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Appendix 1 Properties of Common Solvents

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Appendix 1 Properties of Common Solvents Appendix 1 Properties of common solvents B.p. M.p. I)I H 1)13C Preliminary Rigorous TLV Solvent E Density CC) CC) (300MHz, CDCI3) (300MHz, CDCI3) drylng drying (ppm) Acetic acid 118 17 6.19 1.049 2.08 s, 10-13 br s var 20.7, 177.6 Acetic anhydride Acetic anhydride 10 Acetone 56 -94 20.7 0.790 2.13 s 30.7, 206.5 3Asieve 3A sieve 1000 Acetonitrile 82 -46 36.2 0.777 1.97 s 1.7, 116.2 Potassium carbonate Phosphorus pentoxide 40 Benzene 80 5.5 2.28 0.879 7.37 s 128.3 Not necessary Calcium hydride 10 t-Butanol 82 25 3.49 0.850 1.24 s, 1.35 br s var 31.2, 69.2 Calcium hydride Calcium hydride Carbon tetrachloride 76 -23 2.23 1.460 - 96.2 Alumina Phosphorus pentoxide 10 Chlorobenzene 132 -46 5.62 1.106 7.28 brm 126, 129, 130, 134 Not necessary Calci um hydride 75 Chloroform 62 -63 4.70 1.480 7.24 s 77.0 Alumina Phosphorus pentoxide 10 Dichloroethane 83 -35 10.4 1.235 3.71 s 44.4 Not necessary Calcium hydride 10 Dichloromethane 40 -97 8.9 1.325 5.28 s 53.4 Not necessary Calcium hydride 100 Diethyl ether 35 -116 4.34 0.714 1.18 t, 3.45 q 15.2, 65.8 Calcium chloride; Na SodiunVbenzophenone 400 ~ Dimethoxyethane 83 -58 0.850 3.36 s, 3.51 s 59.0, 71.8 Calcium chloride; Na SodiunVbenzophenone g Calcium hydride Dimethylformarnide 152 -61 36.7 0.945 2.81 s, 2.89 s, 7.94 s 31.4, 36.4, 162.4 Phosphous pentoxide 10 ~ Dimethyl sulphoxide 189 18 49.0 1.101 2.62 s 40.6 Distillation 4A sieve Dioxan 102 12 2.21 1.034 3.66 s 67.0 Calcium chloride: Na SodiunVbenzophenone 50 Ethanol 78 -114 24.3 0.785 1.18 t, 2.05 br s, 3.65q 18.3, 58.2 Magnesium 3A sieve 1000 Ethyl acetate 77 -84 6.02 0.900 1.22 t, 2.01 s, 4.09 q 14.1,20.9,60.3,171.0 Potassium carbonate 4A sieve 400 HMPA 235 7 1.030 2.59 d 36.8 Calcium hydride Calcium hydride Methanol 64 -97 32.6 0.791 1.94 br s var, 3.42 s 50.5 Magnesium 3A sieve 200 Nitromethane 101 -28 38.6 1.137 4.33 s 62.4 Calcium chloride 4A sieve 100 Pyridine 116 -42 12.3 0.982 7.24 m, 7.63 m, 8.58 m 123.6, 135.8, 149.8 Calcium hydride Calcium hydride 5 Tetrahydrofuran 66 -65 18.5 0.805 1.82 m, 3.72 m 25.6, 67.9 Calcium chloride; Na SodiunVbenzophenone 200 Toluene 111 -95 2.38 0.867 2.32 s, 7.17 br s 21,125,128,129,138 Not necessary Calcium hydride ~OO Water 100 0 78.5 1.000 ~ w Appendix 2 Properties of common gases t Denslty Density Hazardous Gas Mol. B.p.- M.p.b TLV' Notes weigbt o( gas· of IIquldd propertles· a. at 1atm Acetylene 26.04 -84 1.109 As, Fl, Note g °c Ammonia 17.03 -33 -78 0.71 0.68 To, Co, Fl 25 b. oe Argon 39.944 -189 -186 1.66 1,4 As c. g/l at 2QoC at 1atm 12.5 -107 4.85 To,Co Boron trichloride 117.19 d. g/ml at b.p. Baron trifluoride 67.81 -100 -127 3 1.59 To,Co 1 e. As = Asphyxiant Carbon dioxide 44.01 -78 1.83 Co 5000 Co = Conosive Carbon monoxide 28.01 -191 -207 1.16 0.79 To, Fl 50 Fl = Flammable -34 -101 2.97 1.56 To,Co 1 Chlorine 70.914 Ox = Oxidising Ethylene 28.05 -104 -170 1.17 0.57 Fl Ethylene oxide 44.05 10.7 -112 1.82 0.88 To, Fl 5 To= Toxic f. ppm ~ 1.57 1.5 Fl,Co 1 Fluorine 37.997 -188 -220 g. Potenliallyexplosive ~ -269 -272 0.17 0.12 As Helium 4.0026 when pressurised ~ Hydrogen 2.016 -253 0.08 0.07 Fl ~ Hydrogen bromide 80.917 -67 -87 3.34 2.16 To,Co 3 Hydrogen chloride 36.461 -85 -114 1.52 1.19 To,Co 5 Hydrogen fluoride 20.006 19.5 -83 0.94 To,Co 3 Hydrogen ~ulphide 34.08 -60 -85 1.43 1.0 To, Co, Fl 10 Isobutylene 56.11 -6.9 -140 2.39 0.63 Fl Methanethiol 48.107 6 -121 2.14 0.89 To, Fl 0.5 Nitric oxide (NO) 30.006 -152 -164 1.24 1.27 To 25 Nitrogen 28.0134 -196 1.25 0.8 As Nitrogen dioxide (NOV 46.0055 21 -9.3 3.3 1,45 To,Co 3 Oxygen 32.0 -183 -218 1.33 1.14 Ox Phosgene 98.92 8.2 -128 4.1 1.41 To,Co 0.1 Sulphur dioxide 64.063 -10 -75 2.70 1.46 To,Co 2 Appendix 3 Approximate * pKa values for some common deprotonations cf. some common bases Rea2ent to be deprotonated pKa Bases pKa (of BH) ArSH 7 RCH2N02 9 RCOCH2CN 9 RCOCH 2COR 9 RSH 10 Et3N 11 RCOCH2C02R 11 Et2NH 11 RC02CH2C02R 13 ~ Cyclopentadiene 15 Na+-OH 16 9 H Na+ -OEt ~ RC 2CHO 17 18 ~ RC=CH 25 K+ -OtBu 19 CH3COCH3 20 CH3C02Et 25 Na+-H 35 CH3CN 25 Na+-NH2 35 PhH 41 U+ -NiPr2 36 H2C=CHCH3 43 H2C=CH2 44 U+ -nBu 50 U+ -tBu ------- - - - -- >50 *These figures are very approximate. A pKa difference of >4 between base and reagent will cause complete deprotonation. ~ U1 Appendix 4 Lewis acids ~ Lewis acid Compatlble solvents Comments 0\ Aluminium trichloride Hydrocarbons, halogenated Slrong, widely used in Friedel-Crafts Boron tribromide Hydrocarbons, halogenated Slrong, used to cleave ethers, acetals Boron trichloride Hydrocarbons, halogenated Slrong, used to cleave ethers, acetals Boron trifluoride etherate Many solvents Moderate, very versatile DiethyWuminium chloride Hydrocarbons, halogenated Moderate, useful for proton-sensitive reactions EthyWuminium dichloride Hydrocarbons, halogenated Moderate, useful for proton-sensitive reactions Feme chloride Hydrocarbons, halogenated Moderate Mercuric chloride Many solvents Weak, useful for cleaving C-S bonds Lanthanide Many solvents Weak, useful for reactions involving sensitive shift reagents dienes, ethers i::l Magnesium bromide Hydrocarbons, halogenated Moderate [ Magnesium chloride.etherate Hydrocarbons, halogenated, ethers Moderate Sil ver chloride Many solvents Moderate, used to generate carbonium ions Sil ver triflate Many solvents Moderate, used to generate carbonium ions Stannie chloride Hydrocarbons, haIogenated Slrong, very versatile Titanium tetrachloride Hydrocarbons, halogenated Slrong, very versatile Trimethylsilyl iodide Hydrocarbons, halogenated, MeCN Strong, used to cleave ethers, acetals, esters Trimethylsilyl triflate Hydrocarbons, halogenated Strong, used with silylated reagents Zinc bromide Hydrocarbons, halogenated Moderate, versatile Zinc chloride Hydrocarbons, halogenated, ethers Moderate, versatile ~- ----- Appendix 5 Common reducing reagents 1. Hydride reducing agents Reagent Typical solvents Temperature Functional groups (OC) reduced LiB14 Tetrahydrofuran o to RT ester ~ alcohol Qithium borohydride) ketone ~ alcohol aldehyde ~ alcohol Li[Et3BH] (Superhydride) Tetrahydrofuran -78 to RT ester ~ alcohol Qithium triethylborohydride) ketone ~ alcohol aldehyde ~ alcohol alkyl halide ~ alkane ~ epoxide ~ alcohol g Li[SBu3BH] (L-Selectride) Tetrahydrofuran -78 to RT ketone ~ alcohol [ Qithium tri-sec-butylborohydride) aldehyde ~ alcohol alkyl halide ~ alkane NaB14 Alcohols, ethers o toRT ketone ~ alcohol (sodium borohydride) aldehyde ~ alcohol Na[BH3CN] Alcohols, water, o toRT ketone ~ alcohol (sodium cyanoborohydride) DMSO aldehyde ~ alcohol alkyl halide ~ alkane imine ~ amine Na[BH(OAc)3] Aceticacid o toRT ketone ~ alcohol ~ I (sodium triacetoxyborohydride) aldehyde ~ alcohol -.l ~ Appendix 5 cont'd 00 Reagent Typical solvents Temperature Functional groups (OC) reduced Zn(Bl4h Ethers OtoRT ketone -+ alcohol (zinc borohydride) aldehyde -+ alcohol nBu.tNBI4 Dichloromethane, OtoRT ketone -+ alcohol (tetra-n-butylammonium borohydride) ethers aldehyde -+ alcohol LiAIH4 Ethers -78 to RT ester -+ alcohol (lithium aluminium hydride) ketone -+ alcohol aldehyde -+ alcohol alkyl halide -+ alkane acetylene -+ trans alkene f epoxide -+ alcohol imine -+ amine r- amide -+ amine Li[(tBu0}JAlHJ Tetrnhydrofuran -78 acid chloride -+ aldehyde (lithium tri-tert-butoxyaluminium RT ketone -+ alcohol hydride) aldehyde -+ alcohol Na[AIH2(OCH2CH2OCH3hJ (RED-AL) Ethers, toluene -78 to RT ester -+ alcohol (sodium bis-[2-methoxyethoxyJ- ketone -+ alcohol aluminium hydride) aldehyde -+ alcohol alkyl halide -+ alkane epoxide -+ alcohol a.ß-unsaturated enone -+ allylic alcohol Appendix 5 cont'd B2% Dichloromethane, -78 to RT carboxylic acid ~ alcohol (diborane) tetrahydrofuran amide ~ amine RT ketone ~ alcohol aldehyde ~ alcohol BH3S(CH3h Tetrahydrofuran, -78 to RT carboxylic acid ~ alcohol RT amide ~ amine (borane-dimethylsulphide complex) dimethyl sulphide I ketone ~ alcohol aldehyde ~ alcohol (SiahBH Tetrahydrofuran -78 to RT ketone ~ alcohol ~ (disiamylborane) aldehyde ~ alcohol g lactone ~ lactol ft f)l AlH3 Ethers -78 to RT ester ~ alcohol (alane) ketone ~ alcohol I aldehyde ~ alcohol alkyl halide ~ alkane epoxide ~ alcohol lactone ~ cyclic ether iBu2AlH (DIBAL) Dichloromethane, -78 ester ~ aldehyde (Di-isobutylaluminium hydride) ethers, toluene lactone ~ lactol amide ~ aldehyde nitrile ~ aldehyde -78 to RT ketone ~ alcohol aldehyde ~ alcohol a,ß-unsaturated ketone ~ allylic alcohol \0~ acetylene ~ cis-alkene t-> U\ Appendix 5 cont'd o 2. Single electron transfer reducing agents Reagent Typical Solvents Temperature Functional Groups (OC) Reduced Li/NH3 Liquid ammonia -78 a,ß-unsaturated ketone ~ ketone (lithium in ammonia) -78 to -33 ketone ~ alcohol aldehyde ~ alcohol aryl ring ~ dihydroaryl ring LiClOH8 Tetrahydrofuran -78 to RT sulphide ~ alkane (lithium naphthalenide) sulphone ~ alkane ~ NaHg Methanol O-RT ketone ~ alcohol '§ (sodium amalgam) aldehyde ~ alcohol sulphone ~ alkane - - r- 3. Common hydrogenation catalysts Catalyst Solvent Temperature H2 Pressure Functional Groups ("C) (bar) Reduced Ni Alcohols, toluene 5 to 100 3-10 alkene ~ alkane ketone ~ alcohol aldehyde ~ alcohol Pd/C Alcohols 5 to 50 1-5 aromatic nitto ~ aromatic amine Alcohols, acetic acid 5 to 100 1-10 nitrile ~ amine Toluene 5 to 100 1-10 acetylene ~ alkane alkyl halide ~ alkane '-------- ,~- -~ ~- , .~ ~ ------ Appendix 5 cont'd Alcohols, toluene 510100 3-10 alkene ~ alkane Toluene 5010150 3-50 imines ~ amine alkyl nitro ~ amine Aceticacid epoxide ~ alcohol Pd/BaS°4 Alcohols, toluene 51050 1-3 acetylene ~ cis alkene PtfC Alcohols 5 to 50 1-5 aromatic nitro ~ aromatic amine Alcohols, toluene 510100 3-10 olefin ~ alkane ketone
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