[ CAS No. 83088-26-0 ] {[proInfo.proName]}

Name: 83088-26-0|(E)-4-(3,5-Dimethoxystyryl)-1,2-dimethoxybenzene|97%
Brand: Ambeed
SKU: A1262996
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Quality Control of [ 83088-26-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 83088-26-0 ]

SDS Specification

Alternatived Products of [ 83088-26-0 ]

Product Details of [ 83088-26-0 ]

CAS No. :	83088-26-0	MDL No. :	MFCD09033675
Formula :	C₁₈H₂₀O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PTVAOGIYBMTHSN-AATRIKPKSA-N
M.W :	300.35	Pubchem ID :	5387294
Synonyms :

Calculated chemistry of [ 83088-26-0 ]

Physicochemical Properties

Num. heavy atoms :	22
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.22
Num. rotatable bonds :	6
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	87.78
TPSA :	36.92 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.87 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.76
Log Po/w (XLOGP3) :	4.6
Log Po/w (WLOGP) :	3.67
Log Po/w (MLOGP) :	2.66
Log Po/w (SILICOS-IT) :	4.2
Consensus Log Po/w :	3.78

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-4.61
Solubility :	0.00741 mg/ml ; 0.0000247 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.1
Solubility :	0.00239 mg/ml ; 0.00000794 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.5
Solubility :	0.000941 mg/ml ; 0.00000313 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.61

Safety of [ 83088-26-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 83088-26-0 ]

* 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 [ 83088-26-0 ]

[ 83088-26-0 ] Synthesis Path-Downstream 1~40

1
[ 7311-34-4 ]
[ 78055-65-9 ]
[ 83088-26-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate 1.) DMF, 0 deg C, 30 min, 2.) a) DMF, from 0 deg C to RT, 1.5 h, b) 95-100 deg C, 1 h, c) RT, overnight; Multistep reaction;

Reference： [1]Cushman, Mark; Nagarathnam, Dhanapalan; Gopal, D.; Chakraborti, Asit K.; Lin, Chii M.; Hamel, Ernest [Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2579 - 2588]

2
[ 7311-34-4 ]
[ 159386-47-7 ]
[ 83088-26-0 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium 1.) THF, hexane, 0 deg C, 10 min; 2.) THF, r.t., 12 h; Yield given. Multistep reaction;

Reference： [1]Brown; Brown, Karen M.; Lawrence; Lawrence, Nicholas J.; Liddle; Liddle, John; Muhammad; Muhammad, Faiz; Jackson; Jackson, David A. [Tetrahedron Letters, 1994, vol. 35, # 36, p. 6733 - 6736]

3
[ 83088-26-0 ]
[ 22318-87-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With hydrogen In ethanol
40%	With ammonium formate In methanol for 2h; Heating;
	With palladium on activated charcoal In methanol for 3h; Ambient temperature;

With palladium 10% on activated carbon; hydrogen In ethanol for 3h;

2.6.2 General procedure General procedure: Dihydro derivatives of compounds 7, 9, 11, 13, 15, 17, 19, 21, and 23 were prepared by hydrogenation of corresponding stilbenes. A standard protocol was followed,32 with minor modifications. Solutions of each stilbene (10mg) in absolute EtOH (5ml) were stirred under H2 for 3h in the presence of 10% Pd/C. The reaction mixtures were filtered over Celite to remove the catalyst, and evaporated to dryness. The resulting residues were purified by flash column chromatography, using a hexane/EtOAc gradient, to afford target compounds 8, 10, 12, 14, 16, 18, 20, 22, and 24, respectively, in yields of 85-95%. The spectroscopic data of compounds were in agreement with the literature, except for compound 24, for which no report was found (1H NMR spectrum is provided as Supporting information).32-41

Reference： [1]Talvitie, Antti; Mannila, Erkki; Kolehmainen, Erkki [Liebigs Annalen der Chemie, 1992, # 4, p. 399 - 402]
[2]Alonso, Emma; Ramon, Diego J.; Yus, Miguel [Journal of Organic Chemistry, 1997, vol. 62, # 2, p. 417 - 421]
[3]Juneja; Sharma; Tandon [Phytochemistry, 1985, vol. 24, # 2, p. 321 - 324]
[4]Rueda, Diana C.; Schöffmann, Angela; De Mieri, Maria; Raith, Melanie; Jähne, Evelyn A.; Hering, Steffen; Hamburger, Matthias [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 4, p. 1276 - 1284]

4
[ 4670-10-4 ]
[ 120-14-9 ]
[ 83088-26-0 ]
(Z)-3-(3,4-Dimethoxy-phenyl)-2-(3,5-dimethoxy-phenyl)-acrylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
300 mg	With piperidine at 160 - 170℃; for 20h; Yields of byproduct given;
600 mg	With piperidine at 160 - 170℃; for 20h; Yields of byproduct given;

Reference： [1]Prakash, Satya; Khan, Mushtaq A.; Khan, Khaliquz Zaman; Zaman, Asif [Phytochemistry, 1985, vol. 24, # 3, p. 622 - 624]
[2]Prakash, Satya; Khan, Mushtaq A.; Khan, Khaliquz Zaman; Zaman, Asif [Phytochemistry, 1985, vol. 24, # 3, p. 622 - 624]

5
[ 83088-26-0 ]
[ 75-36-5 ]
[ 134029-77-9 ]

Yield	Reaction Conditions	Operation in experiment
79%	With triethylamine In benzene at 0℃; for 0.5h;

Reference： [1]Cushman, Mark; Nagarathnam, Dhanapalan; Gopal, D.; Chakraborti, Asit K.; Lin, Chii M.; Hamel, Ernest [Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2579 - 2588]

6
[ 32507-66-7 ]
[ 77-78-1 ]
[ 83088-26-0 ]

Reference： [1]Liebigs Annalen der Chemie,1992,p. 399 - 402
[2]Canadian Journal of Chemistry,1968,vol. 46,p. 2525 - 2529

7
3,5,4',5'-tetramethoxystilbene-8-carboxylic acid [ No CAS ]
[ 83088-26-0 ]

Yield	Reaction Conditions	Operation in experiment
250 mg	With Cu-bronz In quinoline at 240 - 260℃; for 7h;

Reference： [1]Juneja; Sharma; Tandon [Phytochemistry, 1985, vol. 24, # 2, p. 321 - 324]

8
[ 908094-01-9 ]
[ 62502-00-5 ]
[ 83088-26-0 ]

Yield	Reaction Conditions	Operation in experiment
	In diethyl ether

Reference： [1]Aritomi,M.; Donnelly,D.M.X. [Phytochemistry, 1976, vol. 15, p. 2006 - 2008]

9
[ 83088-26-0 ]
[ 10083-24-6 ]

Yield	Reaction Conditions	Operation in experiment
		4.5 ml of chlorobenzene and 15.7 g of triethylamine (155.1 mmol; 21 mol. eq.) are introduced into a three-necked round-bottomed flask. A nitrogen atmosphere is applied, the mixture is cooled to 0-50C and 12.8 g of anhydrous aluminium chloride (95 mmol; 13 mol. eq.) are added in 30 min. The medium is brought to 60C for 1 h. 2.2 g of tetramethylpiceatannol (7.3 mmol) dissolved in 4.5 ml of chlorobenzene are introduced at this temperature over 1 h and the reaction medium is maintained at this temperature for 4 h and then at 80C for 4 h. It is brought back to ambient temperature, separation by settling is carried out and the heavy phase is recovered and hydrolysed by running dropwise onto 40 g of a 50/50 water/ice mixture. The mixture is kept stirred at this temperature for 1 h 30. The medium is extracted with 4 times 25 ml of methyl ethyl ketone and the organic phase is washed with a saturated sodium bicarbonate solution and then with water. 1.62 g of crude (E)-piceatannol are recovered in the form of a brown solid.The product is purified from a 5/95 mixture of methanol/water in order to result in piceatannol exhibiting a melting point of 233-34C. <n="13"/>The proton and 13C NMR spectra are in agreement with the structure of (E)- piceatannol.

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 5571 - 5578
[2]Journal of Organic Chemistry,1997,vol. 62,p. 417 - 421
[3]Journal of Agricultural and Food Chemistry,1999,vol. 47,p. 3974 - 3977
[4]Patent: WO2009/43761,2009,A1 .Location in patent: Page/Page column 10

10
[ 185249-90-5 ]
[ 83088-26-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	In dimethyl sulfoxide for 2h; Heating;

Reference： [1]Alonso, Emma; Ramon, Diego J.; Yus, Miguel [Journal of Organic Chemistry, 1997, vol. 62, # 2, p. 417 - 421]

11
rhapontigenin [ No CAS ]
[ 74-88-4 ]
[ 83088-26-0 ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium hydride In N,N-dimethyl-formamide at 20℃; for 2h;

Reference： [1]Matsuda, Hisashi; Morikawa, Toshio; Toguchida, Iwao; Park, Ji-Young; Harima, Shoichi; Yoshikawa, Masayuki [Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 1, p. 41 - 50]
[2]Matsuda, Hisashi; Kageura, Tadashi; Morikawa, Toshio; Toguchida, Iwao; Harima, Shoichi; Yoshikawa, Masayuki [Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 4, p. 323 - 327]
[3]Kageura, Tadashi; Matsuda, Hisashi; Morikawa, Toshio; Toguchida, Iwao; Harima, Shoichi; Oda, Mamiko; Yoshikawa, Masayuki [Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 7, p. 1887 - 1893]

12
[ 120-14-9 ]
[ 397333-50-5 ]
[ 83088-26-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: 3,4-dimethoxy-benzaldehyde; (3,5-dimethoxy-benzyl)phosphonic acid dimethyl ester With potassium hydroxide; 18-crown-6 ether In dichloromethane at 20℃; Stage #2: With iodine In n-heptane for 12h; Heating; Further stages.;

Reference： [1]Kim; Ko; Jae Eun Park; Jung; Sang Kwang Lee; Chun [Journal of Medicinal Chemistry, 2002, vol. 45, # 1, p. 160 - 164]

13
[ 6380-23-0 ]
[ 25245-27-6 ]
[ 83088-26-0 ]
C₁₈H₂₀O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With N-Methyldicyclohexylamine; tetrabutylammomium bromide In N,N-dimethyl acetamide; water at 120℃; for 14h;

Reference： [1]Botella, Luis; Nájera, Carmen [Tetrahedron, 2004, vol. 60, # 26, p. 5563 - 5570]

14
[ 120-14-9 ]
[ 108957-75-1 ]
[ 83088-26-0 ]

Yield	Reaction Conditions	Operation in experiment
55%	With sodium methylate In N,N-dimethyl-formamide at 100℃; for 1.5h;
1.65 g (55%)	With sodium methylate	4 EXAMPLE 4 EXAMPLE 4 3,3',4',5-Tetramethoxystilbene was synthesised as described in Example 1 from: 10 mmol (2.48 g) of diethyl-(3,5-dimethoxybenzyl)phosphonate, 20 mmol (1.12 g) of sodium methoxide and 10 mmol (1.661 g) of 3,4-dimethoxybenzaldehyde. Yield: 1.65 g (55%).
	With sodium methylate In N,N-dimethyl-formamide at 0 - 100℃; for 26.5h; diastereoselective reaction;

Reference： [1]Murias, Marek; Handler, Norbert; Erker, Thomas; Pleban, Karin; Ecker, Gerhard; Saiko, Philipp; Szekeres, Thomas; Jäger, Walter [Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 21, p. 5571 - 5578]
[2]Current Patent Assignee: SZEKERES - US2007/191627, 2007, A1
[3]Cardullo, Nunzio; Spatafora, Carmela; Musso, Nicolò; Barresi, Vincenza; Condorelli, Daniele; Tringali, Corrado [Journal of Natural Products, 2015, vol. 78, # 11, p. 2675 - 2683]

15
[ 6380-23-0 ]
[ 40243-87-6 ]
[ 83088-26-0 ]
[ 18513-98-9 ]
(E)-3,3',5,5'-tetramethoxystilbene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	In dichloromethane Heating;

Reference： [1]Velder, Janna; Ritter, Stefanie; Lex, Johann; Schmalz, Hans-Guenther [Synthesis, 2006, # 2, p. 273 - 278]

16
[ 108957-73-9 ]
[ 74-88-4 ]
[ 83088-26-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate In acetone for 5h; Heating;

17
[ 1003857-14-4 ]
[ 83088-26-0 ]

Yield	Reaction Conditions	Operation in experiment
68.6%	With potassium <i>tert</i>-butylate In toluene for 3h; Heating / reflux;	20 Example 20; Synthesis of (E)-tetramethylpiceatannol:; 2.6 g (5.0 mmol) of N-[l-(3,5-dimethoxyphenyl)-2-(3,4-dimethoxyphenyl)ethylidene]- N '-tosylhydrazine prepared according to Example 15, 1.24 g (11.4 mmol) of potassium tert-butoxide and 0.13 g of Triton X100 are introduced into 25 ml of toluene in a 100 ml three-necked round-bottomed flask. The mixture is brought to reflux for 3 h. The temperature is brought back to approximately 900C, 15 ml of water are added dropwise, the medium is separated by settling at approximately 600C, the organic phase is washed with 15 ml of water and the organic phase is concentrated on a rotary evaporator to recover 1.55 g of a slightly brown oil. This oil is taken up in 10 ml of methanol. The temperature is brought back to ambient temperature and the mixture is maintained at ambient temperature for 2 h. The precipitate is filtered off and washed on the filter with 3 ml of methanol. 1.03 g of (E)-tetramethylpiceatannol are recovered in the form of a white, slightly cream, precipitate, i.e. a yield of 68.6% with respect to the starting hydrazone, which exhibits a melting point of 68°C.NMR (CDCl3) 200 MHzProton: δ 3.8 s (6H); δ 3.88 s (3H); δ 3.92 s (3H); δ 6.401 (IH); δ 6.68 d (2H); 6.85 d (IH); δ 6.95 d (IH); δ 6.98-7.12 m (3H).C13 (Dept 135): δ 55.38 and 55.97 (OCH3); δ 99.75; 104.40; 108.84; 120.08 (arom. CH); δ 126.81; 129.03 (ethylen. CH).
59.1%	With sodium methylate In toluene for 5h; Heating / reflux;	22 Example 22; Synthesis of (E)-tetramethylpiceatannol:; 2 g (3.86 mmol) of N-[l-(3,5-dimethoxyphenyl)-2-(3,4-dimethoxyphenyl)ethylidene]- N'-tosylhydrazine prepared according to Example 15, 0.431 g of sodium methoxide and 0.10 g of Triton X100 are introduced into 20 ml of toluene in a 50 ml three-necked round-bottomed flask. The medium is brought to reflux for 5 h, and cooled to approximately 600C, 10 ml of water are slowly added and separation by settling is carried out at this temperature. The toluene phase is washed with 5 ml of water and the organic phase is concentrated on a rotary evaporator to result in 1.18 g of an orangey oil. This oil is brought to reflux in 6 ml of methanol, the temperature is brought back to ambient temperature, the mixture is kept stirred for 2 h and the precipitate is filtered off and washed on the filter with 2 ml of methanol. 0.68 g of (E)-tetramethylpiceatannol is recovered in the form of a white, slightly yellow, precipitate, i.e. a yield of 59.1% with respect to the starting hydrazone.
57.4%	With sodium hydride for 3h; Heating / reflux;	23 Example 23; Synthesis of (E)-tetramethylpiceatannol:; The same reaction is carried out as in Example 22 but with 0.34 g of 60% NaH in oil (8.5 mmol) which has been washed beforehand in the round-bottomed flask with 2 times 5 ml of cyclohexane. The mixture is maintained by reflux for 3 h and the treatment is carried out as in Example 22 to produce 1.32 g of an orangey-yellow oil. After precipitating from 7 ml of methanol as in Example 22, 0.66 g of a white, slightly orangey, solid formed of (E)-tetramethylpiceatannol is recovered, i.e. a yield of 57.4% with respect to the starting hydrazone.

47.8%

With potassium <i>tert</i>-butylate In 1,3,5-trimethyl-benzene for 2h; Heating / reflux;

21 Example 21; Synthesis of (E)-tetramethylpiceatannol:; 2 g (3.86 mmol) of N-[l-(3,5-dimethoxyphenyl)-2-(3,4-dimethoxyphenyl)ethylidene]- N'-tosylhydrazine prepared according to Example 15, 0.97 g of potassium tert-butoxide (2.1 eq.) and 0.10 g of Triton X100 are introduced into 20 ml of mesitylene in a 50 ml three-necked round-bottomed flask. The medium is brought to reflux for 2 h and then brought back to a temperature of 600C, 10 ml of water are added, separating by settling is carried out and the organic phase is recovered and washed with 5 ml of water. The organic phase is concentrated up to 800C under 5 mmHg. 1.06 g of a yellow oil are recovered. This oil is brought to reflux in 6 ml of methanol, the temperature is brought back to ambient temperature, the mixture is kept stirred for 2 h and the precipitate is filtered off and washed on the filter with 2 ml of methanol. 0.55 g of (E)- tetramethylpiceatannol is recovered in the form of a white, slightly yellow, precipitate, i.e. a yield of 47.8% with respect to the starting hydrazone.

Reference： [1]Current Patent Assignee: Weylchem (in: Internat. Chemicals Investors); INTERNATIONAL CHEMICALS INVESTORS SE - WO2008/12321, 2008, A1 Location in patent: Page/Page column 30-31
[2]Current Patent Assignee: Weylchem (in: Internat. Chemicals Investors); INTERNATIONAL CHEMICALS INVESTORS SE - WO2008/12321, 2008, A1 Location in patent: Page/Page column 32
[3]Current Patent Assignee: Weylchem (in: Internat. Chemicals Investors); INTERNATIONAL CHEMICALS INVESTORS SE - WO2008/12321, 2008, A1 Location in patent: Page/Page column 32
[4]Current Patent Assignee: Weylchem (in: Internat. Chemicals Investors); INTERNATIONAL CHEMICALS INVESTORS SE - WO2008/12321, 2008, A1 Location in patent: Page/Page column 31

18
[ 621-59-0 ]
[ 83088-26-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: 92 percent / triethylamine / dimethylformamide / 20 °C 2.1: n-BuLi / tetrahydrofuran / 3 h / -78 °C 2.2: tetrahydrofuran / 5 h / 20 °C 3.1: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C 4.1: 92 percent / potassium carbonate / acetone / 5 h / Heating

19
[ 877-88-3 ]
[ 83088-26-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: 90 percent / toluene / 14 h / Heating 2.1: n-BuLi / tetrahydrofuran / 3 h / -78 °C 2.2: tetrahydrofuran / 5 h / 20 °C 3.1: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C 4.1: 92 percent / potassium carbonate / acetone / 5 h / Heating
	Multi-step reaction with 2 steps 1.1: 93 percent / 8 h / 180 °C 2.1: KOH; 18-crown-6 / CH₂Cl₂ / 20 °C 2.2: 92 percent / I₂ / heptane / 12 h / Heating
	Multi-step reaction with 2 steps 1: 5 h / 130 °C 2: sodium methylate / N,N-dimethyl-formamide / 26.5 h / 0 - 100 °C

Reference： [1]Gao, Mingzhang; Wang, Min; Miller, Kathy D.; Sledge, George W.; Hutchins, Gary D.; Zheng, Qi-Huang [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 22, p. 5767 - 5772]
[2]Kim; Ko; Jae Eun Park; Jung; Sang Kwang Lee; Chun [Journal of Medicinal Chemistry, 2002, vol. 45, # 1, p. 160 - 164]
[3]Cardullo, Nunzio; Spatafora, Carmela; Musso, Nicolò; Barresi, Vincenza; Condorelli, Daniele; Tringali, Corrado [Journal of Natural Products, 2015, vol. 78, # 11, p. 2675 - 2683]

20
[ 24131-30-4 ]
[ 83088-26-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-BuLi / tetrahydrofuran / 3 h / -78 °C 1.2: tetrahydrofuran / 5 h / 20 °C 2.1: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C 3.1: 92 percent / potassium carbonate / acetone / 5 h / Heating

21
[ 97315-18-9 ]
[ 83088-26-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-BuLi / tetrahydrofuran / 3 h / -78 °C 1.2: tetrahydrofuran / 5 h / 20 °C 2.1: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C 3.1: 92 percent / potassium carbonate / acetone / 5 h / Heating

22
[ 586410-27-7 ]
[ 83088-26-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C 2: 92 percent / potassium carbonate / acetone / 5 h / Heating

23
[ 705-76-0 ]
[ 83088-26-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: Et₃N / tetrahydrofuran / 1 h / 0 - 20 °C 2: 31 percent / Li, naphthalene / tetrahydrofuran / 2 h / 0 °C 3: 99 percent / dimethylsulfoxide / 2 h / Heating

Reference： [1]Alonso, Emma; Ramon, Diego J.; Yus, Miguel [Journal of Organic Chemistry, 1997, vol. 62, # 2, p. 417 - 421]

24
[ 185249-83-6 ]
[ 83088-26-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 31 percent / Li, naphthalene / tetrahydrofuran / 2 h / 0 °C 2: 99 percent / dimethylsulfoxide / 2 h / Heating

Reference： [1]Alonso, Emma; Ramon, Diego J.; Yus, Miguel [Journal of Organic Chemistry, 1997, vol. 62, # 2, p. 417 - 421]

25
[ 120-14-9 ]
[ 83088-26-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 61 percent / decalin / 3 h / Heating 2: 63 percent / NaBH₄ / dimethylsulfoxide / 12 h / 70 °C 3: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 10 min; 2.) THF, r.t., 12 h

26
[ 159386-44-4 ]
[ 83088-26-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 63 percent / NaBH₄ / dimethylsulfoxide / 12 h / 70 °C 2: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 10 min; 2.) THF, r.t., 12 h

27
[ 4670-10-4 ]
[ 83088-26-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.3 g / various solvent(s) / 20 h / 160 °C 2: 250 mg / Cu-bronz / quinoline / 7 h / 240 - 260 °C

Reference： [1]Juneja; Sharma; Tandon [Phytochemistry, 1985, vol. 24, # 2, p. 321 - 324]

28
[ 93-02-7 ]
[ 83088-26-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.3 g / various solvent(s) / 20 h / 160 °C 2: 250 mg / Cu-bronz / quinoline / 7 h / 240 - 260 °C

Reference： [1]Juneja; Sharma; Tandon [Phytochemistry, 1985, vol. 24, # 2, p. 321 - 324]

29
[ 62501-99-9 ]
[ 83088-26-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: HCl / methanol 2: diethyl ether

Reference： [1]Aritomi,M.; Donnelly,D.M.X. [Phytochemistry, 1976, vol. 15, p. 2006 - 2008]

Yield	Reaction Conditions	Operation in experiment
55%

31
[ 83088-26-0 ]
cis-3,3',4',5-tetramethoxystilbene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol Inert atmosphere; UV-irradiation;
8 mg	In tetrahydrofuran at 20℃; for 4.16667h; UV-irradiation;

Reference： [1]Location in patent: experimental part Mazué, Frédéric; Colin, Didier; Gobbo, Jessica; Wegner, Maria; Rescifina, Antonio; Spatafora, Carmela; Fasseur, Dominique; Delmas, Dominique; Meunier, Philippe; Tringali, Corrado; Latruffe, Norbert [European Journal of Medicinal Chemistry, 2010, vol. 45, # 7, p. 2972 - 2980]
[2]Zaki, Mohamed A.; Balachandran, Premalatha; Khan, Shabana; Wang, Mei; Mohammed, Rabab; Hetta, Mona H.; Pasco, David S.; Muhammad, Ilias [Journal of Natural Products, 2013, vol. 76, # 4, p. 679 - 684]

32
[ 6380-23-0 ]
[ 25245-27-6 ]
[ 83088-26-0 ]

Yield	Reaction Conditions	Operation in experiment
58.8%	With triethanolamine; palladium diacetate at 100℃; for 24h; Inert atmosphere; stereoselective reaction;	4.2. General procedure for the Mizoroki-Heck reactions General procedure: A mixture of the styrene (3 mmol), the halogenated benzene (3 mmol), triethanolamine (3 mmol) and Pd (II) acetate (0.03 g) was stirred under argon at 100 °C for 24 h. The reaction was cooled to 25 °C, quenched by the addition of dil. aq. hydrochloric acid (2 N, 10 ml), and extracted with ether (3 × 100 ml). The organic phases were dried (Na2SO4), the solvents evaporated, and the crude product was subjected to chromatography (silica gel, hexane/ethyl acetate mixtures).

Reference： [1]Location in patent: experimental part Csuk, Rene; Albert, Sabrina; Siewert, Bianka; Schwarz, Stefan [European Journal of Medicinal Chemistry, 2012, vol. 54, p. 669 - 678]

33
[ 83088-26-0 ]
cis-3,3',4',5-tetramethoxystilbene [ No CAS ]
[ 22318-84-9 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran at 20℃; UV-irradiation;

Reference： [1]Zaki, Mohamed A.; Balachandran, Premalatha; Khan, Shabana; Wang, Mei; Mohammed, Rabab; Hetta, Mona H.; Pasco, David S.; Muhammad, Ilias [Journal of Natural Products, 2013, vol. 76, # 4, p. 679 - 684]

34
[ 83088-26-0 ]
[ 1182284-01-0 ]

Yield	Reaction Conditions	Operation in experiment
	With 3-chloro-benzenecarboperoxoic acid

Reference： [1]Sarpietro, Maria Grazia; Spatafora, Carmela; Accolla, Maria Lorena; Cascio, Orazio; Tringali, Corrado; Castelli, Francesco [Journal of Natural Products, 2013, vol. 76, # 8, p. 1424 - 1431]

35
[ 83088-26-0 ]
C₁₈H₂₀O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 0.583333h; regioselective reaction;

Reference： [1]Cardullo, Nunzio; Spatafora, Carmela; Musso, Nicolò; Barresi, Vincenza; Condorelli, Daniele; Tringali, Corrado [Journal of Natural Products, 2015, vol. 78, # 11, p. 2675 - 2683]

36
[ 83088-26-0 ]
(2S,3R,4S,5S)-2-[2-(3,4-dimethoxystyryl)-4,6-dimethoxyphenoxy]tetrahydro-6-hydroxymethyl-2H-pyran-3,4,5-triol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.58 h / 20 °C 2.1: potassium carbonate / methanol; water / 0.25 h / 20 °C 2.2: 24 h / 60 °C

Reference： [1]Cardullo, Nunzio; Spatafora, Carmela; Musso, Nicolò; Barresi, Vincenza; Condorelli, Daniele; Tringali, Corrado [Journal of Natural Products, 2015, vol. 78, # 11, p. 2675 - 2683]

37
[ 83088-26-0 ]
(2S,3R,4S,5R)-2-[2-(3,4-dimethoxystyryl)-4,6-dimethoxyphenoxy]tetrahydro-6-hydroxymethyl-2H-pyran-3,4,5-triol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.58 h / 20 °C 2.1: potassium carbonate / methanol; water / 0.25 h / 20 °C 2.2: 24 h / 60 °C

Reference： [1]Cardullo, Nunzio; Spatafora, Carmela; Musso, Nicolò; Barresi, Vincenza; Condorelli, Daniele; Tringali, Corrado [Journal of Natural Products, 2015, vol. 78, # 11, p. 2675 - 2683]

38
(3,4-Dimethoxy-benzylidene)-triphenyl-λ⁵-phosphane [ No CAS ]
[ 705-76-0 ]
cis-3,3',4',5-tetramethoxystilbene [ No CAS ]
[ 83088-26-0 ]

Yield	Reaction Conditions	Operation in experiment
80 % de	at 70℃; for 1h; Overall yield = 64 %; diastereoselective reaction;	4 Application of Rucat for Wittig Type Olefination Reaction General procedure: 50 mL round bottom flask was charged with Rucat (0.250 g), alcohol (0.1 mol) and phosphorus ylide (0.11 mol) was added to the reaction mixture. The combined reaction mass was allowed to react at 70 °C for 1 h. Again, after removing all the volatile organic impurities from the reaction mass, product was isolated by ether washing (5 × 2 mL). The diastereomeric selectivity was calculated using 1H NMR spectroscopic analyses. After the successful isolation of product, catalytic system was further reduced under hydrogen atmosphere (4 bar) at 50 °C for 3 h before going to the next catalytic run. Sequential addition of reactants was carried out as per above mentioned protocol for the same.

Reference： [1]Srivastava, Vivek [Catalysis Letters, 2017, vol. 147, # 3, p. 693 - 703]

39
[ 2859-78-1 ]
[ 1073354-86-5 ]
[ 83088-26-0 ]

Yield	Reaction Conditions	Operation in experiment
84%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane; water at 80℃; for 6h; Schlenk technique; Inert atmosphere;

Reference： [1]Qiu, Xiaodong; Li, Yangyang; Zhou, Li; Chen, Peishan; Li, Fan; Zhang, Yanan; Ling, Yong [Organic Letters, 2020, vol. 22, # 16, p. 6424 - 6428]

40
C₁₁H₁₄O₃ [ No CAS ]
[ 83088-26-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: bis(acetylacetonate)nickel(II); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; zinc; potassium phosphate / toluene; cyclohexane / 24 h / 120 °C / Schlenk technique; Inert atmosphere 2: potassium phosphate; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / 1,4-dioxane; water / 6 h / 80 °C / Schlenk technique; Inert atmosphere

Reference： [1]Qiu, Xiaodong; Li, Yangyang; Zhou, Li; Chen, Peishan; Li, Fan; Zhang, Yanan; Ling, Yong [Organic Letters, 2020, vol. 22, # 16, p. 6424 - 6428]

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Ghs Precautionary Statements

Precautionary Statements-General
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
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P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
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P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
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P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
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Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
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P308	IF exposed or concerned:
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P310	Immediately call a POISON CENTER or doctor/physician.
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P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
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P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
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Physical hazards
Code	Phrase
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
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
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
H270	May cause or intensify fire; oxidizer
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
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

[ CAS No. 83088-26-0 ] {[proInfo.proName]}

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[ 83088-26-0 ] Synthesis Path-Downstream 1~40

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Aryls

Alkenes

Ethers

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[ 83088-26-0 ]