3D Mol Similar

4'-Hydroxypropiophenone

Iupac Name：1-(4-hydroxyphenyl)propan-1-one

CAS No.: 70-70-2

Molecular Weight：150.1745

Modify Date.: 2022-11-25 00:54

Introduction:

P-Hydroxypropiophenone is a member of acetophenones.

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1. Names and Identifiers

1.1 Name: 4'-Hydroxypropiophenone
1.2 Synonyms: 1-(4-Hydroxyphenyl)-1-propanone 1-(4-hydroxyphenyl)propan-1-one 1-Propanone, 1-(4-hydroxyphenyl)- 4′-Hydroxypropiophen 4'-hydroxy-propiophenone 4-Hydroxypropiophenone 4-HYDROXYPROPIOPHENONE / PAROXYPROPIONE 4''-HYDROXYPROPRIOPHENONE B 360 Bio-Fren EINECS 202-815-9 Frenon H-365 Hypostat Mepal MFCD00008745 P-acetone PARA-ETHYLKETOPHENOL para-hydroxy-propiophenone PARA-PROPIONYLPHENOL Paroxon paroxypropione p-HOC6H4COEt PHP p-Hydroxypropiophenone POP VANATONE

1.3 CAS No.: 70-70-2

1.4 CID: 6271

1.5 EINECS(EC#): 200-743-2

1.6 Molecular Formula: C9H10O2 (isomer)

1.7 Inchi: InChI=1S/C9H10O2/c1-2-9(11)7-3-5-8(10)6-4-7/h3-6,10H,2H2,1H3

1.8 InChkey: RARSHUDCJQSEFJ-UHFFFAOYSA-N

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

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

2. Properties

2.1 Density: 1.104

2.1 Melting point: 148-152℃

2.1 Boiling point: 152-154 °C at 26 mm Hg(lit.)

2.1 Refractive index: 1.542

2.1 Flash Point: 180℃

2.1 Precise Quality: 150.06800

2.1 PSA: 37.30000

2.1 logP: 1.98490

2.1 Solubility: methanol: 0.1?g/mL, clear

2.2 Appearance: white powder

2.3 Storage: Ambient temperatures.

2.4 Chemical Properties: white powder

2.5 Color/Form: Powder

2.6 pKa: 8.87±0.26(Predicted)

2.7 Water Solubility: 0.34 g/l (15 oC)

2.8 StorageTemp: Store below +30°C.

3. Use and Manufacturing

3.1 Purification Methods: 4'-Hydroxypropiophenone [70-70-2] M 150.2, m 149o, b 140-145o/0.5mm, 8.05. Crystallise the phenone from H2O (m 149.8-150.2o) or EtOH (m 147o). The benzoyl derivative has m 117o, and the semicarbazone has m 183o (EtOH). [Beilstein 8 H 102, 8 II 104, 8 III 379.] 4'-Hydroxypropiophenone Preparation Products And Raw materials Raw materials

3.2 Usage: gonadotropic hormone inhibitor

4. Safety and Handling

4.1 Hazard Codes: Xn; Xi

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S24/25

4.1 RIDADR: 25kgs

4.1 Safety Profile: Poison by intraperitoneal, subcutaneous, and parenteral routes. An experimental teratogen. Other experimental reproductive effects. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also KETONES.

4.2 WGK Germany: 3

4.2 RTECS: UH1925000

4.2 Report: Reported in EPA TSCA Inventory.

4.3 Safety: Hazard Codes: Xn,?Xi
Risk Statements: 36/37/38?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 37-24/25-36-26?
S37:Wear suitable gloves.?
S24/25:Avoid contact with skin and eyes.?
S36:Wear suitable protective clothing.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3
RTECS: UH1925000
HS Code: 29145000
Hazardous Substances Data: 70-70-2(Hazardous Substances Data)
Poison by intraperitoneal, subcutaneous, and parenteral routes. An experimental teratogen. Other experimental reproductive effects. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also KETONES.

4.4 Specification: ?Paroxypropione (CAS NO.70-70-2) is also named as 1-(4-Hydroxyphenyl)-1-propanone ; 1-(p-Hydroxyphenyl)-1-propanone ; 4-08-00-00441 (Beilstein Handbook Reference) ; 4-Hydroxypropiophenone ; 4-Propionylphenol ; AI3-03719 ; B 360 ;?Ethyl p-hydroxyphenyl ketone ; Frenantol ; Frenohypon ; Frenon ; Frenormon ; H 365 ; Paroxipropiona ; Paroxipropiona [INN-Spanish] ; Paroxon ; Possipione ; Profenone ; Proxiphenon ; Sterofenon ; UNII-X9952001TG ; USAF EK-3302 ; p-Hydroxyphenyl-1-propanone ; p-Hydroxypropiophenone ; p-Oxypropiophenone ; p-Propionylphenol ; p-Propiophenol .?Paroxypropione (CAS NO.70-70-2) is white powder. It is?slightly soluble in water, soluble in boiling water, with alcohol, ether immiscibility.

4.5 Toxicity

1.	???	ims-rbt TDLo:1600?mg/kg (female 15-30D post):TER	???	AOGNAX ?? Archivio di Ostetricia e Ginecologia. 66 (1961),286.
2.	???	orl-mus LD50:3?mg/kg	???	85JDAH ?? Organophosphorus Pesticides: Organic and Biological Chemistry Eto, M.,Cleveland, OH.:?CRC Press, Inc.,1974,197.
3.	???	ipr-mus LD50:200?mg/kg	???	NTIS** ?? National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD277-689 .
4.	???	scu-mus LD50:1130?μg/kg	???	AIPTAK ?? Archives Internationales de Pharmacodynamie et de Therapie. 124 (1960),212.
5.	???	par-frg LD50:91?mg/kg	???	AIPTAK ?? Archives Internationales de Pharmacodynamie et de Therapie. 124 (1960),212.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	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. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
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

1H NMR : 90 MHz in CDCl3

gas

IR : KBr disc

IR : nujol mull

SOLID (KBr DISC) VS KBr

Mass

7. Synthesis Route

70-70-2Total: 22 Synthesis Route

121-97-1 123 Suppliers

70-70-2 241 Suppliers

Literatures:
DONG WHA PHARMACEUTICAL. IND. CO., LTD. Patent: WO2006/14087 A1, 2006 ; Location in patent: Page/Page column 67 ;
Yield: ~68%

637-27-4 15 Suppliers

70-70-2 241 Suppliers

Literatures:
Viswanathan; Kodgule; Chaudhari Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 15 p. 3532 - 3535
Yield: ~58%

628-13-7 166 Suppliers

70-70-2 241 Suppliers

Literatures:
Recueil des Travaux Chimiques des Pays-Bas, , vol. 68, p. 781,785
Yield: null

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8. Precursor and Product

precursor:

68-12-2

53946-87-5

84234-15-1

7446-70-0

142-82-5

628-13-7

802294-64-0

75-15-0

925-90-6

99-93-4

610-99-1

79-03-8

637-27-4

79119-31-6

80-46-6

192067-89-3

10035-10-6

79-34-5

142-96-1

4495-66-3

64-19-7

121-97-1

108-95-2

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product :

88737-51-3

501-97-3

88737-50-2

83022-58-6

84-16-2

198480-21-6

1929-29-9

4495-66-3

53946-87-5

35081-45-9

88737-43-3

50916-44-4

5736-90-3

88737-60-4

645-56-7

5736-93-6

29644-98-2

85068-38-8

889-26-9

5736-96-9

36116-14-0

62932-89-2

7507-01-9

62634-51-9

35081-48-2

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9. Other Information

9.0 Mesh Entry Terms: 4-hydroxypropiophenone

9.1 Manufacturing Info: 1-Propanone, 1-(4-hydroxyphenyl)-: ACTIVE

9.2 Merck: 14,7044

9.3 BRN: 907511

9.4 Chemical Properties: white powder

9.5 Uses: gonadotropic hormone inhibitor

9.6 Uses: p-Hydroxypropiophenone is a 4-hydroxyphenyl ketone used in the preparation of potential antitumor agents. p-Hydroxypropiophenone is a lignin degrradation product.

9.7 Uses: Intermediates of Liquid Crystals

9.8 Preparation: Preparation by Fries rearrangement of phenyl propionate
with aluminium chloride in refluxing carbon disulfide ? then at 130–150° for 2–3 h after solvent elimination (45–50%)
with aluminium chloride in nitrobenzene at 50° for 18 h (72%) or at ? 20° for 48 h (60%)
with aluminium chloride in nitromethane at 20° for 7–8 days (80%)
with aluminium chloride in chlorobenzene using microwave irradiation for ? 3 min at 106° (62%)
with aluminium chloride in ethylene dichloride at 95° for 5 h or in heptane at ? 80–90° for 7 h (36%), in benzene or in tetrachloroethane at 80°; with aluminium chloride in the presence of propionyl chloride at 50–60° for ? 6 h (49%)
with aluminium chloride without solvent at 50° for 10 h
with titanium tetrachloride in nitromethane at 20° for 7 days (56%) or ? without solvent at 50° for 10 h (39%)
with polyphosphoric acid at 100° (61%)
with boron trifluoride at 50° for 3 h (46%)
with stannic chloride at 50° for 3 h (10%).

9.9 Synthesis Reference(s): The Journal of Organic Chemistry, 30, p. 2491, 1965 DOI: 10.1021/jo01018a528

9.10 Safety Profile: Poison by intraperitoneal, subcutaneous, and parenteral routes. An experimental teratogen. Other experimental reproductive effects. A flammable liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also KETONES.

9.11 Purification Methods: 4'-Hydroxypropiophenone [70-70-2] M 150.2, m 149o, b 140-145o/0.5mm, 8.05. Crystallise the phenone from H2O (m 149.8-150.2o) or EtOH (m 147o). The benzoyl derivative has m 117o, and the semicarbazone has m 183o (EtOH). [Beilstein 8 H 102, 8 II 104, 8 III 379.]

10. Computational chemical data

Molecular Weight: 150.1745g/mol
Molecular Formula: C₉H₁₀O₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 150.068079557
Monoisotopic Mass: 150.068079557
Complexity: 135
Rotatable Bond Count: 2
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 37.3
Heavy Atom Count: 11
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: AAADccBwMAAAAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAGgAACAAADASAmAAyBoAAAgCIAqBSAAACAAAkIAAIiAEGCMgIJjKCFRKAcQAkwBEImYeIzKDOIAAAAAAAAABAAAAAAAAAAAAAAAAAAA==