Pentaerythritol tribromide
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Pentaerythritol tribromide
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CAS No:
1522-92-5
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Formula:
C5H9Br3O
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Chemical Name:
Pentaerythritol tribromide
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Synonyms:
1-Propanol,3-bromo-2,2-bis(bromomethyl)-;3-Bromo-2,2-bis(bromomethyl)-1-propanol;Pentaerythritol tribromide;2,2,2-Tris(bromomethyl)ethanol;Tribromoneopentyl alcohol;2,2-Bis(bromomethyl)-3-bromo-1-propanol;3-Bromo-2,2-bis(bromomethyl)propanol;Pentaerythritol tribromohydrin;3-Bromo-2,2-bis(bromomethyl)propyl alcohol;FR 1360;FR 513;NSC 20521;Tribromoneopentanol
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CAS No:
Description
PHYSICAL DESCRIPTION: White solid. (NTP, 1992)
3-bromo-2,2-bis(bromomethyl)propanol is a white solid. (NTP, 1992)
3-bromo-2,2-bis(bromomethyl)propanol is a white solid. (NTP, 1992)
Pentaerythritol tribromide Basic Attributes
324.83600
324.84
253-057-0
8HZ2FQ3KUC
20521
DTXSID9024641
2905590090
Characteristics
20.23000
1.9
3-bromo-2,2-bis(bromomethyl)propanol is a white solid. (NTP, 1992)
2.192g/cm3
90-95 °C
131 °C @ Press: 2.5 Torr
153.8ºC
1.589
H2O: insoluble
Keep in a cool, dry, dark location in a tightly sealed container or cylinder. Keep away from incompatible materials, ignition so
Insoluble in water.
Alcohols and Polyols
A brominated alcohol. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.
Safety Information
R20/21/22
26-36/37/39
UA7410000
Stable. Combustible. Incompatible with strong oxidizing agents.
P264, P280, P305+P351+P338, P33, P313
H319
The flash point of this compound has not been determined, but it is probably combustible. (NTP, 1992)
|Warning|H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]|P264, P280, P305+P351+P338, and P337+P313|Aggregated GHS information provided by 42 companies from 4 notifications to the ECHA C&L Inventory.
Fires involving this material can be controlled with dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, you should dampen the solid spill material with alcohol, then transfer the dampened material to a suitable container. Use absorbent paper dampened with alcohol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminate area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
Drug Information
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
3-BBBMP
Pentaerythritol tribromide Use and Manufacturing
A 2-l Erlenmeyer flask was charged withpentaerythritol (136 g, 1 mol), 48percent hydrobromic acid (680 ml, 1006.4 g, 6 mol), acetic acid (100 ml, 105.1 g, 1.75 mol), and then sulfuric acid (250 ml, 458.5 g, 4.5 mol) was carefully added while stirring the reaction mixture. The obtainedsolution was refluxed for 10 h. After that, the reactionmixture was cooled to 15°. The bottom (organic) layerwas separated by using a separatory funnel, and the top(aqueous) layer was extracted with chloroform (3×200 ml).The extracts were combined with the organic phase, theobtained solution was washed with water (3×75 ml). Theorganic phase was dried over anhydrous K2CO3 (20 g) forseveral hours. Then the chloroform solution wasevaporated, providing a brown liquid (275.4 g) with thefollowing composition (according to 1 NMR spectrum):3-bromo-2, 2-bis(bromomethyl)propan-1-ol (3a), 3-bromo-2, 2-bis(bromomethyl)propyl acetate (3b), 2, 2-bis(bromomethyl)-1, 3-propanediol (4a), 3-bromo-2-(bromomethyl)-2-(hydroxymethyl)propyl acetate (4b).3-Bromo-2, 2-bis(bromomethyl)propan-1-ol (3a). Yield134.7 g (48.9percent). 1H NMR spectrum (DMSO-d6), δ, ppm(J, Hz): 3.41 (2, d, J = 5.0, 2OH); 3.49 (6, s, CH2Br);5.26 (1H, t, J = 5.0, OH).3-Bromo-2, 2-bis(bromomethyl)propyl acetate (3b).Yield 101.9 g (37.0percent). 1H NMR spectrum (DMSO-d6), δ, ppm: 2.06 (3, s, OC(O)CH3); 3.57 (6, s, CH2Br); 4.06(2, s, CH2OC(O)CH3).2, 2-Bis(bromomethyl)-1, 3-propanediol (4a). Yield6.3 g (2.3percent). 1H NMR spectrum (DMSO-d6), δ, ppm(J, Hz): 3.41 (4, d, J = 5.0, 2OH); 3.44 (4, s, CH2Br);4.84 (1H, t, J = 5.0, OH).3-Bromo-2-(bromomethyl)-2-(hydroxymethyl)propylacetate (4b). Yield 32.5 g (11.8percent). 1H NMR spectrum(DMSO-d6), δ, ppm (J, Hz): 2.03 (3, s, OC(O)CH3); 3.40(2H, d, J = 4.1, CH2OH); 3.50 (4, s, CH2Br); 3.98 (2, s, CH2OC(O)CH3); 5.10 (1H, t, J = 4.6, OH). 13C NMRspectrum (CDCl3), δ, ppm: 171.22; 170.15; 63.95; 63.78;63.32; 62.33; 61.82; 44.50; 44.23; 42.67; 42.31; 34.83;34.51; 34.09; 33.53; 20.78 (for mixture 3a, b and 4a, b).The yield calculated for the target compounds 3a and 3bwas 236.6 g (69.2percent).
Tribromoneopentanol is an brominated flame retardant, previously shown to be a multisite carcinogen in experimental animals.
Computed Properties
Molecular Weight:324.84
XLogP3:1.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:4
Exact Mass:323.81830
Monoisotopic Mass:321.82035
Topological Polar Surface Area:20.2
Heavy Atom Count:9
Complexity:64.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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