[ CAS No. 624-51-1 ] {[proInfo.proName]}

Name: 624-51-1|Nonan-3-ol|98%
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Quality Control of [ 624-51-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 624-51-1 ]

CAS No. :	624-51-1	MDL No. :	MFCD00014411
Formula :	C₉H₂₀O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	144.25	Pubchem ID :	-
Synonyms :

Safety of [ 624-51-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P305+P351+P338+P337+P313	UN#:	N/A
Hazard Statements:	H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 624-51-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 624-51-1 ]

[ 624-51-1 ] Synthesis Path-Downstream 1~50

1
[ 111-71-7 ]
[ 557-20-0 ]
[ 624-51-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	In toluene for 12h; Ambient temperature;
86%	With 1-[α(R)-(N,N-dimethylamino)ethyl]-2-(diphenylhydroxymethyl)benzene * Cr(CO)3
76%	With 15-crown-5; sodium iodide In toluene at 0 - 23℃; for 24h; Inert atmosphere; Schlenk technique;

55%	In hexane for 20h; Ambient temperature;
51%	With tetra-n-butylphosphonium chloride In toluene at 0 - 23℃; Inert atmosphere; chemoselective reaction;
78 % Chromat.	With 1,2-O-isopropylidene-3-O-methyl-6-deoxy-6-N,N-N'-trimethylamino-α-D-glucofuranose In toluene at 25℃; for 10h; enantioselectivity of diethylzinc addition to heptanal, other reagents: 1,2-O-isopropylidene-3-(O-methyl- or deoxy)-6-deoxy-6-(N,N-diethylamino- or pyrrolidino- or piperidino- or morpholino)-α-D-glucopyranose;
	man zerlegt das Gemisch nach Zweimonatigem Stehen mit Wasser;
78 % Chromat.	With 1,2-O-isopropylidene-3-O-methyl-6-deoxy-6-N,N-N'-trimethylamino-α-D-glucofuranose In toluene at 25℃; for 10h;
	With (1R,3R,5R)-3-(diphenylhydroxymethyl)-2-azabicyclo<3.3.0>octane In toluene for 48h;
	Schlenk technique;

Reference： [1]Cho, Byung Tae; Kim, Namdu [Tetrahedron Letters, 1994, vol. 35, # 24, p. 4115 - 4118]
[2]Uemura, Motokazu; Miyake, Ryuta; Nakayama, Kazuo; Shiro, Motoo; Hayashi, Yuji [Journal of Organic Chemistry, 1993, vol. 58, # 5, p. 1238 - 1244]
[3]Werner, Thomas; Bauer, Matthias; Riahi, Abdol Majid; Schramm, Heiko [European Journal of Organic Chemistry, 2014, vol. 2014, # 22, p. 4876 - 4883]
[4]Watanabe, Makoto; Araki, Shuki; Butsugan, Yasuo [Journal of Organic Chemistry, 1991, vol. 56, # 6, p. 2218 - 2224]
[5]Location in patent: experimental part Werner, Thomas; Riahi, Abdol Majid; Schramm, Heiko [Synthesis, 2011, # 21, p. 3482 - 3490]
[6]Cho; Kim [Synthetic Communications, 1996, vol. 26, # 5, p. 855 - 865]
[7]Wagner [Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1884, vol. 16, p. 307]
[8]Cho; Kim [Synthetic Communications, 1996, vol. 26, # 5, p. 855 - 865]
[9]Wilken, Joerg; Winter, Martin; Stahl, Ingfried; Martens, Juergen [Tetrahedron Asymmetry, 2000, vol. 11, # 5, p. 1067 - 1071]
[10]Escorihuela, Jorge; Burguete, M. Isabel; Ujaque, Gregori; Lledós, Agustí; Luis, Santiago V. [Organic and Biomolecular Chemistry, 2016, vol. 14, # 47, p. 11125 - 11136]

2
[ 925-78-0 ]
[ 624-51-1 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium aluminium tetrahydride; diethyl ether
	With lithium aluminium tetrahydride; ethanol; (R,R)-TADDOL 1.) THF, from -76 deg C to RT, 4 h, 2.) 105-135 deg C, 16 torr; Yield given. Multistep reaction;
	With cis-[Ru(6,6'-Me₂bipy)2(H₂O)2](OTf)2; potassium <i>tert</i>-butylate In isopropyl alcohol at 85℃; for 14h; Inert atmosphere;

With sodium borohydrid In methanol

VII 3-Nonanol EXAMPLE VII 3-Nonanol 20.5 g (144 mmol) of 3-nonanone are initially charged in 200 ml of methanol, 5.45 g (144 mmol) of sodium borohydride are added a little at a time at room temperature and the mixture is stirred overnight. The solvent is removed under reduced pressure and the mixture is then acidified and extracted with dichloromethane. The organic phase is dried over sodium sulphate. Removal of the solvent gives 20 g (96%) of a colourless oil. 200 MHz-1H-NMR (CDCl3, ppm): 3.52, m, 1H; 1.48, m, 13H; 0.95, t, 3H; 0.89, t, 3H.

Reference： [1]Zeiss; Tsutsui [Journal of the American Chemical Society, 1953, vol. 75, p. 897,899]
[2]Seebach, Dieter; Beck, Albert K.; Dahinden, Robert; Hoffmann, Matthias; Kuehnle, Florian N. M. [Croatica Chemica Acta, 1996, vol. 69, # 2, p. 459 - 484]
[3]Liu, Pei Nian; Ju, Kun Dong; Lau, Chak Po [Advanced Synthesis and Catalysis, 2011, vol. 353, # 2-3, p. 275 - 280]
[4]Current Patent Assignee: BAYER AG - US6458796, 2002, B1

3
[ 624-51-1 ]
[ 925-78-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium hypochlorite; sodium hydrogencarbonate; potassium bromide In dichloromethane at 0℃; for 5h;
	Oxydation;
	With chromium(VI) oxide; sulfuric acid

Reference： [1]Gheorghe, Alexandru; Matsuno, Ai; Reiser, Oliver [Advanced Synthesis and Catalysis, 2006, vol. 348, # 9, p. 1016 - 1020]
[2]Wagner [Journal fur praktische Chemie (Leipzig 1954), 1891, vol. <2>44, p. 261 Anm.]
[3]Dominguez,J. et al. [Helvetica Chimica Acta, 1962, vol. 45, p. 129 - 138]

4
[ 624-51-1 ]
[ 61925-49-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With alcohol dehydrogenase from Lactobacillus kefir; alcohol dehydrogenase from Rhodococcus ruber DSM 44541; YcnD-oxidoreductase at 30℃; for 3h; aq. buffer; Resolution of racemate; Enzymatic reaction; optical yield given as %ee; enantiospecific reaction;
	Durch Spaltung der racemischen Form ueber den sauren Phthalsaeureester und dessen Cinchonidinsalz;

Reference： [1]Voss, Constance V.; Gruber, Christian C.; Faber, Kurt; Knaus, Tanja; Macheroux, Peter; Kroutil, Wolfgang [Journal of the American Chemical Society, 2008, vol. 130, # 42, p. 13969 - 13972]
[2]Levene; Rothen; Kuna [Journal of Biological Chemistry, 1937, vol. 120, p. 789]
[3]Orrenius, Christian; Oehrner, Niklas; Rotticci, Didier; Mattson, Anders; Hult, Karl; Norin, Torbjoern [Tetrahedron Asymmetry, 1995, vol. 6, # 5, p. 1217 - 1220] Nakamura, Kaoru; Kawasaki, Masashi; Ohno, Atsuyoshi [Bulletin of the Chemical Society of Japan, 1996, vol. 69, # 4, p. 1079 - 1085]

5
[ 624-51-1 ]
[ 273384-45-5 ]

Yield	Reaction Conditions	Operation in experiment
86%	With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 20℃; Inert atmosphere; Cooling with ice;
85%	With cerium(III) chloride; sodium iodide In acetonitrile for 96h; Heating;
	With phosphorus; iodine

Reference： [1]Ren, Peng; Vechorkin, Oleg; Von Allmen, Kim; Scopelliti, Rosario; Hu, Xile [Journal of the American Chemical Society, 2011, vol. 133, # 18, p. 7084 - 7095]
[2]Di Deo, Milena; Marcantoni, Enrico; Torregiani, Elisabetta; Bartoli, Giuseppe; Bellucci, Maria Cristina; Bosco, Marcella; Sambri, Letizia [Journal of Organic Chemistry, 2000, vol. 65, # 9, p. 2830 - 2833]
[3]Bagard [Bulletin de la Societe Chimique de France, 1907, vol. <4>1, p. 359]

6
[ 624-51-1 ]
[ 28123-68-4 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; thionyl chloride
	With thionyl chloride

Reference： [1]Schlenk,W. [Justus Liebigs Annalen der Chemie, 1973, p. 1156 - 1178]
[2]Liu, Yu-Ping; Guan, Wei; Yin, De-Cai; Tian, Hong-Yu; Sun, Bao-Guo [Journal of Chemical Research, 2012, vol. 36, # 8, p. 492 - 494]

7
[ 624-51-1 ]
[ 65950-02-9 ]

Yield	Reaction Conditions	Operation in experiment
	With p-toluenesulfonyl chloride In pyridine at 0℃;

Reference： [1]Zavada,J.; Pankova,M. [Collection of Czechoslovak Chemical Communications, 1977, vol. 42, p. 3421 - 3438]

8
[ 624-51-1 ]
[ 87-69-4 ]
(R,R)-Weinsaeure-di(3-nonyl)ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With methanesulfonic acid In toluene Heating;

Reference： [1]Prelog, Vladimir; Stojanac, Zarko; Kovacevic, Krunoslav [Helvetica Chimica Acta, 1982, vol. 65, # 1, p. 377 - 384]

9
[ 54583-22-1 ]
[ 676-58-4 ]
[ 624-51-1 ]
[ 628-99-9 ]
[ 818-81-5 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran at -40 - 20℃; for 40h; Yield given. Yields of byproduct given;
	In tetrahydrofuran at -40 - 50℃; for 3h; Yield given. Yields of byproduct given;

Reference： [1]Bourgain-Commercon, Monique; Normant, Jean F. [Bulletin de la Societe Chimique de France, 1980, vol. 2, # 5-6, p. 289 - 294]
[2]Bourgain-Commercon, Monique; Normant, Jean F. [Bulletin de la Societe Chimique de France, 1980, vol. 2, # 5-6, p. 289 - 294]

10
[ 81372-32-9 ]
[ 624-51-1 ]

Yield	Reaction Conditions	Operation in experiment
72%	With potassium <i>tert</i>-butylate In water; dimethyl sulfoxide at 80℃; for 20h;

Reference： [1]Hudrlik, Paul F.; Holmes, Peter E.; Hudrlik, Anne M. [Tetrahedron Letters, 1988, vol. 29, # 49, p. 6395 - 6398]

11
[ 3839-31-4 ]
[ 2984-50-1 ]
[ 624-51-1 ]
[ 133930-58-2 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium methyl(cyano)cuprate In tetrahydrofuran; diethyl ether at -78℃; for 1.5h; Yield given. Yields of byproduct given;

Reference： [1]Singer, Robert D.; Oehlschlager, Allan C. [Journal of Organic Chemistry, 1991, vol. 56, # 11, p. 3510 - 3514]

12
[ 624-51-1 ]
[ 201230-82-2 ]
6-Ethyl-3-propyl-tetrahydro-pyran-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With lead(IV) acetate In benzene at 40℃; for 72h;

Reference： [1]Tsunoi, Shinji; Ryu, Ilhyong; Sonoda, Noboru [Journal of the American Chemical Society, 1994, vol. 116, # 12, p. 5473 - 5474]

13
[ 624-51-1 ]
[ 61925-50-6 ]

Yield	Reaction Conditions	Operation in experiment
99%	With alcohol dehydrogenase from Thermoanaerobium brockii; NADH-specific (R)-selective-ADH; YcnD-oxidoreductase at 30℃; for 6h; aq. buffer; Resolution of racemate; Enzymatic reaction; optical yield given as %ee; enantiospecific reaction;
	Multi-step reaction with 2 steps 1: 64 percent / Candida antarctica B lipase / heptane / 20 °C / Enzymatic reaction 2: 71 percent / K₂CO₃ / methanol / 0.5 h

Reference： [1]Voss, Constance V.; Gruber, Christian C.; Faber, Kurt; Knaus, Tanja; Macheroux, Peter; Kroutil, Wolfgang [Journal of the American Chemical Society, 2008, vol. 130, # 42, p. 13969 - 13972]
[2]Orrenius, Christian; Oehrner, Niklas; Rotticci, Didier; Mattson, Anders; Hult, Karl; Norin, Torbjoern [Tetrahedron Asymmetry, 1995, vol. 6, # 5, p. 1217 - 1220]
[3]Mayer, Sandra F.; Mang, Harald; Steinreiber, Andreas; Saf, Robert; Faber, Kurt [Canadian Journal of Chemistry, 2002, vol. 80, # 4, p. 362 - 369]

14
[ 624-51-1 ]
3-Nitrooxy-nonane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; nitric acid

Reference： [1]Schneider, Manfred; Ballschmiter, Karlheinz [Chemistry - A European Journal, 1996, vol. 2, # 5, p. 539 - 544]

15
[ 75-24-1 ]
[ 2984-50-1 ]
[ 624-51-1 ]
[ 818-81-5 ]

Yield	Reaction Conditions	Operation in experiment
	With water In hexane; dichloromethane at -23℃; for 1h; Yield given. Yields of byproduct given;

Reference： [1]Miyazawa, Masahiro; Ishibashi, Naoki; Ohnuma, Satoshi; Miyashita, Masaaki [Tetrahedron Letters, 1997, vol. 38, # 19, p. 3419 - 3422]

16
tert-Butyl-(1-ethyl-heptyloxy)-dimethyl-silane [ No CAS ]
[ 624-51-1 ]

Yield	Reaction Conditions	Operation in experiment
97%	With cerium(III) chloride; sodium iodide In acetonitrile for 24h; Heating;

Reference： [1]Bartoli, Giuseppe; Bosco, Marcella; Marcantoni, Enrico; Sambri, Letizia; Torregiani, Elisabetta [Synlett, 1998, # 2, p. 209 - 211]

17
tert-Butyl-(1-ethyl-heptyloxy)-diphenyl-silane [ No CAS ]
[ 624-51-1 ]

Yield	Reaction Conditions	Operation in experiment
94%	With cerium(III) chloride; sodium iodide In acetonitrile for 36h; Heating;

Reference： [1]Bartoli, Giuseppe; Bosco, Marcella; Marcantoni, Enrico; Sambri, Letizia; Torregiani, Elisabetta [Synlett, 1998, # 2, p. 209 - 211]

18
[ 624-51-1 ]
[ 39482-46-7 ]
[ 214853-60-8 ]

Yield	Reaction Conditions	Operation in experiment
96%	With triethylamine In dichloromethane at 25℃; for 15h;

Reference： [1]Crimmins, Michael T.; Carroll, Charlotte A.; Wells, Angela J. [Tetrahedron Letters, 1998, vol. 39, # 39, p. 7005 - 7008]

19
[ 624-51-1 ]
[ 201230-82-2 ]
(3R,6R)-6-Ethyl-3-propyl-tetrahydro-pyran-2-one [ No CAS ]
(3R,6S)-6-Ethyl-3-propyl-tetrahydro-pyran-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lead(IV) acetate In benzene at 40℃; Yield given. Yields of byproduct given;

Reference： [1]Tsunoi, Shinji; Ryu, Ilhyong; Okuda, Tohru; Tanaka, Minoru; Komatsu, Mitsuo; Sonoda, Noboru [Journal of the American Chemical Society, 1998, vol. 120, # 34, p. 8692 - 8701]

20
1-(1-ethyl-heptyloxymethyl)-4-methoxy-benzene [ No CAS ]
[ 624-51-1 ]

Yield	Reaction Conditions	Operation in experiment
88%	With cerium(III) chloride; sodium iodide In acetonitrile for 48h; Heating;

Reference： [1]Cappa, Anna; Marcantoni, Enrico; Torregiani, Elisabetta; Bartoli, Giuseppe; Bellucci, Maria Cristina; Bosco, Marcella; Sambri, Letizia [Journal of Organic Chemistry, 1999, vol. 64, # 15, p. 5696 - 5699]

21
[ 111-71-7 ]
ethyl potassium ; compound with diethyl zinc [ No CAS ]
[ 624-51-1 ]
[ 16000-65-0 ]
[ 111-70-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 85% 2: 2% 3: 9%	In toluene for 0.166667h; Title compound not separated from byproducts.;

Reference： [1]Musser; Richey Jr. [Journal of Organic Chemistry, 2000, vol. 65, # 23, p. 7750 - 7756]

22
[ 111-71-7 ]
ethyl sodium ; compound with diethyl zinc [ No CAS ]
[ 624-51-1 ]
[ 16000-65-0 ]
[ 111-70-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 90% 2: 2% 3: 3%	In toluene for 0.166667h; Title compound not separated from byproducts.;

Reference： [1]Musser; Richey Jr. [Journal of Organic Chemistry, 2000, vol. 65, # 23, p. 7750 - 7756]

23
[ 111-71-7 ]
C₄H₁₀Zn*C₂H₅Li [ No CAS ]
[ 624-51-1 ]
[ 111-70-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 95% 2: 2%	In toluene for 24h; Title compound not separated from byproducts.;

Reference： [1]Musser; Richey Jr. [Journal of Organic Chemistry, 2000, vol. 65, # 23, p. 7750 - 7756]

24
[ 108-05-4 ]
[ 624-51-1 ]
[ 61925-49-3 ]
Acetic acid (R)-1-ethyl-heptyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With Candida antarctica B lipase In n-heptane at 20℃; Enzymatic reaction;

Reference： [1]Mayer, Sandra F.; Mang, Harald; Steinreiber, Andreas; Saf, Robert; Faber, Kurt [Canadian Journal of Chemistry, 2002, vol. 80, # 4, p. 362 - 369]

25
2-(isopropoxy-dimethyl-silanyl)-nonan-3-ol [ No CAS ]
[ 624-51-1 ]
[ 2216-38-8 ]

Yield	Reaction Conditions	Operation in experiment
76%	With 18-crown-6 ether; potassium <i>tert</i>-butylate In water; dimethyl sulfoxide at 20℃; for 20h;

Reference： [1]Hudrlik, Paul F.; Gebreselassie, Petros; Tafesse, Laykea; Hudrlik, Anne M. [Tetrahedron Letters, 2003, vol. 44, # 16, p. 3409 - 3412]

26
[ 99-50-3 ]
[ 624-51-1 ]
3-nonanyl 3,4-dihydroxybenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	With dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃;
	With dicyclohexyl-carbodiimide

Reference： [1]Kubo, Isao; Fujita, Ken-Ichi; Nihei, Ken-Ichi [Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 19, p. 4255 - 4262]
[2]Nihei, Ken-Ichi; Nihei, Atsuko; Kubo, Isao [Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 22, p. 3993 - 3996]

27
[ 111-84-2 ]
[ 624-51-1 ]
[ 628-99-9 ]
[ 143-08-8 ]

Yield	Reaction Conditions	Operation in experiment
	With cytochrome P₄₅₀ BM₃ from Bacillus megaterium 77-9H mutation; oxygen; NADPH In phosphate buffer; ethanol at 25℃; for 12h; Title compound not separated from byproducts;

Reference： [1]Meinhold, Peter; Peters, Matthew W.; Hartwick, Adam; Hernandez, Alisha R.; Arnold, Frances H. [Advanced Synthesis and Catalysis, 2006, vol. 348, # 6, p. 763 - 772]

28
(3SR,4RS)-3,4-epoxynonane [ No CAS ]
[ 5932-79-6 ]
[ 624-51-1 ]

Yield	Reaction Conditions	Operation in experiment
	With cyclohexa-1,4-diene; 2,4,6-collidine hydrochloride; zinc In tetrahydrofuran at 20℃; Title compound not separated from byproducts.;

Reference： [1]Gansaeuer, Andreas; Fan, Chun-An; Keller, Florian; Keil, Jutta [Journal of the American Chemical Society, 2007, vol. 129, # 12, p. 3484 - 3485]

29
[ 624-51-1 ]
[ 108-24-7 ]
[ 60826-15-5 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap for 2h;

Reference： [1]Gruber, Christian C.; Oberdorfer, Gustav; Voss, Constance V.; Kremsner, Jennifer M.; Kappe, C. Oliver; Kroutil, Wolfgang [Journal of Organic Chemistry, 2007, vol. 72, # 15, p. 5778 - 5783]

30
(3-hexyl-oxiranyl)-isopropoxy-dimethyl-silane [ No CAS ]
[ 624-51-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 84 percent / CuCN / diethyl ether / 4 h / -70 °C 2: 76 percent / KOt-Bu; 18-crown-6 / dimethylsulfoxide; H₂O / 20 h / 20 °C

Reference： [1]Hudrlik, Paul F.; Gebreselassie, Petros; Tafesse, Laykea; Hudrlik, Anne M. [Tetrahedron Letters, 2003, vol. 44, # 16, p. 3409 - 3412]

31
[ 624-51-1 ]
[ 156575-43-8 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane	VIII 1-Ethyl-heptyl Methanesulphonate EXAMPLE VIII 1-Ethyl-heptyl Methanesulphonate 20 g (138.6 mmol) of 3-nonanol and 15.43 g of triethylamine are dissolved in 150 ml of dichloromethane and admixed dropwise with 17.47 g (152.5 mmol) of mesyl chloride. The mixture is stirred at room temperature for 4 hours. The organic phase is extracted twice with water and dried over sodium sulphate and the solvent is removed under reduced pressure. This gives 30.7 g (95%) of a yellow liquid. 200 MHz-1H-NMR (CDCI3, ppm): 4.67, quin., 1H; 3.00, s, 3H; 1.71, m, 4H; 1.30, m, 8H; 0.99, t, 3H; 0.90, t, 3H.

Reference： [1]Current Patent Assignee: BAYER AG - US6458796, 2002, B1

32
[ 624-51-1 ]
[ 959230-91-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 20 °C / Inert atmosphere; Cooling with ice 2: C₃₂H₃₀ClN₂NiP / tetrahydrofuran; N,N-dimethyl acetamide / 2 h / -20 °C / Inert atmosphere

Reference： [1]Ren, Peng; Vechorkin, Oleg; Von Allmen, Kim; Scopelliti, Rosario; Hu, Xile [Journal of the American Chemical Society, 2011, vol. 133, # 18, p. 7084 - 7095]

33
[ 624-51-1 ]
[ 618-58-6 ]
[ 1346758-18-6 ]

Yield	Reaction Conditions	Operation in experiment
97%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h;

Reference： [1]Location in patent: experimental part Suda, Kiyoshi; Akagi, Kazuo [Macromolecules, 2011, vol. 44, # 24, p. 9473 - 9488]

34
petroleum [ No CAS ]
[ 624-51-1 ]
[ 87-42-3 ]
[ 1237126-87-2 ]

Yield	Reaction Conditions	Operation in experiment
	With diisopropyl (E)-azodicarboxylate; triphenylphosphine In tetrahydrofuran; ethyl acetate	(rac)-6-Chloro-9-(nonan-3-yl)-9H-purine (rac)-6-Chloro-9-(nonan-3-yl)-9H-purine Diisopropyl azodicarboxylate (2.33 mL, 12.0 mmol) was added to a mixture of nonan-3-ol (1.26 mL, 7.20 mmol), 6-chloro-9H-purine (0.93 g, 6.00 mmol) and triphenylphosphine (2.36 g, 9.00 mmol) in tetrahydrofuran (50 mL) at room temperature and stirred for 48 h. TLC (4:1 light petroleum/ethyl acetate) indicated consumption of nonan-3-ol (Rf 0.59) and formation of a product component (Rf 0.28). The reaction mixture was filtered through a short silica gel column, washing with light petroleum/ethyl acetate (1:1, 100 mL). Evaporation of the filtrate gave a crude yellow oil that was chromatographed on a silica gel column (80 g). Gradient elution with light petroleum/ethyl acetate (9:1, 1 L; 7:1, 800 mL; 5:1, 840 mL) gave 6-chloro-9-(nonan-3-yl)-9H-purine (1.30 g, 4.63 mmol; 77%) as a dense pale yellow oil: δH (200 MHz; CDCl3): 8.70 (1H, s), 8.08 (1H, s), 4.47 (1H, m), 2.07-1.88 (4H, m), 1.27-1.10 (8H, m), 0.83-0.72 (6H, m); δC (50 MHz; CDCl3): 152.25 (C), 151.88 (CH), 151.14 (C), 144.15 (CH), 131.91 (C), 59.01 (CH), 34.75 (CH2), 31.65 (CH2), 28.90 (CH2), 28.29 (CH2), 26.23 (CH2), 22.63 (CH2), 14.15 (CH3), 10.84 (CH3).

Reference： [1]Current Patent Assignee: ITI SCOTLAND LIMITED - US2012/202287, 2012, A1

35
[ 624-51-1 ]
[ 20445-31-2 ]
[ 139199-71-6 ]
[ 139199-72-7 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide In dichloromethane for 12h;
	With dmap; dicyclohexyl-carbodiimide In dichloromethane Inert atmosphere; Cooling with ice;	(2S)-Nonan-3-yl-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate 25aa General procedure: The enantiomeric excess of 24a was determined by NMR for its (R)-(+)-MTPA ester (Mosher’s ester). General procedure for MTPA ester preparation: A solution of 24a (1 equiv), (R)-(+)-MTPA ((R)-2-methoxy-3,3,3-trifluoro-2-phenylpropanoic acid) (2 equiv), and DMPA (catalytic) in DCM was cooled with an ice bath. To this solution was added DCC (4 equiv) and stirred until TLC showed completion of reaction. Then this was diluted with hexane, filtered, concentrated, and purified by column chromatography (230-400mesh silica gel, 50% EtOAc/hexane) to obtain 24aa. The MTPA ester was made by following the same procedure as for 24aa. 1H NMR (400MHz, CDCl3, δ): 7.57-7.55 (m, 2H), 7.41-7.39 (m, 4H), 5.06-5.03 (m, 1H), 3.58-3.56 (m, 3H), 1.70-1.56 (m, 4H), 1.28-1.20 (m, 8H), 0.95-0.82 (m, 6H). 13C NMR (100.6MHz, CDCl3, δ): 166.4, 132.6, 129.5, 128.3, 127.4, 78.8, 55.4, 33.0, 31.6, 29.0, 26.7, 24.8, 22.5, 14.0, 9.6. IR (KBr): 3065 (CH), 2932 (CH), 2857 (CH), 1744 (C=O), 1452 (C=C), 716 (CH aromatic) cm-1. Ee: 83% (ee was determined by 19F NMR (376.49MHz, CDCl3, δ): -71.27 (R), -71.35 (S); integration ratio of R:S=1.00:11.05).

Reference： [1]Location in patent: experimental part Wu, Pei-Shan; Chen, Chinpiao [Journal of the Chinese Chemical Society, 2012, vol. 59, # 6, p. 768 - 781]
[2]Shih, Yi-Shan; Boobalan, Ramalingam; Chen, Chinpiao; Lee, Gene-Hsian [Tetrahedron Asymmetry, 2014, vol. 25, # 4, p. 327 - 333]

36
[ 624-51-1 ]
methyl 4-ethyldecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: thionyl chloride 2.1: magnesium; iodine; ethylene dibromide / tetrahydrofuran / 70 °C / Heating 2.2: 3 h / -10 °C

Reference： [1]Liu, Yu-Ping; Guan, Wei; Yin, De-Cai; Tian, Hong-Yu; Sun, Bao-Guo [Journal of Chemical Research, 2012, vol. 36, # 8, p. 492 - 494]

37
[ 624-51-1 ]
[ 25234-31-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: thionyl chloride 2.1: magnesium; iodine; ethylene dibromide / tetrahydrofuran / 70 °C / Heating 2.2: 3 h / -10 °C 3.1: potassium hydroxide / methanol; water / 3 h / Reflux

Reference： [1]Liu, Yu-Ping; Guan, Wei; Yin, De-Cai; Tian, Hong-Yu; Sun, Bao-Guo [Journal of Chemical Research, 2012, vol. 36, # 8, p. 492 - 494]

38
[ 624-51-1 ]
[ 98-59-9 ]
[ 65950-02-9 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine at 0 - 20℃; Inert atmosphere;

Reference： [1]Polster, Johannes; Schieberle, Peter [Journal of Agricultural and Food Chemistry, 2015, vol. 63, # 5, p. 1419 - 1432]

39
[ 624-51-1 ]
C₁₁H₂₂OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: pyridine / 0 - 20 °C / Inert atmosphere 2: N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere

Reference： [1]Polster, Johannes; Schieberle, Peter [Journal of Agricultural and Food Chemistry, 2015, vol. 63, # 5, p. 1419 - 1432]

40
[ 624-51-1 ]
nonane-3-thiol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: pyridine / 0 - 20 °C / Inert atmosphere 2: N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere 3: lithium aluminium tetrahydride / diethyl ether / 2 h / 0 - 20 °C / Inert atmosphere

Reference： [1]Polster, Johannes; Schieberle, Peter [Journal of Agricultural and Food Chemistry, 2015, vol. 63, # 5, p. 1419 - 1432]

41
[ 624-51-1 ]
3-(methylthio)nonane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: pyridine / 0 - 20 °C / Inert atmosphere 2.1: N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere 3.1: lithium aluminium tetrahydride / diethyl ether / 2 h / 0 - 20 °C / Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / 0 - 20 °C / Inert atmosphere 4.2: 0.33 h / 0 - 20 °C / Inert atmosphere

Reference： [1]Polster, Johannes; Schieberle, Peter [Journal of Agricultural and Food Chemistry, 2015, vol. 63, # 5, p. 1419 - 1432]

42
[ 111-84-2 ]
[ 624-51-1 ]
[ 628-99-9 ]
[ 623-93-8 ]

Yield	Reaction Conditions	Operation in experiment
	With cytochrome P₄₅₀ BM-3 enzyme mutant 9-10A-F₈₇A Enzymatic reaction;	3 Regiospecific Activity General procedure: Table 11 shows product distributions for hydroxylation of alkanes catalyzed by cytochrome P450 BM-3 variants wt F87A and 9-10A F87A.
	With cytochrome P₄₅₀ BM-3 enzyme mutant wt F₈₇A Enzymatic reaction;	3 Regiospecific Activity General procedure: Table 11 shows product distributions for hydroxylation of alkanes catalyzed by cytochrome P450 BM-3 variants wt F87A and 9-10A F87A.

Reference： [1]Current Patent Assignee: CALIFORNIA INSTITUTE OF TECHNOLOGY - US2016/24482, 2016, A1 Location in patent: Paragraph 0341
[2]Current Patent Assignee: CALIFORNIA INSTITUTE OF TECHNOLOGY - US2016/24482, 2016, A1 Location in patent: Paragraph 0341

43
[ 111-84-2 ]
[ 624-51-1 ]
(R)-2-nonanol [ No CAS ]
[ 70419-06-6 ]

Yield	Reaction Conditions	Operation in experiment
60 % ee	With cytochrome P₄₅₀ BM-3 enzyme mutant 9-10A Enzymatic reaction; regiospecific reaction;	3 Regiospecific Activity General procedure: Mutant 9-10A exhibits high activity towards alkanes as small as propane. The alkane hydroxylation properties of this mutant are detailed in Tables 5 and 6. (0324) In Table 5 the product distribution is determined as ratio of a specific alcohol product to the total amount of all alcohol products (given in %). The product distribution for ketones was similar to alcohol product distribution. The numbers reported here are the (%) total of all ketones relative to total products (alcohols+ketones). The favored enantiomer is listed in parentheses.

Reference： [1]Current Patent Assignee: CALIFORNIA INSTITUTE OF TECHNOLOGY - US2016/24482, 2016, A1 Location in patent: Paragraph 0323; 0324

44
[ 624-51-1 ]
[ 108-95-2 ]
[ 20012-44-6 ]

Yield	Reaction Conditions	Operation in experiment
47%	With di-isopropyl azodicarboxylate; triethylamine; triphenylphosphine In tetrahydrofuran; toluene at 0 - 20℃; for 24h; Inert atmosphere;

Reference： [1]Higashi, Tomomi; Ueda, Takahiro; Mochida, Tomoyuki [Physical Chemistry Chemical Physics, 2016, vol. 18, # 15, p. 10041 - 10048]

45
[ 624-51-1 ]
[ 141-78-6 ]
[ 60826-15-5 ]

Yield	Reaction Conditions	Operation in experiment
89%	With iodine for 3h; Reflux; chemoselective reaction;	2. Typical procedure for alcohol acetylation General procedure: To a solution of benzyl alcohol (0.108 g, 1 mmol) in ethyl acetate (2 mL), iodine (0.1 mmol)was added and the mixture was heated at reflux for 2 h. When the reaction was complete(monitored by TLC), it was cooled and a saturated sodium thiosulfate solution (5 mL) was added. The reaction mixture was extracted with ethyl acetate (3x10 mL). The combined organiclayers were washed with brine, dried over anhydrous sodium sulphate and concentrated invacuo. The crude was then purified by column chromatography to give 1a in 97% yield (145mg, 0.97 mmol).

Reference： [1]Basumatary, Grace; Bez, Ghanashyam [Tetrahedron Letters, 2017, vol. 58, # 45, p. 4312 - 4315]

46
[ 21964-44-3 ]
[ 925-78-0 ]
[ 624-51-1 ]
[ 6434-78-2 ]
[ 6434-77-1 ]

Yield	Reaction Conditions	Operation in experiment
1: 58.333 % de 2: 17 %Chromat. 3: 14 %Chromat.	With methanol; toluene-4-sulfonic acid at 25℃; for 5h; Inert atmosphere; Sealed tube; Irradiation;

Reference： [1]Takada, Yuki; Caner, Joaquim; Kaliyamoorthy, Selvam; Naka, Hiroshi; Saito, Susumu [Chemistry - A European Journal, 2017, vol. 23, # 71, p. 18025 - 18032]

47
[ 93-58-3 ]
[ 624-51-1 ]
nonan-3-yl benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With tetramethylammonium methyl carbonate In toluene for 3h; Molecular sieve; Reflux; Green chemistry;

Reference： [1]Hatano, Manabu; Tabata, Yuji; Yoshida, Yurika; Toh, Kohei; Yamashita, Kenji; Ogura, Yoshihiro; Ishihara, Kazuaki [Green Chemistry, 2018, vol. 20, # 6, p. 1193 - 1198]

48
[ 624-51-1 ]
3-azidononane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: triethylamine / dichloromethane 2: dimethyl sulfoxide

Reference： [1]Current Patent Assignee: BAYER AG - US6458796, 2002, B1

49
[ 624-51-1 ]
[ 2524-64-3 ]
nonan-3-yl diphenyl phosphate [ No CAS ]
nonan-3-yl diphenyl phosphate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap In dichloromethane at 20℃; for 3h;

Reference： [1]Fu, Gregory C.; Yang, Ze-Peng [Journal of the American Chemical Society, 2020]

50
[ 624-51-1 ]
2,7-nonadiol [ No CAS ]
[ 307975-17-3 ]

Yield	Reaction Conditions	Operation in experiment
1: 63% 2: 14%	With C₄₀H₆₈F₆FeN₄O₆S₂Si₂; dihydrogen peroxide; acetic acid at 0℃; for 0.5h; chemoselective reaction;

Reference： [1]Bietti, Massimo; Borrell, Margarida; Costas, Miquel; Gil-Caballero, Sergio [ACS Catalysis, 2020, vol. 10, # 8, p. 4702 - 4709]

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Physical hazards
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
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H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
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H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
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H336	May cause drowsiness or dizziness
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H370	Causes damage to organs
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H372	Causes damage to organs through prolonged or repeated exposure
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Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 624-51-1 ] {[proInfo.proName]}

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[ 624-51-1 ] Synthesis Path-Downstream 1~50

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Aliphatic Chain Hydrocarbons

Alcohols

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[ 624-51-1 ]