3839-35-8|Hexyl p-Toluenesulfonate| Ambeed

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Quality Control of [ 3839-35-8 ] Purity: 95% SDS Specification

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Product Details of [ 3839-35-8 ]

CAS No. :	3839-35-8
Formula :	C₁₃H₂₀O₃S
M.W :	256.36
SMILES Code :	CC1=CC=C(S(=O)(OCCCCCC)=O)C=C1
MDL No. :	MFCD00059439
InChI Key :	IVQOVYWBHRSGJI-UHFFFAOYSA-N
Pubchem ID :	220448

Safety of [ 3839-35-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 3839-35-8 ]

* 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 [ 3839-35-8 ]

[ 3839-35-8 ] Synthesis Path-Downstream 1~38

1
[ 98-59-9 ]
[ 111-27-3 ]
[ 3839-35-8 ]

Yield	Reaction Conditions	Operation in experiment
95.0%	With pyridine;	Step v) Production of n-hexyl p-toluenesulfonate 20 ml of pyridine was added to 5.02 g (49.2 mM) of n-hexanol, followed by stirring below 0 C. To the mixture, 11.24 g (59.0 mM) of p-toluenesulfonyl chloride was added. The mixture was stirred for 6 hours below 0 C. After the reaction, the reaction mixture was poured into iced water and acidified with conc. HCl, followed by two times of extraction with dichloromethane, two times of washing with water, drying with sodium sulfate and distilling-off of the solvent to obtain 12.0 g (46.8 mM) of an objective product (yield: 95.0%).
95%	With dmap; triethylamine; In dichloromethane; at 0 - 20℃; for 1h;	To a solution of Tscl (2.86 g, 15 mmol) and DMAP (166 mg,1 mmol) in DCM (30 mL), triethylamine (2.1 mL, 15 mmol) and hexyl alcohol (1.58 mL, 10 mmol) in DCM (20 mL) was addeddropwise at 0 C, and the mixture was allowed warm to rt andstirred for 1 h, the solvent was evaporated in vacuo, the residuewasdissolved by ethyl acetate (EA) and washed with satd aq NaHCO3,the organic layer was dried with Na2SO4, filtered, concentrated, andpurified by column chromatography to afford 11 as yellow solid(2.7 g, 95%). 1H NMR (400 MHz, CDCl3): d 7.78 (d, J8.4 Hz, 2H), 7.34(d, J8.0 Hz, 2H), 4.02 (t, J6.4 Hz, 2H), 2.44 (s, 3H), 1.66e1.59 (m,2H), 1.33e1.17 (m, 6H), 0.84 (t, J7.0 Hz, 3H) ppm.
95%	With dmap; In dichloromethane; for 1h;	The toluene sulfonyl chloride (compound 29, 2.86g, 15mmol) and DMAP (166 mg, 1mmol) dissolved in anhydrous dichloromethane (30 ml), add triethylamine (2.1 ml, 15mmol), compound 29 (1.58 ml, 10mmol) dissolved in dichloromethane (20 ml) is dropped into the, mixing 1h, decompression turns on lathe methylene chloride, the residue is dissolved in ethyl acetate (150 ml) is dissolved, the organic phase with saturated sodium bicarbonate solution and saturated salt water washing, dry anhydrous sodium sulfate, concentrated, the residue is dissolved in silica gel column chromatography to obtain compound 30 (2.7g, 95

93.2%	With triethylamine; In dichloromethane; at 10℃; for 6h;Large scale;	1-hexanol (1.2 kg, 11.70 mol), TsCl (2.7 kg, 14.0 mol), methylene chloride (12.0 L) are stirred,Triethylamine (2.4 kg, 23.40 mol) was added dropwise while maintaining an internal temperature of 10 C. or lower.After completion of dropwise addition, the internal temperature was maintained at 10 C. or lower and stirred for 6 hours.After 5 L of purified water was added, the separated organic layer was concentrated under reduced pressure to obtain the title compound (2.8 kg, 93.2%).
	With pyridine; at 10 - 20℃; for 3h;	General procedure: 4-Methylbenzenesulphonyl chloride (55 mmol) was added slowly to a mixture of a primary alcohol (50 mmol) and 20 ml of pyridine at 10 C. The reaction mixture was stirred for 3 h at 20 C. After that 120 ml of 25 % hydrochloric acid was slowly added. The reaction mixture was then extracted with chloroform, organic layer dried with Na2SO4 and evaporated to yield alkyl 4-methylbenzenesulphonate as colourless oily liquid or white solid, which was used without further purification. Ethyl 4-methylbenzenesulphonate was purchased from Fluka.
	With pyridine; for 6h;Cooling with ice;	100 Ml reaction flask by adding the magnetic coil, is provided with a thermometer, adding 9.5 g of toluene sulfonyl chloride (0.05 µM), dissolved in 20 ml of pyridine in, the reaction bottle is located in the ice water bath and stirring, by way instillment hexyl alcohol, is hexanol adding amount is 5.1 g (0.05 µM), reaction time is 6 h, inverted ice water in the reaction liquid, adding concentrated hydrochloric acid until its [...], extraction, water vapor direct distillation, is paratoluene sulfonic acid hexyl pure product.

References: [1]Patent: US5118441,1992,A .
[2]Tetrahedron,2014,vol. 70,p. 7763 - 7769.
[3]Patent: CN103601742,2016,B .Location in patent: Paragraph 0143-0146.
[4]Patent: KR2020/2720,2020,A .Location in patent: Paragraph 0081-0083.
[5]Organic Letters,2009,vol. 11,p. 1757 - 1759.
[6]New Journal of Chemistry,2017,vol. 41,p. 4743 - 4746.
[7]Il Farmaco,1992,vol. 47,p. 1457 - 1476.
[8]Chemical Communications,2020,vol. 56,p. 11855 - 11858.
[9]Journal of the Chemical Society,1953,p. 1785,1791.
[10]Chemische Berichte,1933,vol. 66,p. 360,363.
[11]Journal of the American Chemical Society,1969,vol. 91,p. 4824 - 4837.
[12]Synthetic Communications,2002,vol. 32,p. 2651 - 2655.
[13]Helvetica Chimica Acta,2006,vol. 89,p. 304 - 319.
[14]Russian Journal of Applied Chemistry,2005,vol. 78,p. 1646 - 1650.
[15]Angewandte Chemie - International Edition,2011,vol. 50,p. 3904 - 3907.
[16]Organic and Biomolecular Chemistry,2011,vol. 9,p. 5220 - 5227.
[17]Angewandte Chemie - International Edition,2012,vol. 51,p. 528 - 532.
[18]Organic Letters,2014,vol. 16,p. 6342 - 6345.
[19]European Journal of Medicinal Chemistry,2015,vol. 93,p. 263 - 273.
[20]Chemistry - A European Journal,2014,vol. 20,p. 15334 - 15338.
[21]Patent: CN109942436,2019,A .Location in patent: Paragraph 0064-0065; 0068; 0071; 0074; 0077.

2
[ 2444-28-2 ]
[ 3839-35-8 ]
[ 75169-13-0 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1980,p. 910 - 914.
Zhurnal Organicheskoi Khimii,1980,vol. 16,p. 1034 - 1039.

3
[ 3839-35-8 ]
[ 6928-78-5 ]
[ 16967-02-5 ]

References: [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1987,vol. 36,p. 1888 - 1892.
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1987,p. 2037 - 2041.

4
[ 3839-35-8 ]
diisobutylaluminum benzenetellurolate [ No CAS ]
[ 85055-59-0 ]

References: [1]Chemistry Letters,1991,p. 415 - 418.

5
[ 3839-35-8 ]
indolactam V [ No CAS ]
(-)-14-O-hexyl indolactam V [ No CAS ]

References: [1]Agricultural and Biological Chemistry,1985,vol. 49,p. 1441 - 1446.

6
[ 3839-35-8 ]
[ 52056-08-3 ]
[ 7732-99-2 ]

References: [1]Journal of the American Chemical Society,1988,vol. 110,p. 7737 - 7745.

7
[ 3839-35-8 ]
[ 6926-45-0 ]

References: [1]Il Farmaco,1992,vol. 47,p. 1457 - 1476.

8
[ 3839-35-8 ]
[ 536-57-2 ]
[ 111-27-3 ]

References: [1]Phosphorus and Sulfur and the Related Elements,1982,vol. 13,p. 301 - 308.

9
[ 27126-76-7 ]
[ 638-45-9 ]
[ 3839-35-8 ]

References: [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1983,vol. 32,p. 1530 - 1531.
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1983,p. 1682.

10
[ 7182-86-7 ]
[ 638-45-9 ]
[ 544-10-5 ]
[ 3839-35-8 ]

References: [1]Journal of Organic Chemistry,1985,vol. 50,p. 1872 - 1876.

11
[ 94957-45-6 ]
[ 3839-35-8 ]

References: [1]Journal of the American Chemical Society,1987,vol. 109,p. 228.

12
[ 3839-35-8 ]
[ 336184-12-4 ]
[ 336184-13-5 ]

References: [1]European Journal of Organic Chemistry,2001,p. 779 - 786.

13
[ 107-10-8 ]
[ 124-38-9 ]
[ 3839-35-8 ]
n-hexyl n-propylcarbamate [ No CAS ]

References: [1]Monatshefte fur Chemie,2006,vol. 137,p. 459 - 463.
[2]Synthetic Communications,2002,vol. 32,p. 2651 - 2655.

14
[ 124-38-9 ]
[ 3839-35-8 ]
[ 108-91-8 ]
n-hexyl cyclohexylcarbamate [ No CAS ]

References: [1]Monatshefte fur Chemie,2006,vol. 137,p. 459 - 463.
[2]Synthetic Communications,2002,vol. 32,p. 2651 - 2655.

15
[ 3839-35-8 ]
[ 693-04-9 ]
[ 124-18-5 ]

References: [1]Chemistry Letters,2003,vol. 32,p. 890 - 891.

16
[ 1142-19-4 ]
[ 3839-35-8 ]
[ 59693-91-3 ]

References: [1]Synthetic Communications,2004,vol. 34,p. 2337 - 2343.
[2]Synthetic Communications,2004,vol. 34,p. 1685 - 1690.

17
[ 103-19-5 ]
[ 3839-35-8 ]
[ 5342-83-6 ]

References: [1]Synthetic Communications,2004,vol. 34,p. 2337 - 2343.
[2]Synthetic Communications,2004,vol. 34,p. 1685 - 1690.

18
[ 3839-35-8 ]
[ 882-33-7 ]
[ 943-78-2 ]

References: [1]Synthetic Communications,2004,vol. 34,p. 2337 - 2343.
[2]Synthetic Communications,2004,vol. 34,p. 1685 - 1690.

19
[ 107-10-8 ]
[ 75-15-0 ]
[ 3839-35-8 ]
n-hexyl n-propyldithiocarbamate [ No CAS ]

References: [1]Monatshefte fur Chemie,2006,vol. 137,p. 465 - 469.

20
[ 619-14-7 ]
[ 3839-35-8 ]
[ 885620-30-4 ]

References: [1]Helvetica Chimica Acta,2006,vol. 89,p. 304 - 319.

21
[ 616-82-0 ]
[ 3839-35-8 ]
[ 885620-29-1 ]

References: [1]Helvetica Chimica Acta,2006,vol. 89,p. 304 - 319.

22
[ 75-15-0 ]
[ 3839-35-8 ]
[ 108-91-8 ]
S-n-hexyl cyclohexyldithiocarbamate [ No CAS ]

References: [1]Monatshefte fur Chemie,2006,vol. 137,p. 465 - 469.

23
[ 75-15-0 ]
[ 3839-35-8 ]
[ 62-53-3 ]
n-hexyl phenyldithiocarbamate [ No CAS ]

References: [1]Monatshefte fur Chemie,2006,vol. 137,p. 465 - 469.

24
[ 124-38-9 ]
[ 3839-35-8 ]
[ 62-53-3 ]
[ 7461-26-9 ]

References: [1]Monatshefte fur Chemie,2006,vol. 137,p. 459 - 463.

25
[ 355-80-6 ]
[ 3839-35-8 ]
1-(2,2,3,3,4,4,5,5-octafluoropentoxy)hexane [ No CAS ]

References: [1]Russian Journal of Applied Chemistry,2005,vol. 78,p. 1646 - 1650.

26
[ 335-99-9 ]
[ 3839-35-8 ]
1-(1,1,7-trihydroperfluoroheptoxy)hexane [ No CAS ]

References: [1]Russian Journal of Applied Chemistry,2005,vol. 78,p. 1646 - 1650.

27
[ 3839-35-8 ]
trihexylheptaphosphine [ No CAS ]

References: [1]Russian Chemical Bulletin,2007,vol. 56,p. 298 - 303.

28
[ 3839-35-8 ]
hexyl 4-hydroxy-3-aminobenzoate [ No CAS ]

References: [1]Helvetica Chimica Acta,2006,vol. 89,p. 304 - 319.

29
[ 3839-35-8 ]
hexyl 3-hydroxy-4-aminobenzoate [ No CAS ]

References: [1]Helvetica Chimica Acta,2006,vol. 89,p. 304 - 319.

30
[ 3839-35-8 ]
hexyl 2-[4-(hexyloxy)phenyl]benzoxazole-6-carboxylate [ No CAS ]

References: [1]Helvetica Chimica Acta,2006,vol. 89,p. 304 - 319.

31
[ 3839-35-8 ]
hexyl-2-[4-(hexyloxy)phenyl]benzoxazole-5-carboxylate [ No CAS ]

References: [1]Helvetica Chimica Acta,2006,vol. 89,p. 304 - 319.

32
[ 3839-35-8 ]
4-[1-(4-Hexyloxy-phenyl)-meth-(E)-ylidene]-amino}-3-hydroxy-benzoic acid hexyl ester [ No CAS ]

References: [1]Helvetica Chimica Acta,2006,vol. 89,p. 304 - 319.

33
[ 3839-35-8 ]
3-[1-(4-Hexyloxy-phenyl)-meth-(E)-ylidene]-amino}-4-hydroxy-benzoic acid hexyl ester [ No CAS ]

References: [1]Helvetica Chimica Acta,2006,vol. 89,p. 304 - 319.

34
[ 3839-35-8 ]
(Z)-7-tetradecene [ No CAS ]

References: [1]Journal of Chemical Research, Miniprint,1982,p. 321 - 351.

35
[ 27126-76-7 ]
[ 3839-35-8 ]

References: [1]Journal of the American Chemical Society,1987,vol. 109,p. 228.

36
[ 94957-42-3 ]
[ 3839-35-8 ]

References: [1]Journal of the American Chemical Society,1987,vol. 109,p. 228.

37
[ 3839-35-8 ]
[ 137615-41-9 ]

Yield	Reaction Conditions	Operation in experiment
88%	In N-methyl-acetamide;	PREPARATION EXAMPLE 2 1.4 g (5 mmol) of the product (8-1) obtained in Preparation Example 1 was dissolved in 20 ml of dimethylformamide, and the solution was added with 0.24 g (6 mmol) of sodium hydride (content: 60%) and stirred at room temperature for one hour. This was followed by addition of 1.5 g (6 mmol) of n-hexyl p-toluenesulfonate and stirring at room temperature for 3 hours. The reaction mixture was poured into water and extracted with ethyl acetate, and the obtained organic layer was washed with water and brine dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (eluent: toluene/hexane (1/1)) to obtain 1.6 g of (+)-4-benzyloxy-1-(1-hexyloxy-2,2,2-trifluoroethyl)benzene (9-1). Yield: 88%; [α]D20 =+36.6 (c=1, CHCl3).

References: [1]Patent: US5238598,1993,A .

38
[ 3839-35-8 ]
(+)-2-benzyloxy-6-(1-hexyloxyethyl)naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%		Preparation Example 99 In a flask, 1.4 g (5 mmoles) of the compound (XLIII) obtained in Preparation 98 and 20 ml of dimethylformamide were added to form a solution, and 0.3 g (8 mmoles) of sodium hydride (content: 60%) was added, then stirred at room temperature for 1 hour. Thereafter 2.1 g (8 mmole) of n-hexyl p-toluenesulfonate was added thereto, and stirred at 70-80 C. for 10 hours. After completion of the reaction, the resultant mixture was poured into water, the organic layer thus obtained was washed successively with water and saturated aqueous sodium chloride solution, dried with anhydrous magnesium sulfate, subjected to silica gel column chromatography (eluent: toluene/ethyl acetate=40/1) to give 1.5 g of (+)-2-benzyloxy-6-(1-hexyloxyethyl)naphthalene (XLII-1) [Yield: 81%, [α]D20 =+53.0 C. (c=1, CHCl3)].

References: [1]Patent: US5422038,1995,A .

Historical Records

Technical Information

• Nucleophilicity of Sulfur Compounds • Reactions of Benzene and Substituted Benzenes

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H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
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
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
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

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CAS No.: 3839-35-8

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CAS No.: 3839-35-8

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[ 3839-35-8 ] Synthesis Path-Downstream 1~38

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