[ CAS No. 24106-05-6 ] {[proInfo.proName]}

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Quality Control of [ 24106-05-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 24106-05-6 ]

Product Details of [ 24106-05-6 ]

CAS No. :	24106-05-6	MDL No. :	MFCD00017779
Formula :	C₉H₁₀BrNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	228.09	Pubchem ID :	-
Synonyms :

Safety of [ 24106-05-6 ]

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

Application In Synthesis of [ 24106-05-6 ]

* 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 [ 24106-05-6 ]
Downstream synthetic route of [ 24106-05-6 ]

[ 24106-05-6 ] Synthesis Path-Upstream 1~9

1
[ 24106-05-6 ]
[ 40598-76-3 ]

Reference： [1] Chemische Berichte, 1922, vol. 55, p. 1141,1157

2
[ 24106-05-6 ]
[ 465529-56-0 ]

Reference： [1] Chemische Berichte, 1922, vol. 55, p. 1141,1157

3
[ 24106-05-6 ]
[ 465529-57-1 ]

Reference： [1] Chemische Berichte, 1922, vol. 55, p. 1141,1157
[2] Chemische Berichte, 1922, vol. 55, p. 1141,1157

4
[ 24106-05-6 ]
[ 4692-98-2 ]

Reference： [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 3, p. 564 - 574

5
[ 24106-05-6 ]
[ 2362-12-1 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1975, vol. 48, p. 2127 - 2133

6
[ 24106-05-6 ]
[ 329944-72-1 ]

Reference： [1] Journal of the Chemical Society, 1915, vol. 107, p. 849

7
[ 24106-05-6 ]
[ 54932-72-8 ]

Reference： [1] Journal of the Indian Chemical Society, 1959, vol. 36, p. 329,333

8
[ 24106-05-6 ]
[ 78881-21-7 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 7, p. 1860 - 1864

9
[ 24106-05-6 ]
[ 76153-06-5 ]

Reference： [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1980, vol. 19, # 12, p. 1035 - 1037

Yield	Reaction Conditions	Operation in experiment
94%	With hydrogen bromide; Selectfluor; In water; at 20℃; for 0.25h;	General procedure: 1a as example: To a stirred suspension of N-(p-tolyl)acetamide 1a (75 mg, 0.5 mmol) and Selectfluor (213 mg, 0.6 mmol) in water (3.0 mL) was added HBr (40% aqueous, 0.08 mL, 0.55 mmol), and the mixture was stirred for 5 min at room temperature. After 1a was consumed, as indicated by TLC, the reaction mixture was quenched with saturated aqueous Na2S2O3 (2.0 mL) and water (20.0 mL), and extracted with CH2Cl2 (10.0 mL) three times. The residue obtained after evaporation of the solvent was purified by column chromatography on silica gel (petroleum ether-ethyl acetate = 6:1, v/v) to afford N-(2-bromo-4-methylphenyl)acetamide 2a as a white solid (108 mg, 95% yield).
	With bromine; acetic acid; at 50 - 55℃; for 1.5h;	To a stirred solution of step-a product (24 g, 0.16 mol) in acetic acid (88 ml, 3.7 times), bromine (25.6 g (8.3 ml), 0.16 mol) was added drop wise at rt. Heated the reaction mass to 50 - 550C and allowed stirred for 1.5 hrs at the same temperature. Progress of the reaction was monitored by TLC (50% ethyl acetate/hexane, Rr0.6). On completion of the reaction, poured the reaction contents into ice cold water. The solid thrown out was filtered and dried to obtain the crude product as a pale pink solid (55g, crude). The crude obtained was directly used for the next step without any further purification.
		A mixture of 2-methylaniline (5 g, 47 mmol, 1 eq.), acetic anhydride (5 g, 49 mmol, 1.1 eq.) and hexamethylphosphoramide (trace) was stirred at room temperature. The reaction was monitored by TLC or HPLC. After completion of amide formation, aqueous hydrobromic acid (40%, 9.53 g, 47 mmol, 1.0 eq.) was added to the resulting solution of /V-(2-methylphenyl)acetamide and the mixture was cooled to 0 0C. Aqueous hydrogen peroxide (30%, 5.48 g, 47 mmol, 1.0 eq.) was then added slowly within 30 min and stirring was continued overnight. A white precipitate formed and was collected by filtration. The filtrate was concentrated using a rotary evaporator and a second crop of white solid was collected by filtration. The combined white solid was washed with water and aqueous sodium carbonate and dried to give Lambda£(4-bromo- 2-methylphenyl)acetamide as a white solid. Yield: 8.50 g (80%).1H NMR (400 MHz, DMSO-fe): delta 9.32 (s, 1H), 7.41 (d, J= 2.0 Hz, 1H), 7.40 (d, J = 8.8 Hz, 1 H), 7.32 (dd, J = 2.0 Hz, J= 8.8 Hz, 1 H), 2.19 (s, 3H), 2.05 (s, 3H). 13C NMR (100 MHz, DMSO-alphafe): delta 168.8, 136.4, 134.5, 133.1 , 129.1, 127.0, 117.4, 23.8, 18.0.

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: 4'-bromo-2'-methylacetanilide With hydrogenchloride In ethanol; water for 3h; Reflux; Stage #2: With sodium hydroxide In water at 20℃; for 0.5h;	6.6.12.c Step-b product (55 g, 0.28 mol) was dissolved in ethanol (65 ml, 1 time) and heated to a reflux temperature. While boiling the contents, cone. HCI (65 ml) was added and the reaction mass was refluxed for 3 hrs. Progress of the reaction was monitored by TLC (50% ethyl acetate/hexane, RrO.8). On completion of the reaction, cooled the contents to rt and the solid thrown out was filtered. The solid obtained was dried (35 g) and dissolved in water (93 ml). A solution of sodium hydroxide (16.3 g, 0.4 mol, 2.7 eq) in water (81.5 ml) was added and the reaction mass was stirred for 30 min at rt. Progress of the reaction was monitored by TLC (50% ethyl acetate/hexane, RrO.8). On completion of the reaction, solid thrown out was filtered. The solid obtained was dissolved in ethyl acetate (250 ml), dried over sodium sulfate and concentrated under reduced pressure. The crude obtained was washed with hexane and dried to yield the required product as a brown colored solid (22 g, 63% yield).
50%	Stage #1: 4'-bromo-2'-methylacetanilide With hydrogenchloride In ethanol for 3h; Reflux; Stage #2: With water; sodium hydroxide at 20℃; for 0.5h;	3 Step3: Compound [91] ( 15.0g, 0.65mol, 1 eq.) was taken in 25 ml ethanol in two necked RBF. The mixture was refluxed. Con HCl (20 ml) was added to the mixture drop wise and refluxing was continued for 3 hrs. After completion, the mixture was cooled to RT and solid was filtered. The solid obtained was dissolved in water, basified with aq. NaOH ad stirred at RT for 30 min. The solution was extracted with ethyl acetate (3 X 200 ml), organic layer was separated, dried over Na2SC>4, concentrated under reduced pressure to obtain compound [92] (7.25g, 50%) brown colored solid. ESIMS: 188 (M+ + 1)
	With hydrogenchloride

Yield	Reaction Conditions	Operation in experiment
96%	With triethylamine In dichloromethane from 0 deg C to RT;
86%	In ethyl acetate at 20℃; for 3h;
	In dichloromethane at 20℃;

Yield	Reaction Conditions	Operation in experiment
25.0 g (94%)		PREPARATION 14 N-(4-Fluoro-2-methylphenyl)acetamide In the manner of Preparation 5, 20 g (0.160 mol) of 5-fluoro-2-methylaniline was converted into the title compound: yield 25.0 g (94%); m.p. 131-132 C., [lit. m.p. 133.5-134 C.: E. A. Steck, L. T. Fletcher, J. Am. Chem. Soc. 70, 439-440 (1948)].

Yield	Reaction Conditions	Operation in experiment
11.1 g (94%)		PREPARATION 21 N-(4-Iodo-2-methylphenyl)acetamide In the manner of Preparation 5, 10 g (0.043 mol) of <strong>[83863-33-6]5-iodo-2-methylaniline</strong> was converted into the title compound: yield 11.1 g (94%); m.p. 182-183 C. Analysis calculated for C9 H10 INO: C, 39.29; H, 3.66; N, 5.09%. Found: C, 39.61; H, 3.77; N, 4.96%.

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: hydrogenchloride / ethanol / 3 h / Reflux 1.2: 0.5 h / 20 °C 2.1: water / 0.25 h / 20 °C 2.2: 0 - 5 °C 3.1: 18-crown-6 ether; potassium acetate / chloroform / 2 h / 20 °C 4.1: trifluoroacetic acid / ethyl acetate 5.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 18 h / 100 °C / Inert atmosphere

Yield	Reaction Conditions	Operation in experiment
90%	With Imidazole hydrochloride at 150℃; for 6h; Sealed tube;	3.2. General Procedures for the Synthesis of N-Acetamides 1a-1w General procedure: To a mixture of aromatic or aliphatic or heterocyclic amine (3.0 mmol, 1.0 equiv.), Imidazolium chloride (1.0 mmol, 0.3 equiv.), N,N-Dimethyl acetamide (2.0 mL) was added. The mixture was refluxed at 150 °C and the progress of the reaction was monitored by TLC visualized with UV short wavelength followed by iodine stain. After completion, the mixture was diluted with cold water(10 mL) then extracted with EtOAc (10 mL). The EtOAc layer was washed with 1 M hydrochloric acid (3.0 15 mL). Adsorption of pigment with activated carbon, filtration of filtrate. The filtrate was dried over anhydrous Na2SO4 and concentrated under vacuum to obtain crude N-acetamide amine, the N-acetamide amine product was isolated by column chromatography eluting with petroleum ether:ethyl acetate (10:1) mixtures.
82%	With potassium <i>tert</i>-butylate at 20℃; Sealed tube; Inert atmosphere;

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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.
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P251	Pressurized container: Do not pierce or burn, even after use.
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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:
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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.
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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:
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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
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P378
P380	Evacuate area.
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
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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.
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P401
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Physical hazards
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H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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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
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H319	Causes serious eye irritation
H320	Causes eye irritation
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H361d	Suspected of damaging the unborn child
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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

[ CAS No. 24106-05-6 ] {[proInfo.proName]}

Quality Control of [ 24106-05-6 ]

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Application In Synthesis of [ 24106-05-6 ]

[ 24106-05-6 ] Synthesis Path-Upstream 1~9

[ 24106-05-6 ] Synthesis Path-Downstream 1~17

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