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[ CAS No. 99747-74-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

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Limited Quantity	USD 15-60
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Inaccessible (Haz class 6.1), International	USD 150+
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2D 3D

Chemical Structure| 99747-74-7

Chemical Structure| 99747-74-7

Structure of 99747-74-7 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 99747-74-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 99747-74-7 ]

SDS Specification

Alternatived Products of [ 99747-74-7 ]

Product Details of [ 99747-74-7 ]

CAS No. :	99747-74-7	MDL No. :	MFCD00192340
Formula :	C₁₁H₇F₃O₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WQWUQDVFRYMMCY-UHFFFAOYSA-N
M.W :	276.23	Pubchem ID :	378884
Synonyms :

Calculated chemistry of [ 99747-74-7 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.09
Num. rotatable bonds :	3
Num. H-bond acceptors :	6.0
Num. H-bond donors :	0.0
Molar Refractivity :	59.6
TPSA :	51.75 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.98 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.95
Log Po/w (XLOGP3) :	4.23
Log Po/w (WLOGP) :	5.41
Log Po/w (MLOGP) :	2.91
Log Po/w (SILICOS-IT) :	2.3
Consensus Log Po/w :	3.36

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.43
Solubility :	0.0102 mg/ml ; 0.0000371 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.03
Solubility :	0.00259 mg/ml ; 0.00000939 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.62
Solubility :	0.00657 mg/ml ; 0.0000238 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.59

Safety of [ 99747-74-7 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P321-P363-P405-P501	UN#:	3265
Hazard Statements:	H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 99747-74-7 ]

* 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.

Upstream synthesis route of [ 99747-74-7 ]
Downstream synthetic route of [ 99747-74-7 ]

[ 99747-74-7 ] Synthesis Path-Upstream 1~1

1
[ 99747-74-7 ]
[ 90-14-2 ]

Reference： [1] Journal of the American Chemical Society, 2017, vol. 139, # 25, p. 8621 - 8627

[ 99747-74-7 ] Synthesis Path-Downstream 1~88

1
[ 100-42-5 ]
[ 99747-74-7 ]
[ 28358-65-8 ]
[ 2840-87-1 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 3558 - 3563

2
[ 88-12-0 ]
[ 99747-74-7 ]
[ 141171-87-1 ]
[ 141171-93-9 ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 7421 - 7426

3
[ 108-05-4 ]
[ 99747-74-7 ]
[ 826-74-4 ]
[ 141171-96-2 ]
[ 141171-95-1 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 3558 - 3563
[2]Journal of Organic Chemistry,1992,vol. 57,p. 3558 - 3563

4
[ 598-32-3 ]
[ 99747-74-7 ]
[ 3506-84-1 ]
[ 141171-89-3 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 3558 - 3563

5
[ 111-34-2 ]
[ 99747-74-7 ]
[ 941-98-0 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 3654 - 3655
[2]Journal of Organic Chemistry,1990,vol. 55,p. 3654 - 3655
[3]Journal of Organic Chemistry,1992,vol. 57,p. 3558 - 3563
[4]Journal of Organic Chemistry,1993,vol. 58,p. 7421 - 7426

6
[ 111-34-2 ]
[ 99747-74-7 ]
[ 134576-01-5 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 1808 - 1812
[2]Tetrahedron Letters,1991,vol. 32,p. 1753 - 1756
[3]Journal of Organic Chemistry,1992,vol. 57,p. 1481 - 1486
[4]Journal of Organic Chemistry,2003,vol. 68,p. 6639 - 6645
[5]Journal of the American Chemical Society,2012,vol. 134,p. 443 - 452

7
[ 3622-76-2 ]
[ 99747-74-7 ]
[ 154318-67-9 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 1808 - 1812
[2]Tetrahedron,1994,vol. 50,p. 285 - 304

8
[ 3195-78-6 ]
[ 99747-74-7 ]
[ 141171-88-2 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 3558 - 3563

9
[ 3195-78-6 ]
[ 99747-74-7 ]
[ 141171-88-2 ]
[ 141171-92-8 ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 7421 - 7426

10
[ 7001-18-5 ]
[ 99747-74-7 ]
[ 113337-47-6 ]

Reference： [1]Tetrahedron Letters,1987,vol. 28,p. 3039 - 3042

11
[ 35356-70-8 ]
[ 99747-74-7 ]
[ 131305-18-5 ]

Reference： [1]Tetrahedron,1990,vol. 46,p. 7151 - 7164

12
[ 358-23-6 ]
[ 90-15-3 ]
[ 99747-74-7 ]

Yield	Reaction Conditions	Operation in experiment
96%		General procedure: To a solution of aryl alcohol (1.0 equiv, 0.5 M) in CH2Cl2, was added pyridine (1.2 equiv) at 0 C. The mixture wasallowed to stir at 0 C for 5 min followed by dropwise addition of Tf2O (1.2 equiv). The reaction mixture waswarmed up to room temperature, and allowed to stir until full consumption of starting materials (monitored by TLC).The resulting mixture was quenched with DI water (approx. 20 mL), and extracted with CH2Cl2 (3 × 20 mL). Thecombined organic layer was dried over Na2SO4 and filtered. The filtrate was concentrated under reduced pressureand purified by flash column chromatography.
95%	With pyridine; In dichloromethane; at 0 - 25℃; for 5h;Inert atmosphere;	Synthesis of aryl and heteroaryl triflates. [00147] General Procedure: Under argon, a 100 mL Schlenk flask was charged successively with phenol (10.0 mmol), dry dichloromethane (30 mL) and analytical-grade pyridine (1.2 mL, 15.0 mmol). The solution was cooled to 0 C in an ice bath, and treated with dropwise addition of triflic anhydride (2.0 mL, 12.0 mmol). The resulting mixture was slowly warmed up to 25 o C and kept stirred for additional 5 hours. At the end of the reaction (monitored by TLC), the mixture was passed through a pad of silica gel (-80 g) with 1 :30 Ethyl acetate hexane washings, until no more aryl triflate was eluted out. The filtrate was concentrated on a rotary evaporator and the residue was subjected to flash silica gel chromatography to afford the desired aryl triflate. [00148] 1-Naphthyl trifluoromethanesulfonate [99747-74-7]. [00149] Flash chromatography (60: 1 hexane EtOAc) yielded the target compound as colorless oil (95%). Ή NMR (300 MHz, CDC13): δ 8.09 (d, J = 8.3 Hz, 1H), 7.94-7.85 (m, 2H), 7.69- 7.58 (m, 2H), 7.53-7.46 (m, 2H).
88.34%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 10℃; for 2h;	alpha-Naphthol (4 g, 27.74 mmol) was dissolved in DCM (200 mL) in a 3 neck flask. The reaction was cooled to 10C in a water bath. N-ethyl-N-isopropylpropan-2-amine (4.846 ml, 27.74 mmol) and trifluoromethanesulfonic anhydride (4.668 ml, 27.74 mmol) were added to the solution dropwise. The reaction was stirred at 10C for 2 hours. TLC (25% EtOAc, UV vis) showed reaction complete. The organics were with water (2X) and brine (2X). The organics were dried over MgS04 and concentrated in vacuo. The concentrate was purified using normal phase chromatography on the CombiFlash (0%-12% EtOAc :Hexanes). All fractions containing clean product were combined and conentrated in vacuo to give naphthalen-l-yl trifluoromethanesulfonate (6.77 g, 24.51 mmol, 88.34 % yield).

88.34%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 10℃; for 2h;	alpha-Naphthol (4 g, 27.74 mmol) was dissolved in DCM (200 mL) in a 3 neck flask. The reaction was cooled to 10° C. in a water bath. N-ethyl-N-isopropylpropan-2-amine (4.846 ml, 27.74 mmol) and trifluoromethanesulfonic anhydride (4.668 ml, 27.74 mmol) were added to the solution dropwise. The reaction was stirred at 10° C. for 2 hours. TLC (25% EtOAc, UV vis) showed reaction complete. The organics were with water (2 ) and brine (2 ). The organics were dried over MgSO 4 and concentrated in vacuo. The concentrate was purified using normal phase chromatography on the CombiFlash (0%-12% EtOAc:Hexanes). All fractions containing clean product were combined and concentrated in vacuo to give naphthalen-1-yl trifluoromethanesulfonate (6.77 g, 24.51 mmol, 88.34% yield).
88.34%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 10℃; for 2h;	alpha-Naphthol (4 g, 27.74 mmol) was dissolved in DCM (200 mL) in a 3 neck flask. The reaction was cooled to l0C in a water bath. N-ethyl-N-isopropylpropan-2-amine (4.846 ml, 27.74 mmol) and trifluoromethanesulfonic anhydride (4.668 ml, 27.74 mmol) were added to the solution dropwise. The reaction was stirred at 10C for 2 hours. TLC (25% EtOAc, UV vis) showed reaction complete. The organics were with water (2X) and brine (2X). The organics were dried over MgS04 and concentrated in vacuo. The concentrate was purified using normal phase chromatography on the CombiFlash (0%-l2% EtOAc:Hexanes). All fractions containing clean product were combined and conentrated in vacuo to give naphthalen-l -yl trifluoromethanesulfonate (6.77 g, 24.51 mmol, 88.34 % yield).
88.34%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 10℃; for 2h;	alpha-Naphthol (4 g, 27.74 mmol) was dissolved in DCM (200 L) in a 3 neck flask. The reaction was cooled to 10C in a water bath. N- ethyl-N-isopropylpropan-2-amine (4.846 ml, 27.74 mmol) and trifluoromethanesulfonic anhydride (4.668 ml, 27.74 mmol) were added to the solution dropwise. I he reaction was stirred at 10C for 2 hours. TLC (25% EtOAc, UV vis) showed reaction complete. The organics were with water (2X) and brine (2X). The organics were dried over MgS04 and concentrated in vacuo. The concentrate was purified using normal phase chromatography on the CombiFlash (0%-12% EtOAc:Hexanes). All fractions containing clean product were combined and concentrated in vacuo to give naphthalen-l-yl trifluoromethanesulfonate (6.77 g, 24.51 mmol, 88.34 % yield).
	With pyridine; In dichloromethane; at 0 - 20℃; for 5h;	General procedure: To a solution of phenol (1.0 equiv) and pyridine (2.0 equiv) in DCM was added dropwise trifluoromethanesulfonic anhydride (1.2 equiv) at 0 C. Then the mixture was warmed to room temperature and stirred for 5 hours. The reaction was quenched with HCl (1M). The mixture was diluted with ethyl acetate. The organic layer was washed with sat. NaHCO3, water, brine successively and concentrated under reduced pressure. The crude residue was purified with a flash column chromatography.

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 4983 - 4987
[2]European Journal of Organic Chemistry,2021,vol. 2021,p. 309 - 313
[3]Tetrahedron,2018,vol. 74,p. 3325 - 3328
[4]Journal of the American Chemical Society,2011,vol. 133,p. 15882 - 15885
[5]Patent: WO2013/28132,2013,A1 .Location in patent: Paragraph 00147-00149
[6]Synthesis,2005,p. 547 - 550
[7]Chemical Communications,2013,vol. 49,p. 9425 - 9427
[8]Research on Chemical Intermediates,2013,vol. 39,p. 321 - 345
[9]Journal of the American Chemical Society,1987,vol. 109,p. 5478
[10]Angewandte Chemie - International Edition,2012,vol. 51,p. 5915 - 5919
[11]Patent: WO2017/201161,2017,A1 .Location in patent: Paragraph 0258
[12]Patent: US2019/144444,2019,A1 .Location in patent: Paragraph 0430-0431
[13]Patent: WO2020/47192,2020,A1 .Location in patent: Paragraph 0292
[14]Patent: WO2020/146613,2020,A1 .Location in patent: Paragraph 0288
[15]Bulletin de la Societe Chimique de France,1995,vol. 132,p. 499 - 508
[16]Journal of Organic Chemistry,1990,vol. 55,p. 350 - 353
[17]Tetrahedron,2007,vol. 63,p. 1270 - 1280
[18]Chemistry - A European Journal,2007,vol. 13,p. 1432 - 1441
[19]Organic and Biomolecular Chemistry,2017,vol. 15,p. 9903 - 9909
[20]Journal of Organic Chemistry,2004,vol. 69,p. 1137 - 1143
[21]Chinese Journal of Chemistry,2018,vol. 36,p. 1031 - 1034
[22]Australian Journal of Chemistry,1988,vol. 41,p. 1711 - 1716
[23]Organometallics,2017,vol. 36,p. 1662 - 1672
[24]Journal of the Chemical Society. Chemical communications,1987,p. 904 - 905
[25]Journal of Organic Chemistry,1999,vol. 64,p. 3266 - 3270
[26]Tetrahedron,1999,vol. 55,p. 14479 - 14490
[27]Chemistry - A European Journal,2007,vol. 13,p. 5937 - 5943
[28]Tetrahedron,2009,vol. 65,p. 1951 - 1956
[29]Journal of Organic Chemistry,2012,vol. 77,p. 10468 - 10472
[30]Angewandte Chemie - International Edition,2015,vol. 54,p. 12134 - 12138
Angew. Chem.,2015,vol. 127,p. 12302 - 12306,5
[31]Organic Letters,2019,vol. 21,p. 36 - 39
[32]Tetrahedron,2019,vol. 75,p. 4186 - 4191
[33]Organic and Biomolecular Chemistry,2019,vol. 17,p. 5916 - 5919
[34]Organometallics,2020,vol. 39,p. 2189 - 2196
[35]Journal of Organic Chemistry,2021,vol. 86,p. 466 - 474
[36]European Journal of Organic Chemistry,2021,vol. 2021,p. 4616 - 4619
[37]Journal of Organic Chemistry,2021,vol. 86,p. 12318 - 12325

13
[ 201230-82-2 ]
[ 38858-74-1 ]
[ 99747-74-7 ]
[ 127931-52-6 ]

Reference： [1]Tetrahedron,1991,vol. 47,p. 3935 - 3946

14
[ 201230-82-2 ]
[ 60068-19-1 ]
[ 99747-74-7 ]
[ 127931-49-1 ]

Reference： [1]Tetrahedron,1991,vol. 47,p. 3935 - 3946

15
[ 201230-82-2 ]
[ 99747-74-7 ]
[ 86-55-5 ]

Reference： [1]Tetrahedron Letters,1992,vol. 33,p. 3939 - 3942

16
[ 201230-82-2 ]
[ 58207-97-9 ]
[ 99747-74-7 ]
[ 89244-73-5 ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 1557

17
[ 201230-82-2 ]
[ 82101-76-6 ]
[ 99747-74-7 ]
[ 22422-69-1 ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 1557

18
[ 201230-82-2 ]
[ 99747-74-7 ]
[ 594-27-4 ]
[ 941-98-0 ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 1557

19
[ 201230-82-2 ]
[ 99747-74-7 ]
[ 55723-10-9 ]
[ 112533-22-9 ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 1557

20
[ 99747-74-7 ]
[ 91-20-3 ]

Reference： [1]Tetrahedron Letters,1987,vol. 28,p. 1381 - 1384
[2]Journal of Organic Chemistry,1990,vol. 55,p. 350 - 353
[3]Tetrahedron,1999,vol. 55,p. 14479 - 14490
[4]Organic Letters,2020,vol. 22,p. 5582 - 5588

21
[ 99747-74-7 ]
[ 107-18-6 ]
[ 33244-71-2 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 3558 - 3563
[2]Angewandte Chemie - International Edition,2011,vol. 50,p. 4983 - 4987
[3]Angewandte Chemie - International Edition,2020,vol. 59,p. 10814 - 10818
Angew. Chem.,2020,vol. 132,p. 10906 - 10910,5

22
[ 99747-74-7 ]
[ 107-13-1 ]
[ 56477-58-8 ]
[ 111686-30-7 ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 7421 - 7426

23
[ 99747-74-7 ]
[ 107-13-1 ]
[ 70067-70-8 ]
[ 141171-98-4 ]
[ 93863-65-1 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 3558 - 3563

24
[ 99747-74-7 ]
[ 79-06-1 ]
[ 107624-88-4 ]
2-(naphthalen-1-yl)acrylamide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 7421 - 7426

25
[ 99747-74-7 ]
[ 292638-85-8 ]
[ 22837-81-6 ]

Reference： [1]Journal of Organic Chemistry,1992,vol. 57,p. 3558 - 3563

26
[ 99747-74-7 ]
[ 292638-85-8 ]
[ 22837-81-6 ]
[ 335208-46-3 ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 7421 - 7426

27
[ 99747-74-7 ]
[ 604-53-5 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 261 - 274
[2]Journal of Organic Chemistry,1997,vol. 62,p. 261 - 274
[3]Journal of Organic Chemistry,1997,vol. 62,p. 261 - 274

28
[ 201230-82-2 ]
[ 99747-74-7 ]
[ 2243-81-4 ]

Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 2835 - 2838
[2]Tetrahedron Letters,1998,vol. 39,p. 2835 - 2838

29
[ 99747-74-7 ]
[ 134-32-7 ]

Reference： [1]Journal of the American Chemical Society,1998,vol. 120,p. 7651 - 7652
[2]Tetrahedron,2009,vol. 65,p. 1951 - 1956

30
[ 124-38-9 ]
[ 99747-74-7 ]
[ 86-55-5 ]

Reference： [1]European Journal of Organic Chemistry,1998,p. 1811 - 1821
[2]Organic Letters,2019,vol. 21,p. 4632 - 4637
[3]Organic Letters,2019,vol. 21,p. 4486 - 4489

31
[ 99747-74-7 ]
[ 25015-63-8 ]
[ 91-20-3 ]
[ 68716-52-9 ]

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 164 - 168

32
[ 556-56-9 ]
[ 99747-74-7 ]
[ 2489-86-3 ]

Reference： [1]Journal of Organic Chemistry,2002,vol. 67,p. 8265 - 8268
[2]Chemistry - An Asian Journal,2011,vol. 6,p. 2147 - 2157

33
[ 99747-74-7 ]
[ 14296-00-5 ]
[ 1127-76-0 ]

Reference： [1]Synthesis,2003,p. 302 - 306

34
[ 99747-74-7 ]
5-tri-n-butylstannyl-2-furannecarbaldehyde [ No CAS ]
[ 51792-36-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 663 - 673

35
[ 99747-74-7 ]
Et₃Al [ No CAS ]
[ 91-20-3 ]
[ 1127-76-0 ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 8593 - 8595

36
[ 591-87-7 ]
[ 99747-74-7 ]
[ 2489-86-3 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 1165 - 1168
[2]Advanced Synthesis and Catalysis,2004,vol. 346,p. 1641 - 1645
[3]Chemistry - A European Journal,2007,vol. 13,p. 5197 - 5206

37
[ 25240-59-9 ]
[ 99747-74-7 ]
[ 68716-52-9 ]

Reference： [1]Synthesis,2005,p. 547 - 550

38
[ 99747-74-7 ]
[ 75336-86-6 ]
[ 439081-68-2 ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 2548 - 2558

39
[ 99747-74-7 ]
[ 74879-18-8 ]
[ 439081-70-6 ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 2548 - 2558

40
[ 99747-74-7 ]
[ 731852-88-3 ]
6-naphthalen-1-yl-3,4-dihydro-2H-pyridine-1-carboxylic acid benzyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 7324 - 7330

41
[ 99747-74-7 ]
[ 98-80-6 ]
[ 605-02-7 ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 4101 - 4111
[2]Journal of Organic Chemistry,2006,vol. 71,p. 685 - 692
[3]Chemistry - A European Journal,2007,vol. 13,p. 5937 - 5943
[4]Organic Letters,2013,vol. 15,p. 3950 - 3953
[5]Organometallics,2017,vol. 36,p. 1662 - 1672

42
[ 99747-74-7 ]
[ 107035-97-2 ]
[ 28530-21-4 ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 2210 - 2211

43
Diethyl phosphonate [ No CAS ]
[ 99747-74-7 ]
[ 25944-75-6 ]

Reference： [1]Angewandte Chemie - International Edition,2006,vol. 45,p. 7248 - 7251

44
[ 1191-99-7 ]
[ 99747-74-7 ]
2-(1-naphthyl)-2,3-dihydrofuran [ No CAS ]
(R)-2-(naphthalen-1-yl)-2,5-dihydrofuran [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 941 - 946
[2]Chemistry - A European Journal,2007,vol. 13,p. 3296 - 3304
[3]Chemistry - A European Journal,2010,vol. 16,p. 3434 - 3440

45
[ 99747-74-7 ]
[ 100-46-9 ]
[ 6361-33-7 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 1218 - 1224

46
[ 99747-74-7 ]
[ 594-27-4 ]
[ 941-98-0 ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 1557

47
[ 82101-76-6 ]
[ 99747-74-7 ]
[ 22422-69-1 ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 1557

48
[ 58207-97-9 ]
[ 99747-74-7 ]
[ 89244-73-5 ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 1557
[2]Journal of the American Chemical Society,1988,vol. 110,p. 1557

49
1-(tri-n-butylstannyl)-1-propenyl 3-tetrahydropyranyl ether [ No CAS ]
[ 99747-74-7 ]
(E)-1-naphthalenyl-4-tetrahydropyranyloxy-2-buten-1-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 1557
[2]Journal of the American Chemical Society,1988,vol. 110,p. 1557
[3]Journal of the American Chemical Society,1988,vol. 110,p. 1557

50
indium(III) benzenethiolate [ No CAS ]
[ 99747-74-7 ]
[ 7570-98-1 ]

Yield	Reaction Conditions	Operation in experiment
95%		Preparation of 1-phenylnaphthylsulfide [formula 7]A solution of palladium acetate (4.5 mg, 0.02 mmol) and Xantphos (12.7 mg, 0.022 mmol) in DMF (1 mL) was stirred for 5 minutes under a nitrogen atmosphere. To this solution was added 1-naphthyltrifluoromethanesulfonate (138. lmg, 0.5 mmol) dissolved in 0.5 mL of DMF and then the reaction mixture was stirred for 10 minutes at room temperature. In(SPh)3 (74mg, 0.167 mmol) in DMF ( 1 mL) and diisopropylethyl amine (65 mg, 0.5 mmol) were added to this reaction mixture. The reaction mixture was maintained for 2 hours at 100 degrees Celsius. The solution was cooled to room temperature and then 1 mL of hydrochloric acid (5 % of aqueous solution) was added to stop the reaction. The crude product was extracted with diethyl ether (15 mL, 3 times) and sequentially washed with 10 mL of water, a saturated NaHCO3 (10 mL) solution and a saturated NaCl (20 mL) solution. The extracted organic compound was dried over anhydrous MgSO4 and then filtered. After evaporation of solvents, the crude product was purified by column chromatography to give 1-phenylnaphthylsulfide (112 mg, 95 %) ( formula7).1H-NMR (300 MHz, CDCl3) δ 8.40-8.38(m, IH), 7.90~7.85(m, 2H), 7.67(d, J=7.2Hz, IH),7.52- 7.49(m, 2H), 7.43(t, J=8.4Hz, IH), 7.25-7.17(m, 5H).

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 7413 - 7416
[2]Patent: WO2009/69888,2009,A2 .Location in patent: Page/Page column 10

51
[ 89033-18-1 ]
[ 99747-74-7 ]
[ 1127562-68-8 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 3291 - 3306

52
[ 2423-65-6 ]
[ 99747-74-7 ]
2-(naphthalen-1-yl)pyrazine 1-oxide [ No CAS ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 4977 - 4983

53
[ 18668-68-3 ]
[ 99747-74-7 ]
[ 46267-11-2 ]

Reference： [1]Chemical Communications,2009,p. 1873 - 1875

54
[ 99747-74-7 ]
[ 321-38-0 ]

Yield	Reaction Conditions	Operation in experiment
76%	With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; di-tert-butyl(2',4',6'-triisopropyl-3,6-dimethoxy-[1,1':3',1''-terphenyl]-2-yl)phosphane; cesium fluoride; In toluene; at 100℃; for 18h;Sealed tube; Inert atmosphere;	To an oven-dried flask equipped with a magnetic stir bar was added 3.9 mg (0.0075 mmol) of [Pd(cinnamy)Cl]2, 8.4 mg (0.015 mmol) of 25OMe-TIP-tBu*Phine, 151.9 mg (1.0 mmol) of CsF, 138.1 mg (0.5 mmol) of 1-naphthyl-triflate and 2.5 mL of anhydrous toluene. The flask was crimp sealed with a Teflon-lined cap under argon, heated to 100 C. in an oil bath and vigorously stirred for 18 h. Upon reaction completion, the mixture was cooled to room temperature, diluted with EtOAc and filtered through a pad of Celite. Several portions of EtOAc were used to rinse the Celite and the filtrate was consolidated then concentrated to dryness. The crude residue was purified by column-chromatography on silica gel using petroleum ether as the eluent to give the pure product as a colorless liquid (56 mg, 76%). 1H NMR (600 MHz, Chloroform-d) δ 8.18-8.11 (m, 1H), 7.91-7.85 (m, 1H), 7.65 (d, J=8.3 Hz, 1H), 7.59-7.53 (m, 2H), 7.41 (td, J=8.0, 5.4 Hz, 1H), 7.17 (ddd, J=10.7, 7.6, 1.0 Hz, 1H). 13C NMR (151 MHz, Chloroform-d) δ 159.59, 134.87, 127.51, 127.48, 126.79, 126.15, 126.14, 125.60, 125.54, 123.63, 123.60, 120.53, 120.49, 109.45, 109.32. 19F NMR (280 MHz, Chloroform-d) δ-124.6.
52%	With cesium fluoride;5-(di-tert-butylphosphino)-1′, 3′, 5′-triphenyl-1′H-[1,4′]bipyrazole; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; In toluene; at 150℃; for 18h;Sealed tube;Product distribution / selectivity;	Example 2 Synthesis of Fluoroarenes from Trifluoromethanesulfonates 1-Fluoronaphthalene. To an oven-dried screw-cap test tube equipped with a magnetic stir bar was added <strong>[99747-74-7]1-naphthyl trifluoromethanesulfonate</strong> (25 μL, 0.127 mmol, 1.0 eq), cesium fluoride (29.3 mg, 0.191 mmol, 1.5 eq), [Pd(cinnamyl)Cl]2 (3.3 mg, 7 μmol, 5 mol %) and L1 (6.6 mg, 13 μmol, 10 mol %) inside a glovebox. See . The test tube was then sealed off with a screw-cap and taken out of the glovebox. Toluene (2 mL) was promptly added via syringe in such a manner that any reagent on the side of the test tube was washed down to the bottom of the tube. The test tube was then placed in a pre-heated oil bath at the indicated temperature and it was stirred for 18 h. After cooling to room temperature, dodecane (28.9 μL) was added, the reaction was diluted with EtOAc (~1 mL) and the resulting mixture was filtered through a plug of Celite and it was analyzed by GC.

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 15757 - 15766
[2]Patent: US2016/207034,2016,A1 .Location in patent: Paragraph 0553
[3]Patent: US2011/15401,2011,A1 .Location in patent: Page/Page column 19
[4]Journal of Organic Chemistry,2013,vol. 78,p. 4184 - 4189
[5]Patent: US2011/15401,2011,A1 .Location in patent: Page/Page column 17-18
[6]Science,2009,vol. 325,p. 1661 - 1664
[7]Angewandte Chemie - International Edition,2011,vol. 50,p. 8900 - 8903
[8]Journal of the American Chemical Society,2011,vol. 133,p. 18106 - 18109

55
[ 99747-74-7 ]
[ 58521-27-0 ]
[ 14743-46-5 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 1000 - 1003

56
[ 1208611-64-6 ]
[ 99747-74-7 ]
[ 1239886-94-2 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 1486 - 1489

57
[ 99747-74-7 ]
[ 199604-10-9 ]
[ 218-38-2 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 1486 - 1489

58
[ 99747-74-7 ]
[ 1071-36-9 ]
[ 132-75-2 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 4470 - 4474

59
[ 99747-74-7 ]
[ 72658-10-7 ]
[ 1334591-58-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With zinc(II) fluoride; (R)-2-(dicyclohexylphosphino)-2'-(2-naphthylmethoxy)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl; lithium acetate; bis(dibenzylideneacetone)-palladium(0); at 50℃; for 24h;Inert atmosphere; Sealed tube;	[00198] Typical procedure of the asymmetric arylation of silyl ketene acetals using Pd(dba)2 [00199] Synthesis of {S)-tert-bv y 2-(l '-naphthyl)propionate. In an argon-filled glove box, a dry 4 mL vial was charged with Pd(dba)2 (5.8 mg, 0.010 mmol), (/?)-2-(dicyclohexyl- phosphino)-2'-(2-naphthylmethoxy)-5,5',6,6,,7,7',8,8'-octahydro-l,r-binaphthyl L6 (7.4 mg, 0 0.012 mmol) and 1.0 mL of dry α,α,α-trifluorotoluene. After stirring at 25 C for 30 minutes, the mixture was treated successively with anhydrous LiOAc (66 mg, 1.0 mmol), ZnF2 co- activator (10 mg, 0.10 mmol), <strong>[99747-74-7]1-naphthyl trifluoromethanesulfonate</strong> (138 mg, 0.50 mmol), (1£)- l-½r/-butoxy-l-(trimethylsiloxy)propene (152 mg, 0.75 mmol) and GC standard n-dodecane (50 0 uL). The vial was capped tightly and the mixture was heated with stirring in a 50 C (internal 0 temperature) heating block. After aryl triflate was fully consumed within 24 hours at 50 C o (monitored by GC and TLC), the reaction mixture was cooled to 25 C and filtered through a pad of silica gel with diethyl ether washings (20 mL). The filtrate was concentrated and the residue was purified by flash silica gel chromatography with ethyl acetate/hexane (1:50) as eluent to give the title compound as colorless oil (127 mg, 99% yield). The ee of the purified products was determined to be 92% by chiral HPLC analysis (Daicel CHIRALCEL OJ-H; hexanes: /-PrOH = 98:2; detection wavelengths = 254 nm and 227 nm; flow rate = 0.5 mL/min). TR = 13.2 min (major) and 15.8 min (minor). [a]20D = +95.5 (c = 2.2, CHC13). 1H NMR (400 MHz, CDC13): δ 8.11 (d, J = 8.4 Hz, 1H), 7.87 (dd, J = 7.8, 1.8 Hz, 1H), 7.78-7.75 (m, 1H), 7.56-7.42 (m, 4H), 4.42 (q, J = 7.2 Hz, 1H), 1.61 (d, J = 7.2 Hz, 3H), 1.42 (s, 9H). 13C NMR (100 MHz, CDC13): 5 174.4, 137.7, 134.2, 131.7, 129.1, 127.6, 126.2, 125.77, 125.69, 124.4, 123.6, 80.9, 42.5, 28.1, 18.3. GCMS (EI): calcd for Ci7H20O2 M: 256.15. Found: 256.07.

Reference： [1]Patent: WO2013/28132,2013,A1 .Location in patent: Paragraph 00198-00199
[2]Journal of the American Chemical Society,2011,vol. 133,p. 15882 - 15885

60
[ 363-72-4 ]
[ 99747-74-7 ]
[ 14743-46-5 ]

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 2289 - 2299

61
[ 99747-74-7 ]
[ 931-88-4 ]
[ 1461737-21-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	With (R)-7-bis(m-xylyl)phosphino-7-bis(3,5-dimethylphenyl)phosphinyl-1,1'-spirobiindane; N-ethyl-N,N-diisopropylamine; bis(dibenzylideneacetone)-palladium(0); In 1,4-dioxane; at 27℃; for 60h;Inert atmosphere; Glovebox;	General procedure: A. Examples of asymmetric Heck reaction of cyclic olefinsGeneral procedureIn an argon-filled glove box, Pd(dba)2 (7.2 mg, 0.013 mmol) and (R)-Xyl-SDP(O) (10.8 mg, 5 0.015 mmol) were stirred in dry 1,4-dioxane (0.50 mL) for 10 to 20 mm in a 4-mL vial, followedby addition of n-C14H30 (25 tL, GC internal standard), aryl triflate (0.50 mmol), Nethyldiisopropylamine (170 iL, 1.0 mmol, 2 equiv) and cyclic olefin (2.0 mmol, 4 quiv). The mixture was vigorously stirred in a preheated oil bath at a set temperature until the aryl triflate was fully consumed (monitored by GC). The reaction mixture was cooled to RT and subjected to10 flash chromatography (basic alumina, Brockmann grade I, pentane/Et20) to give the purified product. Silica gel may be also used for purification. The olefinic selectivity of Heck isomers in the crude mixture was determined by GC. The ee of the purified product was determined by chiral HPLC analysis with Daicel Chiralcel columns or by chiral GC analysis. Racemic products were prepared using the racemic ligand to facilitate determination of ee.

Reference： [1]Chemical Communications,2013,vol. 49,p. 9425 - 9427
[2]Patent: WO2014/196930,2014,A1 .Location in patent: Page/Page column 39; 40

62
[ 5417-32-3 ]
[ 99747-74-7 ]
[ 1461737-24-5 ]

Yield	Reaction Conditions	Operation in experiment
	With (R)-7-bis(m-xylyl)phosphino-7-bis(3,5-dimethylphenyl)phosphinyl-1,1'-spirobiindane; lithium carbonate; bis(dibenzylideneacetone)-palladium(0); In 1,4-dioxane; at 50℃; for 44h;Inert atmosphere; Glovebox;	General procedure: A. Examples of asymmetric Heck reaction of cyclic olefinsGeneral procedureIn an argon-filled glove box, Pd(dba)2 (7.2 mg, 0.013 mmol) and (R)-Xyl-SDP(O) (10.8 mg, 5 0.015 mmol) were stirred in dry 1,4-dioxane (0.50 mL) for 10 to 20 mm in a 4-mL vial, followedby addition of n-C14H30 (25 tL, GC internal standard), aryl triflate (0.50 mmol), Nethyldiisopropylamine (170 iL, 1.0 mmol, 2 equiv) and cyclic olefin (2.0 mmol, 4 quiv). The mixture was vigorously stirred in a preheated oil bath at a set temperature until the aryl triflate was fully consumed (monitored by GC). The reaction mixture was cooled to RT and subjected to10 flash chromatography (basic alumina, Brockmann grade I, pentane/Et20) to give the purified product. Silica gel may be also used for purification. The olefinic selectivity of Heck isomers in the crude mixture was determined by GC. The ee of the purified product was determined by chiral HPLC analysis with Daicel Chiralcel columns or by chiral GC analysis. Racemic products were prepared using the racemic ligand to facilitate determination of ee.

Reference： [1]Chemical Communications,2013,vol. 49,p. 9425 - 9427
[2]Patent: WO2014/196930,2014,A1 .Location in patent: Page/Page column 41

63
[ 58101-60-3 ]
[ 99747-74-7 ]
[ 1499187-57-3 ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 11758 - 11760

64
[ 225931-80-6 ]
[ 1160861-53-9 ]
[ 99747-74-7 ]
C₄₁H₅₆O₂PPd⁽¹⁺⁾*CF₃O₃S^(1-) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 15757 - 15766

65
[ 99747-74-7 ]
[ 6972-81-2 ]
[ 1461737-23-4 ]
C₁₇H₁₇NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (R)-7-bis(m-xylyl)phosphino-7-bis(3,5-dimethylphenyl)phosphinyl-1,1'-spirobiindane; N-ethyl-N,N-diisopropylamine; bis(dibenzylideneacetone)-palladium(0); In 1,4-dioxane; at 50℃; for 44h;Inert atmosphere; Glovebox;	General procedure: A. Examples of asymmetric Heck reaction of cyclic olefinsGeneral procedureIn an argon-filled glove box, Pd(dba)2 (7.2 mg, 0.013 mmol) and (R)-Xyl-SDP(O) (10.8 mg, 5 0.015 mmol) were stirred in dry 1,4-dioxane (0.50 mL) for 10 to 20 mm in a 4-mL vial, followedby addition of n-C14H30 (25 tL, GC internal standard), aryl triflate (0.50 mmol), Nethyldiisopropylamine (170 iL, 1.0 mmol, 2 equiv) and cyclic olefin (2.0 mmol, 4 quiv). The mixture was vigorously stirred in a preheated oil bath at a set temperature until the aryl triflate was fully consumed (monitored by GC). The reaction mixture was cooled to RT and subjected to10 flash chromatography (basic alumina, Brockmann grade I, pentane/Et20) to give the purified product. Silica gel may be also used for purification. The olefinic selectivity of Heck isomers in the crude mixture was determined by GC. The ee of the purified product was determined by chiral HPLC analysis with Daicel Chiralcel columns or by chiral GC analysis. Racemic products were prepared using the racemic ligand to facilitate determination of ee.

Reference： [1]Patent: WO2014/196930,2014,A1 .Location in patent: Page/Page column 40; 41

66
[ 99747-74-7 ]
[ 142-29-0 ]
4-(1-naphthyl)cyclopentene [ No CAS ]
[ 1461737-02-9 ]

Yield	Reaction Conditions	Operation in experiment
	With (R)-7-bis(m-xylyl)phosphino-7-bis(3,5-dimethylphenyl)phosphinyl-1,1'-spirobiindane; N-ethyl-N,N-diisopropylamine; bis(dibenzylideneacetone)-palladium(0); In 1,4-dioxane; at 50℃; for 2.5h;Inert atmosphere; Glovebox;	General procedure: A. Examples of asymmetric Heck reaction of cyclic olefinsGeneral procedureIn an argon-filled glove box, Pd(dba)2 (7.2 mg, 0.013 mmol) and (R)-Xyl-SDP(O) (10.8 mg, 5 0.015 mmol) were stirred in dry 1,4-dioxane (0.50 mL) for 10 to 20 mm in a 4-mL vial, followedby addition of n-C14H30 (25 tL, GC internal standard), aryl triflate (0.50 mmol), Nethyldiisopropylamine (170 iL, 1.0 mmol, 2 equiv) and cyclic olefin (2.0 mmol, 4 quiv). The mixture was vigorously stirred in a preheated oil bath at a set temperature until the aryl triflate was fully consumed (monitored by GC). The reaction mixture was cooled to RT and subjected to10 flash chromatography (basic alumina, Brockmann grade I, pentane/Et20) to give the purified product. Silica gel may be also used for purification. The olefinic selectivity of Heck isomers in the crude mixture was determined by GC. The ee of the purified product was determined by chiral HPLC analysis with Daicel Chiralcel columns or by chiral GC analysis. Racemic products were prepared using the racemic ligand to facilitate determination of ee.

Reference： [1]Patent: WO2014/196930,2014,A1 .Location in patent: Page/Page column 28

67
[ 1191-99-7 ]
[ 99747-74-7 ]
2-(1-naphthyl)-2,3-dihydrofuran [ No CAS ]
(S)-2-(naphthalen-1-yl)-2,5-dihydrofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (R)-7-bis(m-xylyl)phosphino-7-bis(3,5-dimethylphenyl)phosphinyl-1,1'-spirobiindane; N-ethyl-N,N-diisopropylamine; bis(dibenzylideneacetone)-palladium(0); In 1,4-dioxane; at 50℃; for 4h;Inert atmosphere; Glovebox;	General procedure: A. Examples of asymmetric Heck reaction of cyclic olefinsGeneral procedureIn an argon-filled glove box, Pd(dba)2 (7.2 mg, 0.013 mmol) and (R)-Xyl-SDP(O) (10.8 mg, 5 0.015 mmol) were stirred in dry 1,4-dioxane (0.50 mL) for 10 to 20 mm in a 4-mL vial, followedby addition of n-C14H30 (25 tL, GC internal standard), aryl triflate (0.50 mmol), Nethyldiisopropylamine (170 iL, 1.0 mmol, 2 equiv) and cyclic olefin (2.0 mmol, 4 quiv). The mixture was vigorously stirred in a preheated oil bath at a set temperature until the aryl triflate was fully consumed (monitored by GC). The reaction mixture was cooled to RT and subjected to10 flash chromatography (basic alumina, Brockmann grade I, pentane/Et20) to give the purified product. Silica gel may be also used for purification. The olefinic selectivity of Heck isomers in the crude mixture was determined by GC. The ee of the purified product was determined by chiral HPLC analysis with Daicel Chiralcel columns or by chiral GC analysis. Racemic products were prepared using the racemic ligand to facilitate determination of ee.

Reference： [1]Patent: WO2014/196930,2014,A1 .Location in patent: Page/Page column 34

68
[ 628-92-2 ]
[ 99747-74-7 ]
[ 1461737-20-1 ]
(R)-3-(1-naphthyl)cyclohept-1-ene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (R)-7-bis(m-xylyl)phosphino-7-bis(3,5-dimethylphenyl)phosphinyl-1,1'-spirobiindane; N-ethyl-N,N-diisopropylamine; bis(dibenzylideneacetone)-palladium(0); In 1,4-dioxane; at 50℃; for 14h;Inert atmosphere; Glovebox;	General procedure: A. Examples of asymmetric Heck reaction of cyclic olefinsGeneral procedureIn an argon-filled glove box, Pd(dba)2 (7.2 mg, 0.013 mmol) and (R)-Xyl-SDP(O) (10.8 mg, 5 0.015 mmol) were stirred in dry 1,4-dioxane (0.50 mL) for 10 to 20 mm in a 4-mL vial, followedby addition of n-C14H30 (25 tL, GC internal standard), aryl triflate (0.50 mmol), Nethyldiisopropylamine (170 iL, 1.0 mmol, 2 equiv) and cyclic olefin (2.0 mmol, 4 quiv). The mixture was vigorously stirred in a preheated oil bath at a set temperature until the aryl triflate was fully consumed (monitored by GC). The reaction mixture was cooled to RT and subjected to10 flash chromatography (basic alumina, Brockmann grade I, pentane/Et20) to give the purified product. Silica gel may be also used for purification. The olefinic selectivity of Heck isomers in the crude mixture was determined by GC. The ee of the purified product was determined by chiral HPLC analysis with Daicel Chiralcel columns or by chiral GC analysis. Racemic products were prepared using the racemic ligand to facilitate determination of ee.

Reference： [1]Patent: WO2014/196930,2014,A1 .Location in patent: Page/Page column 39

69
[ 99747-74-7 ]
[ 931-88-4 ]
[ 1461737-21-2 ]
(S)-3-(1-naphthyl)cyclooctene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With (R)-7-bis(m-xylyl)phosphino-7-bis(3,5-dimethylphenyl)phosphinyl-1,1'-spirobiindane; N-ethyl-N,N-diisopropylamine; bis(dibenzylideneacetone)-palladium(0); In 1,4-dioxane; at 50℃; for 16h;Inert atmosphere; Glovebox;	General procedure: A. Examples of asymmetric Heck reaction of cyclic olefinsGeneral procedureIn an argon-filled glove box, Pd(dba)2 (7.2 mg, 0.013 mmol) and (R)-Xyl-SDP(O) (10.8 mg, 5 0.015 mmol) were stirred in dry 1,4-dioxane (0.50 mL) for 10 to 20 mm in a 4-mL vial, followedby addition of n-C14H30 (25 tL, GC internal standard), aryl triflate (0.50 mmol), Nethyldiisopropylamine (170 iL, 1.0 mmol, 2 equiv) and cyclic olefin (2.0 mmol, 4 quiv). The mixture was vigorously stirred in a preheated oil bath at a set temperature until the aryl triflate was fully consumed (monitored by GC). The reaction mixture was cooled to RT and subjected to10 flash chromatography (basic alumina, Brockmann grade I, pentane/Et20) to give the purified product. Silica gel may be also used for purification. The olefinic selectivity of Heck isomers in the crude mixture was determined by GC. The ee of the purified product was determined by chiral HPLC analysis with Daicel Chiralcel columns or by chiral GC analysis. Racemic products were prepared using the racemic ligand to facilitate determination of ee.

Reference： [1]Patent: WO2014/196930,2014,A1 .Location in patent: Page/Page column 39; 40

70
[ 2446-83-5 ]
[ 99747-74-7 ]
[ 1334500-65-0 ]

Yield	Reaction Conditions	Operation in experiment
80%		General procedure: To a stirred solution of DIAD (1.2 mmol) in DMF (2 mL) at 0 C,NaH (0.05 g, 1.2 mmol) was added in portions over 20 min.Then, the aryl O-triflate (1.0 mmol), LiI (134 mg, 1mmol), andCu2O (15 mg, 0.1 mmol) were added to the reaction mixture,which was stirred at 80 C for 8 h under N2. The reaction wascooled and quenched by adding CH2Cl2 (2 mL) and sat. aq NH4Cl(3 mL). The mixture was stirred for an additional 30 min, andtwo layers were separated. The aqueous layer was extractedwith CH2Cl2 (3 × 2 mL), the combined organic layers were driedover MgSO4, filtered, and concentrated in vacuo. The residuewas purified by chromatography (silica gel; hexane-EtOAc, 3:1)to give the product.

Reference： [1]Synlett,2015,vol. 26,p. 942 - 944

71
[ 5467-58-3 ]
[ 99747-74-7 ]
[ 94879-53-5 ]

Reference： [1]Nature,2015,vol. 524,p. 454 - 457

72
[ 99747-74-7 ]
[ 134576-01-5 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,1'-bis-(diphenylphosphino)ferrocene; tetrakis(triphenylphosphite)nickel(0); N-Methyldicyclohexylamine; In 1,4-dioxane; at 100℃; for 18h;	General procedure: A flame-dried Schlenk tube was charged sequentially with the corresponding aryl triflate, nickel catalyst (Ni[P(OPh)3]4 or Ni[P(OEt)3]4), diphosphine ligand (dppf or dppe), and Cy2NMe. The mixture was dissolved in toluene or 1,4-dioxane (~6mL mmol-1), followed by the addition of butyl vinyl ether. The reaction vessel was sealed, and stirred at 100 C for 18 h in a preheated oil bath. For the hydrolysis step, the reaction mixture was allowed to cool to room temperature (RT), and then treated with 6M HCl (~6mL mmol-1). The mixture was stirred vigorously at RT for 1 h. After dilution with Et2O (10 mL), the organic layer was separated and fused onto silica gel. Purification by flash column chromatography on silica gave the desired ketone products. 1-Acetylnaphthalene (10a) Following the general procedure, using <strong>[99747-74-7]1-<strong>[99747-74-7]naphthyl triflate</strong></strong> (118 mg, 0.430 mmol, 1.00 equiv.), Ni[P(OPh)3]4 (29.0 mg, 0.022 mmol, 5 mol-%), dppf (12 mg, 0.022 mmol, 5 mol-%), Cy2NMe (276 mL, 1.29 mmol, 3.00 equiv.), butyl vinyl ether (222 mL, 1.72 mmol, 4.00 equiv.), and 1,4-dioxane (3 mL), the desired ketone 10a was obtained after hydrolysis and purification by flash column chromatography (hexanes/EtOAc 100 : 0 - 90 : 10) as a colourless oil (40 mg, 0.24 mmol, 56 %). The spectral data were in accordance with those reported in theliterature.[19] Rf 0.43 (hexanes/EtOAc 90 : 10). δH (CDCl3, 300 MHz) 8.76 (1H, d, J 8.4, Ar-H), 8.03-7.84 (3H, m, 3Ar-H), 7.66-7.45 (3H, m, 3Ar-H), 2.75 (3H, s, CH3).

Reference： [1]Australian Journal of Chemistry,2015,vol. 68,p. 1842 - 1853

73
[ 40841-62-1 ]
[ 99747-74-7 ]
[ 1162-90-9 ]

Yield	Reaction Conditions	Operation in experiment
85%	With palladium diacetate; caesium carbonate; In toluene; at 100℃; for 12h;Inert atmosphere;	1-naphthol trifluoromethanesulfonate 1f (58 mg, 0.21 mmol, 1.05 eq), p-methylbenzoyldiphenylphosphine 2a (60.8 mg, 0.2 mmol, 1.0 eq), palladium acetate 0.006 mmol, 0.03 eq), cesium carbonate (72 mg, 0.22 mmol, 1.1 eq) and 0.5 mL of toluene. The mixture was reacted at 100 C for 12 h under nitrogen. After the reaction was completed, the mixture was concentrated and directly separated by column chromatography to give 53.1 mg of product 3d, isolated in a yield of 85%
45%	With palladium diacetate; caesium carbonate; In toluene; at 100℃; for 12h;Sealed tube; Inert atmosphere;	General procedure: In a sealed vial, under nitrogen, p-methylbenzoyldiphenylphosphine (61 mg, 0.20 mmol, 1.0 equiv), Pd(OAc)2 (1.4 mg, 0.006 mmol), naphthyl bromides or triflates (0.21 mmol, 1.05 equiv), Cs2CO3 (72 mg, 0.22 mmol, 1.1 equiv) and toluene (0.5 mL) were mixed and stirred at 100 oC for 12 h. When reaction completed, the reaction mixture was directly purified by flash column chromatography on silica gel to give pure product.

Reference： [1]Journal of Organic Chemistry,2021,vol. 86,p. 8987 - 8996
[2]Patent: CN106928273,2017,A .Location in patent: Paragraph 0052-0055
[3]Tetrahedron Letters,2016,vol. 57,p. 3404 - 3406

74
[ 542-69-8 ]
[ 99747-74-7 ]
[ 1634-09-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With nickel(II) bromide dimethoxyethane; manganese; bathophenanthroline; lithium bromide; In N,N-dimethyl-formamide; at 20 - 40℃;Inert atmosphere;	General procedure: To a suspension of NiBr2·glyme (3.1 mg, 10 μmol), bathophenanthroline (3.9 mg, 12 μmol), manganese (22 mg, 0.40 mmol), and LiBr (26mg, 0.30 mmol) in DMF (0.4 mL) were added 2-naphthyl nonaflate (3a; 85.3 mg, 0.200 mmol) and 1-iodobutane (34.2 μL, 0.300 mmol) at r.t. After stirring for 14 h at 40 C, the mixture was cooled to r.t. and to this was added aqueous phosphate buffer (pH 7.4, ca. 2 mL). The mixturewas extracted with Et2O (3 × ca. 2 mL) and the combined organic extracts were dried (Na2SO4) and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by chromatography (silica gel, n-hexane) to give 2a

Reference： [1]Synthesis,2017,vol. 49,p. 3590 - 3601

75
[ 99747-74-7 ]
[ 765-30-0 ]
N-cyclopropylnaphthalen-1-amine [ No CAS ]

Reference： [1]ACS Catalysis,2017,vol. 7,p. 6048 - 6059

76
[ 327-54-8 ]
[ 99747-74-7 ]
1-(2',3',5',6'-tetrafluorophenyl)naphthalene [ No CAS ]

Reference： [1]ACS Catalysis,2017,vol. 7,p. 7421 - 7430

77
[ 99747-74-7 ]
[ 607-53-4 ]

Yield	Reaction Conditions	Operation in experiment
86%	With copper(l) iodide; sulfur; sodium t-butanolate; In N,N-dimethyl-formamide; at 120℃; for 6h;Inert atmosphere;	General procedure: A one-necked flask was charged with CuI (10 mg, 0.05 mmol), NaOt-Bu (376 mg, 4.0 mmol), S8 (16 mg, 0.5 mmol), phenolic ester (1 mmol), anhyd DMF (2 mL) under an inert atmosphere. The mixture was magnetically stirred and heated at 120 C for the appropriate reaction time (Table 6). After completion of the reaction, the mixture was cooled to r.t. H2O (4 mL) was added and the product was extracted with EtOAc (3 × 4 mL) and dried (anhyd Na2SO4). Evaporation of the solvent and purification by column chromatography on silica gel (n-hexane/EtOAc) gave the desired symmetrical diaryl sulfides in 75-93% yields.

Reference： [1]Synthesis,2017,vol. 49,p. 5025 - 5038
[2]Applied Organometallic Chemistry,2019,vol. 33

78
[ 99747-74-7 ]
[ 98-80-6 ]
[ 7570-98-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With copper(l) iodide; sulfur; sodium t-butanolate; at 60 - 80℃; for 9h;	General procedure: A one-necked flask was charged with CuI (30 mg, 0.15 mmol), NaOt-Bu (376 mg, 4.0 mmol), S8 (47 mg, 1.5 mmol), phenolic ester (1 mmol), arylboronic acid (1.1 mmol), and PEG200 (2 mL). The mixture was magnetically stirred and heated at 60-80 C for the appropriate reaction time (Table 2). After completion of the reaction, the reaction mixture was cooled to r.t. H2O (4 mL) was added and the product was extracted with EtOAc (3 × 4 mL) and dried (anhyd Na2SO4). Evaporation of the solvent and purification by column chromatography on silicagel (n-hexane/EtOAc) gave the desired unsymmetrical diaryl sulfides in 74-95% yields.

Reference： [1]Synthesis,2017,vol. 49,p. 5025 - 5038
[2]Applied Organometallic Chemistry,2019,vol. 33

79
[ 5720-05-8 ]
[ 99747-74-7 ]
[ 127567-55-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	With copper(l) iodide; sulfur; sodium t-butanolate; at 60 - 80℃; for 11h;	General procedure: A one-necked flask was charged with CuI (30 mg, 0.15 mmol), NaOt-Bu (376 mg, 4.0 mmol), S8 (47 mg, 1.5 mmol), phenolic ester (1 mmol), arylboronic acid (1.1 mmol), and PEG200 (2 mL). The mixture was magnetically stirred and heated at 60-80 C for the appropriate reaction time (Table 2). After completion of the reaction, the reaction mixture was cooled to r.t. H2O (4 mL) was added and the product was extracted with EtOAc (3 × 4 mL) and dried (anhyd Na2SO4). Evaporation of the solvent and purification by column chromatography on silicagel (n-hexane/EtOAc) gave the desired unsymmetrical diaryl sulfides in 74-95% yields.

Reference： [1]Synthesis,2017,vol. 49,p. 5025 - 5038
[2]Applied Organometallic Chemistry,2019,vol. 33

80
[ 99747-74-7 ]
[ 639-58-7 ]
[ 7570-98-1 ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium fluoride; copper diacetate; potassium carbonate; sulfur; at 80℃; for 4h;	General procedure: A one-necked flask was charged with Cu(OAc)2 (30 mg, 0.15 mmol), K2CO3 (414 mg, 3.0 mmol), S8 (48 mg, 1.5 mmol), KF (180 mg, 3 mmol), phenolic ester (1 mmol), triphenyltin chloride (0.35 mmol), and PEG200 (1.5 mL). The mixture was magnetically stirred and heatedat 80 C for the appropriate reaction time (Table 4). After completion of the reaction, the reaction mixture was cooled to r.t. H2O (4 mL) was added and the product was extracted with EtOAc (3 × 4 mL) and dried (anhyd Na2SO4). Evaporation of the solvent and purification by column chromatography on silica gel (n-hexane/EtOAc) gave the desired phenyl aryl sulfides in 79-94% yields.

Reference： [1]Synthesis,2017,vol. 49,p. 5025 - 5038
[2]Applied Organometallic Chemistry,2019,vol. 33

81
[ 421-83-0 ]
[ 90-15-3 ]
[ 99747-74-7 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0℃; for 24h;	General procedure: A mixture of phenol (0.45 g, 5 mmol), trifluoromethanesulfonyl chloride (0.8 mL, 7.5 mmol) and Et3N (1.4 mL, 10 mmol) in THF (30 mL) was stirred at 0 C for 24 h. The solvent was evaporated and to the resulting residue were added H2O (20 mL) and EtOAc (20 mL). The organic phase was decanted and dried (anhyd Na2SO4). Evaporation of the solvent and purification by column chromatography on silica gel (hexane/EtOAc, 4:1) gave the pure triflate in 85% yield (191 mg).

Reference： [1]Synthesis,2017,vol. 49,p. 5025 - 5038

82
[ 80041-89-0 ]
[ 99747-74-7 ]
[ 6158-45-8 ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 9903 - 9909

83
[ 88496-88-2 ]
[ 99747-74-7 ]
[ 56796-83-9 ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 9903 - 9909

84
[ 99747-74-7 ]
[ 13149-00-3 ]
cis-2-(1-naphthoyl)cyclohexane-1-carboxylic acid [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 1191 - 1194

85
[ 5471-63-6 ]
[ 99747-74-7 ]
(Li*2,2,6,6-tetramethylpiperidine)_0.1Li[ZnEt₂(2,2,6,6-tetramethylpiperidine)] [ No CAS ]
[ 138719-98-9 ]

Yield	Reaction Conditions	Operation in experiment
67%	In tetrahydrofuran; hexane; at 20℃; for 21h;Inert atmosphere; Schlenk technique;	General procedure: To a solution of aryl triflate (0.2 mmol, 1.0 equiv) and 1,3-diphenylisobenzofuran (108.1 mg, 0.4 mmol, 2.0 equiv)in THF (to give a final concentration of 0.1 M), was added freshly titrated LiTMP0.1Li[ZnEt2(TMP)] (0.3 mmol, 1.5equiv). The reaction mixture was allowed to stir at room temperature for 21 h and quenched with isopropanol(approx. 0.2 mL). The crude mixture was filtered through a plug of silica gel and washed with ethyl acetate (approx.10 mL). The resulting filtrate was concentrated under reduced pressure and purified by flash columnchromatography.

Reference： [1]Tetrahedron,2018,vol. 74,p. 3325 - 3328

86
[ 6832-87-7 ]
[ 99747-74-7 ]
[ 29103-83-1 ]
[ 13127-50-9 ]

Reference： [1]Organic Letters,2020

87
[ 99747-74-7 ]
[ 91-20-3 ]
[ 68716-52-9 ]

Reference： [1]Organic Letters,2020,vol. 22,p. 5582 - 5588

88
[ 99747-74-7 ]
[ 68716-52-9 ]

Reference： [1]Organic Letters,2020,vol. 22,p. 5582 - 5588

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Ghs Precautionary Statements

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

Ghs Hazard Statements

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