18995-35-2|1-(tert-Butoxy)-4-chlorobenzene| Ambeed

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Quality Control of [ 18995-35-2 ] Purity: 98% SDS Specification

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Product Details of [ 18995-35-2 ]

CAS No. :	18995-35-2
Formula :	C₁₀H₁₃ClO
M.W :	184.66
SMILES Code :	ClC1=CC=C(OC(C)(C)C)C=C1
MDL No. :	MFCD04038411
Boiling Point :	No data available
InChI Key :	NEJWTQIEQDHWTR-UHFFFAOYSA-N
Pubchem ID :	140458

Safety of [ 18995-35-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Application In Synthesis of [ 18995-35-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 18995-35-2 ]

[ 18995-35-2 ] Synthesis Path-Downstream 1~35

1
[ 507-20-0 ]
[ 106-48-9 ]
[ 18995-35-2 ]

References: [1]Journal of Chemical Research - Part S,2000,p. 252 - 253.
[2]Synthesis,1982,p. 186 - 188.

2
[ 6669-13-2 ]
[ 18995-35-2 ]

References: [1]Canadian Journal of Chemistry,1997,vol. 75,p. 1905 - 1912.
[2]Journal of Chemical Research - Part S,1998,p. 662 - 663.
[3]Journal of the Chemical Society. Perkin transactions I,1997,p. 3081 - 3085.

5
[ 27607-77-8 ]
[ 18995-35-2 ]
tris(4-tert-butoxyphenyl)sulfonium trifluoromethanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With thionyl chloride; ammonium chloride; magnesium; In tetrahydrofuran; chloroform; water;	Example 1 Synthesis of tris(4-tert-butoxyphenyl)sulfonium trifluoromethanesulfonate A Grignard reagent was conventionally prepared using 60.7 g (2.5 mol) of magnesium, 461 g (2.5 mol) of <strong>[18995-35-2]4-tert-butoxyphenyl chloride</strong>, and 700 g of THF. The Grignard reagent solution was cooled in an ice water bath whereupon 59.5 g (0.5 mol) of thionyl chloride diluted with 100 g of THF was added dropwise at less 30 C. Reaction mixture was ripened for about 30 minutes. Thereafter, 277.8 g (1.25 mol) of trimethylsilyltrifluoromethane sulfonate was added dropwise at less 20 C. Reaction mixture was further ripened for 1 hour and thereafter, the reaction solution was allowed to stand overnight at room temperature. After the reaction solution was again cooled in an ice water bath, 1,800 g of 16.7% ammonium chloride aqueous solution (NH4 Cl 300 g+H2 O 1,500 g) was added thereto at a temperature not in excess of 30 C. After separation, 1,000 g of chloroform was added to the organic layer, which was washed three times using 1,000 g of water. Thereafter, the solvent was distilled off under reduced pressure by means of a rotary evaporator and the resulting oily residue was recrystallized, isolating tris(4-tert-butoxyphenyl)sulfonium trifluoromethanesulfonate of 99% purity in an amount of 141 g (yield 45%).

References: [1]Patent: US5705702,1998,A .

6
[ 18995-35-2 ]
[ 170632-59-4 ]

Yield	Reaction Conditions	Operation in experiment
60%	With thionyl chloride; In tetrahydrofuran; dichloromethane; water;	Synthesis Example 1 Synthesis of bis(p-tert-butoxyphenyl)sulfoxide A Grignard reagent was prepared in a conventional manner using 24.3 g (1 mol) of metallic magnesium, 203.2 g (1.1 mol) of p-tert-butoxyphenyl chloride and 280 g of THF. The Grignard reagent was diluted with 500 g of THF and cooled below -60 C. with a dry ice methanol bath. To the Grignard reagent solution, a solution of 47.5 g (0.4 mol) of thionyl chloride diluted with 70 g of THF was added dropwise over one hour at a temperature not exceeding 0 C. Stirring was continued for one hour on the ice water bath and 36 g of water then added to decompose the excess of Grignard reagent. To the reaction solution were added 1000 g of methylene chloride, 400 g of saturated ammonium chloride aqueous solution and 300 g of water. After layer separation, the organic solvent layer was washed twice with 700 g of pure water. The organic solvent layer was dried over magnesium sulfate, filtered, and evaporated in vacuo. The resulting oily product was recrystallized, recovering 83 g (yield 60%) of the end product, bis(p-tert-butoxyphenyl)sulfoxide as a white crystal having a purity of 96% and a melting point of 80-82 C.

References: [1]Patent: US5633409,1997,A .

7
[ 74-96-4 ]
[ 18995-35-2 ]
p-tert-butoxyphenylmagnesium chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran;	Example 1 In a one-liter four-necked flask equipped with a stirrer and a reflux condenser, purged with nitrogen and dried was placed 29.2 g (1.2 mol.) of metallic magnesium flakes to which were added 50 ml of anhydrous tetrahydrofuran and 2 ml of ethyl bromide. After confirming initiation of the reaction by bubbling on the surface of the metallic magnesium, a solution of 184.6 g (1.0 mol.) of p-tert-butoxychlorobenzene in 500 ml of anhydrous tetrahydrofuran was added dropwise at the refluxing temperature over approximately 2 hours followed by stirring for 5 hours to give p-tert-butoxyphenylmagnesium chloride. When an aliquot portion of the reaction mixture was taken, decomposed by pouring water and analyzed by gas chromatography, conversion ratio of the Grignard reagent was found to be 99.8%.

References: [1]Patent: EP307106,1989,A1 .

8
[ 102-54-5 ]
[ 18995-35-2 ]
[ 143-66-8 ]
(η6-4-chlorophenyl-tert-butyl ether)(η5-cyclopentadienyl)iron(II) tetraphenylborate [ No CAS ]

References: [1]Journal of Organometallic Chemistry,2006,vol. 691,p. 2641 - 2647.

9
[ 18995-35-2 ]
[ 590-86-3 ]
[ 1070716-48-1 ]

References: [1]Organic Letters,2008,vol. 10,p. 4561 - 4564.

10
[ 106-39-8 ]
[ 865-47-4 ]
[ 18995-35-2 ]

References: [1]Tetrahedron Letters,2009,vol. 50,p. 1478 - 1481.

11
(1-(phenylsulfonyl)-1H-indol-2-yl)boronic acid [ No CAS ]
[ 18995-35-2 ]
[ 1158985-06-8 ]

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 6961 - 6963.

12
[ 13331-23-2 ]
[ 18995-35-2 ]
[ 1158984-98-5 ]

Yield	Reaction Conditions	Operation in experiment
98%		Under ambient atmosphere, to a 40 mL I-Chem vial equipped with a stir bar was added 1-te/t-butoxy-4-chlorobenzene (3a) (0.185 g, 1.00 mmol), dicyclohexylphosphino^δ'-dimethoxy-I J '-biphenyl (SPhos) (41 mg, 0.10 mmol) and Pd(OAc)2 (11 mg, 0.050 mmol). The vial was sealed with a PTFE-lined septum screw- cap, and then placed under an Ar atmosphere. To the vial was added dioxane (9.5 mL) and the resulting mixture was stirred at 23 0C for 10 min. To the vial was added aqueous K3PO4 (3.0 M, 2.5 mL, degassed by sparging with Ar for 30 min). The vial was placed in a 60 0C oil bath, and to the stirred mixture was added dropwise over 3 h via syringe pump freshly prepared 2-furylboronic acid (1a) (0.1 12 g, 1.00 mmol) as a solution in dioxane (3.0 mL). After the addition was complete the reaction mixture was stirred at 60 0C for an additional 3 h. The mixture was cooled to room temperature and was then transferred to a 60 mL separatory funnel and was diluted with aqueous NaOH (1.0 M, 10 mL). The mixture was extracted with Et2θ (3 x 10 mL). The combined organic fractions were dried over MgSO4, filtered and then concentrated in vacuo. The resulting residue was purified by flash chromatography (hexanes: EtOAc, 100:0 -> 9:1) to afford a colorless oil (0.213 g, 98%).

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 6961 - 6963.
[2]Patent: WO2010/36921,2010,A2 .Location in patent: Page/Page column 45, 46, 50-51, 52.

13
[ 6165-68-0 ]
[ 18995-35-2 ]
[ 808142-44-1 ]

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 6961 - 6963.

14
[ 1104636-73-8 ]
[ 18995-35-2 ]
4-tert-butoxystyrene [ No CAS ]

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 6961 - 6963.

15
[ 1104637-36-6 ]
[ 18995-35-2 ]
[ 1158985-08-0 ]

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 6961 - 6963.

16
[ 1158984-93-0 ]
[ 18995-35-2 ]
[ 1158985-01-3 ]

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 6961 - 6963.

17
[ 1158984-94-1 ]
[ 18995-35-2 ]
[ 1158985-03-5 ]

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 6961 - 6963.

18
[ 1158984-95-2 ]
[ 18995-35-2 ]
[ 1158985-06-8 ]

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 6961 - 6963.

19
[ 1158984-90-7 ]
[ 18995-35-2 ]
[ 1158985-01-3 ]

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 6961 - 6963.

20
[ 1104637-62-8 ]
[ 18995-35-2 ]
[ 1158984-98-5 ]

Yield	Reaction Conditions	Operation in experiment
94%		Under ambient atmosphere, to a 40 mL I-Chem vial equipped with a stir bar was added 1 -te/t-butoxy-4-chlorobenzene (3a) (185 mg, 1.00 mmol), the MIDA boronate or freshly-prepared boronic acid (1.00 mmol), 2-dicyclohexylphosphino-2',6'- dimethoxybiphenyl (SPhos) (41 mg, 0.10 mmol) and Pd(OAc)2 (1 1 mg, 0.050 mmol). The vial was sealed with a PTFE-lined septum screw-cap and was placed under Ar atmosphere. To the vial was added dioxane (12.5 mL) and the resulting mixture was stirred at 23 0C for 10 min. To the vial was then added aqueous K3PO4 (3.0 M, 2.5 mL, degassed by sparging with Ar for 30 min). The vial was placed in a 60 0C oil bath with stirring for 6 h. After cooling to room temperature the mixture was transferred to a 60 mL separatory funnel and was diluted with aqueous NaOH (1.0 M, 10 mL) and Et2O (10 mL). The mixture was shaken and the phases were separated. The aqueous phase was extracted with Et2O (3 x 10 mL). The combined organic fractions were dried over MgSO4, filtered and concentrated in vacuo. The crude residue was subjected to flash- chromatography on silica gel (hexanes:EtOAc). This method is depicted in the scheme below, and the yields of cross-coupling are listed in FIG. 2. To form 2-(4-te/t-butoxyphenyl)furan (4a), the general procedure was followed using MIDA boronate 2a (223 mg, 1.00 mmol) to afford 4a as a colorless oil (203 mg, 94%). A parallel reaction using freshly-prepared boronic acid 1a (1 12 mg, 1.00 mmol) under otherwise identical conditions afforded 4a as a colorless oil (147 mg, 68%). TLC (hexanes:EtOAc 20:1) Rf = 0.33, visualized by UV (254 nm). 1H-NMR (500 MHz, CDCI3) δ 7.60 (d, / = 8.5 Hz, 2H), 7.45 (dd, / = 1.5, 0.5 Hz, 1 H), 7.04 (d, / = 8.5 Hz, 2H), 6.58 (d, / = 3.0 Hz, 1 H), 6.46 (dd, / = 3.0, 1.5 Hz, 1 H), 1.38 (s, 9H). 13C-NMR (125 MHz, CDCl3) δ 154.8, 153.9, 141.6, 126.3, 124.4, 124.3, 1 1 1.5, 104.0, 78.7, 28.8. HRMS (Cl +) Calculated for C14H16O2 (M) + : 216.1150, Found: 216.1 151 . IR (thin film, cm-1) 2977, 1612, 1587, 1566, 1512, 1481 , 1414, 1390, 1366, 1245, 1 162, 1 106, 1078, 1007, 904, 895, 854, 798, 730, 667, 594.

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 6961 - 6963.
[2]Patent: WO2010/36921,2010,A2 .Location in patent: Page/Page column 45, 46.

21
[ 1104637-65-1 ]
[ 18995-35-2 ]
[ 1158985-00-2 ]

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 6961 - 6963.
[2]Journal of the American Chemical Society,2013,vol. 135,p. 17707 - 17710.

22
[ 1158984-92-9 ]
[ 18995-35-2 ]
[ 808142-44-1 ]

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 6961 - 6963.

23
[ 98437-24-2 ]
[ 18995-35-2 ]
[ 1158985-00-2 ]

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 6961 - 6963.

24
[ 4363-34-2 ]
[ 18995-35-2 ]
4-tert-butoxystyrene [ No CAS ]

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 6961 - 6963.

25
[ 18995-35-2 ]
[ 135884-31-0 ]
[ 1158985-03-5 ]

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 6961 - 6963.

26
[ 18995-35-2 ]
[ 411235-57-9 ]
[ 1158985-08-0 ]

References: [1]Journal of the American Chemical Society,2009,vol. 131,p. 6961 - 6963.

27
[ 18995-35-2 ]
[ 227275-59-4 ]

References: [1]Journal of Chemical Research,2009,p. 397 - 399.

Yield	Reaction Conditions	Operation in experiment
		Under ambient atmosphere, to a 25 mL Schlenk flask equipped with a stir bar was added 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos) (41 mg, 0.10 mmol), Pd(OAc)2 (1 1 mg, 0.050 mmol) and freshly-prepared 2-furylboronic acid (1a) (106 mg, 0.949 mmol). The flask was placed under Ar atmosphere and to the flask was added dioxane (12.5 mL). To the solution was added dodecane (100 microliters, internal standard) and 1 -te/t-butoxy-4-chlorobenzene (3a) (175 microliters, 0.980 mmol), and the solution was stirred at 23 0C for 10 minutes. The solution was sampled and analyzed by GC to determine the ratio of halide:dodecane. To the dark amber solution was added aqueous K3PO4 (3.0 M, 2.5 mL, degassed by sparging with Ar for 30 min) and the dark mixture was stirred for 5 minutes. The organic phase was sampled as the initial time-point (t = 0), and the mixture was then immediately placed in a 60 0C oil bath with stirring. The organic phase was sampled periodically and the consumption of the halide was determined by GC analysis versus the internal standard. FIG. 4 depicts a graph of the data for cross-coupling conversion of 2-furyl boronic acid 1a with 1-te/t-butoxy-4-chlorobenzene 3a.

29
[ 1227700-43-7 ]
[ 18995-35-2 ]
[ 1374997-11-1 ]

References: [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 2667 - 2672.

30
[ 1227700-44-8 ]
[ 18995-35-2 ]
[ 1374997-12-2 ]

References: [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 2667 - 2672.

31
[ 1227700-46-0 ]
[ 18995-35-2 ]
[ 1374997-14-4 ]

References: [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 2667 - 2672.

32
[ 1227700-48-2 ]
[ 18995-35-2 ]
[ 1374997-15-5 ]

References: [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 2667 - 2672.

33
[ 1227700-42-6 ]
[ 18995-35-2 ]
[ 1374997-10-0 ]

References: [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 2667 - 2672.

34
[ 1227700-45-9 ]
[ 18995-35-2 ]
2-(4-(t-butoxy)phenyl)-6-methoxypyridine [ No CAS ]

References: [1]Journal of the American Chemical Society,2013,vol. 135,p. 17707 - 17710.

35
[ 18995-35-2 ]
[ 593-51-1 ]
4-(tert-butoxy)-N-methylaniline [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 3768 - 3772.
Angew. Chem.,2015,vol. 127,p. 3839 - 3843,5.
[2]Organic Letters,2014,vol. 16,p. 4388 - 4391.

Historical Records

Technical Information

• Alkyl Halide Occurrence • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Nomenclature of Ethers • Preparation of Ethers • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Ethers • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling

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[ 18995-35-2 ]

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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

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CAS No.: 18995-35-2

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