Basic information
- CAS
920-66-1- Standard SMILES
OC(C(F)(F)F)C(F)(F)F- InChIKey
BYEAHWXPCBROCE-UHFFFAOYSA-N- Molecular formula
- C3H2F6O
- Average molar mass
- 168.04 g/mol
- Monoisotopic mass
- 168.000984
Overview
1,1,1,3,3,3-hexafluoro-2-propanol is a clear colorless oily liquid with an aromatic odor. (NTP, 1992) Combustible, may cause burns to skin, eyes and mucous membranes.
Names & identifiers
- Preferred name
- 1,1,1,3,3,3-Hexafluoro-2-propanol
- IUPAC
- 1,1,1,3,3,3-hexafluoropropan-2-ol
- English name
- 1,1,1,3,3,3-Hexafluoro-2-propanol
- Molecular formula
- C3H2F6O
- Molecular weight
- 168.04
Names & synonyms
1,1,1,3,3,3-Hexafluoro-2-propanol920-66-1Hexafluoroisopropanol1,1,1,3,3,3-HEXAFLUOROPROPAN-2-OLHFIPHexafluoroisopropyl alcohol1,1,1,3,3,3-HexafluoroisopropanolBis(trifluoromethyl)methanol2H-Hexafluoroisopropanol1,1,1,3,3,3-Hexafluoroisopropyl alcohol2-Propanol, 1,1,1,3,3,3-hexafluoro-2,2,2-Trifluoro-1-(trifluoromethyl)ethanol
Show more names
HFPHFIPAHEXAFLUORO-2-PROPANOL(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl formatecatalase enzymeN-benzyl-3-methoxy-2-(N-methylacetamido)propanamide1,1,1,3,3,3-HEXAFLUOROPROPANOL
Ethanol, 2,2,2-trifluoro-1-(trifluoromethyl)-1,1,1,3,3,3-Hexafluoro-2-hydroxypropane3D632GYQ50NSC-96336CHEBI:63104RefChem:786091213-059-4hexafluoropropanol
Database identifiers
- CAS
920-66-1- PubChem CID
- 13529
- DTXSID
DTXSID1022134- ChEMBL
CHEMBL1231750- ChEBI
CHEBI:63104- UNII
- 3D632GYQ50
- EC Number
- 213-059-4
- Nikkaji
- J50.987F
Properties
Computed structural properties
- XLogP
- 1.7
- Topological polar surface area
- 20.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 0
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 97.1
Experimental & physicochemical properties
Chemical Classes
Ionic Liquids
Ionic Liquids -> Fluorinated Ionic Liquids
PFAS
PFAS
PFAS -> Suspected persistent, mobile, toxic (PMT) PFAS or PFAS-like compounds
PFAS -> PFAS identified in REACH Regulation EC No. 1272/2008
PFAS -> Identified in migrating and extractable food contact chemical data
PolymersOther Classes -> Alcohols and Polyols, Other
SpringerMaterials PropertiesSchoenflies notation
LogP1.66
Density
1.596 at 68 °F (NTP, 1992) - Denser than water; will sink
1.46 @25 °C
Solubilitygreater than or equal to 100 mg/mL at 68 °F (NTP, 1992)
Flash Point
greater than 200 °F (NTP, 1992)
Flash point > 93 °C
Boiling Point
138 °F at 760 mmHg (NTP, 1992)
59 °C @760 [mm Hg]
Melting Point25 °F (NTP, 1992)
Vapor Pressure
158 mmHg at 72 °F ; 556 mmHg at 124 °F; 1468 mmHg at 167 °F (NTP, 1992)
159.0 [mmHg]
Physical Description
1,1,1,3,3,3-hexafluoro-2-propanol is a clear colorless oily liquid with an aromatic odor. (NTP, 1992) Combustible, may cause burns to skin, eyes and mucous membranes.
Liquid; Gas Vapor
Colorless to light colored liquid; [CAMEO] Melting point = -4 deg C; Miscible in water; [MSDSonline]
Physicochemical properties
- Melting point
- 4 °C · −4 °C(lit.)
- Boiling point
- 59 °C · 59 °C(lit.)
- Density
- 1.596 g/mL · 1.596 g/mL at 25 °C(lit.)
- vapor pressure
- 269 hPa · 269 hPa (30 °C)
- refractive index
- 20 · n20/D 1.275(lit.)
- Flash point
- 4 · 4,4°C
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- soluble in Chloroform, Ethyl Acetate
- pka
- 1 · pK1:9.42 (25°C)
- form
- Solid
- Specific Gravity
- 1.596 · 1.596
- color
- White to yellow
- PH
- 3 · 3-4 (H2O)Aqueous solution
- Water Solubility
- 1000 g/L · 1000 g/L (25 ºC)
- λmax
- 229 nm · 229nm(lit.)
- BRN
- 1841007 · 1841007
- Henry's Law Constant
- 1 · 1.0×10-1 mol/(m3Pa) at 25℃, I. et al. (1999)
- Stability
- Stable. Incompatible with strong acids, strong bases, alkali metals.
- InChI
- 1S/C3H2F6O/c4-2(5,6)1(10)3(7,8)9/h1,10H
- InChIKey
- BYEAHWXPCBROCE-UHFFFAOYSA-N
- SMILES
- OC(C(F)(F)F)C(F)(F)F
- LogP
- 1.5 at · 1.5 at 25℃
- Surface tension
- 67.1 mN/m · 67.1mN/m at 1g/L and 19.8℃
- CAS DataBase Reference
- 920 · 920-66-1(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 3 D632GYQ50 · 3D632GYQ50
- NIST Chemistry Reference
- 2 · 2-Propanol, 1,1,1,3,3,3-hexafluoro-(920-66-1)
- EPA Substance Registry System
- 1 · 1,1,1,3,3,3-Hexafluoro-2-propanol (920-66-1)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 5 · GHS05,GHS08
- Signal word
- Danger
- Hazard statements
- 314 · H314-H361-H373
- Precautionary statements
- 202 · P202-P260-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338
- PPE
- Faceshields, Gloves, Goggles
- Hazard Codes
- C,Xi
- Risk Statements
- 20 · 20/22-34
- Safety Statements
- 26 · 26-36/37/39-45-27
- RIDADR
- 2922 · UN 2922 8/PG 2
- WGK Germany
- 2 · 2
- RTECS
- 6450000 · UB6450000
- F
- 27 · 27
- Hazard Note
- Corrosive
- TSCA
- TSCA listed
- HazardClass
- 8 · 8
- PackingGroup
- II
- HS Code
- 29055910 · 29055910
- Storage Class
- 8 A · 8A - Combustible corrosive hazardous materials
- Hazard Classifications
- 1 Repr · Eye Dam. 1Repr. 2Skin Corr. 1ASTOT RE 2
- Toxicity
- 50 orally · LD50 orally in Rabbit: 1500 mg/kg
- REACH Registrations
- Active
- Limited Quantities
- 1 Kg · 1 Kg (2.2 lbs) (solid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
Danger
H302 (90.5%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P318, P319, P321, P330, P362+P364, P363, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 200 reports by companies from 30 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 2-Propanol, 1,1,1,3,3,3-hexafluoro-
2-Propanol, 1,1,1,3,3,3-hexafluoro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Propanol, 1,1,1,3,3,3-hexafluoro- 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: 05-08-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/21690
1,1,1,3,3,3-Hexafluoro-2-propanol: Does not have an individual approval but may be used under an appropriate group standard
DOT LabelCorrosive
Fire HazardsThis chemical is probably combustible. (NTP, 1992)
Health Hazards
SYMPTOMS: Symptoms of exposure to this compound include a burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, vomiting, abdominal pain; skin irritation, dermatitis, blistering and ulceration of the skin; gangrene, erythema; conjunctivitis, eye injury; dizziness, vertigo, light-headedness; lowered body temperature; cyanosis; respiratory distress; convulsions; collapse; coma; and liver and kidney damage. Inhalation may be fatal as a result of spasm, inflammation and edema of the larynx and bronchi, chemical pneumonitis and pulmonary edema.
Hazards SummaryDestructive to tissues and can cause chemical pneumonitis, liver and kidney injury, convulsions, coma, and death; [CAMEO] Corrosive to skin; Harmful by inhalation; Can cause chemical pneumonitis; [MSDSonline]
Reactive GroupAlcohols and Polyols
Reactivity Profile1,1,1,3,3,3-HEXAFLUORO-2-PROPANOL is incompatible with acids, acid chlorides and oxidizing agents. (NTP, 1992)
Air and Water ReactionsWater soluble.
Hazard Classes and CategoriesAcute Tox. 4 (90.5%)
Safety & protection
Fire FightingFires involving this compound can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid
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.
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
Isolation and EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Protective Action Criteria (PAC)
1.3 [ppm]
15 [ppm]
87 [ppm]
Personal Protective Equipment (PPE)MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves.
Toxicology
Adverse EffectsNeurotoxin - Other CNS neurotoxin
Toxicity DataLC50 (rat) = 1,974 ppm/4h
Safety data
- F
- 27
- PPE
- Faceshields, Gloves, Goggles
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- UB6450000
- ridadr
- UN 2922 8/PG 2
- hs_code
- 29055910
- Toxicity
- LD50 orally in Rabbit: 1500 mg/kg
- risk_code
- 20/22-34
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS08
- hazard_code
- C,Xi
- hazard_note
- Corrosive
- safety_code
- 26-36/37/39-45-27
- hazard_class
- 8
- Storage Class
- 8A - Combustible corrosive hazardous materials
- packing_group
- II
- Hazard statements
- H314-H361-H373
- 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
- Hazard Classifications
- Eye Dam. 1Repr. 2Skin Corr. 1ASTOT RE 2
- Precautionary statements
- P202-P260-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338
Chemistry & industry
Pharmacology
Metabolism/MetabolitesHexafluoroisopropanol has known human metabolites that include (2S,3S,4S,5R)-6-(1,1,1,3,3,3-hexafluoropropan-2-yloxy)-3,4,5-trihydroxyoxane-2-carboxylic acid.
Tissue LocationsKidney
Cellular LocationsCytoplasm
Uses & manufacturing
U.S. Production2023: 1,000,000 - <8,500,000 lb
Consumer UsesMonomers
Industry UsesMonomers
General Manufacturing Information
Pharmaceutical and Medicine Manufacturing
2-Propanol, 1,1,1,3,3,3-hexafluoro-: ACTIVE
Applications
DescriptionHexafluoroisopropanol (HFIP) is a viscous and colorless liquid with scary odorless. It is an ideal solvent for dissolving polyamides and esters, and it can be used to analyze nylon. Typically, a small amount of sodium trifluoroacetate can be added to the eluent to reduce the aggregation of the sample. HFIP has a certain viscosity, but its boiling point is very low, so we need to analyst under the conditions of 40 ° C to reduce the back pressure of the column. Hexafluoroisopropanol is also a highly polar solvent that results in a non-linearity of the calibration curve obtained from the mixed column bed column. Therefore, Agilent has developed a special column-PL HFIPgel column for this solvent, which has a porous structure that is not affected by solvents.
Description1,1,1,3,3,3-Hexafluoro-2-propanol (HFIP) is aclear, colorless, oily, combustible liquid. Odor is describedasaromatic. Molecular weight = 1 68.04; Specific grav-ity = 1.596 .at 20℃; Freezing/Melting point= -4℃;Boiling point = 59℃at 760 mmHg; V apor pressure:556 mmHg at 51℃; 1468 mmHg at 75℃; Flash point: .>93℃. Hazard Identification (based on NFPA-704 MRating System): Health 3; Flammability 0; Reactivity 0.W ater soluble; solubility=≥100 mg/mL at 20℃.
UsesHexafluoroisopropanol is used to produce high-end chemicals, such as fluorinated surfactants, fluorinated emulsifier and fluorinated medicine, etc. HFIP is used as a solvent or cleaner in electronic industry.
UsesUsually used for preparing hexafluoroalcohol-functionalized methacrylate polymers for lithographic/nanopatterning materials.
UsesIt is used as a polar solvent and exhibits strong hydrogen bonding properties.It dissolves substances that are hydrogen-bond acceptors, such as amides, ethers and a wide range of polymers, including those that are not soluble in the most common organic solvents.
Uses1,1,1,3,3,3-Hexafluoro-2-propanol effects the native state of proteins, denaturing them as well as stabilizing the α-helical conformation of unfolded proteins and polypeptides.
General Description1,1,1,3,3,3-Hexafluoro-2-propanol is a solution-phase peptide chemistry solvent. This fluorinated polar solvent of high ionizing power facilitates Friedel–Crafts-type reactions, using covalent reagents in the absence of a Lewis acid catalyst. It also enhances the efficiency of rhodium(I)-catalyzed [4+2] intramolecular cycloaddition of ether-tethered alkynyl dienes and [5+2] cycloaddition of alkynyl vinylcyclopropanes. 1,1,1,3,3,3-Hexafluoro-2-propanol clusters catalyzes the epoxidation of cyclooctene and 1-octene with hydrogen peroxide.
Preparation methods
Preparation1,1,1,3,3,3-Hexafluoro-2-propanol is prepared from hexafluoropropylene through hexafluoroacetone, which is then hydrogenated. (CF3)2CO + H2 → (CF3)2CHOH
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: An organofluorine compound formed by substitution of all the methyl protons in propan-2-ol by fluorine. It is a metabolite of inhalation anesthetic sevoflurane.
Related reactions
320 records
Compound notes
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