常用试剂缩写中英对照Common reagents and abbreviations
84 种试剂 · 7 类
有机合成文献和实验记录中，试剂通常以缩写或俗名表示。下表按作用分为碱、还原剂、氧化剂、保护基及其引入与脱除试剂、缩合试剂、催化剂和其他试剂七类，列出缩写、英文全称、中文名称、作用和典型用途。反应条件为文献中的常见条件，具体用量与温度以原始文献为准。
In the synthetic literature and in laboratory records, reagents are usually written as abbreviations or trivial names. The table groups them by role — bases, reducing agents, oxidising agents, protecting groups with the reagents that install and remove them, coupling reagents, catalysts and other reagents — and gives the abbreviation, full English name, Chinese name, function and typical use. Conditions are those commonly reported; quantities and temperatures should be taken from the original procedure.
碱 Bases
| 缩写 Abbr. | 名称 Name | 作用 Function | 典型用途 Typical use |
|---|---|---|---|
| LDA | 二异丙基氨基锂lithium diisopropylamide | 强碱，位阻大，亲核性弱strong, hindered, weakly nucleophilic base | THF 中 −78 °C 生成酮的动力学烯醇负离子kinetic enolates of ketones in THF at −78 °C |
| LiHMDS | 双(三甲基硅基)氨基锂lithium bis(trimethylsilyl)amide | 强碱，位阻大，碱性弱于 LDAstrong hindered base, weaker than LDA | 生成烯醇负离子，酯、酮的去质子化enolate formation; deprotonation of esters and ketones |
| n-BuLi | 正丁基锂n-butyllithium | 极强碱，亦为碳亲核试剂very strong base and carbon nucleophile | 端炔、芳环的锂化；锂–卤交换lithiation of terminal alkynes and arenes; lithium–halogen exchange |
| NaH | 氢化钠sodium hydride | 强碱，不具亲核性，放出 H₂strong non-nucleophilic base; releases H₂ | 醇去质子化后进行 Williamson 醚合成deprotonating alcohols for Williamson ether synthesis |
| t-BuOK | 叔丁醇钾potassium tert-butoxide | 强碱，位阻大strong, bulky base | E2 消除，主要生成取代较少的烯烃（Hofmann 产物）E2 elimination giving mainly the less substituted alkene (Hofmann product) |
| Et₃N (TEA) | 三乙胺triethylamine | 有机弱碱，中和反应生成的酸weak organic base; scavenges the acid formed | 酰氯酰化、磺酰化；Swern 氧化的最后一步acylation with acyl chlorides, sulfonylation; final step of the Swern oxidation |
| DIPEA | N,N-二异丙基乙胺N,N-diisopropylethylamine (Hünig's base) | 位阻大的叔胺碱，几乎无亲核性hindered tertiary amine base with very low nucleophilicity | 肽偶联、烷基化反应中的缚酸剂acid scavenger in peptide coupling and alkylation |
| DBU | 1,8-二氮杂二环[5.4.0]十一碳-7-烯1,8-diazabicyclo[5.4.0]undec-7-ene | 脒类有机强碱，亲核性弱strong amidine base, weakly nucleophilic | 卤代烃的 E2 消除，温和条件下的去质子化E2 elimination of alkyl halides; deprotonation under mild conditions |
| py | 吡啶pyridine | 弱碱，可兼作溶剂weak base that can also serve as solvent | 醇的酰化、磺酰化（TsCl / py）acylation and sulfonylation of alcohols (TsCl / py) |
| K₂CO₃ | 碳酸钾potassium carbonate | 温和无机碱mild inorganic base | 酚、羧酸的 O-烷基化；乙酸酯在甲醇中的脱除O-alkylation of phenols and acids; removal of acetates in methanol |
还原剂 Reducing agents
| 缩写 Abbr. | 名称 Name | 作用 Function | 典型用途 Typical use |
|---|---|---|---|
| LiAlH₄ (LAH) | 氢化铝锂lithium aluminium hydride | 强负氢还原剂，遇水剧烈反应powerful hydride donor; reacts violently with water | 无水乙醚或 THF 中将酯、羧酸还原为醇，酰胺、腈还原为胺reduces esters and acids to alcohols, amides and nitriles to amines, in dry ether or THF |
| NaBH₄ | 硼氢化钠sodium borohydride | 温和负氢还原剂，可在醇或水中使用mild hydride donor, usable in alcohols or water | 醛、酮还原为醇；一般不还原酯、羧酸aldehydes and ketones to alcohols; esters and acids are normally untouched |
| DIBAL-H | 二异丁基氢化铝diisobutylaluminium hydride | 亲电性负氢还原剂electrophilic hydride reducing agent | −78 °C 将酯还原为醛，腈还原为醛（水解后）esters to aldehydes at −78 °C; nitriles to aldehydes after hydrolysis |
| NaBH₃CN | 氰基硼氢化钠sodium cyanoborohydride | 弱还原剂，弱酸性下选择性还原亚胺离子weak reductant; selectively reduces iminium ions under mildly acidic conditions | 还原胺化reductive amination |
| NaBH(OAc)₃ (STAB) | 三乙酰氧基硼氢化钠sodium triacetoxyborohydride | 温和、选择性的负氢还原剂mild, selective hydride donor | 醛、酮与胺的还原胺化reductive amination of aldehydes and ketones |
| BH₃·THF | 硼烷–四氢呋喃配合物borane–tetrahydrofuran complex | 亲电性硼氢化试剂electrophilic hydroborating agent | 烯烃硼氢化–氧化得反马氏醇；还原羧酸为醇hydroboration–oxidation of alkenes to anti-Markovnikov alcohols; reduction of acids to alcohols |
| Na / NH₃(l) | 钠–液氨sodium in liquid ammonia | 溶解金属还原，单电子转移dissolving-metal reduction by single-electron transfer | Birch 还原芳环；炔烃还原为反式烯烃Birch reduction of arenes; alkynes to trans-alkenes |
| Zn(Hg) / HCl | 锌汞齐–盐酸zinc amalgam and hydrochloric acid | 酸性条件下的金属还原metal reduction under acidic conditions | Clemmensen 还原：芳基酮的 C=O 还原为 CH₂Clemmensen reduction of aryl ketone C=O to CH₂ |
| Sn / HCl | 锡–浓盐酸tin and concentrated hydrochloric acid | 酸性条件下的金属还原metal reduction under acidic conditions | 硝基苯还原为苯胺reduction of nitrobenzene to phenylamine |
氧化剂 Oxidising agents
| 缩写 Abbr. | 名称 Name | 作用 Function | 典型用途 Typical use |
|---|---|---|---|
| PCC | 氯铬酸吡啶鎓盐pyridinium chlorochromate | Cr(VI) 氧化剂，无水条件下使用Cr(VI) oxidant used under anhydrous conditions | CH₂Cl₂ 中伯醇氧化为醛，仲醇氧化为酮primary alcohols to aldehydes and secondary to ketones in CH₂Cl₂ |
| PDC | 重铬酸吡啶鎓盐pyridinium dichromate | Cr(VI) 氧化剂，酸性弱于 PCCCr(VI) oxidant, less acidic than PCC | CH₂Cl₂ 中醇氧化为醛、酮；DMF 中伯醇可氧化为羧酸alcohols to aldehydes and ketones in CH₂Cl₂; primary alcohols to acids in DMF |
| Jones reagent | 琼斯试剂（CrO₃ / H₂SO₄ / 丙酮）chromium(VI) oxide in aqueous sulfuric acid and acetone | 强酸性 Cr(VI) 氧化剂strongly acidic Cr(VI) oxidant | 伯醇氧化为羧酸，仲醇氧化为酮primary alcohols to carboxylic acids, secondary to ketones |
| K₂Cr₂O₇ / H⁺ | 酸性重铬酸钾acidified potassium dichromate(VI) | Cr(VI) 氧化剂，反应后由橙色变为绿色Cr(VI) oxidant; turns from orange to green | 伯醇边蒸馏得醛、回流得羧酸，仲醇得酮；叔醇不反应primary alcohols to aldehydes (distil) or acids (reflux), secondary to ketones; tertiary alcohols do not react |
| DMP | 戴斯–马丁高碘烷Dess–Martin periodinane | 高价碘氧化剂，条件温和、中性hypervalent iodine oxidant; mild, neutral conditions | 室温下醇氧化为醛、酮，不过度氧化alcohols to aldehydes and ketones at room temperature without over-oxidation |
| Swern | 斯文氧化（(COCl)₂ / DMSO / Et₃N）oxalyl chloride, DMSO, then Et₃N | 活化 DMSO 的氧化，不含金属metal-free oxidation by activated DMSO | −78 °C 下醇氧化为醛、酮；副产物为 Me₂Salcohols to aldehydes and ketones at −78 °C; Me₂S is a by-product |
| TEMPO | 2,2,6,6-四甲基哌啶-1-氧自由基(2,2,6,6-tetramethylpiperidin-1-yl)oxyl | 稳定氮氧自由基，催化量使用stable nitroxyl radical used catalytically | 与 NaOCl 合用，伯醇选择性氧化为醛with NaOCl, selective oxidation of primary alcohols to aldehydes |
| mCPBA | 间氯过氧苯甲酸meta-chloroperoxybenzoic acid | 过氧酸，亲电性氧转移试剂peroxyacid; electrophilic oxygen-transfer reagent | 烯烃环氧化；Baeyer–Villiger 氧化酮为酯epoxidation of alkenes; Baeyer–Villiger oxidation of ketones to esters |
| OsO₄ | 四氧化锇osmium(VIII) oxide (osmium tetroxide) | 顺式双羟基化试剂，剧毒，催化量使用syn-dihydroxylating agent; highly toxic, used catalytically | 与 NMO 合用，烯烃转化为顺式 1,2-二醇with NMO, alkenes to syn-1,2-diols |
| NMO | N-甲基吗啉-N-氧化物N-methylmorpholine N-oxide | 共氧化剂，使催化剂再生co-oxidant that regenerates the catalyst | OsO₄ 双羟基化、TPAP 氧化OsO₄ dihydroxylation; TPAP oxidation |
| KMnO₄ | 高锰酸钾potassium manganate(VII) (potassium permanganate) | 强氧化剂，紫色褪去strong oxidant; purple colour discharged | 冷稀碱性得 1,2-二醇；热酸性断裂 C=C；烷基苯氧化为苯甲酸cold dilute alkaline gives 1,2-diols; hot acidic cleaves C=C; alkylbenzenes to benzoic acid |
| O₃ | 臭氧ozone | 臭氧解断裂 C=Ccleaves C=C by ozonolysis | Me₂S 或 Zn 还原后处理得醛、酮；H₂O₂ 氧化后处理得羧酸reductive work-up (Me₂S or Zn) gives aldehydes and ketones; oxidative work-up (H₂O₂) gives acids |
| NaIO₄ | 高碘酸钠sodium periodate | 断裂邻二醇cleaves 1,2-diols | 1,2-二醇氧化断裂为两分子羰基化合物oxidative cleavage of 1,2-diols to two carbonyl compounds |
| DDQ | 2,3-二氯-5,6-二氰基-1,4-苯醌2,3-dichloro-5,6-dicyano-1,4-benzoquinone | 高电势醌类氧化剂high-potential quinone oxidant | 脱氢芳构化；氧化脱除 PMB 保护基dehydrogenation to aromatics; oxidative removal of PMB groups |
保护基及引入、脱除试剂 Protecting groups and their reagents
| 缩写 Abbr. | 名称 Name | 作用 Function | 典型用途 Typical use |
|---|---|---|---|
| Boc | 叔丁氧羰基tert-butoxycarbonyl | 胺的保护基，对碱和氢化稳定amine protecting group, stable to base and hydrogenation | Boc₂O 引入；TFA 或 HCl 脱除installed with Boc₂O; removed with TFA or HCl |
| Boc₂O | 二碳酸二叔丁酯di-tert-butyl dicarbonate | 引入 Boc 基的试剂reagent that installs the Boc group | 胺与 Boc₂O 在碱存在下生成 Boc 氨基甲酸酯amine + Boc₂O with a base gives the Boc carbamate |
| Cbz (Z) | 苄氧羰基benzyloxycarbonyl | 胺的保护基，对酸较稳定amine protecting group, fairly stable to acid | CbzCl 引入；H₂、Pd/C 氢解脱除installed with CbzCl; removed by hydrogenolysis over Pd/C |
| Fmoc | 9-芴甲氧羰基9-fluorenylmethoxycarbonyl | 胺的保护基，对酸稳定、碱不稳定amine protecting group, acid-stable and base-labile | 固相肽合成；哌啶的 DMF 溶液脱除solid-phase peptide synthesis; removed with piperidine in DMF |
| TFA | 三氟乙酸trifluoroacetic acid | 强有机酸strong organic acid | CH₂Cl₂ 中脱除 Boc、叔丁酯removal of Boc groups and tert-butyl esters in CH₂Cl₂ |
| TMS | 三甲基硅基trimethylsilyl | 醇的硅醚保护基，极易水解silyl ether protecting group for alcohols; very easily hydrolysed | TMSCl / Et₃N 引入；稀酸或 F⁻ 脱除；也用于端炔保护installed with TMSCl / Et₃N; removed with dilute acid or F⁻; also protects terminal alkynes |
| TBS (TBDMS) | 叔丁基二甲基硅基tert-butyldimethylsilyl | 醇的硅醚保护基，稳定性高于 TMSsilyl ether protecting group for alcohols, more robust than TMS | TBSCl / 咪唑 / DMF 引入；TBAF 或酸脱除installed with TBSCl / imidazole / DMF; removed with TBAF or acid |
| TBDPS | 叔丁基二苯基硅基tert-butyldiphenylsilyl | 醇的硅醚保护基，耐酸性强于 TBSsilyl ether protecting group, more acid-stable than TBS | TBDPSCl / 咪唑引入；TBAF 脱除installed with TBDPSCl / imidazole; removed with TBAF |
| TBAF | 四正丁基氟化铵tetra-n-butylammonium fluoride | 可溶于有机溶剂的氟离子源fluoride source soluble in organic solvents | THF 中脱除硅醚（Si–F 键很强）cleavage of silyl ethers in THF (the Si–F bond is very strong) |
| Bn | 苄基benzyl | 醇、胺的保护基，对酸碱稳定protecting group for alcohols and amines, stable to acid and base | BnBr / NaH 引入；H₂、Pd/C 氢解脱除installed with BnBr / NaH; removed by hydrogenolysis over Pd/C |
| PMB | 对甲氧基苄基para-methoxybenzyl | 醇的保护基，可氧化脱除alcohol protecting group removable by oxidation | PMBCl / NaH 引入；DDQ 脱除installed with PMBCl / NaH; removed with DDQ |
| THP | 四氢吡喃-2-基tetrahydropyran-2-yl | 醇的缩醛型保护基，对碱稳定acetal-type alcohol protecting group, stable to base | 二氢吡喃（DHP）/ 酸催化引入；稀酸脱除installed with dihydropyran (DHP) and acid catalyst; removed with dilute acid |
| Ac | 乙酰基acetyl | 醇、胺的酯型或酰胺型保护基ester or amide protecting group for alcohols and amines | Ac₂O / 吡啶引入；K₂CO₃ / MeOH 或碱水解脱除installed with Ac₂O / pyridine; removed with K₂CO₃ / MeOH or base hydrolysis |
| acetal (dioxolane) | 缩酮（1,3-二氧戊环）1,3-dioxolane from ethane-1,2-diol | 醛、酮的保护形式，对碱和负氢试剂稳定protected form of aldehydes and ketones, stable to base and hydride reagents | 乙二醇 / TsOH 引入（除水）；稀酸水解脱除formed with ethane-1,2-diol / TsOH (removing water); removed by aqueous acid |
缩合试剂 Coupling reagents
| 缩写 Abbr. | 名称 Name | 作用 Function | 典型用途 Typical use |
|---|---|---|---|
| DCC | N,N′-二环己基碳二亚胺N,N′-dicyclohexylcarbodiimide | 碳二亚胺类脱水缩合剂，活化羧酸carbodiimide dehydrating agent that activates carboxylic acids | 酰胺、酯的生成；副产物 DCU 不溶，过滤除去amide and ester formation; the insoluble urea DCU is filtered off |
| EDC (EDCI) | 1-乙基-3-(3-二甲氨基丙基)碳二亚胺1-ethyl-3-(3-dimethylaminopropyl)carbodiimide | 水溶性碳二亚胺缩合剂，常以盐酸盐使用water-soluble carbodiimide, usually as the hydrochloride | 酰胺偶联；脲副产物可水洗除去amide coupling; the urea by-product is removed by aqueous wash |
| DIC | N,N′-二异丙基碳二亚胺N,N′-diisopropylcarbodiimide | 液态碳二亚胺缩合剂liquid carbodiimide coupling agent | 固相肽合成，脲副产物可溶solid-phase peptide synthesis; the urea by-product is soluble |
| HOBt | 1-羟基苯并三唑1-hydroxybenzotriazole | 缩合添加剂，生成活性酯coupling additive that forms an active ester | 与碳二亚胺合用，抑制消旋化used with carbodiimides to suppress racemisation |
| HATU | 2-(7-氮杂苯并三唑-1-基)-N,N,N′,N′-四甲基脲六氟磷酸盐1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate | 脲盐型缩合剂，活性高highly reactive uronium-type coupling reagent | 与 DIPEA 合用，用于位阻大的酰胺偶联with DIPEA, for hindered amide couplings |
| CDI | N,N′-羰基二咪唑1,1′-carbonyldiimidazole | 羰基转移试剂，活化羧酸为酰基咪唑carbonyl-transfer reagent; activates acids as acylimidazoles | 酰胺、酯、脲、氨基甲酸酯的生成formation of amides, esters, ureas and carbamates |
| DEAD / DIAD | 偶氮二甲酸二乙酯 / 二异丙酯diethyl / diisopropyl azodicarboxylate | 与 PPh₃ 组成 Mitsunobu 试剂with PPh₃, forms the Mitsunobu reagent | Mitsunobu 反应：醇与酸性亲核体缩合，碳构型翻转Mitsunobu reaction: condensation of an alcohol with an acidic nucleophile, with inversion at carbon |
催化剂 Catalysts
| 缩写 Abbr. | 名称 Name | 作用 Function | 典型用途 Typical use |
|---|---|---|---|
| Pd/C | 钯碳palladium on carbon | 多相加氢催化剂heterogeneous hydrogenation catalyst | H₂ 下还原 C=C、C≡C、硝基；氢解脱除 Bn、Cbzwith H₂, reduces C=C, C≡C and nitro groups; hydrogenolysis of Bn and Cbz |
| Lindlar catalyst | 林德拉催化剂Pd on CaCO₃ poisoned with lead(II) acetate and quinoline | 活性降低的钯催化剂deactivated (poisoned) palladium catalyst | 炔烃部分加氢为顺式烯烃partial hydrogenation of alkynes to cis-alkenes |
| PtO₂ | 二氧化铂（亚当斯催化剂）platinum(IV) oxide (Adams' catalyst) | 多相加氢催化剂前体precursor of a heterogeneous hydrogenation catalyst | 烯烃、芳环的催化加氢catalytic hydrogenation of alkenes and arenes |
| Raney Ni | 雷尼镍Raney nickel | 多孔镍加氢催化剂，吸附氢porous nickel catalyst carrying adsorbed hydrogen | 催化加氢；硫缩醛脱硫为 CH₂catalytic hydrogenation; desulfurisation of thioacetals to CH₂ |
| Pd(PPh₃)₄ | 四(三苯基膦)钯(0)tetrakis(triphenylphosphine)palladium(0) | 零价钯交叉偶联催化剂Pd(0) cross-coupling catalyst | Suzuki、Stille、Sonogashira 偶联Suzuki, Stille and Sonogashira couplings |
| Pd(OAc)₂ | 乙酸钯(II)palladium(II) acetate | 钯催化剂前体，原位还原为 Pd(0)palladium precatalyst reduced to Pd(0) in situ | Heck 反应等交叉偶联Heck reaction and other cross-couplings |
| Wilkinson's catalyst | 威尔金森催化剂（三(三苯基膦)氯化铑）chloridotris(triphenylphosphine)rhodium(I), RhCl(PPh₃)₃ | 均相加氢催化剂homogeneous hydrogenation catalyst | 取代较少的 C=C 选择性加氢selective hydrogenation of less substituted C=C bonds |
| Grubbs catalyst | 格拉布催化剂ruthenium benzylidene phosphine complexes | 钌卡宾烯烃复分解催化剂ruthenium carbene olefin-metathesis catalyst | 关环复分解（RCM）、交叉复分解ring-closing metathesis (RCM) and cross-metathesis |
| DMAP | 4-二甲氨基吡啶4-(dimethylamino)pyridine | 亲核性酰基转移催化剂nucleophilic acyl-transfer catalyst | 位阻醇的酰化；与 DCC 合用进行 Steglich 酯化acylation of hindered alcohols; Steglich esterification with DCC |
| AlCl₃ | 三氯化铝aluminium chloride | Lewis 酸Lewis acid | Friedel–Crafts 烷基化、酰基化Friedel–Crafts alkylation and acylation |
| FeBr₃ | 溴化铁iron(III) bromide | Lewis 酸，极化 Br₂Lewis acid that polarises Br₂ | 芳环亲电溴代electrophilic bromination of arenes |
| TsOH (PTSA) | 对甲苯磺酸para-toluenesulfonic acid | 可溶于有机溶剂的强酸strong acid soluble in organic solvents | 缩醛、缩酮的生成，Fischer 酯化，脱水acetal formation, Fischer esterification, dehydration |
其他试剂 Other reagents
| 缩写 Abbr. | 名称 Name | 作用 Function | 典型用途 Typical use |
|---|---|---|---|
| RMgX | 格氏试剂（烃基卤化镁）Grignard reagent (alkyl- or arylmagnesium halide) | 碳亲核试剂和强碱，须无水carbon nucleophile and strong base; needs anhydrous conditions | 与醛、酮、酯、CO₂ 加成生成新 C–C 键adds to aldehydes, ketones, esters and CO₂ to form new C–C bonds |
| RLi | 有机锂试剂organolithium reagent | 活性高于格氏试剂的碳亲核试剂carbon nucleophile more reactive than Grignard reagents | 与羰基加成；作强碱进行锂化addition to carbonyls; lithiation as a strong base |
| R₂CuLi | 吉尔曼试剂（二烃基铜锂）Gilman reagent (lithium dialkylcuprate) | 软碳亲核试剂soft carbon nucleophile | α,β-不饱和羰基化合物的 1,4-共轭加成；与卤代烃偶联1,4-conjugate addition to α,β-unsaturated carbonyls; coupling with alkyl halides |
| Ph₃P=CHR | 维蒂希试剂（磷叶立德）Wittig reagent (phosphonium ylide) | 将 C=O 转化为 C=Cconverts C=O into C=C | 醛、酮的 Wittig 烯化Wittig olefination of aldehydes and ketones |
| NBS | N-溴代丁二酰亚胺N-bromosuccinimide | 低浓度 Br₂ 或 Br⁺ 的来源source of Br₂ at low concentration, or of Br⁺ | 引发剂存在下烯丙位、苄位溴代；水溶液中生成溴代醇allylic and benzylic bromination with an initiator; bromohydrins in aqueous solvent |
| NCS | N-氯代丁二酰亚胺N-chlorosuccinimide | 亲电氯化试剂electrophilic chlorinating agent | 烯丙位、芳环的氯代allylic and aromatic chlorination |
| AIBN | 偶氮二异丁腈2,2′-azobis(2-methylpropanenitrile) (azobisisobutyronitrile) | 自由基引发剂，受热分解放出 N₂radical initiator; decomposes on heating, releasing N₂ | NBS 溴代、Bu₃SnH 还原、自由基聚合的引发initiates NBS brominations, Bu₃SnH reductions and radical polymerisation |
| Bu₃SnH | 三丁基氢化锡tributyltin hydride | 氢原子供体，自由基链反应试剂hydrogen-atom donor in radical chain reactions | 与 AIBN 合用，卤代烃还原脱卤、自由基环化with AIBN, reductive dehalogenation and radical cyclisation |
| TsCl | 对甲苯磺酰氯para-toluenesulfonyl chloride (tosyl chloride) | 将醇的 OH 转化为好离去基团 OTsconverts an alcohol OH into the good leaving group OTs | 吡啶中生成对甲苯磺酸酯，碳构型保持tosylates formed in pyridine with retention at carbon |
| MsCl | 甲磺酰氯methanesulfonyl chloride (mesyl chloride) | 将 OH 转化为离去基团 OMsconverts OH into the leaving group OMs | Et₃N 存在下生成甲磺酸酯mesylates formed with Et₃N |
| Tf₂O | 三氟甲磺酸酐trifluoromethanesulfonic anhydride | 生成极好的离去基团 OTfforms the excellent leaving group OTf | 醇、酚、烯醇转化为三氟甲磺酸酯converts alcohols, phenols and enols into triflates |
| SOCl₂ | 亚硫酰氯（氯化亚砜）thionyl chloride (sulfur dichloride oxide) | 氯化试剂，副产物 SO₂ 和 HCl 为气体chlorinating agent; by-products SO₂ and HCl are gases | 醇转化为氯代烃，羧酸转化为酰氯alcohols to chloroalkanes, carboxylic acids to acyl chlorides |
| PBr₃ | 三溴化磷phosphorus tribromide | 溴化试剂brominating agent | 伯醇、仲醇转化为溴代烃primary and secondary alcohols to bromoalkanes |
| PCl₅ | 五氯化磷phosphorus pentachloride | 氯化试剂，与 OH 反应放出 HClchlorinating agent; releases HCl with OH groups | 醇转化为氯代烃，羧酸转化为酰氯；检验 –OHalcohols to chloroalkanes, acids to acyl chlorides; test for –OH |
| DAST | 二乙氨基三氟化硫diethylaminosulfur trifluoride | 亲核氟化试剂nucleophilic fluorinating agent | 醇转化为氟代烃，醛、酮转化为偕二氟化物alcohols to fluoroalkanes; aldehydes and ketones to gem-difluorides |
| Lawesson's reagent | 劳森试剂2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide | 硫化试剂thionating agent | 酮、酰胺的 C=O 转化为 C=Sconverts C=O of ketones and amides into C=S |
| TMSCHN₂ | 三甲基硅基重氮甲烷(trimethylsilyl)diazomethane | 重氮甲烷的替代试剂substitute for diazomethane | 甲醇中将羧酸转化为甲酯converts carboxylic acids to methyl esters in methanol |
| NaN₃ | 叠氮化钠sodium azide | 叠氮负离子亲核试剂，剧毒azide nucleophile; highly toxic | SN2 生成有机叠氮，再还原为伯胺；点击化学SN2 to organic azides, then reduction to primary amines; click chemistry |