Name: 33670-32-5|(Methoxymethyl)triphenylphosphonium bromide|95%
Brand: Ambeed
SKU: A192754
Price: 7.0 USD
Availability: InStock
Rating: 92 (25 reviews)

1
[ 117835-14-0 ]
[ 33670-32-5 ]
1-(1R,2R,4R)-Bicyclo[2.2.1]hept-5-en-2-yl-2-methoxy-2-(triphenyl-λ⁵-phosphanylidene)-ethanone [ No CAS ]

Reference： [1]Monatshefte fur Chemie,1966,vol. 97,p. 1797 - 1820

2
[ 33670-32-5 ]
[ 4023-34-1 ]
[ 6395-78-4 ]

Reference： [1]Monatshefte fur Chemie,1966,vol. 97,p. 1797 - 1820

3
[ 33670-32-5 ]
[ 4891-38-7 ]
[ 13883-34-6 ]

Reference： [1]Monatshefte fur Chemie,1966,vol. 97,p. 1797 - 1820

4
[ 33670-32-5 ]
[ 638-29-9 ]
[ 6395-82-0 ]

Reference： [1]Monatshefte fur Chemie,1966,vol. 97,p. 1797 - 1820

5
[ 33670-32-5 ]
[ 79-30-1 ]
[ 6395-80-8 ]

Reference： [1]Monatshefte fur Chemie,1966,vol. 97,p. 1797 - 1820

6
[ 33670-32-5 ]
[ 102-92-1 ]
Methoxy-cinnamoyl-triphenylphosphoranyliden-methan [ No CAS ]

Reference： [1]Monatshefte fur Chemie,1966,vol. 97,p. 1797 - 1820

7
[ 33670-32-5 ]
[ 5006-22-4 ]
[ 6395-75-1 ]

Reference： [1]Monatshefte fur Chemie,1966,vol. 97,p. 1797 - 1820

8
[ 33670-32-5 ]
[ 2614-88-2 ]
[ 13883-36-8 ]

Reference： [1]Monatshefte fur Chemie,1966,vol. 97,p. 1797 - 1820

9
[ 63995-82-4 ]
[ 33670-32-5 ]
[ 95887-49-3 ]

Reference： [1]Chemistry Letters,1984,p. 2149 - 2152

10
[ 63995-86-8 ]
[ 33670-32-5 ]
[ 95887-37-9 ]

Reference： [1]Chemistry Letters,1984,p. 2149 - 2152

11
[ 33235-14-2 ]
[ 33670-32-5 ]
[ 113426-73-6 ]

Reference： [1]Synthetic Communications,1987,vol. 17,p. 1261 - 1272

12
[ 80360-20-9 ]
[ 33670-32-5 ]
[ 110128-40-0 ]
[ 110128-39-7 ]

Reference： [1]Monatshefte fur Chemie,1989,vol. 120,p. 157 - 162

13
[ 33670-32-5 ]
[ 104596-33-0 ]
(Z)-7-[(1R,2S,3R,4S)-3-((E)-2-Methoxy-vinyl)-7-oxa-bicyclo[2.2.1]hept-2-yl]-hept-5-enoic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 2335 - 2347

14
[ 33670-32-5 ]
[ 133559-68-9 ]
[ 133585-57-6 ]

Reference： [1]Bulletin de la Societe Chimique de France,1990,p. 714 - 718

15
[ 33670-32-5 ]
[ 133559-66-7 ]
[ 133559-70-3 ]

Reference： [1]Bulletin de la Societe Chimique de France,1990,p. 714 - 718

16
[ 33670-32-5 ]
[ 133559-67-8 ]
[ 133559-71-4 ]

Reference： [1]Bulletin de la Societe Chimique de France,1990,p. 714 - 718

17
[ 33670-32-5 ]
[ 122172-27-4 ]
[ 122172-28-5 ]

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 3831 - 3836

18
[ 33670-32-5 ]
[ 77092-51-4 ]
[ 77092-52-5 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1980,p. 1241 - 1242

19
[ 33670-32-5 ]
[ 124293-81-8 ]
[ 113660-49-4 ]

Reference： [1]Monatshefte fur Chemie,1989,vol. 120,p. 157 - 162

20
[ 33670-32-5 ]
potassium dicyanoaurate [ No CAS ]
methoxymethyltriphenylphosphonium dicyanoaurate [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1980,vol. 53,p. 3436 - 3438

21
[ 33670-32-5 ]
potassium dicyanoargentate(I) [ No CAS ]
methoxymethyltriphenylphosphonium dicyanoargentate [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1980,vol. 53,p. 3436 - 3438

22
[ 33670-32-5 ]
[ 98577-13-0 ]
4-(1-bromo-2-bicyclo<2.2.2>octyl)-1-methoxy-1-butene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1985,vol. 50,p. 4605 - 4608

23
[ 33670-32-5 ]
2-sec-butyl-4,4-ethylenedioxybutanal [ No CAS ]
2-[2-((E)-2-Methoxy-vinyl)-3-methyl-pentyl]-[1,3]dioxolane [ No CAS ]

Reference： [1]Gazzetta Chimica Italiana,1986,vol. 116,p. 307 - 316

24
[ 33670-32-5 ]
[ 20763-19-3 ]

Reference： [1]Tetrahedron Letters,1990,vol. 31,p. 157 - 160
[2]Journal of Organic Chemistry,1997,vol. 62,p. 8535 - 8539

25
[ 13057-17-5 ]
[ 603-35-0 ]
[ 33670-32-5 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1980,vol. 53,p. 3436 - 3438
[2]Organic Letters,2020

26
[ 33670-32-5 ]
[ 2043-61-0 ]
[ 80434-60-2 ]
cis-2-cyclohexyl-1-methoxyethylene [ No CAS ]

Reference： [1]Chemische Berichte,1993,vol. 126,p. 2493 - 2500

27
[ 700-58-3 ]
[ 33670-32-5 ]
[ 72590-63-7 ]

Reference： [1]Synthetic Communications,1972,vol. 2,p. 79 - 81

28
[ 33670-32-5 ]
(+/-)-(1R,2S/1S,2R)-2-[2-(phenyl)cyclohexyloxy]propenal [ No CAS ]
(Z)-1-methoxy-3-(2-phenylcyclohexyloxy)buta-1,3-diene [ No CAS ]
(E)-1-methoxy-3-(2-phenylcyclohexyloxy)buta-1,3-diene [ No CAS ]

Reference： [1]Synthesis,1997,p. 967 - 974

29
[ 872831-71-5 ]
[ 33670-32-5 ]
[ 872832-14-9 ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 10538 - 10551

30
[ 33670-32-5 ]
[ 312920-87-9 ]
[ 312920-65-3 ]
(E)-9-N-(tert-butoxycarbonyl)-N-methylaminomethyl-6-methoxy-9b-(2-methoxyvinyl)-3,4,4a,9b-tetrahydrodibenzofuran [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 14785 - 14803
[2]Journal of the American Chemical Society,2000,vol. 122,p. 11262 - 11263

31
[ 33670-32-5 ]
[ 446061-84-3 ]
Z-5-methoxy-pent-4-enoic acid 2-(trimethylsilyl)-ethyl ester [ No CAS ]
E-5-methoxy-pent-4-enoic acid 2-(trimethylsilyl)-ethyl ester [ No CAS ]

Reference： [1]Organic Letters,2002,vol. 4,p. 2293 - 2296

32
[ 29978-83-4 ]
[ 33670-32-5 ]
[ 251445-09-7 ]

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 3513 - 3519

33
[ 2426-87-1 ]
[ 33670-32-5 ]
[ 210173-72-1 ]

Reference： [1]European Journal of Organic Chemistry,2006,p. 2970 - 2976

34
[ 156265-95-1 ]
[ 33670-32-5 ]
1,3-difluoro-5-(4-(methoxymethylene)cyclohexyl)benzene [ No CAS ]

Reference： [1]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,2001,vol. 364,p. 899 - 910

35
3-(dimethyl-phenyl-silanyl)-2-methyl-pent-4-enal [ No CAS ]
[ 33670-32-5 ]
((E)-(1R,2S)-4-Methoxy-2-methyl-1-vinyl-but-3-enyl)-dimethyl-phenyl-silane [ No CAS ]

Reference： [1]Organic Letters,2006,vol. 8,p. 4871 - 4874

36
1,2,5,5-tetramethyl-1,2,3,5,6,7,8,8a-octahydro-naphthalin-1-carbaldehyde [ No CAS ]
[ 33670-32-5 ]
5-(2-methoxy-vinyl)-1,1,5,6-tetramethyl-1,2,3,4,4a,5,6,7-octahydro-naphthaline [ No CAS ]
5-(2-methoxy-vinyl)-1,1,5,6-tetramethyl-1,2,3,4,4a,5,6,7-octahydro-naphthaline [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 13171 - 13178

37
[ 1136-86-3 ]
[ 33670-32-5 ]
[ 931103-19-4 ]

Yield	Reaction Conditions	Operation in experiment
73%		To a flame dried 250 mL round-bottom flask was added <strong>[33670-32-5]methoxymethyltriphenylphosphonium bromide</strong> (10.28 g, 30.0 mmol). THF (100 mL) was added and the solution cooled to 0 C. n-BuLi (14.0 mL, 30.0 mmol, 2.2 M) was added dropwise and the solution stirred at 0 C. for 30 min. 3,4,5-Trimethoxyacetophenone (5.26 g, 25.0 mmol) in THF (25 mL) was added dropwise. The reaction was stirred at 0 C. for 30 min, and then water (30 mL) was added. The layers were separated, and the aqueous layer was extracted with Et2O (3×20 mL). The combined organics were washed with brine (30 mL), dried over anhydrous Na2SO4, and concentrated. The residue was purified by flash chromatography (SiO2, 50 g) using 5% EtOAc in hexanes as eluent to afford the enol ether (4.35 g, 73%). The enol ether (4.35 g, 18.26 mmol) was dissolved in THF (37.0 mL). Concentrated HCl (3.0 mL) was added and the solution heated to reflux. The solution was stirred at reflux for 3 h and allowed to cool to room temperature. Water (10 mL) was added, and the organics were washed with sat. NaHCO3 (10 mL) and brine (10 mL), dried over anhydrous Na2SO4, and concentrated. The residue was purified by flash chromatography (SiO2, 50 g) using 20% EtOAc in hexanes as the eluent to afford 2-(3,4,5-trimethoxyphenyl)propanal (3.82 g, 93%). Spectra were the identical to literature values CBr4 (8.47 g, 25.55 mmol) was dissolved in DCM (150 mL) and cooled to 0 C. Ph3P (13.4 g, 51.09 mmol) was added and the solution stirred at 0 C. for 5 min. 2-(3,4,5-trimethoxyphenyl)propanal (3.82 g, 17.03 mmol) in DCM (20 mL) was added dropwise. The reaction was stirred at 0 C. for 30 min and then poured into ice-cooled Et2O (500 mL). The solids were filtered through Celite and washed with Et2O (3×50 mL). The combined organics were concentrated. The residue was filtered through a plug of silica and washed with hexanes (100 mL) followed by 10% EtOAc in hexanes (5×100 mL). The combined organics were concentrated to give the intermediate dibromide (4.86 g, 75%) which was used directly for the next reaction. Mg (0.621 g, 25.57 mmol) was suspended in THF (2.0 mL). 1,2-Dibromoethane (0.442 mL, 5.12 mmol) was added and the reaction stirred at 25 C. for 30 min. The dibromide (4.86 g, 12.79 mmol) in THF (11.0 mL) was added dropwise and the solution heated to reflux where it was stirred for 1 h. The solution was cooled to room temperature and the solvent removed. The residue was purified by flash chromatography (SiO2, 150 g) using 10% EtOAc in hexanes as the eluent to afford 5-(But-3-yn-2-yl)-1,2,3-trimethoxybenzene as a colorless oil (1.97 g, 70%): Rf=0.29 (4:1, Hex:EtOAc); 1H NMR (CDCl3) delta 6.62 (s, 2H), 3.88 (s, 6H), 3.84 (s, 3H), 3.74-3.69 (m, 1H), 2.29 (d, J) 2.7 Hz, 1H), 1.52 (d, J) 7.1 Hz, 3H); 13C NMR (CDCl3) delta 153.4, 138.5, 136.9, 104.0, 104.0, 87.2, 70.5, 61.0, 56.3, 32.1, 24.5; HRFAB[M+Li]227.1243 (calculated C13H16O3Li: 227.1259).

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 940 - 950
[2]Patent: US2009/105287,2009,A1 .Location in patent: Page/Page column 27-28

38
[ 172498-90-7 ]
[ 33670-32-5 ]
5-(2-methoxyvinyl)-1-trityl-1H-imidazole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4728 - 4745

39
C₂₄H₃₁ClO₇ [ No CAS ]
[ 33670-32-5 ]
C₂₆H₃₅ClO₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; In tetrahydrofuran;	Wittig reaction of lactol 15 with Ph3P+CH2OMe Cl- in the the presence of potassium t-butoxide in THF affords enol ether 16 as a mixture of enol ether olefin geometrical isomers.

Reference： [1]Patent: US6353014,2002,B1 .Location in patent: Page column 16

41
[ 983-05-1 ]
[ 33670-32-5 ]
19-nor-10β-(2-methoxy-vinyl)-3β,17β-androst-5-ene diol 3,17-diacetate [ No CAS ]
19-nor-10β-(2-methoxy-vinyl)-3β,17β-androst-5-ene diol 3,17-diacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A solution of nButyllithium (3.12 mL of 1.6 M hexane solution, 5 mmol) was added to a cold (0C) suspension of methoxymethyl triphenylphosphonium bromide (1.53 g, 5 mmol) in anhydrous tetrahydrofuran (10 mL). Solid l9-oxo-3ss, 17ss-androst-5-ene diol diacetate (390 mg, 1.0 mmol) was then added. The mixture was allowed to warm to room temperature and stirred at room temperature for 3 days. The reaction mixture was partitioned between ether and a pH 5 biphthalate/hydroxide buffer solution. The aqueous layer was extracted with ether and the combined organic layers were washed with saturated sodium chloride, dried over magnesium sulfate, filtered, and concentrated under vacuum to afford an amber oil. The residue was dissolved in pyridine the acetic anhydride (0.66 mL, 7 mmol) and 4-dimethylaminopyridine (10 mg) were added. The resulting solution was stirred at room temperature overnight. The solvent was removed under vacuum and the residue was partitioned between ether and a pH 5 biphthalate/hydroxide buffer solution. The aqueous layer was extracted with ether and the combined organic layers were dried over magnesium sulfate, filtered, and concentrated under vacuum to afford an amber oil. The crude product was purified by silica gel chromatography eluted with 6: 1 hexane: ethyl acetate to afford the title compound as an oil which was a mixture of cis and trans olefin isomers.

Reference： [1]Patent: WO2005/51972,2005,A1 .Location in patent: Page/Page column 39

42
[ 3612-18-8 ]
[ 33670-32-5 ]
[ 123-11-5 ]
1-(1-ethylpiperidin-4-yl)-3-(4-methoxyphenyl)indoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; oxalic acid; sodium hydrogencarbonate; phenylhydrazine; In ethyl acetate; isopropyl alcohol;	Example 241 Synthesis of 1-(1-ethylpiperidin-4-yl)-3-(4-methoxyphenyl)indoline Methoxymethyltriphenylphosphonium bromide (7.113 g) and 4-anisaldehyde (2.6 ml) were treated as in Production Example 41-1 to give a pale yellow, oil (2.235 g). Then this product was dissolved in isopropanol (25 ml) and 2 N hydrochloric acid (25 ml). After adding phenylhydrazine (1.0 ml), the resultant mixture was heated under reflux for 1 hr. Then the reaction solution was allowed to cool and concentrated under reduced pressure. Next, ethyl acetate was added thereto and the layers were separated. The organic layer was washed with saturated aqueous solution of sodium bicarbonate and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate system) to give a yellow oil (1.249 g). The resulting product was treated as in Production Example 54 to give a yellow oil (0.534 g). Subsequently, this product and 1-ethyl-4-piperidone were treated as in Example 16 to give the title compound (0.307 g) as a yellow oil (yield: 4.4%). Next, oxalic acid (41 mg) was added thereto to give a salt followed by recrystallization from ethanol. Thus the oxalate (0.151 g) of the title compound was obtained as pale yellow crystals. m.p. (oxalate): 143 C.

Reference： [1]Patent: US2002/19531,2002,A1

43
[ 192947-78-7 ]
[ 33670-32-5 ]
[ 77-92-9 ]
[ 192947-71-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; In tetrahydrofuran;	EXAMPLE 4 Methyl E-alpha-{2-(1-[4-chlorophenyl]-3-pyrazolyloxy)phenyl}-beta-methoxyacrylate A solution of 0.38 g of potassium tert-butoxide in 3 ml of tetrahydrofuran was added dropwise at not more than 5 C to a suspension of 1.4 g of <strong>[33670-32-5]methoxymethyltriphenylphosphonium bromide</strong> ("Wittig reagent") in 15 ml of anhydrous tetrahydrofuran. 1.0 g of methyl 2-[1-(4-chlorophenyl)-3-pyrazolyloxy]phenylglyoxalate (cf. Ex. 1) in 5 ml of tetrahydrofuran was added to the dark red suspension, and the batch was allowed to come to room temperature. Wittig reagent was metered in twice more until all of the keto ester had reacted. For working-up, the batch was stirred into 20% by weight of aqueous citric acid and the mixture was extracted three times with methyl tert-butyl ether. The combined organic phases were washed until neutral, dried over sodium sulfate and subsequently concentrated. The crude product (3.2 g) was chromatographed over silica gel (eluent: toluene/ethyl acetate, 95/5). The resulting E/Z mixture was separated by medium-pressure chromatography on silica gel (eluent heptane/ethyl acetate, 9/1?7/3). This gave 0.5 g of the title compound and 0.15 g of the Z isomer. E compound: m.p. 109-110 C. 1 H NMR (CDCl3): 3.65 (s,3H); 3.8 (s,3H); 5.95 (d,1H); 7.1-7.4 (m,6H); 7.5 (s,1H); 7.55 (d,2H); 7.75 (d,1H). Z compound: 1 H NMR (CDCl3): 3.6 (s,3H); 3.85 (s,3H); 5.9 (d,1H);

Reference： [1]Patent: US6075149,2000,A

44
2-t-butyl-5-methoxycarbonyloxymethyl-6-methylimidazolo-[2,1-b]-1,3,4-thiadiazole [ No CAS ]
[ 865-47-4 ]
[ 33670-32-5 ]
[ 170013-07-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	In 1,4-dioxane;	EXAMPLE 2 Preparation of 2-t-butyl-5-(1-methoxycarbonyl-2-methoxyethen-1-yl)-6-methylimidazolo[2,1-b]-1,3,4-thiadiazole (Compound No. 2) 9 g of potassium t-butylate are added at ambient temperature to a solution of 28 g of triphenylmethoxymethylphosphonium bromide in 200 cm3 of dioxane. After 2 hours a solution of 4.5 g of 2-t-butyl-5-methoxycarbonyloxymethyl-6-methylimidazolo-[2,1-b]-1,3,4-thiadiazole in 20 cm3 of dioxane is added by dropping. The resultant solution is left under agitation at 20 C. for 1 hour and then refluxed for 4 hours. The solution is left overnight under agitation at ambient temperature and is then poured into an ammonium chloride solution and extracted twice with ethyl acetate. The organic phases obtained are pooled, washed with water, dried over sodium sulphate and evaporated under reduced pressure. The impure residue obtained is purified by silica gel chromatography using as eluent a 4/6 ethyl acetate/hexane mixture. 2.7 g of E isomer and 1.8 g of Z isomer of compound No. 2 are obtained with an overall yield of 90%, its structure being deducible from Table 1.

Reference： [1]Patent: US5716974,1998,A

45
[ 33670-32-5 ]
[ 150930-57-7 ]
[ 927823-90-3 ]

Yield	Reaction Conditions	Operation in experiment
84%		Example 4; 2-(1,2,3,4,8,8alpha-hexahydro-8alpha-methylspiro[1',3'-dithiolane-2',6(7H)naphthalen]-1-yl)acetaldehyde (Structure 7); A solution of potassium hexamethyldisalazide in toluene (0.5 M, 70 ml, 35 mmol) was added dropwise over 45 min to a solution of <strong>[33670-32-5]methoxymethyltriphenylphosphonium bromide</strong> (12 g, 35 mmol) in 80 ml of dry THF cooled to -30 C. under Ar atmosphere. The resulting mixture was allowed to warm up to 0 C. (ca. 1.5 hrs), then a solution of aldehyde 3 (4.68 g, 17.4 mmol) in 40 ml of dry THF was added dropwise over 30 min. The reaction mixture was allowed to warm to room temperature, then stirred at room temperature for 3 hrs. A mixture of 55 ml of 4N HCl and 55 ml of THF was added dropwise over 1.5 hrs, and the resulting mixture was vigorously stirred for 48 hrs. Water was then added to dissolve the precipitate, the layers were separated, and the aqueous layer was extracted with ether. Organic fractions were combined, washed with brine, dried over anhydrous MgSO4, concentrated under reduced pressure to give brownish solid. The solid was treated with ether, and the white insoluble part was filtered off, washed with ether. Then the insoluble solid was treated with ether again, and the insoluble fraction was filtered off again. Ethereal filtrates were combined, and concentrated under reduced pressure to furnish light-brown solid, 14.30 g. Column chromatography on silica gel afforded the desired aldehyde 7, as a white solid, 3.84 g (78%): 1H NMR (CDCl3) delta 9.73 (dd, J=3.2, 1.2 Hz, 1H), 5.55 (s, 1H), 3.68 (t, J=6.0 Hz, 2H), 3.34-3.38 (m, 3H), 3.20-3.25 (m, 1H), 2.52 (ddd, J=16.0, 2.0, 0.8 Hz, 1H), 2.10-2.19 (m, 4H), 2.03 (ddd, J=14.0, 2.0, 1.8 Hz, 1H), 1.73-1.86 (m, 3H), 1.50-1.61 (m, 2H), 1.55-1.65 (m, 2H), 1.33-1.39 (m, 2H), 0.98 (s, 3H); 13C NMR (CDCl3) delta 202.8, 145.0, 125.6, 65.7, 45.2, 43.2, 40.3, 39.8, 38.0, 37.2, 36.9, 32.4, 28.9, 27.0, 18.4. Column chromatography of the mixed fraction afforded another 0.3 g (6%) of 7, total yield: 4.14 g (84%).

Reference： [1]Patent: US2007/49629,2007,A1 .Location in patent: Page/Page column 25

46
[ 33670-32-5 ]
[ 852324-28-8 ]
[ 1039074-75-3 ]

Reference： [1]Tetrahedron Letters,2008,vol. 49,p. 3995 - 3996

47
[ 33670-32-5 ]
[ 4455-77-0 ]

Reference： [1]Canadian Journal of Chemistry,2008,vol. 86,p. 668 - 675

48
[ 5497-67-6 ]
[ 33670-32-5 ]
[ 39482-40-1 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 4421 - 4430
[2]Tetrahedron Letters,2009,vol. 50,p. 155 - 157
[3]Tetrahedron,2009,vol. 65,p. 4709 - 4713
[4]Angewandte Chemie - International Edition,2013,vol. 52,p. 12705 - 12708
Angew. Chem.,2013,vol. 125,p. 12937 - 12940,4

49
[ 1018968-76-7 ]
[ 33670-32-5 ]
[ 1018968-77-8 ]

Reference： [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 1432 - 1435

50
[ 287106-56-3 ]
[ 33670-32-5 ]
C₂₄H₄₈O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The Wittig reagent (679 mg) was suspended in THF (10 mL) and KHMDS solution (4 [ML] of 0.5 M) added. After 20 minutes, the mixture was cooled to-78 C and the aldehyde (567 mg) in THF [(5] mL) was added. After 15 minutes, the mixture was worked up in the usual manner to give 342 mg.

Reference： [1]Patent: WO2003/99195,2003,A2 .Location in patent: Page 39

51
[ 287107-11-3 ]
[ 33670-32-5 ]
C₄₁H₇₉NO₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The 1.6 M n-butyl lithium in hexanes (1.5 [ML)] was added dropwise to the phosphonium salt (0.797 g) in THF (10 mL) at [0 C.] After stirring for 30 minutes the aldehyde (0.734 g) in THF [(15] mL) was added dropwise. After stirring at room temperature for one hour the reaction was worked up in the usual manner to give 0.193 g.

Reference： [1]Patent: WO2003/99195,2003,A2 .Location in patent: Page 56

52
19-oxo-3β,17β-androst-5-ene diol 3,17-bis-o-tetrahydropyranyl ether [ No CAS ]
[ 33670-32-5 ]
19-nor-10β-(cis-2-methoxy-vinyl)-3β,17β-androst-5-ene diol 3,17-bis-tetrahydropyranyl ether [ No CAS ]
19-nor-10β-(trans-2-methoxy-vinyl)-3β,17β-androst-5-ene diol 3,17-bis-tetrahydropyranyl ether [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Methoxymethyl triphenylphosphonium bromide (0.768 g, 0.0022 mol) was added to a cold (-60 C) solution of nButyllithium (1.40 mL of 1.6 M hexane solution, 0.0022 mmol) in tetrahydrofuran (1 mL). The resulting mixture was stirred at 0 C for 45 minutes then 19-oxo-3 (3, 17 (3- androst-5-ene diol 3, 17-bis-O-tetrahydropyranyl ether (0.20 g, 0.00042 mol) was added. The mixture was stirred at reflux for 2 hours then cooled to room temperature. The reaction was then quenched by addition of saturated aqueous ammonium chloride. The resulting mixture was extracted with dichloromethane (2X) and the combined extracts were dried over magnesium sulfate, filtered, and concentrated under vacuum to afford an amber gum. The crude product was purified by flash chromatography on silica gel eluted initially with 95: 5 hexane: ethyl acetate with the eluent gradually changed to 9: 1 hexane: ethyl acetate (gradient elution) to afford the title compound as a yellow gum as a mixture of cis and trans olefin isomers.

Reference： [1]Patent: WO2005/51972,2005,A1 .Location in patent: Page/Page column 29-30

53
[ 13246-46-3 ]
[ 33670-32-5 ]
C₂₃H₂₂O₃ [ No CAS ]

Reference： [1]Tetrahedron,2010,vol. 66,p. 197 - 207

54
[ 33670-32-5 ]
[ 613-45-6 ]
C₁₁H₁₄O₃ [ No CAS ]
C₁₁H₁₄O₃ [ No CAS ]

Reference： [1]Tetrahedron,2010,vol. 66,p. 197 - 207

55
[ 917836-04-5 ]
[ 33670-32-5 ]
[ 1220639-90-6 ]

Yield	Reaction Conditions	Operation in experiment
		Step 50-1: A mixture of Ph3PCH2OMe-Br (4.97 g) including NaNH2 in THF (20 mL) was stirred under ice cooling for 10 minutes. To the mixture, a THF (80 mL) solution of the compound (1.00 g) obtained in Step 1-4 was slowly added dropwise. After completion of the dropwise addition, the mixture was stirred at room temperature for 4 hours. To the reaction mixture, a saturated aqueous NaHCO3 solution was added and the solution was extracted once with EtOAc and twice with CHCl3. The combined organic layers were washed with brine, dried over MgSU4 and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel 60 N, mobile phase: EtOAc/hexane = 20/80 to 40/60; v/v) to obtain 7- (2- methoxyethenyl) -3,4-dihydroquinolin-2 (IH) -one (0.60 g, a colorless solid) .1H NMR (600 MHz, CDCl3, delta) : 2.48-2.76 (m, 2H), 2.79-3.07 (m, 2H), 3.59-3.84 (m, 3H), 5.10-7.18 (m, 5H), 8.17-8.76 (m, IH); ESI/APCI MS m/z 204 [M+H]+.

Reference： [1]Patent: WO2010/38901,2010,A1 .Location in patent: Page/Page column 64

56
[ 1227062-95-4 ]
[ 33670-32-5 ]
C₁₇H₂₅NO [ No CAS ]

Reference： [1]Synlett,2010,p. 567 - 570

57
C₁₁H₁₄O₃ [ No CAS ]
[ 33670-32-5 ]
C₁₃H₁₈O₃ [ No CAS ]

Reference： [1]Organic Letters,2010,vol. 12,p. 3472 - 3475

58
[ 1018968-76-7 ]
[ 33670-32-5 ]
C₁₅H₁₆O [ No CAS ]
C₁₅H₁₆O [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 11350 - 11363

59
[ 916168-52-0 ]
[ 33670-32-5 ]
5-methoxymethylene-2-pentyl-tetrahydropyran [ No CAS ]

Reference： [1]Patent: WO2006/125550,2006,A1 .Location in patent: Page/Page column 20-21

60
C₁₈H₁₁F₇O₃ [ No CAS ]
[ 33670-32-5 ]
C₂₀H₁₅F₇O₃ [ No CAS ]

Reference： [1]Patent: WO2006/125550,2006,A1 .Location in patent: Page/Page column 25-26

61
[ 1374662-15-3 ]
[ 33670-32-5 ]
[ 1374662-16-4 ]

Yield	Reaction Conditions	Operation in experiment
38%		Ste l; 80 81 tert-Butyl (3aR,5R,6R,7R,7aR)-6,7-bis(4-methoxybenzyloxy)-5-((E)-2-methoxyvinyI)- 5,6,7,7a-tetrahydro-3aH-pyranoi3,2-d]thiazol-2-yl(ethyl)carbamate (81): A solution of Ph3PCH2OCH3Cl (613 mg, 1.79 mmol) in THF (20 mL) was treated with potassium t-butoxide (191 mg, 1,71 mmol) at 0 C in a nitrogen atmosphere for 30 min, and followed by addition of 80 (500 mg, 0.85 mmol) in THF (5 mL). The resulting solution was stirred for 3 hours at 25 C, and then quenched by saturated aqueous NH C1 (20 mL), extracted with dichloromethane (3 x 20 mL). The combined organic layers were washed with brine (2 x 20 mL), dried over anhydrous magnesium sulfate, and concentrated under vacuum to give a residue, which was purified by a silica gel column, eluting with 30 % ethyl acetate in petroleum ether to give compound 81 as a light yellow solid (200 mg, 38 %). (ES, m/z) [M+H]+ 615.3.

Reference： [1]Patent: WO2012/64680,2012,A1 .Location in patent: Page/Page column 104

62
[ 1374661-49-0 ]
[ 33670-32-5 ]
[ 1374661-72-9 ]

Yield	Reaction Conditions	Operation in experiment
14%		Step 1; 11 37(3aR,5Rt6R,7R,7aR,E 6,7-Bis(4-methoxybenzyloxy)-5-(2-methoxyvinyl)-N>N- dimethyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-amine (37) : A solution of Ph3PCH20CH3 r (2.0 g, 5.90 mmol) in THF (30 mL) was treated with t-BuOK (645 mg, 5.76 mmol) at -10 C for 30 mm, and followed by addition of (3a , 5S, 6S; 7R, 7aR)-2- (dimethylamino)-6, 7-bis(4-methoxybenzyloxy)-5, 6, 7, 7a-tetrahydro-3aH-pyrano [3, 2- d] thiazole-5-carbaldehyde (700 mg, 1.37 mmol). After stirred for 3 h at 0C, the resulting solution was quenched with ice-water (20 mL), and extracted with ethyl acetate (2 x 20 mL). The combined organic layers were dried over anhydrous magnesium sulfate and concentrated to give a residue, which was purified by a silica gel column, eluted with 10 - 50 % ethyl acetate in petroleum ether to give the product 37 as a yellow oil (100 mg, 14 %). (ES, m/z)[M+K+ 515.0; NMR (300 MHz, CDCI3) delta 7.15 - 7.35 (m, 4H), 6.84 - 6.98 (m, 4H), 6.45 (d, J= 7.8 Hz, IH ), 6.28 (d, J= 6.3 Hz, IH), 5.21 (m, IH), 4.45 - 4.89 (m, 4H), 4.18 (t, J- 5.7 Hz, IH), 3.94 (t, J= 4.8 Hz, IH), 3.87 - 3.91 (m, IH), 3.78 (s, 6H), 3.56 - 3.65 (m, IH), 3.52 (s, 3H), 2.92 (s, 6H).

Reference： [1]Patent: WO2012/64680,2012,A1 .Location in patent: Page/Page column 57-58

63
[ 79710-86-4 ]
[ 33670-32-5 ]
[ 1050494-76-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium amide; In tetrahydrofuran; for 1h;	[518] Example 118 - 5-(3,3-Dimethyl-but-l-ynyl)-3-\|4-(4-methyl-cyclohexyl)-l-r2-(tetrahydro- furan-3 -yD-ethyll - 1 ,2,5 ,6-tetrahydro-pyridin-3 -yl I -thiophene-2-carboxylic acid; [519] To a mixture of (methoxymethyl)triphenylphosphonium bromide and sodium amide (0.3 mmol, mixture commercially available from Aldrich) in THF (2 mL) is added tetrahydrofuran-3- carboxaldehyde (0.3 mmol). After 1 hr, the reaction mixture is diluted with ether (3 mL) and hexane (5 mL), filtered through silica gel (10 g), and rinsed with ether (10 mL). The filtrate containing 3-(2- methoxy- vinyl) -tetrahydrofuran is concentrated to about 1-2 mL, and to it is added THF (1 mL) and aqueous 3 N HC1 (0.1 mL). The mixture is stirred 16 hr to give (tetrahydrofuran-3-yl)-acetaldehyde in solution. To the resulting solution is added AcOK (0.5 mmol), activated molecule sieves 4A (powder, 0.5 g), 1111 (50 mg), and sodium triacetoxyborohydride (200 mg). After the reaction is stirred at RT for 15 hr, the reaction mixture is filtered through Celite, rinsed with EtOAc (20 mL), and concentrated. Purification and subsequent hydrolysis of the intermediate ester, and extraction to recover the resulting acid are conducted generally as described for 112, to give 118.

Reference： [1]Patent: WO2012/83105,2012,A1 .Location in patent: Page/Page column 116-117

64
[ 33670-32-5 ]
[ 4255-62-3 ]
[ 64416-07-5 ]

Yield	Reaction Conditions	Operation in experiment
		An oven-dried 500 mL one- necked round bottomed flask was charged with (methoxymethyl)triphenylphosphonium bromide (22.4 g, 65.4 mmol) and dry THF (40 mL) and then cooled to -78 C. To this solution was added w-BuLi (2.8 M in hexane, 23.3 mL, 65.4 mmol) over 10 min by syringe. The resultant red ylide solution was then warmed to rt, stirred for 3 hours, and cooled to -78 C. To this ylide solution was added 4-dimethyl-cyclohexanone (5.5 g, 43.6 mmol) in dry THF (5 mL) via syringe over 10 min. After being stirred for 1 hour at -78 C, the reaction mixture was warmed to rt slowly and stirred for 10 hours. After that the reaction mixture was cooled to 0 C, quenched with aq.NaHC03 (60 mL), and extracted with ether (3 x 60 mL). The organic layer was washed with brine (60 mL) and dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica chromatography using hexane-Et20 isocratic 20% as eluant to give the title compound as clear oil. 1H NMR (400 MHz, CDC13) delta 5.75 (bs, 1H), 3.75 (s, 3H), 2.18 (ddd, J = 12.8, 6.4, 1.2 Hz, 2H), 1.95 (ddd, J = 12.8, 6.4, 1.2 Hz, 2H), 1.27 (ddd, J = 12.8, 6.8, 2.0 Hz, 4H), 0.91 (s, 6H). No ionization by LCMS.

Reference： [1]Patent: WO2012/87519,2012,A1 .Location in patent: Page/Page column 94; 95

65
ethyl (trans)-4-[(5-bromo-1,3-thiazol-2-yl)carbonyl]cyclohexane-carboxylate [ No CAS ]
[ 33670-32-5 ]
ethyl trans-4-[1-(5-bromo-1,3-thiazol-2-yl)ethenyl]-cyclohexanecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%		INTERMEDIATE 30: ethyl trara-4-[l-(5-bromo-l,3-thiazol-2-yl)-2- hydroxyethyljcyclohexanecarboxylate Step 1 : Methyl(triphenyl)phosphonium bromide (774 mg, 2.166 mmol) was suspended in anhydrous diethyl ether (5 mL) and potassium tert-butoxide (2.31 1 mmol, 1.78 M in THF, 1.29 mL) was added at 0 C dropwise. The suspension was left 25 min at the same temperature (solution became orange-brown). A solution of diethyl ether (1 ml) and ethyl trara-4-[(5-bromo- l,3-thiazol-2-yl)carbonyl]cyclohexanecarboxylate (500 mg, 1.444 mmol) was added dropwise at 0 C . The mixture was left at the same temperature for 30 min, allowed to reach room temperature, left under stirring additional 90 min, diluted with water and taken up in ethyl acetate. The organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel (0% to 10% EtOAc in hexanes) to afford ethyl rrarcs-4-[l-(5-bromo-l,3-thiazol-2-yl)ethenyl]- cyclohexanecarboxylate (62%) as an oil. MS ESI calc'd. for C14H1 8BrN02S for [M + H]+ 344, 346, found 344, 346. iH NMR (500 MHz, CDCI3) delta 7.55 (s, 1H), 5.60 (s, 1H), 5.19 (s, 1H), 4.04 (q, J= 7.0, 2H), 2.62-2.78 (m, 1H), 2.20-2.30 (m, 1H), 1.90-2.02 (m, 3H), 1.50-1.60 (m, 2H), 1.10-1.30 (m, 2H), 1.17 (t, J = 7.0, 3H), 0.72-0.82 (m, 1H).

Reference： [1]Patent: WO2012/154519,2012,A1 .Location in patent: Page/Page column 54-55

66
((tert-butyldimethylsilanyloxy)-2-furan-2'-yl-4',5'-dimethoxyphenyl)acetaldehyde [ No CAS ]
[ 33670-32-5 ]
tert-butyl-[1-(furan-2-yl-4,5-dimethoxyphenyl)-3-methoxyallyloxy]dimethylsilane [ No CAS ]

Reference： [1]Molecules,2013,vol. 18,p. 2438 - 2448

67
(1RS,5RS,7SR,8RS)-8-but-3-en-1-yl-1-[(triisopropylsilyloxy)methyl]-8-methyl-4,9-dioxobicyclo[3.3.1]non-2-ene-7-carbaldehyde [ No CAS ]
[ 33670-32-5 ]
(1RS,5RS,7SR,8RS)-8-but-3-en-1-yl-1-[(triisopropylsilyloxy)methyl]-8-methyl-7-(2-methoxyeth-2-en-1-yl)-2-methoxybicyclo[3.3.1]non-2-ene-4,9-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%		To a suspension of Ph3P(CH2OMe)Br (411.4 mg, 1.20 mmol, 5.8 equiv) in THF (17.6 mL) was added KHMDS in toluene (2.0 mL, 1.0 mmol, 4.8 equiv) at 0 C, and the reaction mixture was stirred for 1 h. Then, the ylide solution (4.6 mL, ca. 0.228 mmol, ca. 1.1 equiv) was added to a stirred solution of 10b in THF (4.1 mL) and the reaction mixture was stirred at 0 C. After the starting material disappeared, the reaction was quenched with saturated aqueous NH4Cl solution (20 mL). The aqueous layer was extracted with Et2O (20 mL×3). The combined organic layers were washed with brine (60 mL×1), dried (Na2SO4), filtered, and evaporated. The residue was purified by flash chromatography (hexane/ethyl acetate=20/1) to afford 11 (80.1 mg, 79%) as an oil: Rf = 0.50 (hexane/ethyl acetate=3/1); 1H NMR (500 MHz, CDCl3) delta 6.23 (1H, d, J = 13.0 Hz), 5.90 (1H, s), 5.75-5.64 (1H, m), 5.01-4.87 (2H, m), 4.44 (1H, dd, J = 12.5, 10.0 Hz), 4.37 (1H, d, J = 8.5 Hz), 4.18 (1H, d, J = 8.5Hz), 3.79 (3H, s), 3.49 (3H, s), 3.24 (1H, t, J = 4.0 Hz), 2.42-2.31 (1H, m), 2.07-1.95 (2H, m), 1.95-1.81 (2H, m), 1.65-1.51 (1H, m), 1.45-1.34 (1H, m), 1.11-0.95 (21H, brs), 0.76 (3H, s); 13C NMR (125 MHz, CDCl3) delta 204.6 (Cq), 195.1 (Cq), 177.1 (Cq), 149.3 (CH), 138.6 (CH), 114.4 (CH2), 108.0 (CH), 101.4 (CH), 66.3 (Cq), 61.0 (CH), 58.4 (CH2), 56.34 (CH3), 56.32 (CH3), 45.9 (Cq), 40.9 (CH), 37.7 (CH2), 36.1 (CH2), 29.7 (CH2), 17.9 (CH3), 14.1 (CH), 12.0 (CH3); IR (neat) numax 2942, 2865, 1736, 1658, 1593, 1462, 1242, 1216, 1114 cm-1; HRMS (Fab) [M+H]+ calculated for C28H47O5Si: 491.3193, found: 491.3184.

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 2022 - 2025

68
[ 1075216-35-1 ]
[ 33670-32-5 ]
[ 1615677-75-2 ]

Yield	Reaction Conditions	Operation in experiment
74%		To a solution of methoxymethyl(triphenyl)phosphonium chloride (58.2 g, 0.17 mol) in THF (300 mL), LiHMDS (280 mL, 0.28 mol) was added drop-wised at 0 C. The reaction mixture was stirred for 30 min, before a solution of 2-chloro-4-(4-chlorophenyl)benzaldehyde (35.2 g, 0.14 mol) in THF (50 mL) was added. The reaction mixture was allowed to warm to room temperature and stirred overnight. Then, an aq. NH4CI sat. solution was added and the aqueous phase was extracted with MTBE. Upon separation, the organic phase was washed with brine, dried over Na2S04 and concentrated. The crude was purified by silica gel column chromatography (PE : EtOAc = 200:10) to give 2-chloro-4-(4-chlorophenyl)-1 -[(E)-2-methoxyvinyl]benzene (26.0 g, 74%). H-NMR (CDC , 400 MHz) delta = 7.63 (s, 1 H), 7.44-7.48 (m, 6H), 7.12-7.01 (d, J = 12.8 Hz, 1 H), 6.23-6.01 (d, J = 12.8 Hz,1 H), 3.84 (s, 3H).

Reference： [1]Patent: WO2014/95655,2014,A1 .Location in patent: Page/Page column 161

69
2-chloro-4-(4-chlorophenoxy)benzaldehyde [ No CAS ]
[ 33670-32-5 ]
[ 1614262-44-0 ]

Yield	Reaction Conditions	Operation in experiment
93%		The solution of (methoxymethyl)triphenylphosphonium bromide (45.1 g, 0.31 mol) in THF (400 mL), LiHMDS (130 mL, 0.13 mol) was added at 0 C. The reaction mixture was stirred for 1 h and then, a solution of 2-chloro-4-(4-chlorophenoxy)benzaldehyde (32.3 g, 0.12 mol) in THF was added dropwised. The reaction mixture was stirred overnight, which was quenched by the addition of an aq. NH4CI and extracted with MTBE. Upon separation, the organic phase was washed with brine, dried over Na2S04 and concentrated. The crude was purified by silica gel column chromatography (PE : EtOAc = 400 : 1 ) to give 2-chloro-4-(4-chlorophenoxy)-1 -[(E)-2- methoxyvinyl]benzene (33.1 g, 93%) H-NMR (CDCI3, 400 MHz) 5=8.1 (d, J = 8.8 Hz, 1 H), 7.3- 7.2 (m, 2 H), 7.1 (m, 1 H), 7.0 (m, 2 H), 6.9 (m, 1 H), 6.3 (d, J = 7.3 Hz, 1 H), 5.6 (d, J = 7.3 Hz, 1 H), 3.9 (s, 3 H) 3.8 (s, 3 H)

Reference： [1]Patent: WO2014/95655,2014,A1 .Location in patent: Page/Page column 159

70
C₅₃H₆₄O₉ [ No CAS ]
[ 33670-32-5 ]
C₅₄H₆₈O₉ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 14991 - 14995

71
[ 4122-56-9 ]
[ 33670-32-5 ]
[ 136540-80-2 ]

Yield	Reaction Conditions	Operation in experiment
2.3 g		To a suspension of(methoxymethyl)triphenylphosphonium bromide (9.44 g, 27.4mmol) in THF (50 mL) was added NaH (1.46 g, 36.6 mmol) at 0 C portion wise. The mixture was stirred at 0 C for 0.5 hand then a solution ofmethyl2-formylbenzoate (3.0 g, 18.3 mmol)in THF (15 mL) added dropwise and the reaction mixture stirred at RT for 12 h. The mixturewas diluted with water, extracted with EtOAc (30 mL x 2) and the combined organic layerswashed with brine, dried over MgS04, filtered, and concentrated in vacuo. The residue was5 purified by chromatography on silica (petroleum ether: EtOAc = 10: 1 to 3: 1) to give the titlecompound (2.3 g) as a colorless oil.
2.3 g		To a suspension of (methoxymethyl)triphenylphosphonium bromide (9.44 g, 27.4 mmol) in THF (50 mL) was added NaH (1.46 g, 36.6 mmol) at 0 C portion wise. The mixture was stirred at 0 C for 0.5 h and then a solution of methyl 2-formylbenzoate (3.0 g, 18.3 mmol) in THF (15 mL) added dropwise and the reaction mixture stirred at RT for 12 h. The mixture was diluted with water, extracted with EtOAc (30 mL x 2) and the combined organic layers washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by chromatography on silica (petroleum ether: EtOAc = 10: 1 to 3: 1) to give the title compound (2.3 g) as a colorless oil.
		To a suspension of (methoxymethyl)triphenylphosphoniumbromide (9.44 g, 27.4 mmol) in THF (50 mL) was added NaH (1.46 g,36.6 mmol) at 0C portion wise. The mixture was stirred at 0C for 0.5 h and then a solution of methyl 2-formylbenzoate (3.0 g, 18.3mmol) in THF (15 mL) added dropwise and the reaction mixture stirred at RT for 12 h. The mixture was diluted with water, extracted with EtOAc (30 mL x 2) and the combined organic layers washed with brine, dried over MgSO4, filtered, and concentrated invacuo. The residue was purified by chromatography on silica (petroleum ether: EtOAc = 10:1 to 3:1) to give the title compound as an oil.

		To a suspension of (methoxymethyl)triphenylphosphonium bromide (9.44 g, 27.4mmol) in THF (50 mL) was added NaH (i.46 g, 36.6 mmol) at 0 C portion wise. The mixturewas stirred at 0 C for 0.5 h. Then a solution of methyl 2-formylbenzoate (3.0 g, 18.3 mmol) in THF (15 mL) was added dropwise and the reaction mixture was stirred at RT for i2 h. The mixture was diluted with water and extracted with EtOAc (30 mL x 2). The combined organic layers was washed with brine, dried over Mg504, filtered, and concentrated in vacuo. Theresidue was purified by chromatography on silica (petroleum ether: EtOAc = 10: ito 3:1) to give the title compound.
		Intermediate L Step 1 : (EVMethyl 2-(2-methoxyvinyl)benzoate (LI) To a suspension of (methoxymethyl)triphenylphosphonium bromide (9.44 g, 27.4 mmol) in THF (50 mL) was added NaH (1.46 g, 36.6 mmol) at 0 C portion wise. The mixture was stirred at 0 C for 0.5 h. Then a solution of methyl 2-formylbenzoate (3.0 g, 18.3 mmol) in THF (15 mL) was added dropwise and the reaction mixture was stirred at RT for 12 h. The mixture was diluted with water and extracted with EtOAc (30 mL x 2). The combined organic layers was washed with brine, dried over MgSC>4, filtered, and concentrated in vacuo. The residue was purified by chromatography on silica (petroleum ether: EtOAc = 10: 1 to 3: 1) to give the title compound.
		To a suspension of (methoxymethyl)triphenylphosphonium bromide (9.44 g, 27.4 mmol) in THF (50 mL) was added NaH (1.46 g, 36.6 mmol) at 0 C portion wise. The mixture was stirred at 0 C for 0.5 h and then a solution of methyl 2-formylbenzoate (3.0 g, 18.3 mmol) in THF(15 mL) added dropwise and the reaction mixture stirred at room temperature for 12 h. The mixture was diluted with water, extracted with EtOAc (30 mL x 2) and the combined organic layers washed with brine, dried over Mg504, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum ether/EtOAc = 10:1 to 3:1) to give F las an oil.

Reference： [1]Patent: WO2015/18029,2015,A1 .Location in patent: Page/Page column 36; 37
[2]Patent: WO2015/20930,2015,A1 .Location in patent: Page/Page column 42
[3]Patent: WO2016/65585,2016,A1 .Location in patent: Page/Page column 46-47
[4]Patent: WO2016/100157,2016,A2 .Location in patent: Page/Page column 40
[5]Patent: WO2016/100161,2016,A1 .Location in patent: Page/Page column 41
[6]Patent: WO2016/85783,2016,A1 .Location in patent: Page/Page column 37; 38

72
[ 17827-40-6 ]
[ 33670-32-5 ]
[ 51794-08-2 ]

Yield	Reaction Conditions	Operation in experiment
		Example 4. Synthesis of (1,4-Dimethoxy-3-methyl-naphthalen-2-yl)-acetaldehyde Potassium tert-butoxide was added to a 25 ml THF solution of <strong>[33670-32-5]methoxymethyltriphenylphosphonium bromide</strong> (2.6 g, 0.007 mol) at 0C to generate a ylide. After stirring the ylide at this temperature for 30 minutes a solution of 1,4-Dimethoxy-3-methylnaphthalene-2-carbaldehyde (1.0 g, 0.0043 mol) was added dropwise over 15 min. This orange colored reaction mixture was further stirred for 2 hours at which time the TLC indicated the consumption of the starting material. All the contents of the reaction mixture were transferred to a separatory funnel containing EtOAc (150 ml) and the reaction mixture was quenched by the slow addition of brine. The organic layer was separated, and the aqueous layer was extracted with EtOAc (30 ml). The organic layers were combined and washed with brine before drying over MgSO4. The solvent was removed under vacuum to furnish a yellow liquid. The crude product obtained from the reaction was mixed with THF (30 ml) and 10 % aq. HCl (5 ml) and subjected to refluxing. The reaction was found to reach completion in 40 minutes. The THF was removed under vacuum before mixing with EtOAc (100 ml) and the reaction mixture was quenched by addition of saturated NaHCO3. The organic layer was removed under vacuum and the product obtained was found to be solidify at lower temperatures, providing (1,4-Dimethoxy-3-methyl-naphthalen-2-yl)-acetaldehyde as solid. 1H NMR(400 MHz, CDCl3): 9.76 (s, 1H), 8.07 (m, 1H) 7.48 (m, 1H), 7.45 (m, 1H), 7.43 (m, 1H), 3.95 (d, 2H, J = 1.8 Hz) 3.86(s, 3H), 3.84 (s, 3H).
		Example 4 Synthesis of (1,4-Dimethoxy-3-methyl-naphthalen-2-yl)-acetaldehyde Potassium tert-butoxide was added to a 25 ml THF solution of <strong>[33670-32-5]methoxymethyltriphenylphosphonium bromide</strong> (2.6 g, 0.007 mol) at 0 C. to generate a ylide. After stirring the ylide at this temperature for 30 minutes a solution of 1,4-Dimethoxy-3-methyl-naphthalene-2-carbaldehyde (1.0 g, 0.0043 mol) was added dropwise over 15 min. This orange colored reaction mixture was further stirred for 2 hours at which time the TLC indicated the consumption of the starting material. All the contents of the reaction mixture were transferred to a separatory funnel containing EtOAc (150 ml) and the reaction mixture was quenched by the slow addition of brine. The organic layer was separated, and the aqueous layer was extracted with EtOAc (30 ml). The organic layers were combined and washed with brine before drying over MgSO4. The solvent was removed under vacuum to furnish a yellow liquid. The crude product obtained from the reaction was mixed with THF (30 ml) and 10% aq. HCl (5 ml) and subjected to refluxing. The reaction was found to reach completion in 40 minutes. The THF was removed under vacuum before mixing with EtOAc (100 ml) and the reaction mixture was quenched by addition of saturated NaHCO3. The organic layer was removed under vacuum and the product obtained was found to be solidify at lower temperatures, providing (1,4-Dimethoxy-3-methyl-naphthalen-2-yl)-acetaldehyde as solid. 1H NMR (400 MHz, CDCl3): 9.76 (s, 1H), 8.07 (m, 1H) 7.48 (m, 1H), 7.45 (m, 1H), 7.43 (m, 1H), 3.95 (d, 2H, J =1.8 Hz) 3.86 (s, 3H), 3.84 (s, 3H).

Reference： [1]Patent: EP2868658,2015,A1 .Location in patent: Paragraph 0057-0058
[2]Patent: US2015/126763,2015,A1 .Location in patent: Paragraph 0153-0154

73
3-[(triphenylphosphine)gold]pentane-2,4-dione [ No CAS ]
[ 33670-32-5 ]
C₃₈H₃₄AuOP₂⁽¹⁺⁾ [ No CAS ]

Reference： [1]Organometallics,2014,vol. 33,p. 7135 - 7140

74
[ 1308252-53-0 ]
[ 33670-32-5 ]
tert-butyl (E)-3-methoxy-2-(3-methoxyphenyl)acrylate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 10677 - 10682

75
[ 1308252-53-0 ]
[ 33670-32-5 ]
tert-butyl (Z)-3-methoxy-2-(3-methoxyphenyl)acrylate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 10677 - 10682

76
[ 7332-98-1 ]
[ 33670-32-5 ]
tert-butyl (E)-3-methoxy-2-phenylacrylate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 10677 - 10682

77
[ 33670-32-5 ]
(1RS,2SR,4SR)-2-methyl-3-methylidenebicyclo[2.2.1]heptane-2-carbaldehyde [ No CAS ]
(1RS,2RS,4SR)-2-[(Z)-2-methoxyethenyl]-2-methyl-3-methylidenebicyclo[2.2.1]heptane [ No CAS ]

Reference： [1]Chemistry and biodiversity,2014,vol. 11,p. 1470 - 1516

78
[ 33670-32-5 ]
[ 100-52-7 ]
[ 4747-15-3 ]

Reference： [1]Chemical Biology and Drug Design,2015,vol. 86,p. 180 - 189

79
[ 33670-32-5 ]
[ 587-04-2 ]
[ 1428905-31-0 ]

Reference： [1]Chemical Biology and Drug Design,2015,vol. 86,p. 180 - 189

80
[ 33670-32-5 ]
[ 591-31-1 ]
1-methoxy-3-(2-methoxyethenyl)benzene [ No CAS ]

Reference： [1]Chemical Biology and Drug Design,2015,vol. 86,p. 180 - 189

81
[ 33670-32-5 ]
[ 123-11-5 ]
[ 101565-19-9 ]

Reference： [1]Chemical Biology and Drug Design,2015,vol. 86,p. 180 - 189

82
C₁₃H₁₆O₃ [ No CAS ]
[ 33670-32-5 ]
C₁₅H₂₀O₃ [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2016,vol. 358,p. 1229 - 1240

83
[ 695-95-4 ]
[ 33670-32-5 ]
[ 1428757-29-2 ]

Yield	Reaction Conditions	Operation in experiment
32.8%		A mixture of methoxymethyl)triphenyl-phosphine bromide (16.02 g, 46.8 mmol) and THF (100 mL) was placed in an ice/water bath and potassium tert-butoxide (5.25 g, 46.8 mmol) was added. The mixture was then stirred for 15 mins at 0 C. and 90 mins at rt. The mixture was cooled to 0 C. and <strong>[695-95-4]methyl 3-oxocyclobutanecarboxylate</strong> (3 g, 23.41 mmol) was added as a solution in THF (5 mL). The resultant mixture was stirred at rt for 3 hours, then for another three hours at 70 C. The mixture was diluted with EtOAc and washed with water. The organic layer was separated and dried over Na2SO4, and concentrated. The crude product was purified by silica gel column chromatography, (EtOAc/heptane, 0 to 80%) to give product 1.2 g (32.8% yield). 1H NMR (400 MHz, CDCl3): 2.76-2.91 (m, 2H) 2.91-3.01 (m, 2H) 3.07-3.24 (m, 1H) 3.47-3.58 (m, 3H) 3.63-3.74 (m, 4H) 5.80 (quin, J=2.29 Hz, 1H)

Reference： [1]Patent: US2016/166548,2016,A1 .Location in patent: Paragraph 0481

84
(2S,3R,4S,6R)-4-(dimethylamino)-2-(((2R,3R,4R,6R)-4-methoxy-4,6-dimethyl-7-oxo-2-(2,2,5-trimethyl-4-oxo-4H-1,3-dioxin-6-yl)heptan-3-yl)oxy)-6-methyltetrahydro-2H-pyran-3-yl methyl carbonate [ No CAS ]
[ 33670-32-5 ]
C₂₈H₄₇NO₁₀ [ No CAS ]

Reference： [1]Nature,2016,vol. 533,p. 338 - 345

85
C₁₅H₁₇N₃O [ No CAS ]
[ 33670-32-5 ]
C₁₆H₁₉N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%		Synthesis of compound 86.2. To a mixture of (methoxymethyl) triphenylphosphonium bromide (4g, 11.75mmol, l .Oeq) in toluene (30mL) was added KHMDS solution (25ml, 11.75mmol, 3eq) at 0 C. Reaction mixture stirred at 0 C for 1 h and 86.1 (lg, 3.92 mmol, leq) was added. Upon completion of reaction, mixture was transferred into NH4C1 solution, extracted with Et20. Organic layers were combined, washed with brine,, dried over Na2S04 and concentrated under reduced pressure to pressure to obtain crude which was purfified by column chromatography to get pure 86.2 (0.4g, 38%). MS(ES): m/z 270 [M+H]+.

Reference： [1]Patent: WO2017/40757,2017,A1 .Location in patent: Paragraph 00422

86
[ 524945-10-6 ]
[ 33670-32-5 ]
2-methoxy-5-[4-methoxy-3-(3,4,5-trimethoxyphenyl)buta-1,3-dienyl]phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%		General procedure: Under an argon atmosphere, triphenylphosphonium bromide (2.0mmol) with various substitutions was dissolved in dry THF (30mL) and then cooled to -78C. The mixture was slowly added to n-BuLi (2.0mmol), then warmed to room temperature and stirred for 0.5h. Afterward, the mixture was cooled to -78C again, and compound 4 (1.0mmol) in THF solution was added. After being stirred for another 0.5h, the resulting solution was warmed to room temperature and held at that temperature for 12h. The reaction was quenched by the addition of saturated ammonium chloride solution, and extraction was performed using ethyl acetate. The organic layers were dried over anhydrous Na2SO4, and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel to give the target compound 5.

Reference： [1]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 3059 - 3067

87
[ 147610-98-8 ]
[ 33670-32-5 ]
[ 1227610-17-4 ]

Yield	Reaction Conditions	Operation in experiment
81.8%		To a solution (methoxymethyl) triphenylphosphonium bromide (338 mg, 0.87 mmol) in THF (5 mL) was added NaHMDS (1 mL, 1 mmol, 1M in THF) at 0. After stirring for 1h at 0, benzyl 2-oxo-7-azaspiro [3.5] nonane-7-carboxylate (200 mg, 0.73 mmol) was added to the mixture, then the resulting mixture was stirred for 2h at rt. The reaction was quenched with aq NH4Cl (5 mL) and extracted with EtOAc (3 x 10 mL) . The organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The crude product was purified by reverse-phase HPLC (mobile phase: methanol/water (10mM NH4HCO3) ) to give benzyl 2- (methoxymethylene) -7-azaspiro [3.5] nonane-7-carboxylate (180 mg, 81.8) . LRMS m/z (M+H) 302.2 found, 302.2 required.

Reference： [1]Patent: WO2018/68297,2018,A1 .Location in patent: Page/Page column 118

88
[ 108940-96-1 ]
[ 33670-32-5 ]
1,3-dibromo-2-methoxy-5-vinylbenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%		To a cooled (0 C) solution of methoxymethyltriphenylphosphonium Bromide (5.46 g,15.306 mmol) in anhydrous THF (20 mL) was added KOtBu (1.70 g, 15.306 mmol). The mixture was stirred for 20 min at 0 C and then for 1.5 h at room temperature, and a solution of aldehyde 17 (3.0 g, 10.204 mmol) in anhydrous THF (20 mL) was added via cannula at 0 C. T he reaction was allowed to warm to room temperature and stirred 1h. The reaction was filtered through a short silica pad, and the filtrate was then washed with water 10 m L) and brine (20 mL), dried (Na2SO4), and concentrated under reduce dpressure. The residue was purified by silica gel column chromatography (Hexane) as eluent to furnish the styrene, (2.45 g, 8.393 mmol ) as a white solid, 16 yield in 82 %, Rf= 9 0 (in Hexane, silica gel TLC); mp 110-112 C ; 1H NMR (400 MHz, CDCl 3 ) delta 7.52 (s, 1H), 6.53 (dd, J = 17.7, 10.8 Hz, 1H), 5.68 (d, J = 17.7 Hz, 1H), 5.29 (d, J = 11.1 Hz, 1H), 3.88 (s, 3H); 13C NMR (100 MHz, CDCl 3 delta 153.5, 136.3, 133.7, 130.2, 128.5, 118.2, 115.9, 60.7; IR (Neat) 2901, 1676, 1567, 1526, 1452, 1400, 1365, 1244, 975, 862 cm-1 ; HRMS (ESI) m/z : [M + H]+ calcd for C9H9Br2O 290.9015 ; found 290.9009

Reference： [1]Tetrahedron Letters,2019,vol. 60

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CAS No. :	33670-32-5	MDL No. :	MFCD00075442
Formula :	C₂₀H₂₀BrOP	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NOCGROPYCGRERZ-UHFFFAOYSA-M
M.W :	387.25	Pubchem ID :	2773654
Synonyms :

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302+H312+H332-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
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
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
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.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
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.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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. 33670-32-5 ] {[proInfo.proName]}

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[ 33670-32-5 ] Synthesis Path-Upstream 1~1

[ 33670-32-5 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

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