[ CAS No. 27798-39-6 ] {[proInfo.proName]}

Name: 27798-39-6|1-Benzyl-3-bromobenzene|95%
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COA NMR CNMR HPLC LC-MS

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Product Details of [ 27798-39-6 ]

CAS No. :	27798-39-6	MDL No. :	MFCD18432375
Formula :	C₁₃H₁₁Br	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KMBNQIVUWJLMIN-UHFFFAOYSA-N
M.W :	247.13	Pubchem ID :	597532
Synonyms :

Safety of [ 27798-39-6 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 27798-39-6 ]

* 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 [ 27798-39-6 ]
Downstream synthetic route of [ 27798-39-6 ]

[ 27798-39-6 ] Synthesis Path-Upstream 1~1

1
[ 108-86-1 ]
[ 100-52-7 ]
[ 2116-36-1 ]
[ 23450-18-2 ]
[ 27798-39-6 ]

Reference： [1] Tetrahedron Letters, 1998, vol. 39, # 35, p. 6291 - 6294

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Technical Information

• Acid-Catalyzed α -Halogenation of Ketones • Addition of a Hydrogen Halide to an Internal Alkyne • Alcohols from Haloalkanes by Acetate Substitution-Hydrolysis • Alcohols React with PX3 • Alkyl Halide Occurrence • Alkylation of an Alkynyl Anion • An Alkane are Prepared from an Haloalkane • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Conversion of Amino with Nitro • Convert Haloalkanes into Alcohols by SN2 • Deprotonation of Methylbenzene • Directing Electron-Donating Effects of Alkyl • Electrophilic Chloromethylation of Polystyrene • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation of Benzene with Haloalkanes • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation of Alkenes • Halogenation of Benzene • Hiyama Cross-Coupling Reaction • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Methylation of Ammonia • Methylation of Ammonia • Nitration of Benzene • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Preparation of Alkylbenzene • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Dihalides • Reductive Removal of a Diazonium Group • Reverse Sulfonation——Hydrolysis • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Sulfonation of Benzene • Suzuki Coupling • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Nitro Group Conver to the Amino Function • Vilsmeier-Haack Reaction • Williamson Ether Syntheses

Historical Records

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[ 27798-39-6 ]

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Yield	Reaction Conditions	Operation in experiment
97%	With aluminum (III) chloride; lithium aluminium tetrahydride In diethyl ether at -20℃; Inert atmosphere; Reflux;
89%	With triethylsilane; trifluoroacetic acid In dichloromethane at 20℃; for 15h;
86%	With lithium aluminium tetrahydride; aluminium trichloride In diethyl ether for 12h; Heating;

85%	With lithium aluminium tetrahydride; aluminium trichloride In diethyl ether
83%	With lithium aluminium tetrahydride; aluminium trichloride In diethyl ether for 1.5h; Heating;
49%	With indium(III) chloride; dimethylmonochlorosilane In dichloromethane at 20℃; for 2h; Inert atmosphere;
	With triethylsilane; boron trifluoride diethyl etherate In dichloromethane at 20℃;
	Stage #1: 3-bromobenzhydrol With aluminum (III) chloride; lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether at 40℃; for 1h; Stage #2: With water In tetrahydrofuran; diethyl ether at 0℃;	34.2 Step 2: 1-Benzyl-3-bromo-benzene (3-Bromo-phenyl)-phenyl-methanol (from previous step) was dissolved in diethyl ether (10 mL) and the solution was added dropwise to a suspension of lithium aluminum hydride (0.607 g, 16 mmol) and aluminum chloride (2.11 g, 16 mmol) stirring in THF (15 mL). The reaction was heated to 40° C. for 1 hour then cooled to 0° C., quenched with H2O, and submitted to standard aqueous workup. The crude product was purified via silica gel chromatography (0-5% EtOAc in hexanes) to afford the title compound.

Yield	Reaction Conditions	Operation in experiment
92%	With sodium tetrahydroborate; trifluoroacetic acid; In dichloromethane; at 10 - 20℃; for 19.166h;	Step a) 1-Benzyl-3-bromobenzene Under a nitrogen atmosphere, into a cold (10 C.) solution of trifluoroacetic acid (240 mL) was added a solution of <strong>[1016-77-9]3-bromobenzophenone</strong> (11 g, 42.1 mmol) in CH2Cl2 (120 mL) over 10 minutes, followed by slow addition of NaBH4-pellets (19 g) over 1 hour. The reaction mixture was stirred at room temperature for 18 h, poured into ice, basified with NaOH (50%) to pH 8 and extracted with ether. The organic extracts were combined, dried over MgSO4, treated with charcoal and filtered. The filtrate was concentrated in vacuo to give 1-benzyl-3-bromobenzene as an oil (9.65 g, 92% yield) MS m/e (M+H)+ 248; 1H NMR (400 MHZ, DMSOd6) delta 3.89 (s, 2H,), 7.19-7.39 (m, 9H).
79%	With sodium tetrahydroborate; trifluoroacetic acid; In dichloromethane; at 10 - 20℃;	To stirred TEA (2.2 mL), at 10 C, a solution of <strong>[1016-77-9](3-bromophenyl)(phenyl)methanone</strong> (0.10 g, 0.38 mmol)in DCM (1.1 mL) was added drop-wise followed by addition of NaBH4 (0.17 g, 4.56 mmol) portion-wise.The ice-bath was removed and the reaction mixture was stirred overnight at RT. The mixture waspoured into ice, basified with NaOH and extracted with Et20. The organic phase was washed with water,dried and solvent removed under vacuum to give 1-benzyl-3-bromobenzene (p24, 74 mg, y= 79%)1H NMR (CHLOROFORM-d): 6 ppm 7.30 - 7.41 (m, 4 H) 7.23 - 7.30 (m, 1 H) 7.12 - 7.23 (m, 4 H) 3.98(s, 2 H)
	With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at 20℃;	Step 2: (3-Benzyl)phenyl bromide. A solution of (3-bromophenyl)ethanone (4.10 g, 0.0156 mole) and triethylsilane (2.72 g, 3.71 ml, 0.0234 mole) in methylene chloride (40 ml) was chilled to 0 C. under argon with stirring followed by addition of neat boron trifluoride etherate (3.32 g, 2.96 ml, 23.4 mmol). The reaction stirred at room temprature overnight. The reaction mixture was poured into 160 ml saturated NaHCO3 and extracted with EtOAc three times, the combined organic layers were washed with brine and dried over Na2SO4, filtered and evaporated to afford colorless oil. Chromatographic purification using 5% EtOAc/hexanes afforded pure (3-benzyl)phenyl bromide; Rf=0.44 (5% EtOAc/Hexanes) 1H NMR (400 MHz, CDCl3) delta 7.27-7.33 (m, 4H), 7.09-7.23 (m, 5H),3.93 (s, 2H).

Yield	Reaction Conditions	Operation in experiment
	With magnesium 1.) THF; Yield given. Multistep reaction;
	With magnesium 1.) THF, 1,2-dibromoethane, reflux, 2.5 h, 2.) THF, 1,2-dibromoethane, RT, overnight; Yield given. Multistep reaction;

[ CAS No. 27798-39-6 ] {[proInfo.proName]}

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[ 27798-39-6 ] Synthesis Path-Upstream 1~1

[ 27798-39-6 ] Synthesis Path-Downstream 1~51

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[ 27798-39-6 ]

Aryls

Bromides

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Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1-benzyl-3-bromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: N-Methoxy-N-methylacetamide In tetrahydrofuran; hexane at -78 - 20℃; Further stages.;
	Stage #1: 1-benzyl-3-bromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.25h; Stage #2: N-Methoxy-N-methylacetamide In tetrahydrofuran; hexane at -78 - 20℃; Stage #3: With water; potassium hydrogencarbonate In tetrahydrofuran; hexane	7.7 Step 7-1-(3-Benzylphenyl)ethanone (7G) Step 7-1-(3-Benzylphenyl)ethanone (7G) To an oven dried 100 ml 3-neck flask fitted with temperature probe, magnetic stir bar, and argon inlet was added 1.10 g 7F in 26 ml ThF and cooled to -78° C. Following dropwise addition of 1.6 M n-butyl lithium in hexanes (4.90 ml, 49 mmole) over 15 minutes, the reaction was stirred for 1 h at -78° C. before adding neat N-methoxy-N-methylacetamide (551 mg, 53.4 mmole) over 20 minutes. The reaction mixture warmed slowly to room temperature as the bath discharged overnight. The reaction was quenched with 60 ml 10% KHSO4 and extracted with Et2O three times. The combined organic layers were washed with NaHCO3, brine and dried over Na2SO4, filtered and evaporated in vacuo to give a clear yellow oil. Chromatographic purification using EtOAc/hexanes afforded pure 7G.
	Stage #1: 1-benzyl-3-bromobenzene With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 1.25h; Stage #2: N-Methoxy-N-methylacetamide In tetrahydrofuran; hexanes at -78 - 20℃;	4.3 Step 3: 1-(3-Benzylphenyl)ethanone (4B). Step 3: 1-(3-Benzylphenyl)ethanone (4B). To an oven-dried 100 ml 3-neck flask fitted with temperature probe, magnetic stir bar, and argon inlet was added 1.10 g of (3-benzyl)phenyl bromide in 26 ml THF and cooled to -78° C. Following dropwise addition of 1.6 M n-butyl lithium in hexanes (4.90 ml, 49 mmol) over 15 minutes, the reaction was stirred for 1 h at -78° C. before adding neat N-methoxy-N-methylacetamide (551 mg, 53.4 mmol) over 20 minutes. The reaction mixture warmed slowly to room temperature as the bath discharged overnight. The reaction was quenched with 60 ml 10% KHSO4 and extracted with Et2O three times. The combined organic layers were washed with NaHCO3, brine and dried over Na2SO4, filtered and evaporated in vacuo to give a clear yellow oil. Chromatographic purification using EtOAc/hexanes afforded pure 4B. Rf=0.10 (5% EtOAc/hexanes); 0.40 (30 acetone, 70 hexane, 1.5 HOAc); 1H NMR (400 MHz, CDCl3) δ 7.80 (m, 2H), 7.39 (m, 2H),7.29 (m, 2H), 7.19 (m, 3H), 4.05 (s, 2H), 2.6 (s, 3H).

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1.) Mg / 1.) THF, 1,2-dibromoethane, reflux, 2.5 h, 2.) THF, 1,2-dibromoethane, RT, overnight 2: 1.) butyllithium, TMEDA / 1.) hexane, THF, from -70 to -60 deg C, 2.) hexane, THF, from -50 to 0 deg C 3: 98 percent / CrO₃, H₂SO₄ / acetone; H₂O / 0 - 20 °C
	Multi-step reaction with 3 steps 1: 1.) Mg / 1.) THF 2: 62 percent / tetrahydrofuran 3: 98 percent / CrO₃, H₂SO₄ / H₂O; acetone

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) Mg / 1.) THF, 1,2-dibromoethane, reflux, 2.5 h, 2.) THF, 1,2-dibromoethane, RT, overnight 2: 1.) butyllithium, TMEDA / 1.) hexane, THF, from -70 to -60 deg C, 2.) hexane, THF, from -50 to 0 deg C
	Multi-step reaction with 2 steps 1: 1.) Mg / 1.) THF 2: 62 percent / tetrahydrofuran

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 1.) Mg / 1.) THF, 1,2-dibromoethane, reflux, 2.5 h, 2.) THF, 1,2-dibromoethane, RT, overnight 2: 1.) butyllithium, TMEDA / 1.) hexane, THF, from -70 to -60 deg C, 2.) hexane, THF, from -50 to 0 deg C 3: 98 percent / CrO₃, H₂SO₄ / acetone; H₂O / 0 - 20 °C 4: 84 percent / diethylamine / toluene / 6 h / Heating
	Multi-step reaction with 4 steps 1: 1.) Mg / 1.) THF 2: 62 percent / tetrahydrofuran 3: 98 percent / CrO₃, H₂SO₄ / H₂O; acetone 4: 84 percent / Et₂NH / toluene

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 1.) Mg / 1.) THF, 1,2-dibromoethane, reflux, 2.5 h, 2.) THF, 1,2-dibromoethane, RT, overnight 2: 1.) butyllithium, TMEDA / 1.) hexane, THF, from -70 to -60 deg C, 2.) hexane, THF, from -50 to 0 deg C 3: 98 percent / CrO₃, H₂SO₄ / acetone; H₂O / 0 - 20 °C 4: 84 percent / diethylamine / toluene / 6 h / Heating 5: 95 percent / Na₂CrO₇, AcOH / 25 h / 130 °C
	Multi-step reaction with 5 steps 1: 1.) Mg / 1.) THF 2: 62 percent / tetrahydrofuran 3: 98 percent / CrO₃, H₂SO₄ / H₂O; acetone 4: 84 percent / Et₂NH / toluene 5: 95 percent / Na₂Cr₂O₇ / acetic acid

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 98 percent / diethyl ether / 1.5 h / Heating 2: 83 percent / AlCl₃, LiAlH₄ / diethyl ether / 1.5 h / Heating
	Multi-step reaction with 2 steps 1: diethyl ether; tetrahydrofuran / 2 h / -78 °C / Inert atmosphere 2: triethylsilane; trifluoroacetic acid / dichloromethane / 15 h / 20 °C

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 98 percent / diethyl ether 2: 85 percent / LiAlH₄, AlCl₃ / diethyl ether
	Multi-step reaction with 2 steps 1.1: magnesium / diethyl ether / 0.5 h / Reflux 1.2: 0.5 h / Reflux 2.1: aluminum (III) chloride; lithium aluminium tetrahydride / diethyl ether / -20 °C / Inert atmosphere; Reflux
	Multi-step reaction with 2 steps 1: diethyl ether; tetrahydrofuran / 2 h / -78 °C / Inert atmosphere 2: triethylsilane; trifluoroacetic acid / dichloromethane / 15 h / 20 °C

	Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 2 h / 20 °C / Cooling with ice 2: boron trifluoride diethyl etherate / 2 h / 80 °C
	Multi-step reaction with 2 steps 1: tetrahydrofuran / 2 h / -20 - 20 °C 2: indium(III) chloride; dimethylmonochlorosilane / dichloromethane / 2 h / 20 °C / Inert atmosphere

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 1.) Mg / 1.) THF 2: 62 percent / LiAlH₄, AlCl₃ / diethyl ether 3: 1.) Mg / 1.) THF 4: 62 percent / TMEDA / tetrahydrofuran 5: 98 percent / CrO₃, H₂SO₄ / acetone; H₂O 6: 84 percent / Et₂NH / toluene
	Multi-step reaction with 6 steps 1: 1.) Mg / 1.) THF 2: 62 percent / LiAlH₄, AlCl₃ / diethyl ether 4: 62 percent / tetrahydrofuran 5: 98 percent / CrO₃, H₂SO₄ / acetone; H₂O 6: 84 percent / Et₂NH / toluene

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 1.) Mg / 1.) THF 2: 62 percent / LiAlH₄, AlCl₃ / diethyl ether 3: 1.) Mg / 1.) THF 4: 62 percent / TMEDA / tetrahydrofuran 5: 98 percent / CrO₃, H₂SO₄ / acetone; H₂O 6: 84 percent / Et₂NH / toluene 7: 95 percent / Na₂Cr₂O₇ / acetic acid
	Multi-step reaction with 7 steps 1: 1.) Mg / 1.) THF 2: 62 percent / LiAlH₄, AlCl₃ / diethyl ether 4: 62 percent / tetrahydrofuran 5: 98 percent / CrO₃, H₂SO₄ / acetone; H₂O 6: 84 percent / Et₂NH / toluene 7: 95 percent / Na₂Cr₂O₇*2H₂O / acetic acid

Yield	Reaction Conditions	Operation in experiment
91%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,2-dimethoxyethane; water at 100℃; for 4h; Inert atmosphere; Large scale reaction;
4.5 g	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,2-dimethoxyethane; water at 100℃; for 15h;	1.A A) l-benzyl-3-bromobenzene A mixture of (chloromethyl) benzene (3.78 g) , (3- bromophenyl) boronic acid (6.00 g) , Pd(PPh3 ) 4 (1.73 g) , sodium carbonate (3.16 g) , DME (60 mL) and water (30 mL) was stirred at 100°C for 15 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether) to give the title compound (4.50 g) . H NMR (400 MHz, CDC13) 53.94 (2H, s) , 7.10-7.25 (5H, m) , 7.28-7.40 (4H, m) .

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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

[ CAS No. 27798-39-6 ] {[proInfo.proName]}

Quality Control of [ 27798-39-6 ]

Related Doc. of [ 27798-39-6 ]

Product Details of [ 27798-39-6 ]

Safety of [ 27798-39-6 ]

Application In Synthesis of [ 27798-39-6 ]

[ 27798-39-6 ] Synthesis Path-Upstream 1~1

[ 27798-39-6 ] Synthesis Path-Downstream 1~51

Technical Information

Related Functional Groups of [ 27798-39-6 ]

Aryls

Bromides

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 27798-39-6 ]