chemical Dangers | Decomposes on heating. This produces toxic and corrosive fumes. Reacts violently with anhydrides, acid chlorides, mercury salts and alkaline hydroxides or chlorides. This generates explosion hazard. |
| Fire fighting | Fire Extinguishing Agents: Water, alcohol foam, dry chemical, or carbon dioxide (USCG, 1999)Use water spray, alcohol-resistant foam, dry powder, carbon dioxide. |
| First aid measures | Fresh air, rest. Half-upright position. Refer immediately for medical attention.Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer immediately for medical attention.Rinse with plenty of water (remove contact lenses if easily possible). Refer immediately for medical attention.Rinse mouth. Do NOT induce vomiting. Refer immediately for medical attention. |
| Accidental release measures | · 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 | SKIN CONTACT: wash affected skin area thoroughly with water.General First Aid: |
| Safe storage | Separated from incompatible materials. See Chemical Dangers. Cool. Store in an area without drain or sewer access. |
| Exposure control and personal protection | · Wear positive pressure self-contained breathing apparatus (SCBA).0.1 [ppm] |
| Fire fighting procedures | If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams fo water may be ineffective Cool all affected containers with flooding quantities of water. Use "alcohol" foam, dry chemical or carbon dioxide. Keep run-off water out of sewers and water sources. |
| Storage conditions | The storage temperature should be kept below 40 °C and storage times longer than a few months should be avoided because the butynediol flakes tend to set up.... MATERIALS WHICH ARE TOXIC AS STORED OR WHICH CAN DECOMP INTO TOXIC COMPONENTS DUE TO CONTACT WITH HEAT, MOISTURE, ACIDS, OR ACID FUMES, SHOULD BE STORED IN COOL, WELL-VENTILATED PLACE, OUT OF DIRECT RAYS OF SUN, AWAY FROM AREAS OF ... FIRE HAZARD & SHOULD BE PERIODICALLY INSPECTED & MONITORED. |
| Nonfire spill response | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Disposal methods | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. 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 soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Spillage disposal | Evacuate danger area! Consult an expert! Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. |
| Preventive Measures | SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.Personnel protection: Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. If contact with the material anticipated, wear appropriate chemical protective clothing.If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors. |
| Interactions | Toxic action of 1,4-butynediol was prevented by pretreatment with pyrazole which competitively inhibited oxidation of 1,4-butynediol by rat liver alcohol dehydrogenase indicating that toxicity is due to products of oxidative metabolism. |
| Ecotoxicity values | EC50 Daphnia magna 26.8 mg/L48 hr (nominal concentration) immobilization, static test. NOTE: At 100 mg/L all daphnids were immobile after 48 hours.LC50 Pimephales promelas (Fathead minnow) 53.6 mg/L/96 hr (confidence limit 49.3-58.3 mg/L), flow-through bioassay with measured concentrations, 25.1 °C, dissolved oxygen 6.8 mg/L, hardness 46.5 mg/L calcium carbonate, alkalinity 43.5 mg/L calcium carbonate, and pH 7.7EC50 Pimephales promelas (Fathead minnow) 53.6 mg/L/96 hr (confidence limit 49.3-58.3 mg/L), flow-through bioassay with measured concentrations, 25.1 °C, dissolved oxygen 6.8 mg/L, hardness 46.5 mg/L calcium carbonate, alkalinity 43.5 mg/L calcium carbonate, and pH 7.7. Effect: loss of equilibrium was not observed prior to death.LC50 Leuciscus idus (fresh-water cyprinoid fish) 46 mg/L/96 hr /Conditions of bioassay not specified in source examined/For more Ecotoxicity Values (Complete) data for 1,4-BUTYNEDIOL (7 total), please visit the HSDB record page. |
| Environmental fate | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a water solubility of 3.74X10+6 mg/L(2) and a regression-derived equation(3), indicates that 1,4-butynediol is expected to have very high mobility in soil(SRC). Volatilization of 1,4-butynediol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.7X10-11 atm-cu m/mole(SRC), derived from its vapor pressure, 5.56X10-4 mm Hg(4), and water solubility(2). 1,4-Butynediol is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). 1,4-Butynediol has been shown to biodegrade 90% in 4 days using a sewage sludge(5)therefore, biodegradation is expected to be an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a water solubility of 3.74X10+6 mg/L(2) and a regression-derived equation(3), indicates that 1,4-butynediol 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 1.7X10-11 atm-cu m/mole(SRC), derived from its vapor pressure, 5.56X10-4 mm Hg(4), and its water solubility(2). According to a classification scheme(5), an estimated BCF of 0.12(SRC), from its water solubility(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 1,4-Butynediol has been shown to biodegrade 90% in 4 days using a sewage sludge(6)therefore, biodegradation is expected to be an important environmental fate profcess in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,4-butynediol, which has a vapor pressure of 5.56X10-4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,4-butynediol 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 11 hours(SRC), calculated from its rate constant of 3.4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 1,4-Butynediol does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(4). |
| Adverse effects | Neurotoxin - Other CNS neurotoxin |
| Exposure routes | The substance can be absorbed into the body by inhalation, through the skin and by ingestion. Serious local effects by all routes of exposure. |
| Ecotoxicity excerpts | /AQUATIC SPECIES/ ... The test results on /the freshwater fish/ Leuciscus idus /showed that among/ the selected test concentrations (10, 21.5, 46.4 and 100 mg/L) only at the highest two lethal effects were observed. After 96 hours the mortality was 5% at 46.4 mg/L and 100% at 100 mg/L and therefore the LC50 is between 46.4 and 100 mg/Ll. The NOEC was 21.5 mg/L./AQUATIC SPECIES/ The population growth impairment testing was done in the /protozoa/ Tetrahymena pyriformis batch system ... This is a two-day assay using population density measured spectrophotometrically at 540 nm as the endpoint. An EC50 inhibition of growth of 1,343 mg/L after 48 hours was obtained./AQUATIC SPECIES/ In a test ... with /the freshwater algae/ Scenedesmus subspicatus after 96 hours an EC50 of 433 mg/L and an EC20 of 218 mg/L were derived for the reduction of biomass measured fluorometrically./AQUATIC SPECIES/ Using continuous flow diluters, the 96 hr LC50 values were determined for 16 acetylenic alcohols in the fathead minnow (Pimephales promelas). The observed LC50 value for butyn-1,4-diol was 53.6 (49.3-58.3) mg/L. This was 4740 times greater than the predicted LC50 of 254,000 mg/L based on quantitative structure activity relationships (QSAR) for ... /CNS depressant/ lethality./OTHER TERRESTRIAL SPECIES/ In a test with /the soil bacterium/ Pseudomonas putida ... after 17 hours an EC50 of 3,935 mg/L and an EC10 of 1993 were obtained for cell multiplication inhibition measured at 436 nm. |
| Signs and Symptoms | Cough. Sore throat. Burning sensation. Shortness of breath. Laboured breathing.Redness. Pain. Skin burns.Redness. Pain. Burns.Burns in mouth and throat. Burning sensation in the throat and chest. Abdominal pain. |
| Effluent Concentrations | 1,4-Butynediol was reported at 5304 ng/uL of extract in 1 occurrence from the organics and plastics industry(1). |
| ICSC Environmental Data | The substance is harmful to aquatic organisms. |
| Soil Adsorption/Mobility | The Koc of 1,4-butynediol is estimated as 1(SRC), using a water solubility of 3.74X10+6 mg/L(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 1,4-butynediol is expected to have very high mobility in soil. |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ Ten workers with suspicion of allergic contact eczema who were probably accidentally exposed to butynediol were asked for voluntary patch testing for possible sensitisation6 of these 10 workers were willing to undergo the test. Pure butynediol and technical grade butynediol were applied as a 0.5% aqueous solution. Furthermore, formaldehyde which is a precursor for synthesis and an impurity in technical grade butynediol was also tested. Whereas formaldehyde did not show a positive reaction in these individuals, 4/4 tested in 2001 showed clear evidence of sensitisation. Two other workers tested in 1990 and 1994 had positive patch test reactions .../SIGNS AND SYMPTOMS/ ... Reported to be severely irritating to eyes and to penetrate skin and cause severe irritation./CASE REPORTS/ A 20-year old patient whose occupation involved nickel-plating developed itchy dermatitis on the dorsum of his left hand, extending to the upper arm. By patch testing butynediol (1% in water) was identified as the causative agent .../CASE REPORTS/ A 54-yr old male worker developed an itchy dermatitis on his hands and lower arms. Eczematous eruption was seen and contact allergy suspected. He was patch tested. The only substance to give a two plus positive reaction at 48 hr was a 2% butin diol soln in water. At the 72 hr reading, the reaction had increased in severity./CASE REPORTS/ A 41-year-old female cleaner developed dermatitis on the face, hands and forearms after having used a new cleaning agent for a few months. The dermatitis appeared about 12 hours after contact with the agent and settled when she was not using it. Patch testing with the components of the cleaning agent produced a strong reaction to butynediol. The compound was present in the cleaning agent at low concentration (0.7%) as corrosion inhibitor. Patch testing of 55 control persons with 1% butynediol in water was negative ... |
| Artificial Pollution Sources | 1,4-Butynediol's production and use as an intermediate, corrosion inhibitor, electroplating brightener, polymerization accelerator, stabilizer for chlorinated hydrocarbons and cosolvent for paint and varnish removal(1) may result in its release to the environment through various waste streams. Its use as a defoliant(1) (not regristered for this application in the US(2)) will result in its direct release to the environment(SRC). |
| F | 23-10 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges |
| Water hazard class (WGK) | 2 |
| TSCA inventory status | TSCA listed |
| RTECS number | ES0525000 |
| UN transport number | UN 2716 |
| Customs code | 29053980 |
| Toxicity | LD50 orally in Rabbit: 100 mg/kg |
| Risk statements (R) | 21-23/25-34-43-48/22 |
| Signal word | Danger |
| GHS pictogram | GHS05,GHS06,GHS08 |
| Hazard symbols | T,C |
| Safety statements (S) | 25-26-36/37/39-45-46 |
| Hazard class | 6.1Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralEye Dam. 1Skin Corr. 1BSkin Sens. 1STOT RE 2 |
| Storage class | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Packing group | III |
| GHS hazard statements | H301+H311+H331-H314-H372-H370-H317-H402 |
| Limited quantities | 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) |
| REACH registrations | Active |
| Autoignition temperature | 410 °C |
| GHS precautionary statements | P501-P273-P272-P260-P270-P271-P264-P280-P308+P311-P361+P364-P303+P361+P353-P333+P313-P301+P330+P331-P301+P310+P330-P304+P340+P310-P305+P351+P338+P310-P403+P233-P405 |
| Hazardous substances data | 110-65-6(Hazardous Substances Data) |
Applications & Uses
Uses
2-Butyne-1,4-diol is used as a precursor to prepare 1,4-butanediol, 2-butene-1,4-diol and mucochloric acid. It is also used in textile additives, corrosion inhibitors, plasticizers, synthetic resins and polyurethanes. It is an important raw material of vitamin B6. Further, it is used for brightening, preserving and inhibiting nickel plating. In addition, it is used in biological studies for nematocidal activity.
General Description
1,4-butynediol appears as white to light-brown solid or brownish-yellow aqueous solution. Solid sinks and mixes with water. (USCG, 1999)