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[ CAS No. 345-35-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

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Chemical Structure| 345-35-7

Chemical Structure| 345-35-7

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Quality Control of [ 345-35-7 ]

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Product Details of [ 345-35-7 ]

CAS No. :	345-35-7	MDL No. :	MFCD00000892
Formula :	C₇H₆ClF	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	MOBRMRJUKNQBMY-UHFFFAOYSA-N
M.W :	144.57	Pubchem ID :	9580
Synonyms :

Safety of [ 345-35-7 ]

Signal Word:	Danger	Class:	8,3
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	2920
Hazard Statements:	H225-H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 345-35-7 ]

* 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 [ 345-35-7 ]
Downstream synthetic route of [ 345-35-7 ]

[ 345-35-7 ] Synthesis Path-Upstream 1~2

1
[ 345-35-7 ]
[ 51859-98-4 ]

Reference： [1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 44, p. 10942 - 10951

2
[ 345-35-7 ]
[ 73183-34-3 ]
[ 517920-60-4 ]

Yield	Reaction Conditions	Operation in experiment
82%	With iron(III)-acetylacetonate; magnesium In tetrahydrofuran at 0℃; for 3 h; Inert atmosphere	Example 7: In the condition of adding magnesium turnings in situ,The boron esterification of ortho-fluorobenzyl chloride and bis-boronic acid pinacol ester catalyzed by Fe(acac)3 was followed by the addition of the catalyst (3.5 mg, 0.010 mmol, 2 molpercent) under argon atmosphere.Bis(pinacolato)boronic acid ester (127.0 mg, 0.5 mmol),Magnesium turnings (16.8 mg, 0.7 mmol), tetrahydrofuran (1 mL),After addition of o-fluorobenzyl chloride (160 μl, 1.35 mmol) at 0°C,The reaction was carried out for 3 hours, and the reaction was terminated with the addition of water. The reaction product was extracted with ethyl acetate and the yield was 82percent as calculated by gas chromatography.

Reference： [1] Patent: CN107903281, 2018, A, . Location in patent: Paragraph 0030
[2] Tetrahedron Letters, 2003, vol. 44, # 2, p. 233 - 235

[ 345-35-7 ] Synthesis Path-Downstream 1~10

1
[ 143-33-9 ]
[ 345-35-7 ]
[ 326-62-5 ]

Reference： [1]Bulletin des Societes Chimiques Belges,1960,vol. 69,p. 312 - 322
[2]Journal of Heterocyclic Chemistry,1981,vol. 18,p. 815 - 820

2
[ 345-35-7 ]
[ 73183-34-3 ]
[ 517920-60-4 ]

Yield	Reaction Conditions	Operation in experiment
82%	With iron(III)-acetylacetonate; magnesium; In tetrahydrofuran; at 0℃; for 3h;Inert atmosphere;	Example 7: In the condition of adding magnesium turnings in situ,The boron esterification of ortho-fluorobenzyl chloride and bis-boronic acid pinacol ester catalyzed by Fe(acac)3 was followed by the addition of the catalyst (3.5 mg, 0.010 mmol, 2 mol%) under argon atmosphere.Bis(pinacolato)boronic acid ester (127.0 mg, 0.5 mmol),Magnesium turnings (16.8 mg, 0.7 mmol), tetrahydrofuran (1 mL),After addition of o-fluorobenzyl chloride (160 mul, 1.35 mmol) at 0C,The reaction was carried out for 3 hours, and the reaction was terminated with the addition of water. The reaction product was extracted with ethyl acetate and the yield was 82% as calculated by gas chromatography.

Reference： [1]Patent: CN107903281,2018,A .Location in patent: Paragraph 0030
[2]Tetrahedron Letters,2003,vol. 44,p. 233 - 235

3
[ 345-35-7 ]
[ 97731-02-7 ]

Reference： [1]Journal of the American Chemical Society,1950,vol. 72,p. 1806

4
[ 5166-67-6 ]
[ 345-35-7 ]
[ 136081-13-5 ]

Yield	Reaction Conditions	Operation in experiment
12.1 g (74.4%)	With sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; ethyl acetate;	Ethyl 1-methyl-3-(2'-fluorobenzyl-nipecotate To a solution of <strong>[5166-67-6]ethyl 1-methylnipecotate</strong> (10.0 g, 58.4 mmol) in dry tetrahydrofuran (350 ml) was added at -78 C. lithium bis(trimethylsilyl)amide (80.0 ml, 80.0 mmol) as a 1.0M solution in tetrahydrofuran and the resulting solution was allowed to stir at -78 C. for 3 hours. To this was added 2-fluorobenzylchloride (7.0 ml, 8.5 g, 59 mmol) and the resulting solution was allowed to warm to room temperature over 5 hours. Thin-layer chromatography showed reaction was not complete. More 2-fluorobenzylchloride (20 ml, 2.4 g, 17 mmol) was added to the reaction mixture and the resulting solution was allowed to stir overnight, ca. 18 hours. The tetrahydrofuran was removed by evaporation in vacuo and the orange residue was dissolved in ethyl acetate. The organic solution was extracted with 0.5N HCl (4100 ml) and the aqueous acid extracts were combined and made basic with 10N NaOH. The aqueous was then extracted with ethyl acetate (5100 ml) and the combined extracts were dried over MgSO4 and concentrated to yield 12.1 g (74.4%) of ethyl 1-methyl-3-(2'-fluoro)-benzyl-nipecotate as an orange oil. 1 H-NMR (CDCl3) delta: 7.22-7.15 (m, 1H), 7.10-6.95 (m, 3H), 4.14-4.05 (m, 2H), 3.01 (bd, 1H, J=10.3 Hz), 2.87 (s, 2H), 2.58 (bd, 1H, J=10.3 Hz), 2.24 (s, 3H), 2.04-1.95 (m, 3H), 1.69-1.60 (m, 2H), 1.30-1.22 (m, 1H), 1.16 (t, 3H, J=7.1 Hz).

Reference： [1]Patent: US5206240,1993,A

5
[ 1196473-37-6 ]
[ 345-35-7 ]
[ 1222010-58-3 ]

Yield	Reaction Conditions	Operation in experiment
55.7%		6-Hydroxyl-l,3-dihydro-l-hydroxy-2,l-benzoxaborole (lmmol) was dissolved in DMF (1OmL) and cooled to 00C with ice bath. To this solution under nitrogen were added in sequence sodium hydride (160mg, 4mmol, 4.0eq) and 1- (chloromethyl)-2-fluorobenzene (0.485mL, 4mmol, 4.0eq). The reaction mixture was stirred for 2 hours then treated with IM HCl (10ml). After extraction with ethyl acetate, the organic layer was washed with water and brine. The residue after rotary evaporation was purified by column chromatography over silica gel to give the title compound (143.6mg, 55.7percent yield). 1H NMR (300 MHz, DMSO-d6): delta 9.13 (s, IH), 7.58-7.12 (m, 7H), 5.16(s, 2H) and 4.92 (s, 2H) ppm. Mp 129-131°C.

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 1276 - 1287
[2]Patent: WO2010/45503,2010,A1 .Location in patent: Page/Page column 155

6
[ 345-35-7 ]
[ 204205-33-4 ]

Reference： [1]Patent: WO2012/1486,2012,A1
[2]Patent: WO2012/1486,2012,A1
[3]Patent: WO2014/114964,2014,A2
[4]Patent: WO2014/114964,2014,A2

7
[ 773837-37-9 ]
[ 345-35-7 ]
[ 326-62-5 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrabutylammomium bromide; In dichloromethane; water; at 25℃;	Example 1Preparation of 2-Fluorobenzyl cyanideIn a 1 ltr 4-necked flask equipped with a thermometer and mechanical stirrer, 2- fluorobenzyl chloride (100 g, 0.69 moles), tetrabutyl ammonium bromide (4.5 g, 0.014 moles) and dichloromethane (280 ml) is added in a clear solution of Sodium cyanide (41 g, 0.84 moles) in water (280 ml) at 25 C (+/-5 C). Stir the reaction mass for 12 to 16 hrs at 25 C (+/-5 C). Separate the organic after reaction completion. Organic layer washed with water and recover the solvent under vacuum to obtain pure 2- Fluorobenzyl cyanide (95 g, GC purity 99%).

Reference： [1]Patent: WO2012/1486,2012,A1 .Location in patent: Page/Page column 15

8
[ 345-35-7 ]
[ 436-77-1 ]
C₅₈H₅₇F₃N₂O₆⁽²⁺⁾*2Cl^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8.25 g		<strong>[436-77-1]fangchinoline</strong> 6.10g,0.20 g of potassium hydride was dissolved in 100 mL of methanol in a 500 mL three-necked flask.Add 1.50 g of o-fluorobenzyl chloride and stir to heat to boiling.The reaction was stirred for 4 h, and TLC was used to detect the total reaction of <strong>[436-77-1]fangchinoline</strong>.Cool down to room temperature, add 10% hydrochloric acid to neutralize to pH=7-8,Add 3.00 g of the remaining o-fluorobenzyl chloride, stir to heat to a boil and stir to react for 8 h.After distilling off methanol, 100 mL of water was added, and extracted with dichloromethane three times (100 mL×3).TLC traces the separation and purification process of the reaction and the product, and the extract recovers dichloromethane.The solid was dried at 60 C for 4 h to give a product as a pale yellow powder.8.25g. The desired product has the melting point: 202.5-203.9 C, 13C NMR (CDCl3, 100 MHz) delta 160.31, 157.86, 152.79,150.36,148.34,147.81,147.38,146.09,142.95,137.64,137.51,137.33,133.89,133.77,131.71, 131.66, 131.41, 129.71, 129.65, 129.54, 128.26, 128.11, 128.06, 127.77, 127.66,127.54, 126.98, 126.90, 126.89, 126.50, 123.74, 122.76, 122.12, 121.79, 120.81, 119.34,115.20, 113.72, 113.51, 111.84, 110.54, 105.00, 66.33, 63.02, 60.45, 55.11, 54.86,54.76, 44.77, 44.51, 44.38, 43.20, 41.35, 41.28, 40.91, 39.15, 23.57, 21.13. TOF-HRMS: M/e(1005.9838), molecular formula: C58H57O6N2F3Cl2,That is, the compound III1 in Table 2.

Reference： [1]Patent: CN109678872,2019,A .Location in patent: Paragraph 0120-0121

9
[ 345-35-7 ]
[ 5294-61-1 ]
N-(2,6-dimethylphenyl)-2-(4-(2-fluorobenzyl)piperazin-1-yl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium carbonate; In acetonitrile; at 25℃; for 10.0h;	General procedure: To a solution of <strong>[5294-61-1]N-(2,6-dimethylphenyl)-2-(piperazin-1-yl)acetamide</strong> 4 in acetonitrile, different substituted benzyl chlorides 7a-e (0.001 mol) were slowly added drop wise in presence of K2CO3 (0.003 mol). Reaction mixture was stirred for 10 h at 25oC and completion of reaction was checked by TLC. Reaction mixture was poured into ice-cold water and extracted with methylene dichloride. The organic layers was washed with brine solution, dried over anhydrous sodium sulphate and concentrated to get alkylated piperazine derivatives 8a-e in good yield.

Reference： [1]Oriental Journal of Chemistry,2019,vol. 35,p. 157 - 166

10
[ 345-35-7 ]
[ 436-77-1 ]
C₄₄H₄₅FN₂O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17.21 g	With sodium hydride; In methanol; at 65℃; for 72h;	Weigh <strong>[436-77-1]fangchinoline</strong> 18.30g,0.72 g of sodium hydride was dissolved in 200 mL of methanol in a 500 mL three-necked flask.Then add 4.50g of o-fluorobenzyl chloride, stir and heat at 65 C, and stir the reaction for 72 hours.TLC was used to detect the total reaction of the <strong>[436-77-1]fangchinoline</strong>, distilling off the methanol, cooling to room temperature, adding 80 mL of water, and extracting with dichloromethane for 3 times (300 mL×3).TLC traces the separation and purification process of the reaction and the product, and the extract recovers dichloromethane.The solid was dried at 60 C for 4 h to give a product as a pale yellow powder.17.21g.

Reference： [1]Patent: CN109776553,2019,A .Location in patent: Paragraph 0067; 0068

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Technical Information

• Alkyl Halide Occurrence • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Hydrogenolysis of Benzyl Ether • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Preparation of Alkylbenzene • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Vilsmeier-Haack Reaction

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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

; ;