4'-Methylacetophenone 122-00-9 wiki

1. Names and Identifiers

1.1 Name: 4'-Methylacetophenone
1.2 Synonyms: 1-(4-Methylphenyl)ethanone 1-(p-Tolyl)ethanone 1-Acetyl-4-methylbenzene 1-p-Tolylethanone 1VR D1 4&lsquo-Methylacetophenone 4&rsquo-Methylacetophenone 4-Acetyltoluene 4-Methylacetophenone Acetophenone, 4'-methyl- EINECS 204-514-8 Esberiven Ethanone, 1-(4-methylphenyl)- Ethanone,1-(4-methylphenyl)- Melilot Melilotal Methyl 4-methylphenyl ketone Methyl p-tolyl ketone MFCD00000203 p-Acetotoluene p-Acetyltoluene p-Methyl acetophenone p-Methylacetophenone Sweet clover Yellow melilot

1.3 CAS No.: 122-00-9

1.4 CID: 8500

1.5 EINECS(EC#): 204-514-8

1.6 Molecular Formula: C9H10O (isomer)

1.7 Inchi: InChI=1S/C9H10O/c1-7-3-5-9(6-4-7)8(2)10/h3-6H,1-2H3

1.8 InChkey: GNKZMNRKLCTJAY-UHFFFAOYSA-N

1.9 Canonical Smiles: CC1=CC=C(C=C1)C(=O)C

1.10 Isomers Smiles: CC1=CC=C(C=C1)C(=O)C

2. Properties

2.1 Density: 1.005

2.1 Melting point: 22-24℃

2.1 Boiling point: 226℃

2.1 Refractive index: 1.532-1.535

2.1 Flash Point: 92℃

2.1 Precise Quality: 134.07300

2.1 PSA: 17.07000

2.1 logP: 2.19760

2.1 Solubility: 2.07g/l

2.2 Appearance: Clear colorless to pale yellow Liquid

2.3 Storage: Ambient temperatures.

2.4 Chemical Properties: 4?-Methylacetophenone has a fruity, floral odor resembling acetophenone and a sweet, strawberry-like flavor.

2.5 Color/Form: Clear colorless to pale yellow

2.6 Physical: Solid

2.7 Water Solubility: H2O: 0.37 g/L (15 oC)

2.8 Stability: Stable under normal temperatures and pressures.

2.9 StorageTemp: Store below +30°C.

3. Use and Manufacturing

3.1 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 1053 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 1 of 1053 companies. For more detailed information, please visit ECHA C&L website

Of the 7 notification(s) provided by 1052 of 1053 companies with hazard statement code(s):

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
H315 (79.94%): Causes skin irritation [Warning Skin corrosion/irritation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P264, P270, P280, P301+P312, P302+P352, P321, P330, P332+P313, P362, and P501

3.2 Methods of Manufacturing: It can be obtained by freeing essential oils: first made into semicarbazone, then decomposed with 10% oxalic acid aqueous solution and then steam distilled to obtain pure product.?By the reaction of acetyl chloride, toluene and aluminum trichloride.

3.3 Purification Methods: Impurities, including the o-and m-isomers, are removed by forming the semicarbazone (m 212-213.5o) which, after repeated crystallisation, is hydrolysed to the ketone. [Brown & Marino J Am Chem Soc 84 1236 1962.] It can also be purified by distillation under reduced pressure, followed by low temperature crystallisation from isopentane. [Beilstein 7 IV 701.] 4'-Methylacetophenone Preparation Products And Raw materials Preparation Products

3.4 Usage: 4'-Methylacetophenone is a methylated acteophenone used in cosmetics and perfumery. The presence of 4'-Methylacetophenone has been shown to accelerate the photopolymerization of Methyl methacrylate.

4. Safety and Handling

4.1 Symbol: GHS07

4.1 Hazard Codes: Xn

4.1 Signal Word: Warning

4.1 Risk Statements: R22

4.1 Safety Statements: S23;S24/25

4.1 Hazard Declaration: H302-H315

4.1 RIDADR: UN 1325

4.1 Safety Profile: Moderately toxic by ingestion. A human skin irritant. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also KETONES.

4.2 Caution Statement: P301 + P312 + P330

4.2 WGK Germany: 3

4.2 RTECS: AM9463000

4.2 Report

The 4'-Methylacetophenone, with the CAS registry number 122-00-9, has the IUPAC name of 1-(4-methylphenyl)ethanone. For being a kind of colorless oily liquid with a similar smell of acetophenone. This chemical is soluble in ethanol, slightly soluble in propylene glycol and mineral oil while insoluble in water. This chemical can be used as intermediates of spice,? herbicides and used in? organic synthesis.

The characteristics of this chemical are as below: (1)ACD/LogP: 2.00; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.998; (4)ACD/LogD (pH 7.4): 1.998; (5)ACD/BCF (pH 5.5): 19.416; (6)ACD/BCF (pH 7.4): 19.416; (7)ACD/KOC (pH 5.5): 290.859; (8)ACD/KOC (pH 7.4): 290.859; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 17.07; (13)Index of Refraction: 1.511; (14)Molar Refractivity: 41.106 cm³; (15)Molar Volume: 137.239 cm³; (16)Polarizability: 16.296×10^-24 cm³; (17)Surface Tension: 33.472 dyne/cm; (18)Density: 0.978 g/cm³; (19)Flash Point: 85.086 °C; (20)Enthalpy of Vaporization: 44.728 kJ/mol; (21)Boiling Point: 210.996 °C at 760 mmHg; (22)Vapour Pressure: 0.187 mmHg at 25°C; (23)Exact Mass: 134.073165; (24)MonoIsotopic Mass: 134.073165; (25)Topological Polar Surface Area: 17.1; (26)Heavy Atom Count: 10; (27)Complexity: 121; (28)Covalently-Bonded Unit Count: 1.

Production method of this chemical: 1-p-tolyl-ethanol could react to produce 4'-Methylacetophenone. This?reaction could happen?in the presence of the reagent of Cr₂O₃-H₂SO₄.

Use of this chemical: 4'-Methylacetophenone could react with morpholine to produce 4-(p-tolyl-thioacetyl)-morpholine. This reaction could happen in the presence of the reagent of?sulfur.

When you are dealing with this chemical, you should be cautious. This is a kind of harmful chemical which may cause damage to health, it is irritating to eyes, respiratory system and skin and it will be dangerous to our body if by inhalation, in contact with skin and if swallowed. Therefore, you should wear suitable protective clothing, gloves and eye/face protection and then try to avoid contacting with skin and eyes. If in case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Then do remember not to breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer).?

Additionally, you could obtain the molecular structure by converting the following datas:
(1)Canonical SMILES: CC1=CC=C(C=C1)C(=O)C
(2)InChI: InChI=1S/C9H10O/c1-7-3-5-9(6-4-7)8(2)10/h3-6H,1-2H3
(3)InChIKey: GNKZMNRKLCTJAY-UHFFFAOYSA-N?

Below are the toxicity information of this chemical:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LD50	oral	1400mg/kg (1400mg/kg)	?	Food and Cosmetics Toxicology. Vol. 12, Pg. 933, 1974.

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4.3 Specification

The 4'-Methylacetophenone, with the CAS registry number 122-00-9, has the IUPAC name of 1-(4-methylphenyl)ethanone. For being a kind of colorless oily liquid with a similar smell of acetophenone. This chemical is soluble in ethanol, slightly soluble in propylene glycol and mineral oil while insoluble in water. This chemical can be used as intermediates of spice,? herbicides and used in? organic synthesis.

The characteristics of this chemical are as below: (1)ACD/LogP: 2.00; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.998; (4)ACD/LogD (pH 7.4): 1.998; (5)ACD/BCF (pH 5.5): 19.416; (6)ACD/BCF (pH 7.4): 19.416; (7)ACD/KOC (pH 5.5): 290.859; (8)ACD/KOC (pH 7.4): 290.859; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 17.07; (13)Index of Refraction: 1.511; (14)Molar Refractivity: 41.106 cm³; (15)Molar Volume: 137.239 cm³; (16)Polarizability: 16.296×10^-24 cm³; (17)Surface Tension: 33.472 dyne/cm; (18)Density: 0.978 g/cm³; (19)Flash Point: 85.086 °C; (20)Enthalpy of Vaporization: 44.728 kJ/mol; (21)Boiling Point: 210.996 °C at 760 mmHg; (22)Vapour Pressure: 0.187 mmHg at 25°C; (23)Exact Mass: 134.073165; (24)MonoIsotopic Mass: 134.073165; (25)Topological Polar Surface Area: 17.1; (26)Heavy Atom Count: 10; (27)Complexity: 121; (28)Covalently-Bonded Unit Count: 1.

Production method of this chemical: 1-p-tolyl-ethanol could react to produce 4'-Methylacetophenone. This?reaction could happen?in the presence of the reagent of Cr₂O₃-H₂SO₄.

Use of this chemical: 4'-Methylacetophenone could react with morpholine to produce 4-(p-tolyl-thioacetyl)-morpholine. This reaction could happen in the presence of the reagent of?sulfur.

When you are dealing with this chemical, you should be cautious. This is a kind of harmful chemical which may cause damage to health, it is irritating to eyes, respiratory system and skin and it will be dangerous to our body if by inhalation, in contact with skin and if swallowed. Therefore, you should wear suitable protective clothing, gloves and eye/face protection and then try to avoid contacting with skin and eyes. If in case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Then do remember not to breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer).?

Additionally, you could obtain the molecular structure by converting the following datas:
(1)Canonical SMILES: CC1=CC=C(C=C1)C(=O)C
(2)InChI: InChI=1S/C9H10O/c1-7-3-5-9(6-4-7)8(2)10/h3-6H,1-2H3
(3)InChIKey: GNKZMNRKLCTJAY-UHFFFAOYSA-N?

Below are the toxicity information of this chemical:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rat	LD50	oral	1400mg/kg (1400mg/kg)	?	Food and Cosmetics Toxicology. Vol. 12, Pg. 933, 1974.

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4.4 Toxicity: LD50 orally in Rabbit: 1400 mg/kg LD50 dermal Rabbit > 2000 mg/kg

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin irritation, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed H315 Causes skin irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in CDCl3

13C NMR : Predict

1H NMR : 400 MHz in DMSO-d6

1H NMR : Predict

Predict 1H proton NMR

IR : CCl4 solution

IR : liquid film

Raman : 4880 A,200 M,liquid

Mass

7. Synthesis Route

122-00-9Total: 107 Synthesis Route

99-87-6 56 Suppliers

3457-45-2 16 Suppliers

122-00-9 284 Suppliers

Literatures:
Monatshefte fuer Chemie, , vol. 53/54, p. 728
Yield: null

99-87-6 56 Suppliers

1197-01-9 25 Suppliers

734-17-8 1 Suppliers

122-00-9 284 Suppliers

Literatures:
Journal of the Chemical Society, , vol. 77, p. 343
Yield: null

99-87-6 56 Suppliers

1197-01-9 25 Suppliers

536-66-3 125 Suppliers

122-00-9 284 Suppliers

Literatures:
Industrial and Engineering Chemistry, , vol. 34, p. 1028,1032 US2302466 , ; US2302462 , ;
Yield: null

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8. Precursor and Product

precursor:

622-96-8

766-97-2

619-41-0

99-97-8

99-87-6

product :

728-88-1

619-41-0

586-89-0

5465-41-8

7163-50-0

99-94-5

833-85-2

7497-80-5

2103-91-5

4974-59-8

699-02-5

4209-24-9

1443-80-7

2089-33-0

5333-27-7

6595-30-8

586-70-9

536-50-5

6921-64-8

619-55-6

766-97-2

938-94-3

6941-19-1

1197-01-9

622-47-9

View all

9. Other Information

9.0 Usage: 4'-Methylacetophenone is used as a flavoring agent. It reacts with morpholine to get 4-(p-tolyl-thioacetyl)-morpholine in the presence of sulfur as a reagent. Further, it is used as an intermediate in the manufacture of active pharmaceutical ingredients, perfumes and cosmetics.

9.1 BRN: 606053

9.2 Description: 4'-Methylacetophenone has a fruity, floral odor resembling acetophenone and a sweet, strawberry-like flavor. May be prepared by slow addition of acetyl chloride to a mixture of toluene and AlCl in an ice bath and under vacuum, maintaining the temperature at +5°C and then letting it increase to +20°C.

9.3 Chemical Properties: 4?-Methylacetophenone has a fruity, floral odor resembling acetophenone and a sweet, strawberry-like flavor.

9.4 Chemical Properties: clear colourless to pale yellowish liquid

9.5 Chemical Properties: 4'-Methylacetophenone has been identified in Brazilian rosewood oil and in pepper. It occurs as colorless crystals with a floral, sweet odor that is milder than that of acetophenone. 4-Methylacetophenone is prepared from toluene and acetic anhydride or acetyl chloride by a Friedel–Crafts reaction. It is used for blossom notes in mimosaand hawthorn-type perfumes, especially soap perfumes.

9.6 Occurrence: Reported found in the essential oil distilled from the wood of Myrocarpus fastigiatus, Myrocarpus frondo sus, Bois de Rose. Also reported found in sour cherry, orange and grapefruit peel oil, black currants, guava, peach, blackberry, celery, potato, tomato, mentha oils, pepper, parsley, smoked fish, cognac, parmesan cheese, cocoa, tea, soybean, cloudberry, mango, cauliflower, broccoli, rice bran, buckwheat, dried bonito, cherimoya, calabash nutmeg and mastic gum leaf oil, cooked cabbage, mandarin juice.

9.7 Uses: 4'-Methylacetophenone is a methylated acteophenone used in cosmetics and perfumery. The presence of 4'-Methylacetophenone has been shown to accelerate the photopolymerization of Methyl methacrylate.

9.8 Preparation: By slow addition of acetyl chloride to a mixture of toluene and AlCl in an ice bath and under vacuum, maintaining the temperature at +5°C and then letting it increase to +20°C.

9.9 Taste threshold values: Taste characteristics at 20 ppm: sweet, creamy, fruity, cherry and heliotropine-like.

9.10 Synthesis Reference(s): Journal of the American Chemical Society, 110, p. 2560, 1988 DOI: 10.1021/ja00216a032
Tetrahedron Letters, 27, p. 2965, 1986 DOI: 10.1016/S0040-4039(00)84691-2

9.11 General Description: 4′-Methylacetophenone occurs naturally in mango, tomato and orange.

9.12 Storage Conditions: It can be obtained by freeing essential oils: first made into semicarbazone, then decomposed with 10% oxalic acid aqueous solution and then steam distilled to obtain pure product.?By the reaction of acetyl chloride, toluene and aluminum trichloride.

9.13 Mesh Entry Terms: p-methylacetophenone

9.14 Manufacturing Info: Ethanone, 1-(4-methylphenyl)-: ACTIVE

9.15 Use Classification: Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index|Cosmetics -> Masking

10. Computational chemical data

Molecular Weight: 134.178g/mol
Molecular Formula: C₉H₁₀O
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 134.073164938
Monoisotopic Mass: 134.073164938
Complexity: 121
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 1
Topological Polar Surface Area: 17.1
Heavy Atom Count: 10
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBwIAAAAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAGgAAAAAADASAmAAyAIAAAACIAqBSAAACAAAkAAAIiAEAAMgIIDKAFRCAIQAggAAIiYcIiMCOQAAAAAAAAACAAAAAAAAAAAAAAAAAAA==

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