トリフェニルホスフィン

Triphenylphosphine

HCID 11776CAS 603-35-0

基本情報

標準SMILES
c1ccc(P(c2ccccc2)c2ccccc2)cc1
InChIKey
RIOQSEWOXXDEQQ-UHFFFAOYSA-N
分子式
C18H15P
平均分子量
262.3 g/mol
単同位体質量
262.09113711

概要

Triphenyl phosphine appears as white crystals. (NTP, 1992)

名称と識別子

優先名称
Triphenylphosphine
IUPAC
triphenylphosphane
現地名
トリフェニルホスフィン
英語名
Triphenylphosphine
分子式
C18H15P
分子量
262.29

名称と別名

TRIPHENYLPHOSPHINE603-35-0TriphenylphosphaneTriphenyl phosphinePhosphine, triphenyl-TriphenylphosphorusTriphenylphosphideTrifenylfosfinPP 360DTXSID5026251NSC-1026D26OA393
名称をさらに表示
トリフェニルホスフィントリスフェニルホスフィントリフェニルホスファントリフェニルホスフィン リントリフェニルホスフィン, POWDERトリフェニルホスフィン, FLAKEトリフェニルホスフィン, 99%トリフェニルホスフィン, 99+%トリフェニルホスフィン, flake, 99%トリフェニルホスフィン, powder, 99%PPh3TriphenylTriphenyphosphineriphenylphosphineTriphenyl phospinetptbp
NSC-215203DTXCID906251CHEBI:183318RefChem:6333210-036-0Triphenylphosphine resintriphenyl-phosphane39319-11-4

データベース識別子

CAS
603-35-0
PubChem CID
11776
DTXSID
DTXSID5026251
ChEMBL
CHEMBL1448331
ChEBI
CHEBI:183318
UNII
26D26OA393
EC Number
210-036-0
Nikkaji
J1.652G

物性

構造計算による物性

XLogP
4.6
極性表面積
0 Ų
水素結合供与体数
0
水素結合受容体数
0
回転可能結合数
3
重原子数
19

実験および物理化学的性質

Chemical ClassesOther Classes -> Phosphorus Compounds
SpringerMaterials PropertiesSchoenflies notation
LogP5.69
OdorODORLESS
Density · 4 件

1.194 at 77 °F (NTP, 1992) - Denser than water; will sink

1.075 @ 80 °C/4 °C

1.1 g/cm³

1.194 @25 °C

Color/Form · 2 件

MONOCLINIC PLATELETS OR PRISMS FROM ETHER

WHITE CRYSTALLINE SOLID

物理化学的性質

融点
79 · 79-81 °C(lit.)
沸点
377 °C · 377 °C(lit.)
比重(密度)
1.132 · 1.132
蒸気密度
9 · 9 (vs air)
蒸気圧
5 mm · 5 mm Hg ( 20 °C)
屈折率
1.6358 · 1.6358

化学的性質

化学的特性Triphenylphosphine is a white to light tan flaked solid. Insoluble inwater; slightly soluble in alcohol; soluble in benzene, acetone, carbon tetrachloride. Combustible.

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 0.5% (6 of 1290) of reports.

Danger

H302 (97.1%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P261, P264, P264+P265, P270, P272, P273, P280, P301+P317, P302+P352, P305+P354+P338, P317, P319, P321, P330, P333+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1290 reports by companies from 56 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

危険有害性情報

Regulatory Information · 4 件

Chemical: Phosphine, triphenyl-

Phosphine, triphenyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phosphine, triphenyl- 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: 14-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/13659

Triphenylphosphine: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Phosphine, triphenyl-: Human health tier II assessment
DOT LabelClass 9
Fire Hazards · 2 件

This compound is combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.

Health HazardsACUTE/CHRONIC HAZARDS: Toxic; when heated to decomposition, emits highly toxic fumes of phosphine and POx. (NTP, 1992)
Hazards Summary · 1 件

Decomposed by heating forming phosphine and phosphorous oxides; A skin, eye, and respiratory tract irritant; [ICSC] Causes convulsions at lethal doses in animal experiments; [RTECS] A strong reducing agent; [CAMEO] Harmful if ingested; May cause skin sensitization; [Aldrich MSDS] See Phosphine.

安全と保護具

Fire Fighting · 2 件

Fires involving this chemical can be controlled with dry chemical, carbon dioxide, or Halon extinguisher. (NTP, 1992)

Use water spray, foam, powder, carbon dioxide.

First Aid Measures · 4 件

Fresh air, rest. Refer for medical attention.

Wear protective gloves when administering first aid. Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

Rinse with plenty of water for several minutes (remove contact lenses if easily possible). Refer for medical attention.

Rinse mouth. Refer for medical attention .

First Aid · 1 件

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.

Safe StorageSeparated from oxidants and acids. Keep in a well-ventilated room.
Exposure Control and Personal Protection2.0 [mg/m3], inhalable fraction[German Research Foundation (DFG)]
Fire Fighting ProceduresFOAM MAY CAUSE FROTHING.

毒性情報

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Exposure RoutesThe substance can be absorbed into the body by inhalation of its aerosol and by ingestion.
Signs and Symptoms · 4 件

Cough. Sore throat.

Redness.

Redness. Pain.

Cough.

ICSC Environmental DataBioaccumulation of this chemical may occur in the environment.
Non-Human Toxicity Excerpts · 3 件

CNS EFFECTS: WEAKNESS & ATAXIA ONLY SYMPTOMS. IRRITANT EFFECTS: SLIGHT SKIN IRRITANT IN GUINEA PIG. /FROM TABLE/

DURING INHALATION EXPOSURE MALE CHR-CD RATS SHOWED MILD RESP IRRITATION; SEVERE WT LOSS OCCURRED IMMEDIATELY AFTER EXPOSURE, FOLLOWED BY NORMAL RATE OF WT GAIN. MILD WT LOSS OCCURRED DURING 10-DAY EXPOSURE PERIOD, FOLLOWED BY NORMAL WT GAIN.

Triphenylphosphine (TPP) was tested for mutagenicity in the Salmonella/microsome preincubation assay using a protocol approved by the National Toxicology Program. TPP was tested over a wide range of doses (0, 89, 285, 854, 2733 and 8200 ug/plate) in four Salmonella typhimurium strains (TA98, TA100, TA1535, and TA1537) in the presence and absence of Aroclor-induced rat or hamster liver S9. TPP was negative in these tests and the highest ineffective dose level tested (not causing formation of a precipitate) in any Salmonella tester strain was 89 ug/plate.

Toxicity DataLC50 (rat) = 1,135 ppm/4h

安全データ

F
9
wgk
2
tsca
TSCA listed
rtecs
SZ3500000
ridadr
3077
毒性
LD50 orally in Rabbit: 700 mg/kg LD50 dermal Rabbit > 4000 mg/kg

化学と産業

用途と製造

Uses · 4 件

Used as a polymerization initiator and an intermediate to make pharmaceuticals, phosphonium salts, and other phosphorus compounds; [HSDB]

ORGANIC SYNTHESIS; POLYMERIZATION INITIATOR

SYNTHESIS OF PHOSPHONIUM SALTS, OTHER PHOSPHORUS COMPOUNDS

CHEMICAL INTERMEDIATE, EG, FOR PHARMACEUTICALS

U.S. Exports · 2 件

(1977) No Data

(1979) No Data

U.S. Imports · 2 件

(1977) 2.72X10+7 G (PRINCPL CUSTMS DISTS)

(1979) 7.58X10+7 G (PRINCPL CUSTMS DISTS)

U.S. Production · 3 件

2023: 1,000,000 - <2,500,000 lb

(1977) No Data

(1979) No Data

Consumer UsesCatalyst
Industry UsesCatalyst
応用分野 · 4 件

解説トリフェニルホスフィン,三塩化リンと臭化フェニルマグネシウム,あるいはフェニルリチウムとの反応で得られる.無色の板状結晶.融点80.5 ℃,沸点377 ℃(不活性ガス中),188 ℃(133 Pa).d4251.194.pKa 2.30.有機溶媒に可溶.ハロゲンと反応して付加物を与え,ハロゲン化アルキルと反応してホスホニウム塩を生成する.ウィッティヒ反応の試薬,緩和な還元剤,ウィルキンソン錯体のような低原子価遷移金属錯体の配位子など,合成化学に有用な試薬である.LD50 800 mg/kg(ラット,経口).

用途主に錯化剤、還元剤、プロセスレギュレーター、ビタミン及び医薬品の合成中間体として使用される。WITTIG反応(主にビタミン及び医薬品の合成)のための出発原料で、オレフィンのヒドロホルミル化反応の触媒リガンドとして使われる。またポリウレタン合成の添加物及び樹脂の硬化触媒として使われる。更には安定化剤、抑制剤、ペンキ及びラッカーにも応用される。(SIDS (ACCESS ON DEC. 2010))

説明Triphenylphosphine: a member of tertiary phosphines Triphenylphosphine (TPP) is a member of tertiary phosphines, which is phosphane, in which the three hydrogens are replaced by phenyl groups. It has a role as a reducing agent and an NMR chemical shift reference compound. It is a crucial ligand utilized in the Wittig reaction for alkene synthesis. This reaction involves the formation of alkyliden-etriphenylphosphoranes from the action of butyllithium or another base on the quarternary halide. Triphenylphosphine is used to synthesise organic compounds due to its nucleophilicity and reducing character.

使用用途トリフェニルホスフィンは、多種多様な人名化学反応で利用されています。その多くは有機化合物を用いた反応です。 トリフェニルホスフィンを用いた化学反応の具体例として、アッペル反応 (英: Appel reaction) やウィッティヒ反応 (英: Wittig reaction) などが挙げられます。それ以外にも、シュタウディンガー反応 (英: Staudinger reaction) 、光延反応 (英: Mitsunobu reaction) 、ヘック反応 (英: Heck reaction) などがあります。

調製方法 · 2 件

Triphenylphosphine is one of the most widely used phosphorus-containing reagents in organic synthesis for many types of transformations such as the Mitsunobu, the Wittig, and the Staudinger reaction. Triphenylphosphine can be prepared in the laboratory by treatment of phosphorus trichloride with phenylmagnesium bromide or phenyllithium. The industrial synthesis involves the reaction between phosphorus trichloride, chlorobenzene, and sodium. PCl3 + 3 PhCl + 6 Na → PPh3 + 6 NaCl

純化方法It crystallises from hexane, MeOH, diethyl ether, CH2Cl2/hexane or 95% EtOH. Dry it at 65o/<1mm over CaSO4 or P2O5. Chromatograph it through alumina using (4:1) *benzene/CHCl3 as eluent. [Blau & Espenson et al. J Am Chem Soc 108 1962 1986, Buchanan et al. J Am Chem Soc 108 1537 1986, Randolph & Wrighton J Am Chem Soc 108 3366 1986, Asali et al. J Am Chem Soc 109 5386 1987.] It has also been crystallised twice from pet ether and 5 times from Et2O/EtOH to give m 80.5o. Alternatively, dissolve it in conc HCl, and upon dilution with H2O it separates because it is weakly basic, it is then crystallised from EtOH/Et2O. It recrystallises unchanged from AcOH. [Forward et al. J Chem Soc Suppl. p121 1949, Muller et al. J Am Chem Soc 78 3557 1956.] 3Ph3P.4HCl crystallises out when HCl gas is bubbled through an Et2O solution, it has m 70-73o, but recrystallises very slowly and is deliquescent. The hydriodide, made by adding Ph3P to hydriodic acid, is not hygroscopic and decomposes at ~100o. The chlorate (1:1) salt has m 165-167o, but decomposes slowly at 100o. All salts hydrolyse in H2O to give Ph3P [IR, UV: Sheldon & Tyree J Am Chem Soc 80 2117 1958, pK: Henderson & Streuli J Am Chem Soc 82 5791 1960, Kosolapoff, Organophosphorus Compounds, Wiley 1950]. [Beilstein 16 IV 951.] § Available commercially on a polystyrene or polyethyleneglycol support.

上流・下流製品情報

下流製品

2-ジフェニルホスフィノ-6-メチルピリジンイベルメクチンメチルトリフェニルホスホニウム ブロミド2-ブロモ-1,1'-ビナフチル, 98%3'-アジド-3'-デオキシチミジン2-(2-(ジフェニルホスフィノ)エチル)ピリジントリフェニルジブロモホスホラン5-(アミノメチル)ピロリジン-2-オン5-フェニルチオフェン-2-カルボキシアルデヒドアミルトリフェニルホスホニウムブロミド2-(ジフェニルホスフィノ)エチルアミントリス(トリフェニルホスフィン)ルテニウム(II) ジクロリド

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