81093-21-2|1-(Bromomethyl)-2,3-dimethylbenzene| Ambeed

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Quality Control of [ 81093-21-2 ] Purity: 95% SDS Specification

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Product Details of [ 81093-21-2 ]

CAS No. :	81093-21-2
Formula :	C₉H₁₁Br
M.W :	199.09
SMILES Code :	BrCC1=C(C(=CC=C1)C)C
MDL No. :	MFCD03844741
InChI Key :	UFYRPPWFKLXRQV-UHFFFAOYSA-N
Pubchem ID :	113627

Safety of [ 81093-21-2 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H314-H290
Precautionary Statements:	P501-P234-P264-P280-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P406-P405
Class:	8
UN#:	3261
Packing Group:	Ⅱ

Application In Synthesis of [ 81093-21-2 ]

* 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 [ 81093-21-2 ]

[ 81093-21-2 ] Synthesis Path-Downstream 1~35

1
[ 13651-14-4 ]
[ 81093-21-2 ]

References: [1]Journal of Natural Products,2014,vol. 77,p. 2134 - 2137.
[2]Helvetica Chimica Acta,1990,vol. 73,p. 48 - 62.
[3]Bulletin de la Societe Chimique de France,1950,p. 340,344.
[4]Zeitschrift fur Naturforschung,1951,vol. 6b,p. 246,248.
[5]Organic and Biomolecular Chemistry,2013,vol. 11,p. 1463 - 1467.

2
[ 81093-21-2 ]
[ 370069-67-3 ]

References: [1]Bulletin de la Societe Chimique de France,1950,p. 340,344.

3
[ 81093-21-2 ]
[ 108-59-8 ]
(2,3-dimethyl-benzyl)-malonic acid dimethyl ester [ No CAS ]

References: [1]Zeitschrift fur Naturforschung,1951,vol. 6b,p. 246,248.

4
[ 81093-21-2 ]
[ 105-45-3 ]
[ 81093-20-1 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 3087 - 3091.

5
[ 81093-21-2 ]
[ 603-35-0 ]
[ 128266-33-1 ]

References: [1]Helvetica Chimica Acta,1990,vol. 73,p. 48 - 62.
[2]Journal of Natural Products,2014,vol. 77,p. 2134 - 2137.

6
[ 81093-21-2 ]
[ 160056-65-5 ]
[ 1053264-74-6 ]

References: [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 4790 - 4799.

7
[ 24424-99-5 ]
[ 81093-21-2 ]
Ni(II) complex of the Schiff base of glycine with (S)-o-[N-(N-benzylprolyl)amino]benzophenone [ No CAS ]
N-Boc-(S)-2',3'-dimethylphenylalanine [ No CAS ]
[ 96293-17-3 ]

References: [1]Heterocycles,2004,vol. 64,p. 505 - 514.

8
[ 81093-21-2 ]
[ 81093-25-6 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 3087 - 3091.

9
[ 81093-21-2 ]
[ 81093-24-5 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 3087 - 3091.

10
[ 81093-21-2 ]
[ 81093-23-4 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 3087 - 3091.

11
[ 81093-21-2 ]
2-[2-(2,3-Dimethyl-phenyl)-ethyl]-furan-3-carbonyl chloride [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 3087 - 3091.

12
[ 81093-21-2 ]
[ 81093-22-3 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 3087 - 3091.

13
[ 81093-21-2 ]
C₂₂H₂₂N₂O₃S [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 3087 - 3091.

14
[ 81093-21-2 ]
[ 128266-34-2 ]

References: [1]Helvetica Chimica Acta,1990,vol. 73,p. 48 - 62.

15
[ 81093-21-2 ]
[ 128266-40-0 ]

References: [1]Helvetica Chimica Acta,1990,vol. 73,p. 48 - 62.

16
[ 81093-21-2 ]
[ 128266-34-2 ]

References: [1]Helvetica Chimica Acta,1990,vol. 73,p. 48 - 62.

17
[ 81093-21-2 ]
[ 128266-36-4 ]

References: [1]Helvetica Chimica Acta,1990,vol. 73,p. 48 - 62.

18
[ 81093-21-2 ]
[ 128266-41-1 ]

References: [1]Helvetica Chimica Acta,1990,vol. 73,p. 48 - 62.

19
[ 81093-21-2 ]
[ 128266-36-4 ]

References: [1]Helvetica Chimica Acta,1990,vol. 73,p. 48 - 62.

20
[ 603-79-2 ]
[ 81093-21-2 ]

References: [1]Helvetica Chimica Acta,1990,vol. 73,p. 48 - 62.

21
[ 81093-21-2 ]
[ 25173-73-3 ]

References: [1]Zeitschrift fur Naturforschung,1951,vol. 6b,p. 246,248.

Yield	Reaction Conditions	Operation in experiment
		i 1-Bromomethyl-2,3-dimethylbenzene A mixture of 1-hydroxymethyl-2,3-dimethylbenzene (ref) (5 g) and phosphorous tribromide (1.16 ml) in benzene (50 ml) was heated at reflux for 3 hours. The mixture was diluted with toluene, washed with water, dried (MgSO4) and evaporated. Yield 7 g. MS: GC-MS: 200/198 (M)

23
[ 81093-21-2 ]
[ 5779-93-1 ]

Yield	Reaction Conditions	Operation in experiment
	With 2-nitropropane; sodium ethanolate; In ethanol; at 20℃;	Step 1; Sodium ethoxide, 2 , 3-dimethylbenzylbromide and 2-nitropropane in ethanol at about 20 0C. Workup with a solution of sodium hydroxide.

References: [1]Patent: WO2009/53709,2009,A1 .Location in patent: Page/Page column 15.

24
[ 73260-12-5 ]
[ 81093-21-2 ]
3-acetyl-1-(2,3-dimethylbenzyl)-4-methoxy-1H-indole [ No CAS ]

References: [1]Molecules,2011,vol. 16,p. 6858 - 6870.

25
[ 81093-21-2 ]
[ 1351646-18-8 ]

References: [1]Molecules,2011,vol. 16,p. 6858 - 6870.

26
[ 81093-21-2 ]
[ 1351646-48-4 ]

References: [1]Molecules,2011,vol. 16,p. 6858 - 6870.

27
[ 1266727-97-2 ]
[ 81093-21-2 ]
C₃₀H₃₆F₂N₂O₄ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 7399 - 7404.

28
[ 1372540-21-0 ]
[ 81093-21-2 ]
C₂₃H₂₇N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 3h;	To a solution of methyl 2-methyl-5-(4-morpholinyl)-1H-benzimidazole-7-carboxylate, prepared as described in Example 26, step d (0.2 g, 0.726 mmol) in N,N-Dimethylformamide (DMF) (10 mL) was added <strong>[81093-21-2]2,3-dimethylbenzyl bromide</strong> (0.289 g, 1.453 mmol) and potassium carbonate (0.301 g, 2.179 mmol), The resulting reaction mixture was stirred for 3 h at 80 C. The solution was cooled to room temperature and poured into water and was extracted with EtOAc. The combined organic phase was washed with Brine and concentrated. The residue was purified on Biotage Isolera purification system using a Biotage 10 g SNAP silica gel cartridge and eluted with a gradient of DCM to 5% MeOH/DCM over 10 column volumes. The expected compound was collected and evaporated to yield a tan solid. The tan solid was dissolved in tetrahydrofuran (THF) (10.00 mL) followed by the addition of 1M lithium hydroxide solution (10 mL, 10 mmol). The reaction was stirred at 50 C. for 2 h. The reaction was cooled to room temperature and the organic solvent was removed in vacuo. The solution was diluted with water (20 mL) and acidified with 1 N HCl. The mixture was then filtered and the grey solid was purified by reversed phase HPLC with a gradient of acetonitrile (0.1% TFA) and water (0.1% TFA v/v) (20-50%) over 10 minutes. The appropriate fractions were collected and evaporated to yield the desired product (55.2 mg, 0.145 mmol, 20.02% yield). 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 2.31 (s, 3H) 2.36 (s, 3H) 2.85 (s, 3H) 3.13-3.24 (m, 4H) 3.80-3.96 (m, 4H) 5.49-5.61 (m, 2H) 6.29-6.38 (m, 1H) 6.94-6.99 (m, 1H) 7.00-7.07 (m, 1H) 7.14-7.23 (m, 1H) 7.72 (m, 1H). MS(ES+) m/e 379.8 [M+H]+.

References: [1]Patent: US2012/88767,2012,A1 .Location in patent: Page/Page column 53.

29
[ 1415663-76-1 ]
[ 81093-21-2 ]
[ 1415664-03-7 ]

Yield	Reaction Conditions	Operation in experiment
38%	With caesium carbonate; In N,N-dimethyl-formamide; at 120℃; for 1h;	General procedure: A stirred solution of 2-aminothiazole 10 or 17 (0.08 g, 0.27 mmol), an appropriately substituted benzyl bromide (11a-ab) (0.03 mL, 0.29 mmol), and Cs2CO3 (0.11 g, 0.35 mmol) in DMF (5 mL) was heated at 120 C for 1 h Yield 38%, mp 210.6 C; Purity by HPLC: 99.17% (35% acetonitrile); 1H NMR (400 MHz, CDCl3): delta 2.27 (s, 3H), 2.31 (s, 3H), 2.36 (s, 3H), 4.50 (s, 2H), 5.80 (br s, 1H), 7.02 (dd, 1H, J = 7.6, 2.4 Hz), 7.07-7.14 (m, 2H), 7.22 (br d, 1H, J = 7.6 Hz), 7.47-7.54 (m, 3H), 7.60 (dd, 1H, J = 9.2, 1.6 Hz), 8.28 (s, 1H), 8.74 (dd, 1H, J = 1.6, 0.8 Hz); 13C NMR (100 MHz, CDCl3) delta 15.23, 20.67, 24.44, 48.90, 115.31, 117.75, 120.58, 120.77, 122.73, 125.96, 126.86, 128.40, 130.19, 133.25, 134.73, 135.38, 137.06, 137.77, 146.62, 149.65, 152.34, 154.42, 158.21, 167.33; IR (KBr) 3228, 2972, 1551 cm-1; HRMS-ESI m/z [M + H]+ calcd. for C24H23N6S: 427.1699, found 427.1703.

References: [1]European Journal of Medicinal Chemistry,2012,vol. 57,p. 74 - 84.

30
[ 81093-21-2 ]
ethyl 7,8-dimethylquinoline-3-carboxylate [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 1463 - 1467.

31
[ 81093-21-2 ]
1-(azidomethyl)-2,3-dimethylbenzene [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 1463 - 1467.

32
[ 81093-21-2 ]
C₁₄H₁₇NO₂ [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 1463 - 1467.

33
[ 1372540-59-4 ]
[ 81093-21-2 ]
[ 1443541-14-7 ]

Yield	Reaction Conditions	Operation in experiment
71%	With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 3h;	a) 4-(4-bromo-1-(2,3-dimethylbenzyl)-2-methyl-1H-benzo[d]imidazol-6-yl)morpholine To the mixture of 4-(4-bromo-2-methyl-1H-benzo[d]imidazol-6-yl)morpholine (0.4 g, 1.351 mmol) in N,N-Dimethylformamide (DMF) (10 mL) was added <strong>[81093-21-2]1-(bromomethyl)-2,3-dimethylbenzene</strong> (0.323 g, 1.621 mmol) and potassium carbonate (0.560 g, 4.05 mmol). The resulting reaction mixture was stirred at 80 C. for 3 h. It was cooled to room temperature and poured into water (100 mL). The aqueous mixture was extracted with DCM (100 mL*2). The combined organic phases were washed with Brine (100 mL) and concentrated. The crude material was purified on silica column (20?90% EtOAc in Hexane) to give the product as solid (0.4 g, 71%). 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 2.33 (s, 3H) 2.37 (s, 3H) 2.53 (s, 3H) 2.98-3.14 (m, 4H) 3.66-3.93 (m, 4H) 5.24 (s, 2H) 6.24 (d, J=7.58 Hz, 1H) 6.53 (d, J=2.27 Hz, 1H) 6.89-7.00 (m, 1H) 7.06-7.17 (m, 2H); MS (ES+) m/e 414.1[M+H]+

References: [1]Patent: US2013/157977,2013,A1 .Location in patent: Paragraph 0200; 0201.

34
[ 5779-93-1 ]
[ 81093-21-2 ]

References: [1]Journal of Natural Products,2014,vol. 77,p. 2134 - 2137.

35
[ 81093-21-2 ]
(E/Z)-1-(3-isopropyl-4-methoxyphenyl)-2-(2,3-dimethylphenyl)ethene [ No CAS ]

References: [1]Journal of Natural Products,2014,vol. 77,p. 2134 - 2137.

Historical Records

Technical Information

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

Related Functional Groups of
[ 81093-21-2 ]

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Bromides

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Benzyl Bromides

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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.: 81093-21-2

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