:Parachlorobenzotrifluoride
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| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 406280091
| ImageFile = Parachlorobenzotrifluoride.svg
| ImageSize =
| PIN = 1-Chloro-4-(trifluoromethyl)benzene
| OtherNames = {{Unbulleted list
|Benzene, 1-chloro-4-(trifluoromethyl)-
|Parachlorobenzotrifluoride
|4-Chlorobenzotrifluoride
|Oxsol
}}
|Section1={{Chembox Identifiers
| Abbreviations = PCBTF
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 98-56-6
| EINECS = 202-681-1
| PubChem = 7394
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7116
| SMILES = C1=CC(=CC=C1C(F)(F)F)Cl
| InChI = 1/C7H4ClF3/c8-6-3-1-5(2-4-6)7(9,10)11/h1-4H
| InChIKey = QULYNCCPRWKEMF-UHFFFAOYAI
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C7H4ClF3/c8-6-3-1-5(2-4-6)7(9,10)11/h1-4H
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = QULYNCCPRWKEMF-UHFFFAOYSA-N
| Beilstein = 510203
| MeSHName = C037723
| EC_number = 202-681-1
| UNNumber = 2234
| UNII = 694YO34JHC
}}
|Section2={{Chembox Properties
| C=7 | H=4 | Cl=1 | F=3
| Appearance = Colorless liquid
| Density = 1.33-1.35 @ {{convert|22|C|F}}{{cite web |title=PCBTF 900, Technical Grade, Liquid, Bulk Datasheet |url=https://www.univarsolutions.com/pcbtf-900-3735056 |website=UnivarSolutions |publisher=UnivarSolutions |access-date=13 November 2024}}
| MeltingPtC = -32.8
| BoilingPtC = 138.6
| Solubility = 29 mg/L
| SolubleOther =
| Solvent =
| LogP = 3.7 @ {{convert|25|C|F}}
| VaporPressure = {{convert|5.3|mmHg|atm}} @ {{convert|20|C|F}}
| HenryConstant = 0.0347
| AtmosphericOHRateConstant =
| pKa =
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|Section3={{Chembox Structure
| CrystalStruct =
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|Section4={{Chembox Thermochemistry
| DeltaHf =
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|Section5={{Chembox Pharmacology
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|Section6={{Chembox Explosive
| ShockSens =
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| REFactor = }}
|Section7={{Chembox Hazards
| ExternalSDS = https://smc-global.com/wp-content/uploads/2020/07/SMC-msds_m900.pdf
| GHSPictograms = {{GHS02}}{{GHS07}}{{GHS09}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|226|315|319|335|411}}
| PPhrases = {{P-phrases|210|233|240|241|242|243|261|264|271|273|280|302+352|303+361+353|304+340|305+351+338|312|321|332+313|337+313|362|370+378|391|403+233|403+235|405|501}}
| MainHazards =
| NFPA-H = 1
| NFPA-F = 2
| NFPA-R = 1
| NFPA-S =
| FlashPtC = 42.8
| AutoignitionPtC = 600
| ExploLimits = 0.9%-10.5% (V)
| LD50 = {{Unbulleted list
|Oral, rat: 13000 mg/kg
|Dermal, rabbit: > 2000 mg/kg
}}
| LC50 = Inhalation, rat: 33 mg/L
| PEL = }}
|Section8={{Chembox Related
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}}
Parachlorobenzotrifluoride is a synthetic halogenated organic chemical compound with the molecular formula {{chem2|C7H4ClF3}}. It is frequently abbreviated PCBTF. Parachlorobenzotrifluoride is a colorless liquid with a distinct aromatic odor. PCBTF has been commercially-produced since the 1960s, initially as an intermediate in the production of other petrochemicals. But since the 1990s, it has been primarily used as a solvent.{{cite news |last1=Rayner-Canham |first1=Geoff |title=Para-Chlorobenzotrifluoride (PCBTF) – the 'super-solvent' |url=https://uwaterloo.ca/chem13-news-magazine/march-2014/chemistry/para-chlorobenzotrifluoride-pcbtf-super-solvent |access-date=14 December 2022 |work=Chem 13 News Magazine |publisher=The University of Waterloo |date=March 2014}}
History
Occidental Chemical Corporation was a leading producer and sold it as part of its Oxsol® product line, specifically under the brand name of Oxsol 100.[https://www.islechem.com/pdfs/100msds.pdf MSDS provided by Islechem] Occidental Chemical Corporation sold the OXSOL line to an Israeli company, Makhteshim Agan Industries, Ltd., in 2002.{{cite web |title=Trifluoromethylbenzene 98-08-8 |url=https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/trifluoromethylbenzene1_508.pdf |publisher=National Cancer Institute |access-date=14 December 2022}}
Uses
PCBTF is increasingly used as a xylene replacement in cleaners, thinners, and other aromatic hydrocarbon blends.
PCBTF is used as a component (5-12%) of low volatile organic compound (VOC) compliant polyurethane finishes.see MSDS for MINWAX product numbers 13025(5%) and 71029(12%) {{full citation needed|date=July 2019}}
The substance is used as an ink solvent in the printing industry. Parachlorobenzotrifluoride has a high capacity for dissolving many inks used by the printing industry. In most cases, up to 22 grams of ink can be dissolved in 20 grams of PCBTF.{{citation needed|date=August 2021}} An added benefit is that parachlorobenzotrifluoride dissolves most inks faster than toluene.
Health and Environmental effects
Health effects:
- Points of entry: eyes, ingestion, inhalation, skin.
- Target organs: central nervous system, kidneys, liver.
- Irritancy: eyes, respiratory tract, skin
In the troposphere, PCBTF has an estimated half-life of 67 days. It is transformed by reaction with photochemically-produced hydroxyl radicals to give mainly 2-chloro-5-trifluoromethylphenol.
Regulation
PCBTF currently has VOC Exempt status from the U.S. Environmental Protection Agency.{{Cite web|date=2018-01-30|title=EPA Exempt Volatile Organic Compound: Parachlorobenzotrifluoride|url=https://www.govinfo.gov/content/pkg/FR-1994-10-05/pdf/FR-1994-10-05.pdf#page=25|access-date=2019-03-20|website=American Coatings Association|language=en-US}} However, California's Office of Environmental Health Hazard Assessment (OEHHA) has adopted inhalation risk factors for PCBTF as of June 2019, which could have implications for its ongoing VOC Exempt status.{{Cite web|title=Chemical Listed Effective June 28, 2019 as Known to the State Of California To Cause Cancer: P-Chloro-a,a,a-Trifluorotoluene (Para-Chlorobenzotrifluoride, PCBTF)|url=https://oehha.ca.gov/proposition-65/crnr/chemical-listed-effective-june-28-2019-known-state-california-cause-cancer|access-date=2021-08-14|website=oehha.ca.gov}}[https://oehha.ca.gov/media/downloads/crnr/pcbtfiur012820.pdf p-Chloro-α,α,α-trifluorotoluene (p-Chlorobenzotrifluoride, PCBTF) - Cancer Inhalation Unit Risk Factor Scientific Review Panel Draft - January 2020 - California Office of Environmental Health Hazard Assessment]