C-C Bond Forming Reagents

Source reagents used in C–C bond formation and core scaffold construction. Use this page to compare synthetic tools for building complex molecules more efficiently.

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  1. Dimethyl 1,3-Benzodithiol-2-ylphosphonate
    CAS: 62217-35-0 Formula: C9H11O3PS2 Molecular Weight: 262.28
    Out of Stock Item #: D155273
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    Technical Identifiers
    IUPAC Name
    2-dimethoxyphosphoryl-1,3-benzodithiole
    SMILES
    COP(=O)(C1SC2=CC=CC=C2S1)OC
    InChIKey
    VKVOUPYVLWQXLB-UHFFFAOYSA-N
    InChI
    1S/C9H11O3PS2/c1-11-13(10,12-2)9-14-7-5-3-4-6-8(7)15-9/h3-6,9H,1-2H3
    Synonyms
    SCHEMBL1966987 | 2-dimethoxyphosphoryl-1,3-benzodithiole | Dimethyl 1,3-Benzodithiol-2-ylphosphonate | T71133 | D3992...
  2. Triphenylpropylphosphonium bromide
    CAS: 6228-47-3 EC Number: 228-330-2 Formula: C21H22BrP Molecular Weight: 385.28
    In Stock Item #: T100772
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    Technical Identifiers
    IUPAC Name
    triphenyl(propyl)phosphanium;bromide
    SMILES
    CCC[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3.[Br-]
    InChIKey
    XMQSELBBYSAURN-UHFFFAOYSA-M
    InChI
    1S/C21H22P.BrH/c1-2-18-22(19-12-6-3-7-13-19,20-14-8-4-9-15-20)21-16-10-5-11-17-21;/h3-17H,2,18H2,1H3;1H/q+1;/p-1
    Synonyms
    DTXSID80977847 | triphenyl(propyl)phosphanium;bromide | 2-Methyl-4-butanolide | Triphenyl(propyl)phosphonium bromide ...
  3. Triphenylpropargylphosphonium Bromide
    CAS: 2091-46-5 PubChem CID: 2724214 Formula: C21H18BrP Molecular Weight: 381.25
    In Stock Item #: T162760
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    Technical Identifiers
    IUPAC Name
    triphenyl(prop-2-ynyl)phosphanium;bromide
    SMILES
    C#CC[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3.[Br-]
    InChIKey
    AFZDAWIXETXKRE-UHFFFAOYSA-M
    InChI
    1S/C21H18P.BrH/c1-2-18-22(19-12-6-3-7-13-19,20-14-8-4-9-15-20)21-16-10-5-11-17-21;/h1,3-17H,18H2;1H/q+1;/p-1
    Synonyms
    Triphenylpropargylphosphonium bromide | J-013717 | SCHEMBL588651 | SY105980 | ?PROPARGYLTRIPHENYLPHOSPHONIUM BROMIDE ...
  4. (Triphenylphosphoranylidene)ketene
    CAS: 15596-07-3 Formula: C20H15OP Molecular Weight: 302.31
    Solid ≥95%
    Out of Stock Item #: B299956
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    Technical Identifiers
    SMILES
    C1=CC=C(C=C1)P(=C=C=O)(C2=CC=CC=C2)C3=CC=CC=C3
    InChIKey
    MNASRBWCHRURHY-UHFFFAOYSA-N
    InChI
    1S/C20H15OP/c21-16-17-22(18-10-4-1-5-11-18,19-12-6-2-7-13-19)20-14-8-3-9-15-20/h1-15H
    Synonyms
    Bestmann Ylide | Ketenylidene(triphenyl)phosphorane
  5. N-(2-Thiazolyl)-1H-benzotriazole-1-carbothioamide
    CAS: 690634-07-2 Formula: C10H7N5S2 Molecular Weight: 261.33
    Out of Stock Item #: N336466
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    Technical Identifiers
    IUPAC Name
    N-(1,3-thiazol-2-yl)benzotriazole-1-carbothioamide
    SMILES
    C1=CC=C2C(=C1)N=NN2C(=S)NC3=NC=CS3
    InChIKey
    HQCYBFVKEAZBJE-UHFFFAOYSA-N
    InChI
    1S/C10H7N5S2/c16-10(12-9-11-5-6-17-9)15-8-4-2-1-3-7(8)13-14-15/h1-6H,(H,11,12,16)
    Synonyms
    N-(1,3-thiazol-2-yl)benzotriazole-1-carbothioamide | N-(1,3-Thiazol-2-yl)-1H-1,2,3-benzotriazole-1-carbothioamide | D...
  6. (2-Hydroxyethyl)triphenylphosphonium bromide
    CAS: 7237-34-5 Formula: HOCH2CH2P(C6H5)3Br Molecular Weight: 387.25
    In Stock Item #: H332721
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    Technical Identifiers
    IUPAC Name
    2-hydroxyethyl(triphenyl)phosphanium;bromide
    SMILES
    C1=CC=C(C=C1)[P+](CCO)(C2=CC=CC=C2)C3=CC=CC=C3.[Br-]
    InChIKey
    QZJOQNHOOVSESC-UHFFFAOYSA-M
    InChI
    1S/C20H20OP.BrH/c21-16-17-22(18-10-4-1-5-11-18,19-12-6-2-7-13-19)20-14-8-3-9-15-20;/h1-15,21H,16-17H2;1H/q+1;/p-1
    Synonyms
    AKOS015913455 | Phosphonium,(2-hydroxyethyl)triphenyl-,bromide(1:1) | MFCD00011901 | (2-Hydroxyethyl)(triphenyl)phosp...
  7. (3-Benzyloxypropyl)triphenylphosphonium bromide
    CAS: 54314-85-1 Formula: C6H5CH2O(CH2)3P(C6H5)3Br Molecular Weight: 491.4
    In Stock Item #: B341757
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    Technical Identifiers
    IUPAC Name
    triphenyl(3-phenylmethoxypropyl)phosphanium;bromide
    SMILES
    C1=CC=C(C=C1)COCCC[P+](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4.[Br-]
    InChIKey
    DWYCJWXMZGVGJV-UHFFFAOYSA-M
    InChI
    1S/C28H28OP.BrH/c1-5-14-25(15-6-1)24-29-22-13-23-30(26-16-7-2-8-17-26,27-18-9-3-10-19-27)28-20-11-4-12-21-28;/h1-12,14-21H,13,22-24H2;1H/q+1;/p-1
    Synonyms
    MFCD00191781 | triphenyl(3-phenylmethoxypropyl)phosphanium;bromide | [3-(Benzyloxy)propyl]triphenylphosphoniumBromide...
  8. Triphenyl(2-pyridylmethyl)phosphonium chloride hydrochloride
    CAS: 99662-46-1 PubChem CID: 16213046 Formula: C24H21ClNP · HCl Molecular Weight: 426.32
    In Stock Item #: T332291
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    Technical Identifiers
    IUPAC Name
    triphenyl(pyridin-2-ylmethyl)phosphanium;chloride;hydrochloride
    SMILES
    C1=CC=C(C=C1)[P+](CC2=CC=CC=N2)(C3=CC=CC=C3)C4=CC=CC=C4.Cl.[Cl-]
    InChIKey
    JHQWTRCLYUFMSJ-UHFFFAOYSA-M
    InChI
    1S/C24H21NP.2ClH/c1-4-13-22(14-5-1)26(23-15-6-2-7-16-23,24-17-8-3-9-18-24)20-21-12-10-11-19-25-21;;/h1-19H,20H2;2*1H/q+1;;/p-1
    Synonyms
    Triphenyl(2-pyridylmethyl)phosphonium ch loride hydrochloride,98% | Triphenyl[(pyridin-2-yl)methyl]phosphanium chlori...
  9. 1-[(Trimethylsilyl)methyl]benzotriazole
    CAS: 122296-00-8 PubChem CID: 3317323 Formula: C10H15N3Si Molecular Weight: 205.33
    In Stock Item #: T336963
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    Technical Identifiers
    IUPAC Name
    benzotriazol-1-ylmethyl(trimethyl)silane
    SMILES
    C[Si](C)(C)CN1C2=CC=CC=C2N=N1
    InChIKey
    VRGRHLJMRVGQCS-UHFFFAOYSA-N
    InChI
    1S/C10H15N3Si/c1-14(2,3)8-13-10-7-5-4-6-9(10)11-12-13/h4-7H,8H2,1-3H3
    Synonyms
    AKOS015889150 | DTXSID90391398 | SCHEMBL1054916 | 1-((trimethylsilyl)methyl)benzotriazole | 1-((Trimethylsilyl)methyl...
  10. Butyltriphenylphosphonium bromide
    CAS: 1779-51-7 EC Number: 217-219-4 Formula: C22H24BrP Molecular Weight: 399.3
    In Stock Item #: B107826
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    Technical Identifiers
    IUPAC Name
    butyl(triphenyl)phosphanium;bromide
    SMILES
    CCCC[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3.[Br-]
    InChIKey
    IKWKJIWDLVYZIY-UHFFFAOYSA-M
    InChI
    1S/C22H24P.BrH/c1-2-3-19-23(20-13-7-4-8-14-20,21-15-9-5-10-16-21)22-17-11-6-12-18-22;/h4-18H,2-3,19H2,1H3;1H/q+1;/p-1
    Synonyms
    TBP | Q-200774 | (1-BUTYL)TRIPHENYLPHOSPHONIUM BROMIDE;BUTYL TRIPHENYL PHOSPHINE BROMIDE;BUTYL TRIPHENYL PHOSPHOROUS ...
  11. Butyltriphenylphosphonium chloride
    CAS: 13371-17-0 EC Number: 236-443-3 Formula: C22H24ClP Molecular Weight: 354.85
    Solid ≥98%
    In Stock Item #: B102913
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    Technical Identifiers
    IUPAC Name
    butyl(triphenyl)phosphanium;chloride
    SMILES
    CCCC[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3.[Cl-]
    InChIKey
    MFIUDWFSVDFDDY-UHFFFAOYSA-M
    InChI
    1S/C22H24P.ClH/c1-2-3-19-23(20-13-7-4-8-14-20,21-15-9-5-10-16-21)22-17-11-6-12-18-22;/h4-18H,2-3,19H2,1H3;1H/q+1;/p-1
    Synonyms
    butyl(triphenyl)phosphanium chloride | D89162 | Phosphonium, butyltriphenyl-, chloride | triphenylbutylphosphonium ch...
  12. Diethyl (2-Methylbenzyl)phosphonate
    CAS: 62778-16-9 Formula: C12H19O3P Molecular Weight: 242.25
    In Stock Item #: D155196
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    Technical Identifiers
    IUPAC Name
    1-(diethoxyphosphorylmethyl)-2-methylbenzene
    SMILES
    CCOP(=O)(CC1=CC=CC=C1C)OCC
    InChIKey
    SAVIMLRIKAZZCZ-UHFFFAOYSA-N
    InChI
    1S/C12H19O3P/c1-4-14-16(13,15-5-2)10-12-9-7-6-8-11(12)3/h6-9H,4-5,10H2,1-3H3
    Synonyms
    Phosphonic acid, P-((2-methylphenyl)methyl)-, diethyl ester | SCHEMBL916350 | Phosphonic acid,p-[(2-methylphenyl)meth...
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R&D Use Only Products supplied for research and development use

Frequently Asked Questions

How do I choose between C-C Bond Forming Reagents variants?
Match reagent to substrate compatibility, required selectivity, scalability, and downstream purification needs. Different c-c bond forming reagents have distinct reactivity profiles — review reaction conditions and reported yields for each variant.
What specifications matter for C-C Bond Forming Reagents?
Purity, titer (for solution reagents), water content for moisture-sensitive reagents, stabilizer presence, and pack size. Always check certificate of analysis for batch-specific quality data.
How should C-C Bond Forming Reagents be stored and handled?
Many synthesis reagents are moisture- or air-sensitive. Store in sealed containers under inert atmosphere when specified. Solution reagents may degrade after multiple openings — aliquot for long-term storage.
Are research and process scales both available?
Yes. C-C Bond Forming Reagents are available in gram-scale research quantities through kilogram-scale process supplies. Bulk packaging and custom synthesis options are available on request.

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