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tert-Butyl(phenyl)phosphinothioic acid

  1. Rajender Salla

Published Online: 16 SEP 2013

DOI: 10.1002/047084289X.rn01592

e-EROS Encyclopedia of Reagents for Organic Synthesis

e-EROS Encyclopedia of Reagents for Organic Synthesis

How to Cite

Salla, R. 2013. tert-Butyl(phenyl)phosphinothioic acid. e-EROS Encyclopedia of Reagents for Organic Synthesis. .

Author Information

  1. Wayne State University, Michigan, MI, USA

Publication History

  1. Published Online: 16 SEP 2013

Chemistry Terms

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Abstract

(precursor to various optically pure phosphines, resolving agent, and chiral solvating agent)

Physical Data: mp 95–96 °C.

Solubility: soluble in dichloromethane, ethanol, and most organic solvents.

Form Supplied in: crystalline solid.

Preparative Method: racemic tert-butyl(phenyl)phosphinothioic acid is synthesized by reacting dichlorophenylphosphine with tert-butylmagnesium chloride followed by refluxing with molecular sulfur in toluene. Resolution involves treatment with (S)-(−)-α-methylbenzylamine in ether followed by collection of the crystalline, ether-insoluble (R)-(+)-acid-(S)-(−)-amine salt. If the NMR spectrum shows contamination from the diastereomeric salt, the salt is dissolved in chloroform and induced to recrystallize by addition of ether. The crude (−)-acid was recovered from the ether-soluble (S)-(−)-acid-(S)-(−)-amine salt (eq 1).1

original image(1)

Handling, Storage, and Precautions: storage in a cool, dry place is recommended.

Featured Compounds

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  1. 1 - 42
Compound Information
Molecular Weight:178.984
Molecular Formula:C6H5Cl2P
InChIKey:IMDXZWRLUZPMDH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:116.872
Molecular Formula:C4H9ClMg
InChIKey:ZDRJSYVHDMFHSC-UHFFFAOYSA-M
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Compound Information
Molecular Weight:182.1993
Molecular Formula:C10H15OP
InChIKey:BJQBKYYLWCDABM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:74.1216
Molecular Formula:C4H10O
InChIKey:RTZKZFJDLAIYFH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:53.491
Molecular Formula:ClH4N
InChIKey:NLXLAEXVIDQMFP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:36.461
Molecular Formula:ClH
InChIKey:VEXZGXHMUGYJMC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:214.264
Molecular Formula:C10H15OPS
InChIKey:ACQNBIJCKLUKMY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:256.52
Molecular Formula:S8
InChIKey:JLQNHALFVCURHW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:92.1384
Molecular Formula:C7H8
InChIKey:YXFVVABEGXRONW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:121.1796
Molecular Formula:C8H11N
InChIKey:RQEUFEKYXDPUSK-ZETCQYMHSA-N
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Compound Information
Molecular Weight:335.444
Molecular Formula:C18H26NOPS
InChIKey:CVEWLYIGSPNVOW-QIUDTCLKSA-N
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Compound Information
Molecular Weight:335.444
Molecular Formula:C18H26NOPS
InChIKey:CVEWLYIGSPNVOW-OLBMHGAYSA-N
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Compound Information
Molecular Weight:214.264
Molecular Formula:C10H15OPS
InChIKey:ACQNBIJCKLUKMY-LBPRGKRZSA-N
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Compound Information
Molecular Weight:39.9971
Molecular Formula:HNaO
InChIKey:HEMHJVSKTPXQMS-UHFFFAOYSA-M
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Compound Information
Molecular Weight:58.6934
Molecular Formula:Ni
InChIKey:PXHVJJICTQNCMI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:46.0684
Molecular Formula:C2H6O
InChIKey:LFQSCWFLJHTTHZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:WYURNTSHIVDZCO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:107.123
Molecular Formula:C6H14LiN
InChIKey:ZCSHNCUQKCANBX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:18.0153
Molecular Formula:H2O
InChIKey:XLYOFNOQVPJJNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:116.165
Molecular Formula:C2N2S2
InChIKey:DTMHTVJOHYTUHE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:239.274
Molecular Formula:C11H14NOPS
InChIKey:POUXPOJUWJAEFH-CQSZACIVSA-N
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Compound Information
Molecular Weight:84.933
Molecular Formula:CH2Cl2
InChIKey:YMWUJEATGCHHMB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:121.1796
Molecular Formula:C8H11N
InChIKey:RQEUFEKYXDPUSK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:360.453
Molecular Formula:C19H25N2OPS
InChIKey:ANZVJHSVORMMRO-GMTBNIFVSA-N
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Compound Information
Molecular Weight:214.264
Molecular Formula:C10H15OPS
InChIKey:ACQNBIJCKLUKMY-GFCCVEGCSA-N
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Compound Information
Molecular Weight:141.939
Molecular Formula:CH3I
InChIKey:INQOMBQAUSQDDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:228.291
Molecular Formula:C11H17OPS
InChIKey:LXQHGRPQZABCNX-CYBMUJFWSA-N
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Compound Information
Molecular Weight:101.19
Molecular Formula:C6H15N
InChIKey:ZMANZCXQSJIPKH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:244.356
Molecular Formula:C11H17PS2
InChIKey:HXUYBSXCULDBPQ-GFCCVEGCSA-N
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Compound Information
Molecular Weight:404.467
Molecular Formula:C14H14O2P2S4
InChIKey:Not Available
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Compound Information
Molecular Weight:216.644
Molecular Formula:C10H14ClOP
InChIKey:URNNRLLBSQXWBR-ZDUSSCGKSA-N
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Compound Information
Molecular Weight:134.97
Molecular Formula:Cl2O2S
InChIKey:YBBRCQOCSYXUOC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:70.906
Molecular Formula:Cl2
InChIKey:KZBUYRJDOAKODT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:212.291
Molecular Formula:C11H17PS
InChIKey:DXSRUTVZTFYOLZ-LBPRGKRZSA-N
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Compound Information
Molecular Weight:64.055
Molecular Formula:C4H9Li
InChIKey:MZRVEZGGRBJDDB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:430.98
Molecular Formula:C13H29ISn
InChIKey:XEKIDGIZQAEOKB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:517.34
Molecular Formula:C23H43OPSSn
InChIKey:AXSKCPRCRQEWPK-SVZPRBGCSA-N
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Compound Information
Molecular Weight:242.317
Molecular Formula:C12H19OPS
InChIKey:CMFLXPKMSSAVJP-AWEZNQCLSA-N
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Compound Information
Molecular Weight:21.976
Molecular Formula:CH3Li
InChIKey:Not Available
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Compound Information
Molecular Weight:196.2258
Molecular Formula:C11H17OP
InChIKey:SAGFRDRHJPDVFK-ZDUSSCGKSA-N
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