2,3-Dimercapto-1-propanol CAS 59-52-9
Introduction：Basic information about 2,3-Dimercapto-1-propanol CAS 59-52-9, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
2,3-Dimercapto-1-propanol Basic information
| Product Name: | 2,3-Dimercapto-1-propanol |
| Synonyms: | 3-hydroxy-1,2-propanedithiol;1,2-DITHIOGLYCEROL;1,2-Dimercapto-3-propanol;1,2-Dimercaptopropanol;1,2-dithio-glycero;1-Propanol, 2,3-dimercapto-;dimercaprolpropanol;Dimercaptol |
| CAS: | 59-52-9 |
| MF: | C3H8OS2 |
| MW: | 124.22 |
| EINECS: | 200-433-7 |
| Product Categories: | BAL;product antidote |
| Mol File: | 59-52-9.mol |
2,3-Dimercapto-1-propanol Chemical Properties
| Melting point | 77 °C |
| Boiling point | 120 °C15 mm Hg(lit.) |
| density | 1.239 g/mL at 25 °C(lit.) |
| vapor density | 4.3 |
| vapor pressure | 7.4 hPa (100 °C) |
| refractive index | n |
| Fp | >230 °F |
| storage temp. | Store at +2°C to +8°C. |
| solubility | 87g/l (slow decomposition) |
| pka | 9.00±0.25(Predicted) |
| form | Liquid |
| color | Clear colorless to slightly yellow |
| PH | 5.0-6.5 (H2O, 20℃)(saturated solution) |
| Odor | pungent odor |
| biological source | rabbit |
| Water Solubility | 87 g/L (25 ºC) |
| Sensitive | Air Sensitive |
| Merck | 14,3209 |
| BRN | 1732058 |
| Stability: | Stable. Combustible. Incompatible with strong oxidizing agents, many metals. |
| InChI | 1S/C3H8OS2/c4-1-3(6)2-5/h3-6H,1-2H2 |
| InChIKey | WQABCVAJNWAXTE-UHFFFAOYSA-N |
| SMILES | OCC(S)CS |
| CAS DataBase Reference | 59-52-9(CAS DataBase Reference) |
| NIST Chemistry Reference | Dimercaprol(59-52-9) |
| EPA Substance Registry System | 2,3-Dimercaptopropanol (59-52-9) |
Safety Information
| Hazard Codes | Xn,Xi |
| Risk Statements | 22-36/37/38-36/38 |
| Safety Statements | 26-36-24/25-23 |
| RIDADR | UN 2810 6.1/PG 3 |
| WGK Germany | 3 |
| RTECS | UB2625000 |
| F | 8-9-13-23 |
| TSCA | TSCA listed |
| HazardClass | 6.1 |
| PackingGroup | III |
| HS Code | 29309070 |
| Storage Class | 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects |
| Hazard Classifications | Acute Tox. 3 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3 |
| Hazardous Substances Data | 59-52-9(Hazardous Substances Data) |
| Toxicity | LD50 i.m. in rats: 86.7 mg/kg (Zvirblis, Ellin) |
| Description | Dimercaprol (INN) or British anti - Lewisite (abbreviated BAL), is a compound developed by British biochemists at Oxford University during World War II . It was developed secretly as an antidote for lewisite, the now - obsolete arsenic - based chemical warfare agent . Today, it is used medically in treatment of arsenic, mercury , gold, lead, antimony, and other toxic metal poisoning . In addition , it has in the past been used for the treatment of Wilson's disease, a genetic disorder in which the body tends to retain copper. |
| Chemical Properties | colourless oily liquid with a typically offensive mercaptan smell |
| Originator | Bal,Hynson/Westcott,US,1944 |
| Uses | BAL is a chelating agent used as an antidote for the treatment ofmetal poisoning, especially arsenic (organic and inorganic),gold salts, and inorganic mercury. BAL is more effective whengiven soon after toxic exposure because it is more effective inpreventing inhibition of sulfhydryl enzymes than in reactivatingthem. BAL is also used in the treatment of Wilson’s disease.The drug cannot be used in poisonings due to iron, cadmium,tellurium, selenium, vanadium, and uranium. It is contraindicatedin poisonings due to elemental mercury vapor,because it can further increase the metal in the brain. |
| Uses | British Anti-Lewisite. A chelator that inhibits sugar nucleotide degradation.2,3-Dimercaptopropanol is used as a chelating agent involved in the treatment of arsenic, antimony, lead, gold and mercury poisoning. It is also used as an antidote to the warfare agent Lewisite. Further, it is used for the treatment of Wilson's disease. In addition to this, it is used as an adjunct in the treatment of the acute encephalopathy of lead toxicity. |
| Uses | 2,3-Dimercapto-1-propanol has been used in synthesizing novel (2-substituted phenyl-1,3-dithiolan-4-yl) methanol (PDTM) derivatives, which are potent tyrosinase inhibitors. It can also be considered for developing new drugs against AIDS due to its ability to inhibit HIV-1 tat activity. |
| Uses | chelating agent (As, Au, Hg antidote) |
| Definition | ChEBI: A dithiol that is propane-1,2-dithiol in which one of the methyl hydrogens is replaced by a hydroxy group. a chelating agent originally developed during World War II as an experimental antidote against the arsenic-based poison gas Lewisite, it has been use clinically since 1949 for the treatment of poisoning by arsenic, mercury and gold. It can also be used for treatment of poisoning by antimony, bismuth and possibly thallium, and (with sodium calcium edetate) in cases of acute leaad poisoning. Administratin is by (painful) intramuscular injection of a suspension of dimercaprol in peanut oil, typically every 4 hours for 2-10 days depending on the toxicity. In the past, dimercaprol was also used for the treatment of Wilson's disease, a severely debilitating gnetic disorder in which the body tends to retain copper, with resultant liver and brain injury. |
| Manufacturing Process | 1,2-Dithioglycerol is prepared in the following manner: 1,537 parts of sodiummonosulfide nonahydrate and 411 parts of powdered sulfur are dissolved withstirring in 1,345 parts of water. Magnesium hydroxide is precipitated in thestirred sodium trisulfide solution by adding successively 97 parts of sodiumhydroxide dissolved in 180 parts of water and then slowly 246 parts ofmagnesium chloride hexahydrate dissolved in 180 parts of water. Themagnesium hydroxide serves as a dispersing agent to maintain the resultingsulfide polymer in finely divided condition. The mixture is heated and stirredat 50°C while 1,329 parts of glycerol 1,2-dibromohydrin is added continuouslyduring a period of 1.5 hours. The reaction is exothermic and external coolingis employed to maintain the temperature within the range of 50°-55°C. Afterthe addition of the dibromohydrin is complete, the mixture is stirred andheated at 75°C for 6 hours. The finely divided yellow sulfide polymer formed is then allowed to settle andthe reaction liquor is separated by decantation. The product is washed bydecantation five times with water and finally filtered by suction. The moistcake of polymer is then air dried. The yield is 988 parts includingapproximately 75 parts of magnesium hydroxide. Thirty-two hundred fifty parts of the hydroxypropylene trisulfide containingmagnesium hydroxide is charged into a steel autoclave equipped with amechanical agitator. There is also charged into the autoclave 2,550 parts ofdry dioxane and 350 parts of cobalt trisulfide catalyst pasted with 700 parts ofdioxane. Hydrogen is charged into the autoclave to a pressure of 1,000 lb/in2and the autoclave is heated to a temperature of 125°C during 1.5 hours,agitation being employed during this operation. When the temperaturereaches about 110°C the pressure commences to drop and is kept betweenthe limits of 1,000 and 1,300 lb/in2 by the addition of hydrogen. When thetemperature reaches 125°C the pressure is raised to 1,700 lb/in2 withhydrogen. The rate of hydrogenation increases as the temperature rises andthe process is about complete when a temperature of 125°C is reached. After the hydrogen absorption ceases, the autoclave is cooled, vented, andthe reaction mixture is filtered to separate the catalyst. The filtrate is thenheated on a steam bath at 60-80 mm pressure to remove the dioxane. Theless volatile residue consists of 1,933 parts of crude dithioglycerol, a viscousoil. 1,2-Dithioglycerol is isolated from the oil by distillation from an oil heated potthrough a short still. The distillation is carried out at a pressure of less than 1mm and at a bath temperature of 120°-175°C, the dithioglycerol distillingover at a head temperature of 60°-65°C/0.2 mm or 75°-80°C/0.8 mm.Starting from 550 parts of crude dithioglycerol, 340 parts of distillate isobtained which contains 53% of mercapto sulfur and is nearly pure 1,2-dithioglycerol. The overall yield of dithioglycerol from the glyceroldibromohydrin is 48% of theoretical. |
| Brand name | Bal (Akorn). |
| Therapeutic Function | Antidote (heavy metal) |
| Biological Functions | Arsenic and some other heavy metals act by chemically reacting with adjacent thiol residues on metabolic enzymes, creating a chelate complex that inhibits the affected enzyme's activity. Dimercaprol competes with the thiol groups for binding the metal ion, which is then excreted in the urine . Dimercaprol is itself toxic, with a narrow therapeutic range and a tendency to concentrate arsenic in some organs. Other drawbacks include the need to administer it by painful intramuscular injection. Serious side effects include nephrotoxicity and hypertension. Dimercaprol has been found to form stable chelates in vivo with many other toxic metals including inorganic mercury, antimony, bismuth, cadmium, chromium, cobalt, gold, and nickel. However, it is not necessarily the treatment of choice for toxicity to these metals. Dimercaprol has been used as an adjunct in the treatment of the acute encephalopathy of lead toxicity. It is a potentially toxic drug, and its use may be accompanied by multiple side effects. Although treatment with dimercaprol will increase the excretion of cadmium, there is a concomitant increase in renal cadmium concentration, so that its use in case of cadmium toxicity is to be avoided. It does, however, remove inorganic mercury from the kidneys; but is not useful in the treatment of alkylmercury or phenyl mercury toxicity. Dimercaprol also enhances the toxicity of selenium and tellurium, so it is not to be used to remove these elements from the body. |
| General Description | Clear colorless viscous liquid with a pungent offensive odor of mercaptans. Used as a medicine and an antidote to the chemical warfare agent LEWISITE. |
| Air & Water Reactions | Moderately soluble in water with decomposition [Hawley]. |
| Reactivity Profile | 2,3-Dimercapto-1-propanol forms highly stable chelates with a variety of metal ions. Organosulfides are incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. Many of these compounds may liberate hydrogen sulfide upon decomposition or reaction with an acid. |
| Fire Hazard | 2,3-Dimercapto-1-propanol is probably combustible. |
| Pharmaceutical Applications | Dimercaprol (BAL) is a chelating agent used as an antidote for arsenic, antimony, bismuth, gold and mercury poisoning. It has the chemical name 2,3-dimercapto-1-propanol and is a clear, colourless or slightly yellow liquid. |
| Clinical Use | 2,3-Dimercapto-1-propanol, BAL, or dithioglycerol is afoul-smelling, colorless liquid. It is soluble in water (1:20)and alcohol. It was developed by the British during WorldWar II as an antidote for “Lewisite,” hence the name Britishanti-Lewisite or BAL. Dimercaprol is effective topicallyand systematically as an antidote for poisoning caused byarsenic, antimony, mercury, gold, and lead. It can, therefore,also be used to treat arsenic and antimony toxicity associatedwith overdose or accidental ingestion of organoarsenicalsor organoantimonials.The antidotal properties of BAL are associated with theproperty of heavy metals to react with sulfhydryl (SH)groups in proteins (e.g., the enzyme pyruvate oxidase) andinterfere with their normal function. 1,2-Dithiol compoundssuch as BAL compete effectively with such proteins for themetal by reversibly forming metal ring compounds.These are relatively nontoxic, metabolically conjugated(as glucuronides), and rapidly excreted.BAL may be applied topically as an ointment or injectedintramuscularly as a 5% or 10% solution in peanut oil. |
| Safety Profile | Poison via ingestion,intramuscular, parenteral, intraperitoneal,and intravenous routes. Experimentalteratogenic effects. Human systemic effectsby intramuscular route: hemorrhage and dermatitis. Human blood and systemic skineffects by intramuscular route. It causesredness and swelling when applied locally tothe skin, but does not produce blisters orulcers. Intensely irritating to eyes andmucous membranes. Systemic symptoms arecaused by injection. When heated todecomposition, it emits toxic fumes of SO,.Used as an antidote to arsenic, gold, andmercury poisoning. |
| Environmental Fate | BAL is believed to compete with tissue sulfhydryl groups andinterferes with cellular respiration. It also competes withmetallic cofactors of metabolic enzyme systems and increasescapillary permeability. Metabolic degradation and excretion areessentially complete within 4 h. BAL not excreted as dimercaprol–metal complex is quickly metabolized by the liver andexcreted as an inactive product in the urine. Because it isa lipophilic drug, it penetrates rapidly the intracellular spaces.The highest concentrations are found in the liver, kidneys,brain, and small intestine. Due to its lipophilic characteristic,the complexes formed with mercury and other metals may beredistributed into sensitive cells in the brain following dimercaproltreatment. |
| Purification Methods | Precipitate BAL as the Hg mercaptide [see Bj.berg Chem Ber 75 13 1942], regenerate with H2S, and distil it under a vacuum [Rosenblatt & Jean Anal Chem 951 1955]. It is an antidote for heavy metal (As, Hg, Au etc) poisoning. [Beilstein 1 IV 2770.] |
| Toxicity evaluation | BAL is a colorless or slightly yellowish viscous oily liquid andhas a pungent odor. The molecular weight, melting point,boiling point, vapor pressure, and the octanol–water partitioncoefficient (log Kow) are 124.23, 77°C, 120°Cat15 mm Hg, 4.36×103 mm Hg at 25°C, and 0.16,respectively. The Henry’s law constant is 9.39×109 atmm3mol-1 at 25°C. BAL is soluble in ethanol and ether, andslightly soluble in chloroform and vegetable oils. Watersolubility is 8.7 g/100 ml. BAL should be protected from lightand should be stored at temperatures between 2 and 10°C insmall vials. |
2,3-Dimercapto-1-propanol Preparation Products And Raw materials
| Raw materials | Allyl alcohol-->Hydrogen-->Sodium sulfide-->2,3-Dibromo-1-propanol |
| Preparation Products | 1,3-dimercaptopropan-2-ol-->1,2-Dithiolan-4-ol |
